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vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> 3 Chemistry </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Chemistry subsection </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Physical_properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Physical_properties"> <div class="vector-toc-text"> 3.1 Physical properties </div> </a> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Solvent_properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Solvent_properties"> <div class="vector-toc-text"> 3.2 Solvent properties </div> </a> <ul id="toc-Solvent_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Azeotrope_with_water" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Azeotrope_with_water"> <div class="vector-toc-text"> 3.3 Azeotrope with water </div> </a> <ul id="toc-Azeotrope_with_water-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Flammability" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Flammability"> <div class="vector-toc-text"> 3.4 Flammability </div> </a> <ul id="toc-Flammability-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Natural_occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Natural_occurrence"> <div class="vector-toc-text"> 4 Natural occurrence </div> </a> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> 5 Production </div> </a> <button aria-controls="toc-Production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Production subsection </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> 5.1 Sources </div> </a> <ul id="toc-Sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydration" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydration"> <div class="vector-toc-text"> 5.2 Hydration </div> </a> <ul id="toc-Hydration-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fermentation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fermentation"> <div class="vector-toc-text"> 5.3 Fermentation </div> </a> <ul id="toc-Fermentation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Testing" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Testing"> <div class="vector-toc-text"> 5.4 Testing </div> </a> <ul id="toc-Testing-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Purification" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Purification"> <div class="vector-toc-text"> 6 Purification </div> </a> <button aria-controls="toc-Purification-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Purification subsection </button> <ul id="toc-Purification-sublist" class="vector-toc-list"> <li id="toc-Grades_of_ethanol" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Grades_of_ethanol"> <div class="vector-toc-text"> 6.1 Grades of ethanol </div> </a> <ul id="toc-Grades_of_ethanol-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> 7 Reactions </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Reactions subsection </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Ester_formation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ester_formation"> <div class="vector-toc-text"> 7.1 Ester formation </div> </a> <ul id="toc-Ester_formation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dehydration" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dehydration"> <div class="vector-toc-text"> 7.2 Dehydration </div> </a> <ul id="toc-Dehydration-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Combustion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Combustion"> <div class="vector-toc-text"> 7.3 Combustion </div> </a> <ul id="toc-Combustion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acid-base_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid-base_chemistry"> <div class="vector-toc-text"> 7.4 Acid-base chemistry </div> </a> <ul id="toc-Acid-base_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Halogenation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Halogenation"> <div class="vector-toc-text"> 7.5 Halogenation </div> </a> <ul id="toc-Halogenation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation"> <div class="vector-toc-text"> 7.6 Oxidation </div> </a> <ul id="toc-Oxidation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> 7.7 Metabolism </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> 8 Safety </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 9 History </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> 10 See also </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 11 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> 12 Further reading </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> 13 External links </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Ethanol</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 117 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-117" aria-hidden="true" > 117 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Etanol" title="Etanol – Afrikaans" lang="af" hreflang="af" data-title="Etanol" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target">Afrikaans</a></li><li class="interlanguage-link interwiki-als mw-list-item"><a href="https://als.wikipedia.org/wiki/Ethanol" title="Ethanol – Alemannic" lang="gsw" hreflang="gsw" data-title="Ethanol" data-language-autonym="Alemannisch" data-language-local-name="Alemannic" class="interlanguage-link-target">Alemannisch</a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D9%8A%D8%AB%D8%A7%D9%86%D9%88%D9%84" title="إيثانول – Arabic" lang="ar" hreflang="ar" data-title="إيثانول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Etanol" title="Etanol – Aragonese" lang="an" hreflang="an" data-title="Etanol" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target">Aragonés</a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%87%E0%A6%A5%E0%A6%BE%E0%A6%A8%27%E0%A6%B2" title="ইথান'ল – Assamese" lang="as" hreflang="as" data-title="ইথান'ল" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target">অসমীয়া</a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Etanol" title="Etanol – Asturian" lang="ast" hreflang="ast" data-title="Etanol" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target">Asturianu</a></li><li class="interlanguage-link interwiki-awa mw-list-item"><a href="https://awa.wikipedia.org/wiki/%E0%A4%A6%E0%A4%BE%E0%A4%B0%E0%A5%81" title="दारु – Awadhi" lang="awa" hreflang="awa" data-title="दारु" data-language-autonym="अवधी" data-language-local-name="Awadhi" class="interlanguage-link-target">अवधी</a></li><li class="interlanguage-link interwiki-gn mw-list-item"><a href="https://gn.wikipedia.org/wiki/Etanol" title="Etanol – Guarani" lang="gn" hreflang="gn" data-title="Etanol" data-language-autonym="Avañe'ẽ" data-language-local-name="Guarani" class="interlanguage-link-target">Avañe'ẽ</a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Etanol" title="Etanol – Azerbaijani" lang="az" hreflang="az" data-title="Etanol" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%AA%D8%A7%D9%86%D9%88%D9%84" title="اتانول – South Azerbaijani" lang="azb" hreflang="azb" data-title="اتانول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%87%E0%A6%A5%E0%A6%BE%E0%A6%A8%E0%A6%B2" title="ইথানল – Bangla" lang="bn" hreflang="bn" data-title="ইথানল" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target">বাংলা</a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Ethanol" title="Ethanol – Minnan" lang="nan" hreflang="nan" data-title="Ethanol" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target">閩南語 / Bân-lâm-gú</a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Bashkir" lang="ba" hreflang="ba" data-title="Этанол" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target">Башҡортса</a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Belarusian" lang="be" hreflang="be" data-title="Этанол" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target">Беларуская</a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB%D1%8C" title="Этаноль – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Этаноль" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target">Беларуская (тарашкевіца)</a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Etanol" title="Etanol – Central Bikol" lang="bcl" hreflang="bcl" data-title="Etanol" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target">Bikol Central</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%95%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Етанол – Bulgarian" lang="bg" hreflang="bg" data-title="Етанол" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bar mw-list-item"><a href="https://bar.wikipedia.org/wiki/Ethanoi" title="Ethanoi – Bavarian" lang="bar" hreflang="bar" data-title="Ethanoi" data-language-autonym="Boarisch" data-language-local-name="Bavarian" class="interlanguage-link-target">Boarisch</a></li><li class="interlanguage-link interwiki-bo mw-list-item"><a href="https://bo.wikipedia.org/wiki/%E0%BD%A8%E0%BC%8B%E0%BD%A2%E0%BD%82%E0%BC%8B%E0%BD%89%E0%BD%B2%E0%BD%84%E0%BC%8B%E0%BD%81%E0%BD%B4%E0%BC%8D" title="ཨ་རག་ཉིང་ཁུ། – Tibetan" lang="bo" hreflang="bo" data-title="ཨ་རག་ཉིང་ཁུ།" data-language-autonym="བོད་ཡིག" data-language-local-name="Tibetan" class="interlanguage-link-target">བོད་ཡིག</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Etanol" title="Etanol – Bosnian" lang="bs" hreflang="bs" data-title="Etanol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-br mw-list-item"><a href="https://br.wikipedia.org/wiki/Etanol" title="Etanol – Breton" lang="br" hreflang="br" data-title="Etanol" data-language-autonym="Brezhoneg" data-language-local-name="Breton" class="interlanguage-link-target">Brezhoneg</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Etanol" title="Etanol – Catalan" lang="ca" hreflang="ca" data-title="Etanol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Chuvash" lang="cv" hreflang="cv" data-title="Этанол" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target">Чӑвашла</a></li><li class="interlanguage-link interwiki-ceb mw-list-item"><a href="https://ceb.wikipedia.org/wiki/Etanol" title="Etanol – Cebuano" lang="ceb" hreflang="ceb" data-title="Etanol" data-language-autonym="Cebuano" data-language-local-name="Cebuano" class="interlanguage-link-target">Cebuano</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ethanol" title="Ethanol – Czech" lang="cs" hreflang="cs" data-title="Ethanol" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ethanol" title="Ethanol – Welsh" lang="cy" hreflang="cy" data-title="Ethanol" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/%C3%86tanol" title="Ætanol – Danish" lang="da" hreflang="da" data-title="Ætanol" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://de.wikipedia.org/wiki/Ethanol" title="Ethanol – German" lang="de" hreflang="de" data-title="Ethanol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Etanool" title="Etanool – Estonian" lang="et" hreflang="et" data-title="Etanool" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%B9%CE%B8%CE%B1%CE%BD%CF%8C%CE%BB%CE%B7" title="Αιθανόλη – Greek" lang="el" hreflang="el" data-title="Αιθανόλη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Etanol" title="Etanol – Spanish" lang="es" hreflang="es" data-title="Etanol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Etanolo" title="Etanolo – Esperanto" lang="eo" hreflang="eo" data-title="Etanolo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Etanol" title="Etanol – Basque" lang="eu" hreflang="eu" data-title="Etanol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%AA%D8%A7%D9%86%D9%88%D9%84" title="اتانول – Persian" lang="fa" hreflang="fa" data-title="اتانول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-hif mw-list-item"><a href="https://hif.wikipedia.org/wiki/Ethanol" title="Ethanol – Fiji Hindi" lang="hif" hreflang="hif" data-title="Ethanol" data-language-autonym="Fiji Hindi" data-language-local-name="Fiji Hindi" class="interlanguage-link-target">Fiji Hindi</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89thanol" title="Éthanol – French" lang="fr" hreflang="fr" data-title="Éthanol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Etanol" title="Etanol – Western Frisian" lang="fy" hreflang="fy" data-title="Etanol" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target">Frysk</a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Eat%C3%A1n%C3%B3l" title="Eatánól – Irish" lang="ga" hreflang="ga" data-title="Eatánól" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target">Gaeilge</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Etanol" title="Etanol – Galician" lang="gl" hreflang="gl" data-title="Etanol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-gu mw-list-item"><a href="https://gu.wikipedia.org/wiki/%E0%AA%87%E0%AA%A5%E0%AB%87%E0%AA%A8%E0%AB%8B%E0%AA%B2" title="ઇથેનોલ – Gujarati" lang="gu" hreflang="gu" data-title="ઇથેનોલ" data-language-autonym="ગુજરાતી" data-language-local-name="Gujarati" class="interlanguage-link-target">ગુજરાતી</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%97%90%ED%83%84%EC%98%AC" title="에탄올 – Korean" lang="ko" hreflang="ko" data-title="에탄올" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B7%D5%A9%D5%AB%D5%AC_%D5%BD%D5%BA%D5%AB%D6%80%D5%BF" title="Էթիլ սպիրտ – Armenian" lang="hy" hreflang="hy" data-title="Էթիլ սպիրտ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%87%E0%A4%A5%E0%A5%87%E0%A4%A8%E0%A5%89%E0%A4%B2" title="इथेनॉल – Hindi" lang="hi" hreflang="hi" data-title="इथेनॉल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target">हिन्दी</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Etanol" title="Etanol – Croatian" lang="hr" hreflang="hr" data-title="Etanol" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-ilo mw-list-item"><a href="https://ilo.wikipedia.org/wiki/Etanol" title="Etanol – Iloko" lang="ilo" hreflang="ilo" data-title="Etanol" data-language-autonym="Ilokano" data-language-local-name="Iloko" class="interlanguage-link-target">Ilokano</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Etanol" title="Etanol – Indonesian" lang="id" hreflang="id" data-title="Etanol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Etan%C3%B3l" title="Etanól – Icelandic" lang="is" hreflang="is" data-title="Etanól" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target">Íslenska</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Etanolo" title="Etanolo – Italian" lang="it" hreflang="it" data-title="Etanolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%AA%D7%A0%D7%95%D7%9C" title="אתנול – Hebrew" lang="he" hreflang="he" data-title="אתנול" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/%C3%89tanol" title="Étanol – Javanese" lang="jv" hreflang="jv" data-title="Étanol" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target">Jawa</a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%88%E0%B2%A5%E0%B3%88%E0%B2%B2%E0%B3%8D_%E0%B2%86%E0%B2%B2%E0%B3%8D%E0%B2%95%E0%B3%8B%E0%B2%B9%E0%B2%BE%E0%B2%B2%E0%B3%8D" title="ಈಥೈಲ್ ಆಲ್ಕೋಹಾಲ್ – Kannada" lang="kn" hreflang="kn" data-title="ಈಥೈಲ್ ಆಲ್ಕೋಹಾಲ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target">ಕನ್ನಡ</a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%94%E1%83%97%E1%83%90%E1%83%9C%E1%83%9D%E1%83%9A%E1%83%98" title="ეთანოლი – Georgian" lang="ka" hreflang="ka" data-title="ეთანოლი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target">ქართული</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%AD%D1%82%D0%B8%D0%BB_%D1%81%D0%BF%D0%B8%D1%80%D1%82%D1%96" title="Этил спирті – Kazakh" lang="kk" hreflang="kk" data-title="Этил спирті" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-kw mw-list-item"><a href="https://kw.wikipedia.org/wiki/Ethanol" title="Ethanol – Cornish" lang="kw" hreflang="kw" data-title="Ethanol" data-language-autonym="Kernowek" data-language-local-name="Cornish" class="interlanguage-link-target">Kernowek</a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Ethanoli" title="Ethanoli – Swahili" lang="sw" hreflang="sw" data-title="Ethanoli" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target">Kiswahili</a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Ethanolum" title="Ethanolum – Latin" lang="la" hreflang="la" data-title="Ethanolum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target">Latina</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Etanols" title="Etanols – Latvian" lang="lv" hreflang="lv" data-title="Etanols" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Ethanol" title="Ethanol – Luxembourgish" lang="lb" hreflang="lb" data-title="Ethanol" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target">Lëtzebuergesch</a></li><li class="interlanguage-link interwiki-lez mw-list-item"><a href="https://lez.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Lezghian" lang="lez" hreflang="lez" data-title="Этанол" data-language-autonym="Лезги" data-language-local-name="Lezghian" class="interlanguage-link-target">Лезги</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Etanolis" title="Etanolis – Lithuanian" lang="lt" hreflang="lt" data-title="Etanolis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Ethanol" title="Ethanol – Limburgish" lang="li" hreflang="li" data-title="Ethanol" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target">Limburgs</a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Etanol" title="Etanol – Lombard" lang="lmo" hreflang="lmo" data-title="Etanol" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target">Lombard</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Etanol" title="Etanol – Hungarian" lang="hu" hreflang="hu" data-title="Etanol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%95%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Етанол – Macedonian" lang="mk" hreflang="mk" data-title="Етанол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%8E%E0%B4%A5%E0%B4%A8%E0%B5%8B%E0%B5%BE" title="എഥനോൾ – Malayalam" lang="ml" hreflang="ml" data-title="എഥനോൾ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%87%E0%A4%A5%E0%A5%87%E0%A4%A8%E0%A5%89%E0%A4%B2" title="इथेनॉल – Marathi" lang="mr" hreflang="mr" data-title="इथेनॉल" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target">मराठी</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Etanol" title="Etanol – Malay" lang="ms" hreflang="ms" data-title="Etanol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Mongolian" lang="mn" hreflang="mn" data-title="Этанол" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target">Монгол</a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%A1%E1%80%AE%E1%80%9E%E1%80%94%E1%80%B1%E1%80%AC%E1%80%9C%E1%80%BA" title="အီသနောလ် – Burmese" lang="my" hreflang="my" data-title="အီသနောလ်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target">မြန်မာဘာသာ</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ethanol" title="Ethanol – Dutch" lang="nl" hreflang="nl" data-title="Ethanol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ne mw-list-item"><a href="https://ne.wikipedia.org/wiki/%E0%A4%87%E0%A4%A5%E0%A4%BE%E0%A4%A8%E0%A5%8B%E0%A4%B2" title="इथानोल – Nepali" lang="ne" hreflang="ne" data-title="इथानोल" data-language-autonym="नेपाली" data-language-local-name="Nepali" class="interlanguage-link-target">नेपाली</a></li><li class="interlanguage-link interwiki-new mw-list-item"><a href="https://new.wikipedia.org/wiki/%E0%A4%87%E0%A4%A5%E0%A4%BE%E0%A4%A8%E0%A5%8B%E0%A4%B2" title="इथानोल – Newari" lang="new" hreflang="new" data-title="इथानोल" data-language-autonym="नेपाल भाषा" data-language-local-name="Newari" class="interlanguage-link-target">नेपाल भाषा</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%82%BF%E3%83%8E%E3%83%BC%E3%83%AB" title="エタノール – Japanese" lang="ja" hreflang="ja" data-title="エタノール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Etanool" title="Etanool – Northern Frisian" lang="frr" hreflang="frr" data-title="Etanool" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target">Nordfriisk</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Etanol" title="Etanol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Etanol" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Etanol" title="Etanol – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Etanol" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target">Norsk nynorsk</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Etan%C3%B2l" title="Etanòl – Occitan" lang="oc" hreflang="oc" data-title="Etanòl" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Etil_spirti" title="Etil spirti – Uzbek" lang="uz" hreflang="uz" data-title="Etil spirti" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target">Oʻzbekcha / ўзбекча</a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%88%E0%A8%A5%E0%A9%87%E0%A8%A8%E0%A9%8B%E0%A8%B2" title="ਈਥੇਨੋਲ – Punjabi" lang="pa" hreflang="pa" data-title="ਈਥੇਨੋਲ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target">ਪੰਜਾਬੀ</a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A7%DB%8C%D8%AA%DA%BE%D8%A7%D9%86%D9%88%D9%84" title="ایتھانول – Western Punjabi" lang="pnb" hreflang="pnb" data-title="ایتھانول" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target">پنجابی</a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%DB%90%D8%AA%D9%86%D9%88%D9%84" title="اېتنول – Pashto" lang="ps" hreflang="ps" data-title="اېتنول" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target">پښتو</a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Ethanol" title="Ethanol – Low German" lang="nds" hreflang="nds" data-title="Ethanol" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target">Plattdüütsch</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Etanol" title="Etanol – Polish" lang="pl" hreflang="pl" data-title="Etanol" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Etanol" title="Etanol – Portuguese" lang="pt" hreflang="pt" data-title="Etanol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Etanol" title="Etanol – Romanian" lang="ro" hreflang="ro" data-title="Etanol" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-qu mw-list-item"><a href="https://qu.wikipedia.org/wiki/Ethanul" title="Ethanul – Quechua" lang="qu" hreflang="qu" data-title="Ethanul" data-language-autonym="Runa Simi" data-language-local-name="Quechua" class="interlanguage-link-target">Runa Simi</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Russian" lang="ru" hreflang="ru" data-title="Этанол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sah mw-list-item"><a href="https://sah.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Yakut" lang="sah" hreflang="sah" data-title="Этанол" data-language-autonym="Саха тыла" data-language-local-name="Yakut" class="interlanguage-link-target">Саха тыла</a></li><li class="interlanguage-link interwiki-stq mw-list-item"><a href="https://stq.wikipedia.org/wiki/Ethanol" title="Ethanol – Saterland Frisian" lang="stq" hreflang="stq" data-title="Ethanol" data-language-autonym="Seeltersk" data-language-local-name="Saterland Frisian" class="interlanguage-link-target">Seeltersk</a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Etanoli" title="Etanoli – Albanian" lang="sq" hreflang="sq" data-title="Etanoli" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target">Shqip</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Ethanol" title="Ethanol – Simple English" lang="en-simple" hreflang="en-simple" data-title="Ethanol" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Etanol" title="Etanol – Slovak" lang="sk" hreflang="sk" data-title="Etanol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Etanol" title="Etanol – Slovenian" lang="sl" hreflang="sl" data-title="Etanol" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%8E%D8%AA%D8%A7%D9%86%DB%86%D9%84" title="ئێتانۆل – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئێتانۆل" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target">کوردی</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%95%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Етанол – Serbian" lang="sr" hreflang="sr" data-title="Етанол" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Etanol" title="Etanol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Etanol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Etanoli" title="Etanoli – Finnish" lang="fi" hreflang="fi" data-title="Etanoli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Etanol" title="Etanol – Swedish" lang="sv" hreflang="sv" data-title="Etanol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Etanol" title="Etanol – Tagalog" lang="tl" hreflang="tl" data-title="Etanol" data-language-autonym="Tagalog" 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title="ఇథనాల్ – Telugu" lang="te" hreflang="te" data-title="ఇథనాల్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target">తెలుగు</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%AD%E0%B8%97%E0%B8%B2%E0%B8%99%E0%B8%AD%E0%B8%A5" title="เอทานอล – Thai" lang="th" hreflang="th" data-title="เอทานอล" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Tajik" lang="tg" hreflang="tg" data-title="Этанол" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target">Тоҷикӣ</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Etanol" title="Etanol – Turkish" lang="tr" hreflang="tr" data-title="Etanol" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-tyv mw-list-item"><a href="https://tyv.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Этанол – Tuvinian" lang="tyv" hreflang="tyv" data-title="Этанол" data-language-autonym="Тыва дыл" data-language-local-name="Tuvinian" class="interlanguage-link-target">Тыва дыл</a></li><li class="interlanguage-link interwiki-uk badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://uk.wikipedia.org/wiki/%D0%95%D1%82%D0%B0%D0%BD%D0%BE%D0%BB" title="Етанол – Ukrainian" lang="uk" hreflang="uk" data-title="Етанол" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A7%DB%8C%D8%AA%DA%BE%D9%86%D9%88%D9%84" 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print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">For ethanol as a drug or medicine, see <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol (drug)</a> and <a href="/wiki/Alcohols_(medicine)" title="Alcohols (medicine)">Alcohols (medicine)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Ethenol" class="mw-redirect" title="Ethenol">Ethenol</a> or <a href="/wiki/Ethynol" title="Ethynol">Ethynol</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Ethanol </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Ethanol-2D-flat.svg" class="mw-file-description" title="Full structural formula of ethanol"><img alt="Full structural formula of ethanol" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Ethanol-2D-flat.svg/110px-Ethanol-2D-flat.svg.png" decoding="async" width="110" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Ethanol-2D-flat.svg/165px-Ethanol-2D-flat.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/df/Ethanol-2D-flat.svg/220px-Ethanol-2D-flat.svg.png 2x" data-file-width="201" data-file-height="126" /></a><figcaption>Full structural formula of ethanol</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Ethanol-2D-skeletal.svg" class="mw-file-description" title="Skeletal formula of ethanol"><img alt="Skeletal formula of ethanol" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ethanol-2D-skeletal.svg/110px-Ethanol-2D-skeletal.svg.png" decoding="async" width="110" height="42" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ethanol-2D-skeletal.svg/165px-Ethanol-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ethanol-2D-skeletal.svg/220px-Ethanol-2D-skeletal.svg.png 2x" data-file-width="1034" data-file-height="397" /></a><figcaption>Skeletal formula of ethanol</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethanol-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of ethanol"><img alt="Ball-and-stick model of ethanol" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/110px-Ethanol-3D-balls.png" decoding="async" width="110" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/165px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/220px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a><figcaption>Ball-and-stick model of ethanol</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethanol-3D-vdW.png" class="mw-file-description" title="Space-filling model of ethanol"><img alt="Space-filling model of ethanol" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Ethanol-3D-vdW.png/110px-Ethanol-3D-vdW.png" decoding="async" width="110" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Ethanol-3D-vdW.png/165px-Ethanol-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Ethanol-3D-vdW.png/220px-Ethanol-3D-vdW.png 2x" data-file-width="1100" data-file-height="879" /></a><figcaption>Space-filling model of ethanol</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Sample_of_Absolute_Ethanol.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Sample_of_Absolute_Ethanol.jpg/220px-Sample_of_Absolute_Ethanol.jpg" decoding="async" width="220" height="314" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Sample_of_Absolute_Ethanol.jpg/330px-Sample_of_Absolute_Ethanol.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Sample_of_Absolute_Ethanol.jpg/440px-Sample_of_Absolute_Ethanol.jpg 2x" data-file-width="2020" data-file-height="2879" /></a> <div style="text-align:center;">Absolute ethanol</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td>Pronunciation </td> <td><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˈɛθənɒl/</a> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Ethanol<a href="#cite_note-iupac2013-1">[1]</a></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>Absolute alcohol</li><li>Alcohol</li><li>Cologne spirit</li><li>Drinking alcohol</li><li>Ethylic alcohol</li><li>EtOH</li><li>Ethyl alcohol</li><li>Ethyl hydroxide</li><li>Ethylene hydrate</li><li>Ethylol</li><li>Grain alcohol</li><li>Hydroxyethane</li><li>Methylcarbinol</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=64-17-5">64-17-5</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=OCC">Interactive image</a></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B01253">B01253</a></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1718733 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16236">CHEBI:16236</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL545">ChEMBL545</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.682.html">682</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00898">DB00898</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.526">100.000.526</a> <a href="https://www.wikidata.org/wiki/Q153#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>787 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=2299">2299</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00469">C00469</a></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/702">702</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/3K9958V90M">3K9958V90M</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>UN 1170 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9020584">DTXSID9020584</a> <a href="https://www.wikidata.org/wiki/Q153#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LFQSCWFLJHTTHZ-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LFQSCWFLJHTTHZ-UHFFFAOYAB</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">OCC</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C2H6O </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>46.069 g·mol−1 </td></tr> <tr> <td>Appearance </td> <td>Colourless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>wine-like, pungent<a href="#cite_note-2">[2]</a> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.78945 g/cm3 (at 20 °C)<a href="#cite_note-crc2-3">[3]</a> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−114.14 ± 0.03<a href="#cite_note-crc2-3">[3]</a> °C (−173.45 ± 0.05 °F; 159.01 ± 0.03 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>78.23 ± 0.09<a href="#cite_note-crc2-3">[3]</a> °C (172.81 ± 0.16 °F; 351.38 ± 0.09 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td><a href="/wiki/Miscibility" title="Miscibility">Miscible</a> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> </td> <td>−0.18 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>5.95 kPa (at 20 °C) </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (pKa) </td> <td>15.9 (H2O), 29.8 (DMSO)<a href="#cite_note-4">[4]</a><a href="#cite_note-5">[5]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−33.60·10−6 cm3/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (nD)</div> </td> <td>1.3611<a href="#cite_note-crc2-3">[3]</a> </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>1.2 mPa·s (at 20 °C), 1.074 mPa·s (at 25 °C)<a href="#cite_note-crc92-6">[6]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>1.69 D<a href="#cite_note-crc89-7">[7]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals">GHS labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a> <a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a> <a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td>Danger </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H360D: May damage the unborn child">H360D</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_9a02d12247c3a88a" /><map name="ImageMap_9a02d12247c3a88a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704">2</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704">0</a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>14 °C (Absolute)<a href="#cite_note-9">[9]</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;">Lethal dose or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD50 (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>7060 mg/kg (oral, rat)</li><li>3450 mg/kg (mouse)</li></ul></div> <a href="#cite_note-12">[12]</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">NIOSH</a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 1000 ppm (1900 mg/m3)<a href="#cite_note-PGCH-10">[10]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 1000 ppm (1900 mg/m3)<a href="#cite_note-PGCH-10">[10]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>3300 ppm <a href="#cite_note-11">[11]</a> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a href="#cite_note-sigmaaldrichMSDS-8">[8]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li><li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Ethanol_(data_page)" title="Ethanol (data page)">Ethanol (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477167117&page2=Ethanol">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y<img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style>CH3CH2OH. It is an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>, with its formula also written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">C2H5OH, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">C2H6O or EtOH, where Et stands for <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a>. Ethanol is a <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatile</a>, <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a>, colorless liquid with a characteristic <a href="/wiki/Wine" title="Wine">wine</a>-like odor and <a href="/wiki/Pungent" class="mw-redirect" title="Pungent">pungent</a> taste.<a href="#cite_note-13">[13]</a><a href="#cite_note-14">[14]</a> In nature, grape-sugar breaks up by the action of fermentation into alcohol or carbonic acid, without anything being added.<a href="#cite_note-15">[15]</a> As a <a href="/wiki/Psychoactive" class="mw-redirect" title="Psychoactive">psychoactive</a> <a href="/wiki/Depressant" title="Depressant">depressant</a>, it is the active ingredient in <a href="/wiki/Alcoholic_beverage" title="Alcoholic beverage">alcoholic beverages</a>, and the second most consumed drug globally behind <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>.<a href="#cite_note-u385-16">[16]</a> Ethanol is naturally produced by the <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> process of <a href="/wiki/Sugar" title="Sugar">sugars</a> by <a href="/wiki/Yeast" title="Yeast">yeasts</a> or via <a href="/wiki/Petrochemical" title="Petrochemical">petrochemical</a> processes such as <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> hydration. Historically it was used as a <a href="/wiki/General_anesthetic" class="mw-redirect" title="General anesthetic">general anesthetic</a>, and has modern medical applications as an <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a>, <a href="/wiki/Disinfectant" title="Disinfectant">disinfectant</a>, solvent for some medications, and <a href="/wiki/Antidote" title="Antidote">antidote</a> for <a href="/wiki/Methanol_poisoning" class="mw-redirect" title="Methanol poisoning">methanol poisoning</a> and <a href="/wiki/Ethylene_glycol_poisoning" title="Ethylene glycol poisoning">ethylene glycol poisoning</a>.<a href="#cite_note-Powell1996-17">[17]</a><a href="#cite_note-Schnelle-18">[18]</a> It is used as a chemical <a href="/wiki/Solvent" title="Solvent">solvent</a> and in the <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesis</a> of organic compounds, and as a <a href="/wiki/Alcohol_fuel" title="Alcohol fuel">fuel source</a> for lamps, stoves, and internal combustion engines. Ethanol also can be dehydrated to make ethylene, an important chemical feedstock. As of 2023, world production of ethanol fuel was 29,590,000,000 US gallons (112.0 gigalitres), coming mostly from the U.S. (51%) and Brazil (26%).<a href="#cite_note-:0-19">[19]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Name">Name</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=1" title="Edit section: Name">edit</a>]</div> Ethanol is the <a href="/wiki/Systematic_name" title="Systematic name">systematic name</a> <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">defined</a> by the <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> for a compound consisting of an <a href="/wiki/Alkyl_group" title="Alkyl group">alkyl group</a> with two carbon <a href="/wiki/Atom" title="Atom">atoms</a> (prefix "eth-"), having a single bond between them (infix "-an-") and an attached −OH <a href="/wiki/Functional_group" title="Functional group">functional group</a> (suffix "-ol").<a href="#cite_note-Pubchem-20">[20]</a> The "eth-" prefix and the qualifier "ethyl" in "ethyl alcohol" originally came from the name "ethyl" assigned in 1834 to the group C 2H 5− by <a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus Liebig</a>. He coined the word from the <a href="/wiki/German_language" title="German language">German</a> name Aether of the compound C 2H 5−O−C 2H 5 (commonly called "ether" in <a href="/wiki/English_language" title="English language">English</a>, more specifically called "<a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>").<a href="#cite_note-21">[21]</a> According to the <a href="/wiki/Oxford_English_Dictionary" title="Oxford English Dictionary">Oxford English Dictionary</a>, Ethyl is a contraction of the Ancient Greek <a href="https://en.wiktionary.org/wiki/%CE%B1%E1%BC%B0%CE%B8%CE%AE%CF%81#Ancient_Greek" class="extiw" title="wikt:αἰθήρ">αἰθήρ</a> (aithḗr, "upper air") and the Greek word <a href="https://en.wiktionary.org/wiki/%E1%BD%95%CE%BB%CE%B7#Ancient_Greek" class="extiw" title="wikt:ὕλη">ὕλη</a> (hýlē, "wood, raw material", hence "matter, substance").<a href="#cite_note-22">[22]</a> Ethanol was coined as a result of a resolution on naming alcohols and phenols that was adopted at the International Conference on <a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">Chemical Nomenclature</a> that was held in April 1892 in <a href="/wiki/Geneva" title="Geneva">Geneva</a>, Switzerland.<a href="#cite_note-23">[23]</a> The term alcohol now refers to a wider class of substances in chemistry nomenclature, but in common parlance it remains the name of ethanol. It is a medieval loan from <a href="/wiki/Arabic" title="Arabic">Arabic</a> <a href="/wiki/Kohl_(cosmetics)" title="Kohl (cosmetics)">al-kuḥl</a>, a powdered ore of <a href="/wiki/Antimony" title="Antimony">antimony</a> used since antiquity as a cosmetic, and retained that meaning in <a href="/wiki/Middle_Latin" class="mw-redirect" title="Middle Latin">Middle Latin</a>.<a href="#cite_note-24">[24]</a> The use of 'alcohol' for ethanol (in full, "alcohol of wine") was first recorded in 1753. Before the late 18th century the term alcohol generally referred to any sublimated substance.<a href="#cite_note-25">[25]</a> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=2" title="Edit section: Uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=3" title="Edit section: Medical">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alcohol_(medicine)" class="mw-redirect" title="Alcohol (medicine)">Alcohol (medicine)</a></div> Ethanol is the oldest known <a href="/wiki/Sedative" title="Sedative">sedative</a>, used as an oral <a href="/wiki/General_anesthetic" class="mw-redirect" title="General anesthetic">general anesthetic</a> during surgery in ancient <a href="/wiki/Mesopotamia" title="Mesopotamia">Mesopotamia</a> and in <a href="/wiki/Middle_Ages" title="Middle Ages">medieval times</a>.<a href="#cite_note-Powell1996-17">[17]</a><a href="#cite_note-Schnelle-18">[18]</a> Mild intoxication starts at a <a href="/wiki/Blood_alcohol_concentration" class="mw-redirect" title="Blood alcohol concentration">blood alcohol concentration</a> of 0.03-0.05 % and induces <a href="/wiki/Induced_coma" title="Induced coma">anesthetic coma</a> at 0.4%.<a href="#cite_note-26">[26]</a> This use carries the high risk of deadly <a href="/wiki/Alcohol_intoxication" title="Alcohol intoxication">alcohol intoxication</a>, <a href="/wiki/Pulmonary_aspiration" title="Pulmonary aspiration">pulmonary aspiration</a> and vomit, which led to use of alternatives in antiquity, such as <a href="/wiki/Opium" title="Opium">opium</a> and <a href="/wiki/Cannabis" title="Cannabis">cannabis</a>, and later diethyl ether, starting in the 1840s.<a href="#cite_note-Grattan-27">[27]</a> Ethanol is used as an <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a> in medical wipes and <a href="/wiki/Hand_sanitizer" title="Hand sanitizer">hand sanitizer</a> gels for its bactericidal and anti-fungal effects.<a href="#cite_note-28">[28]</a> Ethanol kills <a href="/wiki/Microorganism" title="Microorganism">microorganisms</a> by dissolving their membrane <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid bilayer</a> and <a href="/wiki/Denaturation_(biochemistry)" title="Denaturation (biochemistry)">denaturing</a> their <a href="/wiki/Protein" title="Protein">proteins</a>, and is effective against most <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a> and <a href="/wiki/Virus" title="Virus">viruses</a>. It is ineffective against bacterial <a href="/wiki/Endospore" title="Endospore">spores</a>, which can be treated with <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a>.<a href="#cite_note-29">[29]</a> A solution of 70% ethanol is more effective than pure ethanol because ethanol relies on water molecules for optimal antimicrobial activity. Absolute ethanol may inactivate microbes without destroying them because the alcohol is unable to fully permeate the microbe's membrane.<a href="#cite_note-30">[30]</a><a href="#cite_note-31">[31]</a> Ethanol can also be used as a disinfectant and antiseptic by inducing cell dehydration through disruption of the osmotic balance across the cell membrane, causing water to leave the cell, leading to cell death.<a href="#cite_note-32">[32]</a> Ethanol may be administered as an <a href="/wiki/Antidote" title="Antidote">antidote</a> to <a href="/wiki/Ethylene_glycol_poisoning" title="Ethylene glycol poisoning">ethylene glycol poisoning</a><a href="#cite_note-33">[33]</a> and <a href="/wiki/Methanol_poisoning" class="mw-redirect" title="Methanol poisoning">methanol poisoning</a>.<a href="#cite_note-EM2016-34">[34]</a> It does so by acting as a <a href="/wiki/Competitive_inhibitor" class="mw-redirect" title="Competitive inhibitor">competitive inhibitor</a> against <a href="/wiki/Methanol" title="Methanol">methanol</a> and <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a> for <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a> (ADH).<a href="#cite_note-35">[35]</a> Though it has more side effects, ethanol is less expensive and more readily available than <a href="/wiki/Fomepizole" title="Fomepizole">fomepizole</a> in the role.<a href="#cite_note-36">[36]</a> Ethanol is used to dissolve many water-insoluble medications and related compounds. Liquid preparations of <a href="/wiki/Analgesics" class="mw-redirect" title="Analgesics">pain medications</a>, <a href="/wiki/Cold_medicine" title="Cold medicine">cough and cold medicines</a>, and mouth washes, for example, may contain up to 25% ethanol<a href="#cite_note-37">[37]</a> and may need to be avoided in individuals with adverse reactions to ethanol such as <a href="/wiki/Alcohol-induced_respiratory_reactions" title="Alcohol-induced respiratory reactions">alcohol-induced respiratory reactions</a>.<a href="#cite_note-Ann_Allergy_Asthma_Immunol_2013-38">[38]</a> Ethanol is present mainly as an antimicrobial preservative in over 700 liquid preparations of medicine including <a href="/wiki/Acetaminophen" class="mw-redirect" title="Acetaminophen">acetaminophen</a>, <a href="/wiki/Iron_supplement" title="Iron supplement">iron supplements</a>, <a href="/wiki/Ranitidine" title="Ranitidine">ranitidine</a>, <a href="/wiki/Furosemide" title="Furosemide">furosemide</a>, <a href="/wiki/Mannitol" title="Mannitol">mannitol</a>, <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a>, <a href="/wiki/Trimethoprim/sulfamethoxazole" title="Trimethoprim/sulfamethoxazole">trimethoprim/sulfamethoxazole</a> and <a href="/wiki/Over-the-counter" class="mw-redirect" title="Over-the-counter">over-the-counter</a> <a href="/wiki/Cough_medicine" class="mw-redirect" title="Cough medicine">cough medicine</a>.<a href="#cite_note-39">[39]</a> Some medicinal solutions of ethanol are also known as <a href="/wiki/Tincture" title="Tincture">tinctures</a>. <div class="mw-heading mw-heading3"><h3 id="Pharmacological">Pharmacological</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=4" title="Edit section: Pharmacological">edit</a>]</div> In mammals, ethanol is primarily <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a> and <a href="/wiki/Stomach" title="Stomach">stomach</a> by ADH enzymes.<a href="#cite_note-Farrés-40">[40]</a> These enzymes catalyze the <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of ethanol into <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> (ethanal):<a href="#cite_note-41">[41]</a> <dl><dd>CH3CH2OH + NAD+ → CH3CHO + <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a> + H+</dd></dl> When present in significant concentrations, this metabolism of ethanol is additionally aided by the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> enzyme <a href="/wiki/CYP2E1" title="CYP2E1">CYP2E1</a> in humans, while trace amounts are also metabolized by <a href="/wiki/Catalase" title="Catalase">catalase</a>.<a href="#cite_note-42">[42]</a> The resulting intermediate, acetaldehyde, is a known carcinogen, and poses significantly greater toxicity in humans than ethanol itself. Many of the symptoms typically associated with alcohol intoxication—as well as many of the health hazards typically associated with the long-term consumption of ethanol—can be attributed to acetaldehyde toxicity in humans.<a href="#cite_note-43">[43]</a> The subsequent oxidation of acetaldehyde into <a href="/wiki/Acetate" title="Acetate">acetate</a> is performed by <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> (ALDH) enzymes. A mutation in the ALDH2 gene that encodes for an inactive or dysfunctional form of this enzyme affects roughly 50 % of east Asian populations, contributing to the characteristic <a href="/wiki/Alcohol_flush_reaction" title="Alcohol flush reaction">alcohol flush reaction</a> that can cause temporary reddening of the skin as well as a number of related, and often unpleasant, symptoms of acetaldehyde toxicity.<a href="#cite_note-Eng_et_al.-44">[44]</a> This mutation is typically accompanied by another mutation in the ADH enzyme <a href="/wiki/ADH1B" title="ADH1B">ADH1B</a> in roughly 80 % of east Asians, which improves the catalytic efficiency of converting ethanol into acetaldehyde.<a href="#cite_note-Eng_et_al.-44">[44]</a> <div class="mw-heading mw-heading3"><h3 id="Energy_source">Energy source</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=5" title="Edit section: Energy source">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Food_vs._fuel" title="Food vs. fuel">Food vs. fuel</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Ethanol_fuel" title="Ethanol fuel">Ethanol fuel</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Corn_vs_Ethanol_production.webp" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Corn_vs_Ethanol_production.webp/300px-Corn_vs_Ethanol_production.webp.png" decoding="async" width="300" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Corn_vs_Ethanol_production.webp/450px-Corn_vs_Ethanol_production.webp.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Corn_vs_Ethanol_production.webp/600px-Corn_vs_Ethanol_production.webp.png 2x" data-file-width="1588" data-file-height="406" /></a><figcaption>Corn vs ethanol production in the United States <style data-mw-deduplicate="TemplateStyles:r981673959">.mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}</style><div class="legend">  Total corn production (<a href="/wiki/Bushel" title="Bushel">bushels</a>) (left)</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend">  Corn used for <a href="/wiki/Ethanol_fuel" title="Ethanol fuel">Ethanol fuel</a> (bushels) (left)</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959"><div class="legend">  Percent of corn used for Ethanol (right)</div> </figcaption></figure> <table class="wikitable" style="float:right; margin-left:1em;"> <caption><a href="/wiki/Energy_density" title="Energy density">Energy content</a> (<a href="/wiki/Lower_heating_value" class="mw-redirect" title="Lower heating value">lower heating value</a>) of some fuels compared with ethanol. </caption> <tbody><tr> <th>Fuel type</th> <th>MJ/L</th> <th>MJ/kg</th> <th><a href="/wiki/Octane_rating" title="Octane rating">Research octane number</a> </th></tr> <tr> <td><a href="/wiki/Wood_fuel" title="Wood fuel">Dry wood (20% moisture)</a></td> <td></td> <td>~19.5</td> <td> </td></tr> <tr> <td><a href="/wiki/Methanol" title="Methanol">Methanol</a></td> <td>17.9</td> <td>19.9</td> <td>108.7<a href="#cite_note-Fuel_89_(2010)_2713-2720-45">[45]</a> </td></tr> <tr> <td><a href="/wiki/Ethanol_fuel" title="Ethanol fuel">Ethanol</a></td> <td>21.2<a href="#cite_note-Thomas-46">[46]</a></td> <td>26.8<a href="#cite_note-Thomas-46">[46]</a> </td> <td>108.6<a href="#cite_note-Fuel_89_(2010)_2713-2720-45">[45]</a> </td></tr> <tr> <td><a href="/wiki/E85" title="E85">E85</a> (85% ethanol, 15% gasoline)</td> <td>25.2</td> <td>33.2</td> <td>105 </td></tr> <tr> <td><a href="/wiki/Liquefied_natural_gas" title="Liquefied natural gas">Liquefied natural gas</a></td> <td>25.3</td> <td>~55</td> <td> </td></tr> <tr> <td><a href="/wiki/Autogas" title="Autogas">Autogas</a> (<a href="/wiki/Liquified_petroleum_gas" class="mw-redirect" title="Liquified petroleum gas">LPG</a>) (60% <a href="/wiki/Propane" title="Propane">propane</a> + 40% <a href="/wiki/Butane" title="Butane">butane</a>)</td> <td>26.8</td> <td>50</td> <td> </td></tr> <tr> <td><a href="/wiki/Aviation_gasoline" class="mw-redirect" title="Aviation gasoline">Aviation gasoline</a> (high-octane gasoline, not jet fuel)</td> <td>33.5</td> <td>46.8</td> <td>100/130 (lean/rich) </td></tr> <tr> <td><a href="/wiki/Alcohol_fuel" title="Alcohol fuel">Gasohol</a> (90% gasoline + 10% ethanol)</td> <td>33.7</td> <td>47.1</td> <td>93/94 </td></tr> <tr> <td>Regular gasoline/petrol</td> <td>34.8</td> <td>44.4<a href="#cite_note-47">[47]</a></td> <td>min. 91 </td></tr> <tr> <td>Premium gasoline/petrol</td> <td></td> <td></td> <td>max. 104 </td></tr> <tr> <td><a href="/wiki/Diesel_fuel" title="Diesel fuel">Diesel</a></td> <td>38.6</td> <td>45.4</td> <td>25 </td></tr> <tr> <td><a href="/wiki/Charcoal" title="Charcoal">Charcoal</a>, extruded</td> <td>50</td> <td>23</td> <td> </td></tr></tbody></table> The largest single use of ethanol is as an engine <a href="/wiki/Fuel" title="Fuel">fuel</a> and <a href="/wiki/Fuel_additive" class="mw-redirect" title="Fuel additive">fuel additive</a>. <a href="/wiki/Brazil" title="Brazil">Brazil</a> in particular relies heavily upon the use of ethanol as an engine fuel, due in part to its role as one of the world's leading producers of ethanol.<a href="#cite_note-48">[48]</a><a href="#cite_note-49">[49]</a> <a href="/wiki/Gasoline" title="Gasoline">Gasoline</a> sold in Brazil contains at least 25% <a href="/wiki/Anhydrous" title="Anhydrous">anhydrous</a> ethanol. Hydrous ethanol (about 95% ethanol and 5% water) can be used as fuel in more than 90% of new gasoline-fueled cars sold in the country. The US and many other countries primarily use E10 (10% ethanol, sometimes known as gasohol) and E85 (85% ethanol) ethanol/gasoline mixtures. Over time, it is believed that a material portion of the ≈150-billion-US-gallon (570,000,000 m3) per year market for gasoline will begin to be replaced with fuel ethanol.<a href="#cite_note-rfa1-50">[50]</a> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ethyl_alcohol_usp_grade.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Ethyl_alcohol_usp_grade.jpg/170px-Ethyl_alcohol_usp_grade.jpg" decoding="async" width="170" height="310" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Ethyl_alcohol_usp_grade.jpg/255px-Ethyl_alcohol_usp_grade.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Ethyl_alcohol_usp_grade.jpg/340px-Ethyl_alcohol_usp_grade.jpg 2x" data-file-width="1036" data-file-height="1892" /></a><figcaption><a href="/wiki/Chemical_purity" title="Chemical purity">USP grade</a> ethanol for laboratory use</figcaption></figure> Australian law limits the use of pure ethanol from <a href="/wiki/Sugarcane" title="Sugarcane">sugarcane</a> waste to 10 % in automobiles. Older cars (and vintage cars designed to use a slower burning fuel) should have the engine valves upgraded or replaced.<a href="#cite_note-51">[51]</a> According to an industry <a href="/wiki/Advocacy_group" title="Advocacy group">advocacy group</a>, ethanol as a fuel reduces harmful <a href="/wiki/Tailpipe_emissions" class="mw-redirect" title="Tailpipe emissions">tailpipe emissions</a> of carbon monoxide, particulate matter, <a href="/wiki/Oxides_of_nitrogen" class="mw-redirect" title="Oxides of nitrogen">oxides of nitrogen</a>, and other ozone-forming pollutants.<a href="#cite_note-52">[52]</a> <a href="/wiki/Argonne_National_Laboratory" title="Argonne National Laboratory">Argonne National Laboratory</a> analyzed greenhouse gas emissions of many different engine and fuel combinations, and found that <a href="/wiki/Biodiesel" title="Biodiesel">biodiesel</a>/petrodiesel blend (<a href="/wiki/B20_(biodiesel)" class="mw-redirect" title="B20 (biodiesel)">B20</a>) showed a reduction of 8%, conventional <a href="/wiki/E85" title="E85">E85</a> ethanol blend a reduction of 17% and <a href="/wiki/Cellulosic_ethanol" title="Cellulosic ethanol">cellulosic ethanol</a> 64%, compared with pure gasoline.<a href="#cite_note-53">[53]</a> Ethanol has a much greater research octane number (RON) than gasoline, meaning it is less prone to pre-ignition, allowing for better ignition advance which means more torque, and efficiency in addition to the lower carbon emissions.<a href="#cite_note-54">[54]</a> Ethanol <a href="/wiki/Combustion" title="Combustion">combustion</a> in an <a href="/wiki/Internal_combustion_engine" title="Internal combustion engine">internal combustion engine</a> yields many of the products of incomplete combustion produced by gasoline and significantly larger amounts of <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> and related species such as acetaldehyde.<a href="#cite_note-55">[55]</a> This leads to a significantly larger photochemical reactivity and more <a href="/wiki/Ground_level_ozone" class="mw-redirect" title="Ground level ozone">ground level ozone</a>.<a href="#cite_note-56">[56]</a> This data has been assembled into The Clean Fuels Report comparison of fuel emissions<a href="#cite_note-57">[57]</a> and show that ethanol exhaust generates 2.14 times as much ozone as gasoline exhaust.<a href="#cite_note-58">[58]</a> When this is added into the custom Localized Pollution Index of The Clean Fuels Report, the local pollution of ethanol (pollution that contributes to smog) is rated 1.7, where gasoline is 1.0 and higher numbers signify greater pollution.<a href="#cite_note-59">[59]</a> The <a href="/wiki/California_Air_Resources_Board" title="California Air Resources Board">California Air Resources Board</a> formalized this issue in 2008 by recognizing control standards for formaldehydes as an emissions control group, much like the conventional <a href="/wiki/NOx" title="NOx">NOx</a> and reactive organic gases (ROGs).<a href="#cite_note-60">[60]</a> More than 20% of Brazilian cars are able to use 100% ethanol as fuel, which includes ethanol-only engines and <a href="/wiki/Flex-fuel" class="mw-redirect" title="Flex-fuel">flex-fuel</a> engines.<a href="#cite_note-61">[61]</a> Flex-fuel engines in Brazil are able to work with all ethanol, all gasoline or any mixture of both. In the United States, flex-fuel vehicles can run on 0% to 85% ethanol (15% gasoline) since higher ethanol blends are not yet allowed or efficient. Brazil supports this fleet of ethanol-burning automobiles with large national infrastructure that produces ethanol from domestically grown sugarcane. Ethanol's high <a href="/wiki/Miscibility" title="Miscibility">miscibility</a> with water makes it unsuitable for shipping through modern <a href="/wiki/Pipeline_transport" class="mw-redirect" title="Pipeline transport">pipelines</a> like liquid hydrocarbons.<a href="#cite_note-HornKrupp2009-62">[62]</a> Mechanics have seen increased cases of damage to small engines (in particular, the <a href="/wiki/Carburetor" title="Carburetor">carburetor</a>) and attribute the damage to the increased water retention by ethanol in fuel.<a href="#cite_note-63">[63]</a> Ethanol was commonly used as fuel in early <a href="/wiki/Bipropellant" class="mw-redirect" title="Bipropellant">bipropellant</a> <a href="/wiki/Rocket" title="Rocket">rocket</a> (liquid-propelled) vehicles, in conjunction with an <a href="/wiki/Oxidizer" class="mw-redirect" title="Oxidizer">oxidizer</a> such as liquid oxygen. The German A-4 ballistic rocket of <a href="/wiki/World_War_II" title="World War II">World War II</a> (better known by its propaganda name <a href="/wiki/V-2" class="mw-redirect" title="V-2">V-2</a>),<a href="#cite_note-Ignition-64">[64]</a> which is credited as having begun the space age, used ethanol as the main constituent of <a href="/wiki/B-Stoff" class="mw-redirect" title="B-Stoff">B-Stoff</a>. Under such nomenclature, the ethanol was mixed with 25% water to reduce the combustion chamber temperature.<a href="#cite_note-65">[65]</a><a href="#cite_note-braeunig-66">[66]</a> The V-2's design team helped develop U.S. rockets following World War II, including the ethanol-fueled <a href="/wiki/Redstone_(rocket_family)" title="Redstone (rocket family)">Redstone rocket</a>, which launched the first U.S. astronaut on <a href="/wiki/Suborbital_spaceflight" class="mw-redirect" title="Suborbital spaceflight">suborbital spaceflight</a>.<a href="#cite_note-67">[67]</a><a href="#cite_note-68">[68]</a> Alcohols fell into general disuse as more energy-dense rocket fuels were developed,<a href="#cite_note-braeunig-66">[66]</a> although ethanol is currently used in <a href="/wiki/Light_aircraft" title="Light aircraft">lightweight</a> <a href="/wiki/Mark-III_X-racer" class="mw-redirect" title="Mark-III X-racer">rocket-powered racing aircraft</a>.<a href="#cite_note-sdc20100426-69">[69]</a> Commercial fuel cells operate on reformed natural gas, <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> or methanol. Ethanol is an attractive alternative due to its wide availability, low cost, high purity and low toxicity. There is a wide range of fuel cell concepts that have entered trials including <a href="/wiki/Direct-ethanol_fuel_cell" title="Direct-ethanol fuel cell">direct-ethanol fuel cells</a>, auto-thermal reforming systems and thermally integrated systems. The majority of work is being conducted at a research level although there are a number of organizations at the beginning of the commercialization of ethanol fuel cells.<a href="#cite_note-70">[70]</a> Ethanol fireplaces can be used for home heating or for decoration. Ethanol can also be used as stove fuel for cooking.<a href="#cite_note-71">[71]</a><a href="#cite_note-72">[72]</a> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=6" title="Edit section: Other uses">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></div></td><td class="mbox-text"><div class="mbox-text-span">This section needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a>. Please help <a href="/wiki/Special:EditPage/Ethanol" title="Special:EditPage/Ethanol">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed. (November 2024) (<a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a>)</div></td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol (drug)</a> and <a href="/wiki/Alcoholic_drink" class="mw-redirect" title="Alcoholic drink">Alcoholic drink</a></div> As a <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> <a href="/wiki/Depressant" title="Depressant">depressant</a>, ethanol is one of the most commonly consumed <a href="/wiki/Psychoactive_drug" title="Psychoactive drug">psychoactive drugs</a>.<a href="#cite_note-73">[73]</a> Despite alcohol's psychoactive, addictive, and <a href="/wiki/Alcohol_and_cancer" title="Alcohol and cancer">carcinogenic</a> properties, it is readily available and legal for sale in many countries. There are laws regulating the sale, exportation/importation, taxation, manufacturing, consumption, and possession of alcoholic beverages. The most common regulation is prohibition for minors. Ethanol is an important industrial ingredient. It has widespread use as a precursor for other organic compounds such as ethyl <a href="/wiki/Halide" title="Halide">halides</a>, ethyl <a href="/wiki/Ester" title="Ester">esters</a>, diethyl ether, acetic acid, and ethyl <a href="/wiki/Amine" title="Amine">amines</a>. It is considered a universal <a href="/wiki/Solvent" title="Solvent">solvent</a>, as its <a href="/wiki/Molecular" class="mw-redirect" title="Molecular">molecular</a> structure allows for the dissolving of both <a href="/wiki/Chemical_polarity#Polar_molecules" title="Chemical polarity">polar</a>, <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> and <a href="/wiki/Nonpolar" class="mw-redirect" title="Nonpolar">nonpolar</a>, <a href="/wiki/Hydrophobic" class="mw-redirect" title="Hydrophobic">hydrophobic</a> compounds. As ethanol also has a low <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a>, it is easy to remove from a solution that has been used to dissolve other compounds, making it a popular extracting agent for botanical oils. <a href="/wiki/Cannabis_oil" class="mw-redirect" title="Cannabis oil">Cannabis oil</a> extraction methods often use ethanol as an extraction solvent,<a href="#cite_note-74">[74]</a> and also as a post-processing solvent to remove oils, waxes, and <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a> from solution in a process known as <a href="/wiki/Winterization_of_oil" title="Winterization of oil">winterization</a>. Ethanol is found in <a href="/wiki/Paint" title="Paint">paints</a>, tinctures, markers, and personal care products such as mouthwashes, perfumes and deodorants. <a href="/wiki/Polysaccharides" class="mw-redirect" title="Polysaccharides">Polysaccharides</a> <a href="/wiki/Ethanol_precipitation" title="Ethanol precipitation">precipitate</a> from aqueous solution in the presence of alcohol, and ethanol precipitation is used for this reason in the purification of <a href="/wiki/DNA" title="DNA">DNA</a> and <a href="/wiki/RNA" title="RNA">RNA</a>. Because of its low <a href="/wiki/Freezing_point" class="mw-redirect" title="Freezing point">freezing point</a> of −114 °C (−173 °F) and low toxicity, ethanol is sometimes used in laboratories (with <a href="/wiki/Dry_ice" title="Dry ice">dry ice</a> or other coolants) as a <a href="/wiki/Cooling_bath" title="Cooling bath">cooling bath</a> to keep vessels at temperatures below the freezing point of water. For the same reason, it is also used as the active fluid in <a href="/wiki/Alcohol_thermometer" title="Alcohol thermometer">alcohol thermometers</a>. <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=7" title="Edit section: Chemistry">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></div></td><td class="mbox-text"><div class="mbox-text-span">This section needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a>. Please help <a href="/wiki/Special:EditPage/Ethanol" title="Special:EditPage/Ethanol">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed. (November 2024) (<a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a>)</div></td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Ethanol_(data_page)" title="Ethanol (data page)">Ethanol (data page)</a></div> Ethanol is a 2-carbon <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>. Its <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> is CH3CH2OH. The structure of the molecule of ethanol is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">CH3−CH2−OH (an <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl group</a> linked to a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a>), which indicates that the carbon of a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> (CH3−) is attached to the carbon of a <a href="/wiki/Methylene_group" title="Methylene group">methylene group</a> (−CH2–), which is attached to the oxygen of a hydroxyl group (−OH). It is a constitutional <a href="/wiki/Isomer" title="Isomer">isomer</a> of <a href="/wiki/Dimethyl_ether" title="Dimethyl ether">dimethyl ether</a>. Ethanol is sometimes abbreviated as EtOH, using the common organic chemistry notation of representing the ethyl group (C2H5−) with Et. <div class="mw-heading mw-heading3"><h3 id="Physical_properties">Physical properties</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=8" title="Edit section: Physical properties">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Spiritusflamme_mit_spektrum.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Spiritusflamme_mit_spektrum.png/170px-Spiritusflamme_mit_spektrum.png" decoding="async" width="170" height="257" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/5/5d/Spiritusflamme_mit_spektrum.png 1.5x" data-file-width="214" data-file-height="324" /></a><figcaption>Ethanol burning with its spectrum depicted</figcaption></figure> Ethanol is a volatile, colorless liquid that has a slight odor. It burns with a smokeless blue flame that is not always visible in normal light. The physical properties of ethanol stem primarily from the presence of its hydroxyl group and the shortness of its carbon chain. Ethanol's hydroxyl group is able to participate in hydrogen bonding, rendering it more viscous and less volatile than less polar organic compounds of similar molecular weight, such as <a href="/wiki/Propane" title="Propane">propane</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Ethanol's <a href="/wiki/Adiabatic_flame_temperature" title="Adiabatic flame temperature">adiabatic flame temperature</a> for combustion in air is 2082 °C or 3779 °F.<a href="#cite_note-chemss-75">[75]</a> Ethanol is slightly more refractive than water, having a <a href="/wiki/Refractive_index" title="Refractive index">refractive index</a> of 1.36242 (at λ=589.3 nm and 18.35 °C or 65.03 °F).<a href="#cite_note-crc-76">[76]</a> The <a href="/wiki/Triple_point" title="Triple point">triple point</a> for ethanol is 150 ± 20 <a href="/wiki/Kelvin" title="Kelvin">K</a>.<a href="#cite_note-77">[77]</a> <div class="mw-heading mw-heading3"><h3 id="Solvent_properties">Solvent properties</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=9" title="Edit section: Solvent properties">edit</a>]</div> Ethanol is a versatile solvent, <a href="/wiki/Miscible" class="mw-redirect" title="Miscible">miscible</a> with water and with many organic solvents, including <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, diethyl ether, ethylene glycol, <a href="/wiki/Glycerol" title="Glycerol">glycerol</a>, <a href="/wiki/Nitromethane" title="Nitromethane">nitromethane</a>, <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, and <a href="/wiki/Toluene" title="Toluene">toluene</a>. Its main use as a solvent is in making tincture of iodine, cough syrups, etc.<a href="#cite_note-crc-76">[76]</a><a href="#cite_note-merck-78">[78]</a> It is also miscible with light aliphatic hydrocarbons, such as <a href="/wiki/Pentane" title="Pentane">pentane</a> and <a href="/wiki/Hexane" title="Hexane">hexane</a>, and with aliphatic chlorides such as <a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">trichloroethane</a> and <a href="/wiki/Tetrachloroethylene" title="Tetrachloroethylene">tetrachloroethylene</a>.<a href="#cite_note-merck-78">[78]</a> Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms), whose water miscibility decreases sharply as the number of carbons increases.<a href="#cite_note-m_and_b-79">[79]</a> The miscibility of ethanol with <a href="/wiki/Alkane" title="Alkane">alkanes</a> is limited to alkanes up to <a href="/wiki/Undecane" title="Undecane">undecane</a>: mixtures with <a href="/wiki/Dodecane" title="Dodecane">dodecane</a> and higher alkanes show a <a href="/wiki/Miscibility_gap" title="Miscibility gap">miscibility gap</a> below a certain temperature (about 13 °C for dodecane<a href="#cite_note-80">[80]</a>). The miscibility gap tends to get wider with higher alkanes, and the temperature for complete miscibility increases. Ethanol-water mixtures have less volume than the sum of their individual components at the given fractions. Mixing equal volumes of ethanol and water results in only 1.92 volumes of mixture.<a href="#cite_note-crc-76">[76]</a><a href="#cite_note-ChemTech-81">[81]</a> Mixing ethanol and water is <a href="/wiki/Exothermic" class="mw-redirect" title="Exothermic">exothermic</a>, with up to 777 J/mol<a href="#cite_note-82">[82]</a> being released at 298 K. <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ethanol-xtal-1976-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Ethanol-xtal-1976-3D-balls.png/220px-Ethanol-xtal-1976-3D-balls.png" decoding="async" width="220" height="163" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Ethanol-xtal-1976-3D-balls.png/330px-Ethanol-xtal-1976-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Ethanol-xtal-1976-3D-balls.png/440px-Ethanol-xtal-1976-3D-balls.png 2x" data-file-width="1100" data-file-height="814" /></a><figcaption>Hydrogen bonding in solid ethanol at −186 °C</figcaption></figure> Hydrogen bonding causes pure ethanol to be <a href="/wiki/Hygroscopic" class="mw-redirect" title="Hygroscopic">hygroscopic</a> to the extent that it readily absorbs water from the air. The polar nature of the hydroxyl group causes ethanol to dissolve many ionic compounds, notably <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium</a> and <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxides</a>, <a href="/wiki/Magnesium_chloride" title="Magnesium chloride">magnesium chloride</a>, <a href="/wiki/Calcium_chloride" title="Calcium chloride">calcium chloride</a>, <a href="/wiki/Ammonium_chloride" title="Ammonium chloride">ammonium chloride</a>, <a href="/wiki/Ammonium_bromide" title="Ammonium bromide">ammonium bromide</a>, and <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>.<a href="#cite_note-merck-78">[78]</a> <a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium</a> and <a href="/wiki/Potassium_chloride" title="Potassium chloride">potassium chlorides</a> are slightly soluble in ethanol.<a href="#cite_note-merck-78">[78]</a> Because the ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances, including most <a href="/wiki/Essential_oil" title="Essential oil">essential oils</a><a href="#cite_note-merckoils-83">[83]</a> and numerous flavoring, coloring, and medicinal agents. The addition of even a few percent of ethanol to water sharply reduces the <a href="/wiki/Surface_tension" title="Surface tension">surface tension</a> of water. This property partially explains the "<a href="/wiki/Tears_of_wine" title="Tears of wine">tears of wine</a>" phenomenon. When wine is swirled in a glass, ethanol evaporates quickly from the thin film of wine on the wall of the glass. As the wine's ethanol content decreases, its surface tension increases and the thin film "beads up" and runs down the glass in channels rather than as a smooth sheet. <div class="mw-heading mw-heading3"><h3 id="Azeotrope_with_water">Azeotrope with water</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=10" title="Edit section: Azeotrope with water">edit</a>]</div> At atmospheric pressure, mixtures of ethanol and water form an <a href="/wiki/Azeotrope" title="Azeotrope">azeotrope</a> at about 89.4 <a href="/wiki/Mol%25" class="mw-redirect" title="Mol%">mol%</a> ethanol (95.6% ethanol by mass,<a href="#cite_note-NIST-SR1828-84">[84]</a> 97% <a href="/wiki/Alcohol_by_volume" title="Alcohol by volume">alcohol by volume</a>), with a boiling point of 351.3 K (78.1 °C).<a href="#cite_note-PembertonMash-85">[85]</a> At lower pressure, the composition of the ethanol-water azeotrope shifts to more ethanol-rich mixtures.<a href="#cite_note-Beebe1942-86">[86]</a> The minimum-pressure azeotrope has an ethanol fraction of 100%<a href="#cite_note-Beebe1942-86">[86]</a> and a boiling point of 306 K (33 °C),<a href="#cite_note-PembertonMash-85">[85]</a> corresponding to a pressure of roughly 70 <a href="/wiki/Torr" title="Torr">torr</a> (9.333 kPa).<a href="#cite_note-PressureSwingDistillation-87">[87]</a> Below this pressure, there is no azeotrope, and it is possible to distill absolute ethanol from an ethanol-water mixture.<a href="#cite_note-PressureSwingDistillation-87">[87]</a> <div class="mw-heading mw-heading3"><h3 id="Flammability">Flammability</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=11" title="Edit section: Flammability">edit</a>]</div> An ethanol–water solution will catch fire if heated above a temperature called its <a href="/wiki/Flash_point" title="Flash point">flash point</a> and an ignition source is then applied to it.<a href="#cite_note-flash_point-88">[88]</a> For 20% alcohol by mass (about 25% by volume), this will occur at about 25 °C (77 °F). The flash point of pure ethanol is 13 °C (55 °F),<a href="#cite_note-NFPA_325-89">[89]</a> but may be influenced very slightly by atmospheric composition such as pressure and humidity. Ethanol mixtures can ignite below average room temperature. Ethanol is considered a flammable liquid (Class 3 Hazardous Material) in concentrations above 2.35% by mass (3.0% by volume; 6 <a href="/wiki/Alcohol_proof" title="Alcohol proof">proof</a>).<a href="#cite_note-49_CFR_173.120-90">[90]</a><a href="#cite_note-Martínez_et_al-91">[91]</a><a href="#cite_note-49_CFR_172.101-92">[92]</a> Dishes using burning alcohol for culinary effects are called <a href="/wiki/Flamb%C3%A9" title="Flambé">flambé</a>. <table class="wikitable mw-collapsible mw-collapsed" style="white-space: nowrap; text-align: center;"> <caption>Flash points of ethanol–water mixtures<a href="#cite_note-Ha_et_al-93">[93]</a><a href="#cite_note-Martínez_et_al-91">[91]</a><a href="#cite_note-eng-94">[94]</a> </caption> <tbody><tr> <th rowspan="2">Ethanol <a href="/wiki/Mole_fraction" title="Mole fraction">mole fraction</a>, % </th> <th colspan="2">Temperature </th></tr> <tr> <th>°C </th> <th>°F </th></tr> <tr> <td>1</td> <td style="text-align:right;">84.5 </td> <td style="text-align:right;">184.1<a href="#cite_note-Martínez_et_al-91">[91]</a> </td></tr> <tr> <td>2</td> <td style="text-align:right;">64 </td> <td style="text-align:right;">147<a href="#cite_note-Martínez_et_al-91">[91]</a> </td></tr> <tr> <td>2.35</td> <td style="text-align:right;">60 </td> <td style="text-align:right;">140<a href="#cite_note-Martínez_et_al-91">[91]</a><a href="#cite_note-49_CFR_173.120-90">[90]</a> </td></tr> <tr> <td>3</td> <td style="text-align:right;">51.5 </td> <td style="text-align:right;">124.7<a href="#cite_note-Martínez_et_al-91">[91]</a> </td></tr> <tr> <td>5</td> <td style="text-align:right;">43 </td> <td style="text-align:right;">109<a href="#cite_note-Ha_et_al-93">[93]</a> </td></tr> <tr> <td>6</td> <td style="text-align:right;">39.5 </td> <td style="text-align:right;">103.1<a href="#cite_note-Martínez_et_al-91">[91]</a> </td></tr> <tr> <td>10</td> <td style="text-align:right;">31 </td> <td style="text-align:right;">88<a href="#cite_note-Ha_et_al-93">[93]</a> </td></tr> <tr> <td>20</td> <td style="text-align:right;">25 </td> <td style="text-align:right;">77<a href="#cite_note-Martínez_et_al-91">[91]</a> </td></tr> <tr> <td>30</td> <td style="text-align:right;">24 </td> <td style="text-align:right;">75<a href="#cite_note-Ha_et_al-93">[93]</a> </td></tr> <tr> <td>50</td> <td style="text-align:right;">20 </td> <td style="text-align:right;">68<a href="#cite_note-Ha_et_al-93">[93]</a><a href="#cite_note-Martínez_et_al-91">[91]</a> </td></tr> <tr> <td>70</td> <td style="text-align:right;">16 </td> <td style="text-align:right;">61<a href="#cite_note-Ha_et_al-93">[93]</a> </td></tr> <tr> <td>80</td> <td style="text-align:right;">15.8 </td> <td style="text-align:right;">60.4<a href="#cite_note-Martínez_et_al-91">[91]</a> </td></tr> <tr> <td>90</td> <td style="text-align:right;">14 </td> <td style="text-align:right;">57<a href="#cite_note-Ha_et_al-93">[93]</a> </td></tr> <tr> <td>100</td> <td style="text-align:right;">12.5 </td> <td style="text-align:right;">54.5<a href="#cite_note-Ha_et_al-93">[93]</a><a href="#cite_note-Martínez_et_al-91">[91]</a><a href="#cite_note-NFPA_325-89">[89]</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=12" title="Edit section: Natural occurrence">edit</a>]</div> Ethanol is a byproduct of the metabolic process of yeast. As such, ethanol will be present in any yeast habitat. Ethanol can commonly be found in overripe fruit.<a href="#cite_note-95">[95]</a> Ethanol produced by symbiotic yeast can be found in <a href="/wiki/Palm_wine" title="Palm wine">bertam palm</a> blossoms. Although some animal species, such as the <a href="/wiki/Pentailed_treeshrew" class="mw-redirect" title="Pentailed treeshrew">pentailed treeshrew</a>, exhibit ethanol-seeking behaviors, most show no interest or avoidance of food sources containing ethanol.<a href="#cite_note-96">[96]</a> Ethanol is also produced during the germination of many plants as a result of natural <a href="/wiki/Anaerobiosis" class="mw-redirect" title="Anaerobiosis">anaerobiosis</a>.<a href="#cite_note-97">[97]</a> Ethanol has been detected in <a href="/wiki/Outer_space" title="Outer space">outer space</a>, forming an icy coating around dust grains in <a href="/wiki/Interstellar_cloud" title="Interstellar cloud">interstellar clouds</a>.<a href="#cite_note-98">[98]</a> Minute quantity amounts (average 196 <a href="/wiki/Parts_per_billion" class="mw-redirect" title="Parts per billion">ppb</a>) of endogenous ethanol and acetaldehyde were found in the exhaled breath of healthy volunteers.<a href="#cite_note-99">[99]</a> <a href="/wiki/Auto-brewery_syndrome" title="Auto-brewery syndrome">Auto-brewery syndrome</a>, also known as gut fermentation syndrome, is a rare medical condition in which intoxicating quantities of ethanol are produced through <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> within the <a href="/wiki/Digestive_system" class="mw-redirect" title="Digestive system">digestive system</a>.<a href="#cite_note-100">[100]</a> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=13" title="Edit section: Production">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ethanol_Flasche.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Ethanol_Flasche.jpg/170px-Ethanol_Flasche.jpg" decoding="async" width="170" height="271" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Ethanol_Flasche.jpg/255px-Ethanol_Flasche.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Ethanol_Flasche.jpg/340px-Ethanol_Flasche.jpg 2x" data-file-width="382" data-file-height="609" /></a><figcaption>94% denatured ethanol sold in a bottle for household use</figcaption></figure> Ethanol is produced both as a <a href="/wiki/Petrochemical" title="Petrochemical">petrochemical</a>, through the hydration of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> and, via biological processes, by fermenting <a href="/wiki/Sugar" title="Sugar">sugars</a> with <a href="/wiki/Yeast" title="Yeast">yeast</a>.<a href="#cite_note-Mills-Ecklund-101">[101]</a> Which process is more economical depends on prevailing prices of <a href="/wiki/Petroleum" title="Petroleum">petroleum</a> and grain feed stocks. <div class="mw-heading mw-heading3"><h3 id="Sources">Sources</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=14" title="Edit section: Sources">edit</a>]</div> World production of ethanol in 2006 was 51 gigalitres (1.3×1010 US gal), with 69% of the world supply coming from Brazil and the U.S.<a href="#cite_note-:0-19">[19]</a> Brazilian ethanol is produced from sugarcane, which has relatively high yields (830% more fuel than the fossil fuels used to produce it) compared to some other <a href="/wiki/Energy_crop" title="Energy crop">energy crops</a>.<a href="#cite_note-WaPo-Brazil-102">[102]</a> Sugarcane not only has a greater concentration of sucrose than corn (by about 30%), but is also much easier to extract. The <a href="/wiki/Bagasse" title="Bagasse">bagasse</a> generated by the process is not discarded, but burned by power plants to produce electricity. Bagasse burning accounts for around 9% of the electricity produced in Brazil.<a href="#cite_note-103">[103]</a> In the 1970s most industrial ethanol in the U.S. was made as a petrochemical, but in the 1980s the U.S. introduced subsidies for <a href="/wiki/Corn-based_ethanol" class="mw-redirect" title="Corn-based ethanol">corn-based ethanol</a>.<a href="#cite_note-WittcoffReuben2004-104">[104]</a> According to the Renewable Fuels Association, as of 30 October 2007, 131 grain ethanol bio-refineries in the U.S. have the capacity to produce 7×10<s style="display:none">^</s>9 US gal (26,000,000 m3) of ethanol per year. An additional 72 construction projects underway (in the U.S.) can add 6.4 billion US gallons (24,000,000 m3) of new capacity in the next 18 months.<a href="#cite_note-rfa1-50">[50]</a> In India ethanol is made from sugarcane.<a href="#cite_note-105">[105]</a> <a href="/wiki/Sweet_sorghum" title="Sweet sorghum">Sweet sorghum</a> is another potential source of ethanol, and is suitable for growing in dryland conditions. The <a href="/wiki/International_Crops_Research_Institute_for_the_Semi-Arid_Tropics" title="International Crops Research Institute for the Semi-Arid Tropics">International Crops Research Institute for the Semi-Arid Tropics</a> is investigating the possibility of growing sorghum as a source of fuel, food, and animal feed in arid parts of <a href="/wiki/Asia" title="Asia">Asia</a> and <a href="/wiki/Africa" title="Africa">Africa</a>.<a href="#cite_note-106">[106]</a> Sweet sorghum has one-third the water requirement of sugarcane over the same time period. It also requires about 22% less water than corn. The world's first sweet sorghum ethanol distillery began commercial production in 2007 in <a href="/wiki/Andhra_Pradesh" title="Andhra Pradesh">Andhra Pradesh</a>, <a href="/wiki/India" title="India">India</a>.<a href="#cite_note-107">[107]</a> Ethanol has been produced in the laboratory by converting <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> via biological and <a href="/wiki/Electrochemical" class="mw-redirect" title="Electrochemical">electrochemical</a> reactions.<a href="#cite_note-108">[108]</a><a href="#cite_note-109">[109]</a> <style data-mw-deduplicate="TemplateStyles:r996643573">.mw-parser-output .block-indent{padding-left:3em;padding-right:0;overflow:hidden}</style><div class="block-indent">CO2 + H 2O → CH 3CH 2OH + side products</div> <div class="mw-heading mw-heading3"><h3 id="Hydration">Hydration</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=15" title="Edit section: Hydration">edit</a>]</div> Ethanol can be produced from petrochemical feed stocks, primarily by the <a href="/wiki/Acid" title="Acid">acid</a>-<a href="/wiki/Catalysis" title="Catalysis">catalyzed</a> <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a> of ethylene. It is often referred to as synthetic ethanol. <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">C2H4 + H2O → C2H5OH</dd></dl> The catalyst is most commonly <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a>,<a href="#cite_note-r_and_c-110">[110]</a><a href="#cite_note-ullmann-111">[111]</a> <a href="/wiki/Adsorption" title="Adsorption">adsorbed</a> onto a porous support such as <a href="/wiki/Silica_gel" title="Silica gel">silica gel</a> or <a href="/wiki/Diatomaceous_earth" title="Diatomaceous earth">diatomaceous earth</a>. This catalyst was first used for large-scale ethanol production by the <a href="/wiki/Shell_Oil_Company" class="mw-redirect" title="Shell Oil Company">Shell Oil Company</a> in 1947.<a href="#cite_note-ECT4_820-112">[112]</a> The reaction is carried out in the presence of high pressure steam at 300 °C (572 °F) where a 5:3 ethylene to steam ratio is maintained.<a href="#cite_note-113">[113]</a><a href="#cite_note-114">[114]</a> This process was used on an industrial scale by <a href="/wiki/Union_Carbide" title="Union Carbide">Union Carbide</a> Corporation and others. It is no longer practiced in the US as fermentation ethanol produced from corn is more economical.<a href="#cite_note-115">[115]</a> In an older process, first practiced on the industrial scale in 1930 by Union Carbide<a href="#cite_note-ECT4_817-116">[116]</a> but now almost entirely obsolete, ethylene was hydrated indirectly by reacting it with concentrated <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> to produce <a href="/wiki/Ethyl_sulfate" title="Ethyl sulfate">ethyl sulfate</a>, which was <a href="/wiki/Hydrolyzed" class="mw-redirect" title="Hydrolyzed">hydrolyzed</a> to yield ethanol and regenerate the sulfuric acid:<a href="#cite_note-s_and_h-117">[117]</a> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">C2H4 + H2SO4 → C2H5HSO4</dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">C2H5HSO4 + H2O → H2SO4 + C2H5OH</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Fermentation">Fermentation</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=16" title="Edit section: Fermentation">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></div></td><td class="mbox-text"><div class="mbox-text-span">This section needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a>. Please help <a href="/wiki/Special:EditPage/Ethanol" title="Special:EditPage/Ethanol">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed. (November 2024) (<a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a>)</div></td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Ethanol_fermentation" title="Ethanol fermentation">Ethanol fermentation</a> and <a href="/wiki/Cellulosic_ethanol" title="Cellulosic ethanol">Cellulosic ethanol</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Yeast_in_winemaking" title="Yeast in winemaking">Yeast in winemaking</a></div> Ethanol in <a href="/wiki/Alcoholic_beverage" title="Alcoholic beverage">alcoholic beverages</a> and fuel is produced by fermentation. Certain species of yeast (e.g., <a href="/wiki/Saccharomyces_cerevisiae" title="Saccharomyces cerevisiae">Saccharomyces cerevisiae</a>) metabolize sugar (namely <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a>), producing ethanol and carbon dioxide. The chemical equations below summarize the conversion: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r996643573"><div class="block-indent"><a href="/wiki/Glucose" title="Glucose">C 6H 12O 6</a> → 2 CH 3CH 2OH + 2 CO2</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r996643573"><div class="block-indent"><a href="/wiki/Sucrose" title="Sucrose">C 12H 22O 11</a> + H 2O → 4 CH 3CH 2OH + 4 CO2</div> Fermentation is the process of culturing yeast under favorable thermal conditions to produce alcohol. This process is carried out at around 35–40 °C (95–104 °F). Toxicity of ethanol to yeast limits the ethanol concentration obtainable by brewing; higher concentrations, therefore, are obtained by <a href="/wiki/Fortified_wine" title="Fortified wine">fortification</a> or <a href="/wiki/Distillation" title="Distillation">distillation</a>. The most ethanol-tolerant yeast strains can survive up to approximately 18% ethanol by volume. To produce ethanol from starchy materials such as <a href="/wiki/Cereal" title="Cereal">cereals</a>, the <a href="/wiki/Starch" title="Starch">starch</a> must first be converted into sugars. In brewing <a href="/wiki/Beer" title="Beer">beer</a>, this has traditionally been accomplished by allowing the grain to germinate, or <a href="/wiki/Malt" title="Malt">malt</a>, which produces the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Amylase" title="Amylase">amylase</a>. When the malted grain is <a href="/wiki/Mashing" title="Mashing">mashed</a>, the amylase converts the remaining starches into sugars. Sugars for <a href="/wiki/Ethanol_fermentation" title="Ethanol fermentation">ethanol fermentation</a> can be obtained from <a href="/wiki/Cellulose" title="Cellulose">cellulose</a>. Deployment of this technology could turn a number of cellulose-containing agricultural by-products, such as <a href="/wiki/Corncob" title="Corncob">corncobs</a>, <a href="/wiki/Straw" title="Straw">straw</a>, and <a href="/wiki/Sawdust" title="Sawdust">sawdust</a>, into renewable energy resources. Other agricultural residues such as sugarcane bagasse and energy crops such as <a href="/wiki/Switchgrass" class="mw-redirect" title="Switchgrass">switchgrass</a> may also be fermentable sugar sources.<a href="#cite_note-118">[118]</a> <div class="mw-heading mw-heading3"><h3 id="Testing">Testing</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=17" title="Edit section: Testing">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:EthanolMIRInfraredSpectra.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/EthanolMIRInfraredSpectra.PNG/300px-EthanolMIRInfraredSpectra.PNG" decoding="async" width="300" height="185" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/EthanolMIRInfraredSpectra.PNG/450px-EthanolMIRInfraredSpectra.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/EthanolMIRInfraredSpectra.PNG/600px-EthanolMIRInfraredSpectra.PNG 2x" data-file-width="985" data-file-height="607" /></a><figcaption>Infrared reflection spectra of liquid ethanol, showing the −OH band centered near 3300 cm−1 and C−H bands near 2950 cm−1</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ethanol_near_IR_spectrum.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Ethanol_near_IR_spectrum.png/300px-Ethanol_near_IR_spectrum.png" decoding="async" width="300" height="209" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Ethanol_near_IR_spectrum.png/450px-Ethanol_near_IR_spectrum.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Ethanol_near_IR_spectrum.png/600px-Ethanol_near_IR_spectrum.png 2x" data-file-width="3500" data-file-height="2442" /></a><figcaption><a href="/wiki/Near-infrared_spectrum" class="mw-redirect" title="Near-infrared spectrum">Near-infrared spectrum</a> of liquid ethanol</figcaption></figure> Breweries and <a href="/wiki/Biofuel" title="Biofuel">biofuel</a> plants employ two methods for measuring ethanol concentration. Infrared ethanol sensors measure the vibrational frequency of dissolved ethanol using the C−H band at 2900 cm−1. This method uses a relatively inexpensive solid-state sensor that compares the C−H band with a reference band to calculate the ethanol content. The calculation makes use of the <a href="/wiki/Beer%E2%80%93Lambert_law" title="Beer–Lambert law">Beer–Lambert law</a>. Alternatively, by measuring the density of the starting material and the density of the product, using a <a href="/wiki/Hydrometer" title="Hydrometer">hydrometer</a>, the change in specific gravity during fermentation indicates the alcohol content. This inexpensive and indirect method has a long history in the beer brewing industry. <div class="mw-heading mw-heading2"><h2 id="Purification">Purification</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=18" title="Edit section: Purification">edit</a>]</div> Ethylene hydration or brewing produces an ethanol–water mixture. For most industrial and fuel uses, the ethanol must be purified. <a href="/wiki/Fractional_distillation" title="Fractional distillation">Fractional distillation</a> at atmospheric pressure can concentrate ethanol to 95.6% by weight (89.5 mole%). This mixture is an azeotrope with a boiling point of 78.1 °C (172.6 °F), and cannot be further purified by distillation. Addition of an entraining agent, such as benzene, <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>, or <a href="/wiki/Heptane" title="Heptane">heptane</a>, allows a new ternary azeotrope comprising the ethanol, water, and the entraining agent to be formed. This lower-boiling ternary azeotrope is removed preferentially, leading to water-free ethanol.<a href="#cite_note-ullmann-111">[111]</a> Apart from distillation, ethanol may be dried by addition of a <a href="/wiki/Desiccant" title="Desiccant">desiccant</a>, such as <a href="/wiki/Molecular_sieves" class="mw-redirect" title="Molecular sieves">molecular sieves</a>, cellulose, or <a href="/wiki/Cornmeal" title="Cornmeal">cornmeal</a>. The desiccants can be dried and reused.<a href="#cite_note-ullmann-111">[111]</a> <a href="/wiki/Molecular_sieve" title="Molecular sieve">Molecular sieves</a> can be used to selectively absorb the water from the 95.6% ethanol solution.<a href="#cite_note-119">[119]</a> Molecular sieves of pore-size 3 <a href="/wiki/%C3%85ngstrom" class="mw-redirect" title="Ångstrom">Ångstrom</a>, a type of <a href="/wiki/Zeolite" title="Zeolite">zeolite</a>, effectively sequester water molecules while excluding ethanol molecules. Heating the wet sieves drives out the water, allowing regeneration of their desiccant capability.<a href="#cite_note-120">[120]</a> Membranes can also be used to separate ethanol and water. Membrane-based separations are not subject to the limitations of the water-ethanol azeotrope because the separations are not based on vapor-liquid equilibria. Membranes are often used in the so-called hybrid membrane distillation process. This process uses a pre-concentration distillation column as the first separating step. The further separation is then accomplished with a membrane operated either in vapor permeation or pervaporation mode. Vapor permeation uses a vapor membrane feed and pervaporation uses a liquid membrane feed. A variety of other techniques have been discussed, including the following:<a href="#cite_note-ullmann-111">[111]</a> <ul><li>Salting using <a href="/wiki/Potassium_carbonate" title="Potassium carbonate">potassium carbonate</a> to exploit its insolubility will cause a phase separation with ethanol and water. This offers a very small potassium carbonate impurity to the alcohol that can be removed by distillation. This method is very useful in purification of ethanol by distillation, as ethanol forms an <a href="/wiki/Azeotrope" title="Azeotrope">azeotrope</a> with water.</li> <li>Direct <a href="/wiki/Electrochemical_reduction_of_carbon_dioxide" title="Electrochemical reduction of carbon dioxide">electrochemical reduction of carbon dioxide</a> to ethanol under ambient conditions using <a href="/wiki/Copper_nanoparticle" title="Copper nanoparticle">copper nanoparticles</a> on a carbon nanospike film as the catalyst;<a href="#cite_note-121">[121]</a></li> <li>Extraction of ethanol from grain mash by <a href="/wiki/Supercritical_carbon_dioxide" title="Supercritical carbon dioxide">supercritical carbon dioxide</a>;</li> <li><a href="/wiki/Pervaporation" title="Pervaporation">Pervaporation</a>;</li> <li><a href="/wiki/Fractional_freezing" title="Fractional freezing">Fractional freezing</a> is also used to concentrate fermented alcoholic solutions, such as traditionally made <a href="/wiki/Applejack_(beverage)" class="mw-redirect" title="Applejack (beverage)">Applejack (beverage)</a>;</li> <li><a href="/wiki/Pressure_swing_adsorption" title="Pressure swing adsorption">Pressure swing adsorption</a>.<a href="#cite_note-122">[122]</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Grades_of_ethanol">Grades of ethanol</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=19" title="Edit section: Grades of ethanol">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Denatured_alcohol" title="Denatured alcohol">Denatured alcohol</a></div> Pure ethanol and alcoholic beverages are heavily <a href="/wiki/Sin_tax" title="Sin tax">taxed</a> as psychoactive drugs, but ethanol has many uses that do not involve its consumption. To relieve the tax burden on these uses, most jurisdictions waive the tax when an agent has been added to the ethanol to render it unfit to drink. These include <a href="/wiki/Bitterant" title="Bitterant">bittering agents</a> such as <a href="/wiki/Denatonium_benzoate" class="mw-redirect" title="Denatonium benzoate">denatonium benzoate</a> and toxins such as methanol, <a href="/wiki/Naphtha" title="Naphtha">naphtha</a>, and pyridine. Products of this kind are called denatured alcohol.<a href="#cite_note-123">[123]</a><a href="#cite_note-124">[124]</a> Absolute or anhydrous alcohol refers to ethanol with a low water content. There are various grades with maximum water contents ranging from 1% to a few parts per million (ppm). If <a href="/wiki/Azeotropic_distillation" title="Azeotropic distillation">azeotropic distillation</a> is used to remove water, it will contain trace amounts of the material separation agent (e.g. benzene).<a href="#cite_note-125">[125]</a> Absolute alcohol is not intended for human consumption. Absolute ethanol is used as a solvent for laboratory and industrial applications, where water will react with other chemicals, and as fuel alcohol. Spectroscopic ethanol is an absolute ethanol with a low absorbance in <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> and visible light, fit for use as a solvent in <a href="/wiki/Ultraviolet-visible_spectroscopy" class="mw-redirect" title="Ultraviolet-visible spectroscopy">ultraviolet-visible spectroscopy</a>.<a href="#cite_note-126">[126]</a> Pure ethanol is classed as 200 <a href="/wiki/Proof_(alcohol)" class="mw-redirect" title="Proof (alcohol)">proof</a> in the US, equivalent to 175 degrees proof in the UK system.<a href="#cite_note-Andrews2007-127">[127]</a> Rectified spirit, an azeotropic composition of 96% ethanol containing 4% water, is used instead of anhydrous ethanol for various purposes. Spirits of wine are about 94% ethanol (188 proof). The impurities are different from those in 95% (190 proof) laboratory ethanol.<a href="#cite_note-128">[128]</a> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=20" title="Edit section: Reactions">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></div></td><td class="mbox-text"><div class="mbox-text-span">This section needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a>. Please help <a href="/wiki/Special:EditPage/Ethanol" title="Special:EditPage/Ethanol">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed. (November 2024) (<a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a>)</div></td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol (chemistry)</a></div> Ethanol is classified as a primary alcohol, meaning that the carbon that its hydroxyl group attaches to has at least two hydrogen atoms attached to it as well. Many ethanol reactions occur at its hydroxyl group. <div class="mw-heading mw-heading3"><h3 id="Ester_formation">Ester formation</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=21" title="Edit section: Ester formation">edit</a>]</div> In the presence of acid catalysts, ethanol reacts with <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> to produce ethyl esters and water: <dl><dd><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">RCOOH</a> + HOCH2CH3 → <a href="/wiki/Ester" title="Ester">RCOOCH2CH3</a> + H2O</dd></dl> This reaction, which is conducted on large scale industrially, requires the removal of the water from the reaction mixture as it is formed. Esters react in the presence of an acid or base to give back the alcohol and a salt. This reaction is known as <a href="/wiki/Saponification" title="Saponification">saponification</a> because it is used in the preparation of soap. Ethanol can also form esters with inorganic acids. <a href="/wiki/Diethyl_sulfate" title="Diethyl sulfate">Diethyl sulfate</a> and <a href="/wiki/Triethyl_phosphate" title="Triethyl phosphate">triethyl phosphate</a> are prepared by treating ethanol with sulfur trioxide and <a href="/wiki/Phosphorus_pentoxide" title="Phosphorus pentoxide">phosphorus pentoxide</a> respectively. Diethyl sulfate is a useful ethylating agent in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. <a href="/wiki/Ethyl_nitrite" title="Ethyl nitrite">Ethyl nitrite</a>, prepared from the reaction of ethanol with <a href="/wiki/Sodium_nitrite" title="Sodium nitrite">sodium nitrite</a> and sulfuric acid, was formerly used as a <a href="/wiki/Diuretic" title="Diuretic">diuretic</a>. <div class="mw-heading mw-heading3"><h3 id="Dehydration">Dehydration</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=22" title="Edit section: Dehydration">edit</a>]</div> In the presence of acid catalysts, alcohols can be converted to alkenes such as ethanol to ethylene. Typically <a href="/wiki/Solid_acid" title="Solid acid">solid acids</a> such as <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">alumina</a> are used.<a href="#cite_note-UllmannEthylene-129">[129]</a> <dl><dd>CH3CH2OH → H2C=CH2 + H2O</dd></dl> Since water is removed from the same molecule, the reaction is known as <a href="/wiki/Dehydration_of_alcohols_to_alkenes" class="mw-redirect" title="Dehydration of alcohols to alkenes">intramolecular dehydration</a>. Intramolecular dehydration of an alcohol requires a high temperature and the presence of an acid catalyst such as sulfuric acid.<a href="#cite_note-130">[130]</a> Ethylene produced from sugar-derived ethanol (primarily in Brazil) competes with ethylene produced from petrochemical feedstocks such as naphtha and ethane.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] At a lower temperature than that of intramolecular dehydration, <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">intermolecular alcohol dehydration</a> may occur producing a symmetrical ether. This is a <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation reaction</a>. In the following example, diethyl ether is produced from ethanol: <dl><dd>2 CH3CH2OH → CH3CH2OCH2CH3 + H2O<a href="#cite_note-131">[131]</a></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Combustion">Combustion</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=23" title="Edit section: Combustion">edit</a>]</div> Complete combustion of ethanol forms carbon dioxide and water: <dl><dd>C2H5OH (l) + 3 O2 (g) → 2 CO2 (g) + 3 H2O (l); −ΔcH = 1371 kJ/mol<a href="#cite_note-132">[132]</a> = 29.8 kJ/g = 327 kcal/mol = 7.1 kcal/g</dd></dl> <dl><dd>C2H5OH (l) + 3 O2 (g) → 2 CO2 (g) + 3 H2O (g); −ΔcH = 1236 kJ/mol = 26.8 kJ/g = 295.4 kcal/mol = 6.41 kcal/g<a href="#cite_note-133">[133]</a></dd></dl> Specific heat = 2.44 kJ/(kg·K) <div class="mw-heading mw-heading3"><h3 id="Acid-base_chemistry">Acid-base chemistry</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=24" title="Edit section: Acid-base chemistry">edit</a>]</div> Ethanol is a neutral molecule and the <a href="/wiki/PH" title="PH">pH</a> of a solution of ethanol in water is nearly 7.00. Ethanol can be quantitatively converted to its <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate base</a>, the <a href="/wiki/Alkoxide" title="Alkoxide">ethoxide</a> ion (CH3CH2O−), by reaction with an <a href="/wiki/Alkali_metal" title="Alkali metal">alkali metal</a> such as <a href="/wiki/Sodium" title="Sodium">sodium</a>:<a href="#cite_note-m_and_b-79">[79]</a> <dl><dd>2 CH3CH2OH + 2 Na → 2 CH3CH2ONa + H2</dd></dl> or a very strong base such as <a href="/wiki/Sodium_hydride" title="Sodium hydride">sodium hydride</a>: <dl><dd>CH3CH2OH + NaH → CH3CH2ONa + H2</dd></dl> The acidities of water and ethanol are nearly the same, as indicated by their <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pKa</a> of 15.7 and 16 respectively. Thus, sodium ethoxide and sodium hydroxide exist in an equilibrium that is closely balanced: <dl><dd>CH3CH2OH + NaOH ⇌ CH3CH2ONa + H2O</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Halogenation">Halogenation</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=25" title="Edit section: Halogenation">edit</a>]</div> Ethanol is not used industrially as a precursor to ethyl halides, but the reactions are illustrative. Ethanol reacts with <a href="/wiki/Hydrogen_halide" title="Hydrogen halide">hydrogen halides</a> to produce <a href="/wiki/Haloalkane" title="Haloalkane">ethyl halides</a> such as <a href="/wiki/Ethyl_chloride" class="mw-redirect" title="Ethyl chloride">ethyl chloride</a> and <a href="/wiki/Ethyl_bromide" class="mw-redirect" title="Ethyl bromide">ethyl bromide</a> via an <a href="/wiki/SN2_reaction" title="SN2 reaction">SN2 reaction</a>: <dl><dd>CH3CH2OH + <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a> → CH3CH2Cl + H2O</dd></dl> HCl requires a catalyst such as <a href="/wiki/Zinc_chloride" title="Zinc chloride">zinc chloride</a>.<a href="#cite_note-s_and_h-117">[117]</a> HBr requires <a href="/wiki/Refluxing" class="mw-redirect" title="Refluxing">refluxing</a> with a sulfuric acid catalyst.<a href="#cite_note-s_and_h-117">[117]</a> Ethyl halides can, in principle, also be produced by treating ethanol with more specialized <a href="/wiki/Halogenation" title="Halogenation">halogenating agents</a>, such as <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">thionyl chloride</a> or <a href="/wiki/Phosphorus_tribromide" title="Phosphorus tribromide">phosphorus tribromide</a>.<a href="#cite_note-m_and_b-79">[79]</a><a href="#cite_note-s_and_h-117">[117]</a> <dl><dd>CH3CH2OH + SOCl2 → CH3CH2Cl + SO2 + HCl</dd></dl> Upon treatment with halogens in the presence of base, ethanol gives the corresponding <a href="/wiki/Haloform" class="mw-redirect" title="Haloform">haloform</a> (CHX3, where X = Cl, Br, I). This conversion is called the <a href="/wiki/Haloform_reaction" title="Haloform reaction">haloform reaction</a>.<a href="#cite_note-134">[134]</a> An intermediate in the reaction with chlorine is the <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> called <a href="/wiki/Chloral" title="Chloral">chloral</a>, which forms <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a> upon reaction with water:<a href="#cite_note-Ull-135">[135]</a> <dl><dd>4 Cl2 + CH3CH2OH → CCl3CHO + 5 HCl</dd> <dd>CCl3CHO + H2O → CCl3C(OH)2H</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Oxidation">Oxidation</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=26" title="Edit section: Oxidation">edit</a>]</div> Ethanol can be oxidized to acetaldehyde and further oxidized to acetic acid, depending on the reagents and conditions.<a href="#cite_note-s_and_h-117">[117]</a> This oxidation is of no importance industrially, but in the human body, these oxidation reactions are catalyzed by the enzyme <a href="/wiki/Liver_alcohol_dehydrogenase" class="mw-redirect" title="Liver alcohol dehydrogenase">liver ADH</a>. The oxidation product of ethanol, acetic acid, is a nutrient for humans, being a precursor to <a href="/wiki/Acetyl_CoA" class="mw-redirect" title="Acetyl CoA">acetyl CoA</a>, where the acetyl group can be spent as energy or used for biosynthesis. <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3>[<a href="/w/index.php?title=Ethanol&action=edit&section=27" title="Edit section: Metabolism">edit</a>]</div> Ethanol is similar to <a href="/wiki/Macronutrients" class="mw-redirect" title="Macronutrients">macronutrients</a> such as proteins, fats, and carbohydrates in that it provides calories. When consumed and metabolized, it contributes 7 kilocalories per gram via <a href="/wiki/Ethanol_metabolism" class="mw-redirect" title="Ethanol metabolism">ethanol metabolism</a>.<a href="#cite_note-136">[136]</a> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=28" title="Edit section: Safety">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Alcohol_(chemistry)#Toxicity" title="Alcohol (chemistry)">Alcohol (chemistry) § Toxicity</a></div> Ethanol is very flammable and should not be used around an open flame. Pure ethanol will irritate the skin and eyes.<a href="#cite_note-137">[137]</a> Nausea, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, and intoxication are symptoms of ingestion. Long-term use by ingestion can result in serious liver damage.<a href="#cite_note-msdset-138">[138]</a> Atmospheric concentrations above one part per thousand are above the European Union <a href="/wiki/Occupational_exposure_limit" title="Occupational exposure limit">occupational exposure limits</a>.<a href="#cite_note-msdset-138">[138]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=29" title="Edit section: History">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Liquor" title="Liquor">Liquor</a></div> The fermentation of sugar into ethanol is one of the earliest <a href="/wiki/Biotechnology" title="Biotechnology">biotechnologies</a> employed by humans. Ethanol has historically been identified variously as spirit of wine or ardent spirits,<a href="#cite_note-139">[139]</a> and as <a href="/wiki/Aqua_vitae" title="Aqua vitae">aqua vitae</a> or aqua vita. The intoxicating effects of its consumption have been known since ancient times. Ethanol has been used by humans since prehistory as the intoxicating ingredient of alcoholic beverages. Dried residue on 9,000-year-old pottery found in China suggests that <a href="/wiki/Neolithic" title="Neolithic">Neolithic</a> people consumed alcoholic beverages.<a href="#cite_note-Roach-140">[140]</a> The inflammable nature of the exhalations of wine was already known to ancient natural philosophers such as <a href="/wiki/Aristotle" title="Aristotle">Aristotle</a> (384–322 BCE), <a href="/wiki/Theophrastus" title="Theophrastus">Theophrastus</a> (<abbr title="circa">c.</abbr> 371–287 BCE), and <a href="/wiki/Pliny_the_Elder" title="Pliny the Elder">Pliny the Elder</a> (23/24–79 CE).<a href="#cite_note-141">[141]</a> However, this did not immediately lead to the isolation of ethanol, despite the development of more advanced distillation techniques in second- and third-century <a href="/wiki/Roman_Egypt" title="Roman Egypt">Roman Egypt</a>.<a href="#cite_note-142">[142]</a> An important recognition, first found in one of the writings attributed to <a href="/wiki/Jabir_ibn_Hayyan" title="Jabir ibn Hayyan">Jābir ibn Ḥayyān</a> (ninth century CE), was that by <a href="/wiki/Salt-effect_distillation" title="Salt-effect distillation">adding salt</a> to boiling wine, which increases the wine's <a href="/wiki/Relative_volatility" title="Relative volatility">relative volatility</a>, the flammability of the resulting vapors may be enhanced.<a href="#cite_note-143">[143]</a> The distillation of wine is attested in Arabic works attributed to <a href="/wiki/Al-Kindi" title="Al-Kindi">al-Kindī</a> (<abbr title="circa">c.</abbr> 801–873 CE) and to <a href="/wiki/Al-Farabi" title="Al-Farabi">al-Fārābī</a> (<abbr title="circa">c.</abbr> 872–950), and in the 28th book of <a href="/wiki/Al-Zahrawi" title="Al-Zahrawi">al-Zahrāwī</a>'s (Latin: Abulcasis, 936–1013) Kitāb al-Taṣrīf (later translated into Latin as Liber servatoris).<a href="#cite_note-144">[144]</a> In the twelfth century, recipes for the production of aqua ardens ("burning water", i.e., ethanol) by distilling wine with salt started to appear in a number of Latin works, and by the end of the thirteenth century it had become a widely known substance among Western European chemists.<a href="#cite_note-145">[145]</a> The works of <a href="/wiki/Taddeo_Alderotti" title="Taddeo Alderotti">Taddeo Alderotti</a> (1223–1296) describe a method for concentrating ethanol involving repeated fractional distillation through a water-cooled <a href="/wiki/Still" title="Still">still</a>, by which an ethanol purity of 90% could be obtained.<a href="#cite_note-146">[146]</a> The medicinal properties of ethanol were studied by <a href="/wiki/Arnald_of_Villanova" class="mw-redirect" title="Arnald of Villanova">Arnald of Villanova</a> (1240–1311 CE) and <a href="/wiki/John_of_Rupescissa" class="mw-redirect" title="John of Rupescissa">John of Rupescissa</a> (<abbr title="circa">c.</abbr> 1310–1366), the latter of whom regarded it as a life-preserving substance able to prevent all diseases (the aqua vitae or "water of life", also called by John the <a href="/wiki/Aether_(classical_element)" title="Aether (classical element)">quintessence</a> of wine).<a href="#cite_note-147">[147]</a> In <a href="/wiki/China" title="China">China</a>, archaeological evidence indicates that the true distillation of alcohol began during the <a href="/wiki/Jin_dynasty_(1115%E2%80%931234)" title="Jin dynasty (1115–1234)">Jin</a> (1115–1234) or <a href="/wiki/Southern_Song_dynasty" class="mw-redirect" title="Southern Song dynasty">Southern Song</a> (1127–1279) dynasties.<a href="#cite_note-haw-148">[148]</a> A still has been found at an archaeological site in Qinglong, <a href="/wiki/Hebei" title="Hebei">Hebei</a>, dating to the 12th century.<a href="#cite_note-haw-148">[148]</a> In India, the true distillation of alcohol was introduced from the Middle East, and was in wide use in the <a href="/wiki/Delhi_Sultanate" title="Delhi Sultanate">Delhi Sultanate</a> by the 14th century.<a href="#cite_note-habib-149">[149]</a> In 1796, German-Russian chemist <a href="/wiki/Johann_Tobias_Lowitz" title="Johann Tobias Lowitz">Johann Tobias Lowitz</a> obtained pure ethanol by mixing partially purified ethanol (the alcohol-water azeotrope) with an excess of anhydrous alkali and then distilling the mixture over low heat.<a href="#cite_note-150">[150]</a> French chemist <a href="/wiki/Antoine_Lavoisier" title="Antoine Lavoisier">Antoine Lavoisier</a> described ethanol as a compound of carbon, hydrogen, and oxygen, and in 1807 <a href="/wiki/Nicolas-Th%C3%A9odore_de_Saussure" class="mw-redirect" title="Nicolas-Théodore de Saussure">Nicolas-Théodore de Saussure</a> determined ethanol's chemical formula.<a href="#cite_note-151">[151]</a><a href="#cite_note-152">[152]</a> Fifty years later, <a href="/wiki/Archibald_Scott_Couper" title="Archibald Scott Couper">Archibald Scott Couper</a> published the structural formula of ethanol, one of the first structural formulas determined.<a href="#cite_note-Couper-153">[153]</a> Ethanol was first prepared synthetically in 1825 by <a href="/wiki/Michael_Faraday" title="Michael Faraday">Michael Faraday</a>. He found that sulfuric acid could absorb large volumes of <a href="/wiki/Coal_gas" title="Coal gas">coal gas</a>.<a href="#cite_note-154">[154]</a> He gave the resulting solution to <a href="/wiki/Henry_Hennell" title="Henry Hennell">Henry Hennell</a>, a British chemist, who found in 1826 that it contained "sulphovinic acid" (ethyl hydrogen sulfate).<a href="#cite_note-155">[155]</a> In 1828, Hennell and the French chemist <a href="/wiki/Georges-Simon_Serullas" title="Georges-Simon Serullas">Georges-Simon Serullas</a> independently discovered that sulphovinic acid could be decomposed into ethanol.<a href="#cite_note-Hennell-156">[156]</a><a href="#cite_note-157">[157]</a> Thus, in 1825 Faraday had unwittingly discovered that ethanol could be produced from ethylene (a component of coal gas) by <a href="/wiki/Acid_catalysis" title="Acid catalysis">acid-catalyzed</a> hydration, a process similar to current industrial ethanol synthesis.<a href="#cite_note-158">[158]</a> Ethanol was used as lamp fuel in the U.S. as early as 1840, but a tax levied on industrial alcohol during the <a href="/wiki/American_Civil_War" title="American Civil War">Civil War</a> made this use uneconomical. The tax was repealed in 1906.<a href="#cite_note-siegel-159">[159]</a> Use as an automotive fuel dates back to 1908, with the <a href="/wiki/Ford_Model_T" title="Ford Model T">Ford Model T</a> able to run on <a href="/wiki/Petrol" class="mw-redirect" title="Petrol">petrol</a> (gasoline) or ethanol.<a href="#cite_note-dipardo-160">[160]</a> It fuels some <a href="/wiki/Spirit_lamps" class="mw-redirect" title="Spirit lamps">spirit lamps</a>. Ethanol intended for industrial use is often produced from ethylene.<a href="#cite_note-myers-161">[161]</a> Ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. In chemistry, it is both a solvent and a feedstock for the synthesis of other products. It has a long history as a fuel for heat and light, and more recently as a fuel for internal combustion engines. <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=30" title="Edit section: See also">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 30em;"> <ul><li><a href="/wiki/Ethanol-induced_non-lamellar_phases_in_phospholipids" title="Ethanol-induced non-lamellar phases in phospholipids">Ethanol-induced non-lamellar phases in phospholipids</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">1-Propanol</a></li> <li><a href="/wiki/2-Propanol" class="mw-redirect" title="2-Propanol">2-Propanol</a></li> <li><a href="/wiki/Rubbing_alcohol" title="Rubbing alcohol">Rubbing alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol">tert-Butyl alcohol</a></li> <li><a href="/wiki/Butanol_fuel" title="Butanol fuel">Butanol fuel</a></li> <li><a href="/wiki/Timeline_of_alcohol_fuel" title="Timeline of alcohol fuel">Timeline of alcohol fuel</a></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=31" title="Edit section: References">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist 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Annalen der Pharmacie (in German). 9 (22): 1–39. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1834AnP...107..337L">1834AnP...107..337L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fandp.18341072202">10.1002/andp.18341072202</a>. <q>From page 18: "Bezeichnen wir die Kohlenwasserstoffverbindung 4C + 10H als das Radikal des Aethers mit E2 und nennen es Ethyl, ..." (Let us designate the hydrocarbon compound 4C + 10H as the radical of ether with E2 and name it ethyl ...).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Pharmacie&rft.atitle=Ueber+die+Constitution+des+Aethers+und+seiner+Verbindungen&rft.volume=9&rft.issue=22&rft.pages=1-39&rft.date=1834&rft_id=info%3Adoi%2F10.1002%2Fandp.18341072202&rft_id=info%3Abibcode%2F1834AnP...107..337L&rft.aulast=Liebig&rft.aufirst=Justus&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1423568&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-22"><a href="#cite_ref-22">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHarper" class="citation web cs1">Harper, Douglas. <a rel="nofollow" class="external text" href="https://www.etymonline.com/?term=ethyl">"ethyl"</a>. <a href="/wiki/Online_Etymology_Dictionary" title="Online Etymology Dictionary">Online Etymology Dictionary</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Online+Etymology+Dictionary&rft.atitle=ethyl&rft.aulast=Harper&rft.aufirst=Douglas&rft_id=https%3A%2F%2Fwww.etymonline.com%2F%3Fterm%3Dethyl&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-23"><a href="#cite_ref-23">^</a> For a report on the 1892 International Conference on Chemical Nomenclature, see: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFArmstrong1892" class="citation journal cs1">Armstrong H (1892). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=LHkCAAAAIAAJ&pg=PA56">"The International Conference on Chemical Nomenclature"</a>. 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Chemistry LibreTexts. 9 February 2016. Retrieved 9 May 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemistry+LibreTexts&rft.atitle=14.4%3A+Dehydration+Reactions+of+Alcohols&rft.date=2016-02-09&rft_id=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FMap%253A_Organic_Chemistry_%28Wade%29%2F14%253A_Reactions_of_Alcohols%2F14.04%253A_Dehydration_Reactions_of_Alcohols&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-131"><a href="#cite_ref-131">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Alkenes/Synthesis_of_Alkenes/Alkenes_from_Dehydration_of_Alcohols">"Alkenes from Dehydration of Alcohols"</a>. Chemistry LibreTexts. 2 October 2013. Retrieved 9 May 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemistry+LibreTexts&rft.atitle=Alkenes+from+Dehydration+of+Alcohols&rft.date=2013-10-02&rft_id=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FSupplemental_Modules_%28Organic_Chemistry%29%2FAlkenes%2FSynthesis_of_Alkenes%2FAlkenes_from_Dehydration_of_Alcohols&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-132"><a href="#cite_ref-132">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRossini1937" class="citation journal cs1">Rossini FD (1937). "Heats of Formation of Simple Organic Molecules". Ind. Eng. Chem. 29 (12): 1424–1430. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fie50336a024">10.1021/ie50336a024</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ind.+Eng.+Chem.&rft.atitle=Heats+of+Formation+of+Simple+Organic+Molecules&rft.volume=29&rft.issue=12&rft.pages=1424-1430&rft.date=1937&rft_id=info%3Adoi%2F10.1021%2Fie50336a024&rft.aulast=Rossini&rft.aufirst=Frederick+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-133"><a href="#cite_ref-133">^</a> Calculated from heats of formation from CRC Handbook of Chemistry and Physics, 49th Edition, 1968–1969. </li> <li id="cite_note-134"><a href="#cite_ref-134">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChakrabartty1978" class="citation book cs1">Chakrabartty SK (1978). Trahanovsky WS (ed.). Oxidation in Organic Chemistry. New York: Academic Press. pp. 343–370.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Oxidation+in+Organic+Chemistry&rft.place=New+York&rft.pages=343-370&rft.pub=Academic+Press&rft.date=1978&rft.aulast=Chakrabartty&rft.aufirst=SK&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-Ull-135"><a href="#cite_ref-Ull_135-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReinhardKoppMcKusickRöderer2007" class="citation book cs1">Reinhard J, Kopp E, McKusick BC, Röderer G, Bosch A, Fleischmann G (2007). "Chloroacetaldehydes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a06_527.pub2">10.1002/14356007.a06_527.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chloroacetaldehydes&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2007&rft_id=info%3Adoi%2F10.1002%2F14356007.a06_527.pub2&rft.isbn=978-3-527-30673-2&rft.aulast=Reinhard&rft.aufirst=Jira&rft.au=Kopp%2C+Erwin&rft.au=McKusick%2C+Blaine+C.&rft.au=R%C3%B6derer%2C+Gerhard&rft.au=Bosch%2C+Axel&rft.au=Fleischmann%2C+Gerald&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-136"><a href="#cite_ref-136">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCederbaum2012" class="citation journal cs1">Cederbaum, Arthur I (16 November 2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3484320">"Alcohol Metabolism"</a>. Clinics in Liver Disease. 16 (4): 667–685. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.cld.2012.08.002">10.1016/j.cld.2012.08.002</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1089-3261">1089-3261</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3484320">3484320</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23101976">23101976</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinics+in+Liver+Disease&rft.atitle=Alcohol+Metabolism&rft.volume=16&rft.issue=4&rft.pages=667-685&rft.date=2012-11-16&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3484320%23id-name%3DPMC&rft.issn=1089-3261&rft_id=info%3Apmid%2F23101976&rft_id=info%3Adoi%2F10.1016%2Fj.cld.2012.08.002&rft.aulast=Cederbaum&rft.aufirst=Arthur+I&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3484320&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-137"><a href="#cite_ref-137">^</a> <a rel="nofollow" class="external text" href="http://www.nfpa.org/Assets/files/AboutTheCodes/704/CLA-AAA_ROPminutes_01-10.pdf">Minutes of Meeting</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210416230440/https://www.nfpa.org/Assets/files/AboutTheCodes/704/CLA-AAA_ROPminutes_01-10.pdf">Archived</a> 16 April 2021 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>. Technical Committee on Classification and Properties of Hazardous Chemical Data (12–13 January 2010). </li> <li id="cite_note-msdset-138">^ <a href="#cite_ref-msdset_138-0">a</a> <a href="#cite_ref-msdset_138-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110714040451/http://msds.chem.ox.ac.uk/ET/ethyl_alcohol.html">"Safety data for ethyl alcohol"</a>. University of Oxford. 9 May 2008. Archived from <a rel="nofollow" class="external text" href="http://msds.chem.ox.ac.uk/ET/ethyl_alcohol.html">the original</a> on 14 July 2011. Retrieved 3 January 2011.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Safety+data+for+ethyl+alcohol&rft.pub=University+of+Oxford&rft.date=2008-05-09&rft_id=http%3A%2F%2Fmsds.chem.ox.ac.uk%2FET%2Fethyl_alcohol.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-139"><a href="#cite_ref-139">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOttley1826" class="citation book cs1">Ottley, William Campbell (1826). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wYcwvwyk2RAC">A dictionary of chemistry and of mineralogy as connected with it</a>. Murray.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+dictionary+of+chemistry+and+of+mineralogy+as+connected+with+it&rft.pub=Murray&rft.date=1826&rft.aulast=Ottley&rft.aufirst=William+Campbell&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwYcwvwyk2RAC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-Roach-140"><a href="#cite_ref-Roach_140-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRoach2005" class="citation journal cs1">Roach J (18 July 2005). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20050722030635/http://news.nationalgeographic.com/news/2005/07/0718_050718_ancientbeer.html">"9,000-Year-Old Beer Re-Created From Chinese Recipe"</a>. National Geographic News. Archived from <a rel="nofollow" class="external text" href="http://news.nationalgeographic.com/news/2005/07/0718_050718_ancientbeer.html">the original</a> on 22 July 2005. Retrieved 3 September 2007.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=National+Geographic+News&rft.atitle=9%2C000-Year-Old+Beer+Re-Created+From+Chinese+Recipe&rft.date=2005-07-18&rft.aulast=Roach&rft.aufirst=J&rft_id=http%3A%2F%2Fnews.nationalgeographic.com%2Fnews%2F2005%2F07%2F0718_050718_ancientbeer.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-141"><a href="#cite_ref-141">^</a> <a href="#CITEREFBerthelotHoudas1893">Berthelot & Houdas 1893</a>, vol. I, p. 137. </li> <li id="cite_note-142"><a href="#cite_ref-142">^</a> <a href="#CITEREFBerthelotHoudas1893">Berthelot & Houdas 1893</a>, vol. I, pp. 138-139. </li> <li id="cite_note-143"><a href="#cite_ref-143">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFal-Hassan2009" class="citation book cs1"><a href="/wiki/Ahmad_Y._al-Hassan" title="Ahmad Y. al-Hassan">al-Hassan, Ahmad Y.</a> (2009). "Alcohol and the Distillation of Wine in Arabic Sources from the 8th Century". Studies in al-Kimya': Critical Issues in Latin and Arabic Alchemy and Chemistry. Hildesheim: Georg Olms Verlag. pp. 283–298.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Alcohol+and+the+Distillation+of+Wine+in+Arabic+Sources+from+the+8th+Century&rft.btitle=Studies+in+al-Kimya%27%3A+Critical+Issues+in+Latin+and+Arabic+Alchemy+and+Chemistry&rft.place=Hildesheim&rft.pages=283-298&rft.pub=Georg+Olms+Verlag&rft.date=2009&rft.aulast=al-Hassan&rft.aufirst=Ahmad+Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> (same content also available on <a rel="nofollow" class="external text" href="http://www.history-science-technology.com/notes/notes7.html">the author's website</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151229003135/http://www.history-science-technology.com/notes/notes7.html">Archived</a> 29 December 2015 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>). </li> <li id="cite_note-144"><a href="#cite_ref-144">^</a> <a href="#CITEREFal-Hassan2009">al-Hassan 2009</a> (same content also available on <a rel="nofollow" class="external text" href="http://www.history-science-technology.com/notes/notes7.html">the author's website</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151229003135/http://www.history-science-technology.com/notes/notes7.html">Archived</a> 29 December 2015 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>); cf. <a href="#CITEREFBerthelotHoudas1893">Berthelot & Houdas 1893</a>, vol. I, pp. 141, 143. Sometimes, sulfur was also added to the wine (see <a href="#CITEREFBerthelotHoudas1893">Berthelot & Houdas 1893</a>, vol. I, p. 143). </li> <li id="cite_note-145"><a href="#cite_ref-145">^</a> <a href="#CITEREFMulthauf1966">Multhauf 1966</a>, pp. 204–206. </li> <li id="cite_note-146"><a href="#cite_ref-146">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHolmyard1957" class="citation book cs1"><a href="/wiki/Eric_John_Holmyard" title="Eric John Holmyard">Holmyard, Eric John</a> (1957). Alchemy. Harmondsworth: Penguin Books. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-486-26298-7" title="Special:BookSources/978-0-486-26298-7"><bdi>978-0-486-26298-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Alchemy&rft.place=Harmondsworth&rft.pub=Penguin+Books&rft.date=1957&rft.isbn=978-0-486-26298-7&rft.aulast=Holmyard&rft.aufirst=Eric+John&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> pp. 51–52. </li> <li id="cite_note-147"><a href="#cite_ref-147">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPrincipe2013" class="citation book cs1"><a href="/wiki/Lawrence_M._Principe" title="Lawrence M. Principe">Principe, Lawrence M.</a> (2013). The Secrets of Alchemy. Chicago: The University of Chicago Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-226-10379-2" title="Special:BookSources/978-0-226-10379-2"><bdi>978-0-226-10379-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Secrets+of+Alchemy&rft.place=Chicago&rft.pub=The+University+of+Chicago+Press&rft.date=2013&rft.isbn=978-0-226-10379-2&rft.aulast=Principe&rft.aufirst=Lawrence+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> pp. 69-71. </li> <li id="cite_note-haw-148">^ <a href="#cite_ref-haw_148-0">a</a> <a href="#cite_ref-haw_148-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaw2006" class="citation book cs1"><a href="/wiki/Stephen_G._Haw" title="Stephen G. Haw">Haw SG</a> (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DSfvfr8VQSEC&pg=PA148">"Wine, women and poison"</a>. Marco Polo in China. Routledge. pp. 147–148. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-134-27542-7" title="Special:BookSources/978-1-134-27542-7"><bdi>978-1-134-27542-7</bdi></a>. Retrieved 10 July 2016. <q>The earliest possible period seems to be the Eastern Han dynasty... the most likely period for the beginning of true distillation of spirits for drinking in China is during the Jin and Southern Song dynasties</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Wine%2C+women+and+poison&rft.btitle=Marco+Polo+in+China&rft.pages=147-148&rft.pub=Routledge&rft.date=2006&rft.isbn=978-1-134-27542-7&rft.aulast=Haw&rft.aufirst=Stephen+G.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDSfvfr8VQSEC%26pg%3DPA148&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-habib-149"><a href="#cite_ref-habib_149-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHabib2011" class="citation book cs1"><a href="/wiki/Irfan_Habib" title="Irfan Habib">Habib, Irfan</a> (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=K8kO4J3mXUAC&pg=PA55">Economic History of Medieval India, 1200–1500</a>. Pearson Education India. pp. 55–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-317-2791-1" title="Special:BookSources/978-81-317-2791-1"><bdi>978-81-317-2791-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Economic+History+of+Medieval+India%2C+1200%E2%80%931500&rft.pages=55-&rft.pub=Pearson+Education+India&rft.date=2011&rft.isbn=978-81-317-2791-1&rft.aulast=Habib&rft.aufirst=Irfan&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DK8kO4J3mXUAC%26pg%3DPA55&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-150"><a href="#cite_ref-150">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLowitz1796" class="citation journal cs1 cs1-prop-foreign-lang-source">Lowitz T (1796). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Zws_AAAAcAAJ">"Anzeige eines, zur volkommen Entwasserung des Weingeistes nothwendig zu beobachtenden, Handgriffs"</a> [Report of a task that must be done for the complete dehydration of wine spirits [i.e., alcohol-water azeotrope])]. Chemische Annalen für die Freunde der Naturlehre, Aerznengelartheit, Haushaltungskunde und Manufakturen (in German). 1: 195–204. <q>See pp. 197–198: Lowitz dehydrated the azeotrope by mixing it with a 2:1 excess of anhydrous alkali and then distilling the mixture over low heat.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemische+Annalen+f%C3%BCr+die+Freunde+der+Naturlehre%2C+Aerznengelartheit%2C+Haushaltungskunde+und+Manufakturen&rft.atitle=Anzeige+eines%2C+zur+volkommen+Entwasserung+des+Weingeistes+nothwendig+zu+beobachtenden%2C+Handgriffs&rft.volume=1&rft.pages=195-204&rft.date=1796&rft.aulast=Lowitz&rft.aufirst=T.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DZws_AAAAcAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-151"><a href="#cite_ref-151">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChisholm1911" class="citation encyclopaedia cs1"><a href="/wiki/Hugh_Chisholm" title="Hugh Chisholm">Chisholm, Hugh</a>, ed. (1911). <a class="external text" href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Alcohol">"Alcohol" </a>. <a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">Encyclopædia Britannica</a>. Vol. 1 (11th ed.). Cambridge University Press. pp. 525–527.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Alcohol&rft.btitle=Encyclop%C3%A6dia+Britannica&rft.pages=525-527&rft.edition=11th&rft.pub=Cambridge+University+Press&rft.date=1911&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-152"><a href="#cite_ref-152">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFde_Saussure1807" class="citation journal cs1">de Saussure T (1807). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=G-UPAAAAQAAJ&pg=PA316">"Mémoire sur la composition de l'alcohol et de l'éther sulfurique"</a>. Journal de Physique, de Chimie, d'Histoire Naturelle et des Arts. 64: 316–354.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+de+Physique%2C+de+Chimie%2C+d%27Histoire+Naturelle+et+des+Arts&rft.atitle=M%C3%A9moire+sur+la+composition+de+l%27alcohol+et+de+l%27%C3%A9ther+sulfurique&rft.volume=64&rft.pages=316-354&rft.date=1807&rft.aulast=de+Saussure&rft.aufirst=Th%C3%A9odore&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DG-UPAAAAQAAJ%26pg%3DPA316&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> In his 1807 paper, Saussure determined ethanol's composition only roughly; a more accurate analysis of ethanol appears on page 300 of his 1814 paper: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFde_Saussure1814" class="citation journal cs1">de Saussure, Théodore (1814). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ch8zAQAAMAAJ&pg=PA273">"Nouvelles observations sur la composition de l'alcool et de l'éther sulfurique"</a>. Annales de Chimie et de Physique. 89: 273–305.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Nouvelles+observations+sur+la+composition+de+l%27alcool+et+de+l%27%C3%A9ther+sulfurique&rft.volume=89&rft.pages=273-305&rft.date=1814&rft.aulast=de+Saussure&rft.aufirst=Th%C3%A9odore&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dch8zAQAAMAAJ%26pg%3DPA273&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-Couper-153"><a href="#cite_ref-Couper_153-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCouper1858" class="citation journal cs1">Couper AS (1858). <a rel="nofollow" class="external text" href="http://web.lemoyne.edu/~giunta/couper/couper.html">"On a new chemical theory"</a> (online reprint). Philosophical Magazine. 16 (104–116). Retrieved 3 September 2007.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Magazine&rft.atitle=On+a+new+chemical+theory&rft.volume=16&rft.issue=104%E2%80%93116&rft.date=1858&rft.aulast=Couper&rft.aufirst=AS&rft_id=http%3A%2F%2Fweb.lemoyne.edu%2F~giunta%2Fcouper%2Fcouper.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-154"><a href="#cite_ref-154">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFaraday1825" class="citation journal cs1">Faraday M (1825). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k559209/f473.image">"On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat"</a>. Philosophical Transactions of the Royal Society of London. 115: 440–466. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstl.1825.0022">10.1098/rstl.1825.0022</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Transactions+of+the+Royal+Society+of+London&rft.atitle=On+new+compounds+of+carbon+and+hydrogen%2C+and+on+certain+other+products+obtained+during+the+decomposition+of+oil+by+heat&rft.volume=115&rft.pages=440-466&rft.date=1825&rft_id=info%3Adoi%2F10.1098%2Frstl.1825.0022&rft.aulast=Faraday&rft.aufirst=M&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k559209%2Ff473.image&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> In a footnote on page 448, Faraday notes the action of sulfuric acid on coal gas and coal-gas distillate; specifically, "The [sulfuric] acid combines directly with carbon and hydrogen; and I find when [the resulting compound is] united with bases [it] forms a peculiar class of salts, somewhat resembling the sulphovinates [i.e., ethyl sulfates], but still different from them." </li> <li id="cite_note-155"><a href="#cite_ref-155">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHennell1826" class="citation journal cs1">Hennell H (1826). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=f05FAAAAcAAJ">"On the mutual action of sulphuric acid and alcohol, with observations on the composition and properties of the resulting compound"</a>. Philosophical Transactions of the Royal Society of London. 116: 240–249. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstl.1826.0021">10.1098/rstl.1826.0021</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:98278290">98278290</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Transactions+of+the+Royal+Society+of+London&rft.atitle=On+the+mutual+action+of+sulphuric+acid+and+alcohol%2C+with+observations+on+the+composition+and+properties+of+the+resulting+compound&rft.volume=116&rft.pages=240-249&rft.date=1826&rft_id=info%3Adoi%2F10.1098%2Frstl.1826.0021&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A98278290%23id-name%3DS2CID&rft.aulast=Hennell&rft.aufirst=H&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Df05FAAAAcAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> On page 248, Hennell mentions that Faraday gave him some sulfuric acid in which coal gas had dissolved and that he (Hennell) found that it contained "sulphovinic acid" (ethyl hydrogen sulfate). </li> <li id="cite_note-Hennell-156"><a href="#cite_ref-Hennell_156-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHennell1828" class="citation journal cs1">Hennell H (1828). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=X-9FAAAAMAAJ&pg=PA365">"On the mutual action of sulfuric acid and alcohol, and on the nature of the process by which ether is formed"</a>. Philosophical Transactions of the Royal Society of London. 118: 365–371. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstl.1828.0021">10.1098/rstl.1828.0021</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:98483646">98483646</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Transactions+of+the+Royal+Society+of+London&rft.atitle=On+the+mutual+action+of+sulfuric+acid+and+alcohol%2C+and+on+the+nature+of+the+process+by+which+ether+is+formed&rft.volume=118&rft.pages=365-371&rft.date=1828&rft_id=info%3Adoi%2F10.1098%2Frstl.1828.0021&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A98483646%23id-name%3DS2CID&rft.aulast=Hennell&rft.aufirst=H&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DX-9FAAAAMAAJ%26pg%3DPA365&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> On page 368, Hennell produces ethanol from "sulfovinic acid" (<a href="/wiki/Ethyl_sulfate" title="Ethyl sulfate">ethyl hydrogen sulfate</a>). </li> <li id="cite_note-157"><a href="#cite_ref-157">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSérullas1828" class="citation journal cs1">Sérullas GS (1828). Guyton de Morveau LB, Gay-Lussac JL, Arago F, Michel Eugène Chevreul, Marcellin Berthelot, Éleuthère Élie Nicolas Mascart, Albin Haller (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ZxUAAAAAMAAJ&pg=PA152">"De l'action de l'acide sulfurique sur l'alcool, et des produits qui en résultent"</a>. Annales de Chimie et de Physique. 39: 152–186.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=De+l%27action+de+l%27acide+sulfurique+sur+l%27alcool%2C+et+des+produits+qui+en+r%C3%A9sultent&rft.volume=39&rft.pages=152-186&rft.date=1828&rft.aulast=S%C3%A9rullas&rft.aufirst=Georges-Simon&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DZxUAAAAAMAAJ%26pg%3DPA152&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> On page 158, Sérullas mentions the production of alcohol from "sulfate acid d'hydrogène carboné" (hydrocarbon acid sulfate). </li> <li id="cite_note-158"><a href="#cite_ref-158">^</a> In 1855, the French chemist <a href="/wiki/Marcellin_Berthelot" title="Marcellin Berthelot">Marcellin Berthelot</a> confirmed Faraday's discovery by preparing ethanol from pure ethylene. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBerthelot1855" class="citation journal cs1">Berthelot M (1855). Arago F, Gay-Lussac JL (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=1ClCAAAAcAAJ&pg=PA385">"Sur la formation de l'alcool au moyen du bicarbure d'hydrogène (On the formation of alcohol by means of ethylene)"</a>. Annales de Chimie et de Physique. 43: 385–405.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Sur+la+formation+de+l%27alcool+au+moyen+du+bicarbure+d%27hydrog%C3%A8ne+%28On+the+formation+of+alcohol+by+means+of+ethylene%29&rft.volume=43&rft.pages=385-405&rft.date=1855&rft.aulast=Berthelot&rft.aufirst=Marcellin&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D1ClCAAAAcAAJ%26pg%3DPA385&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> (Note: The chemical formulas in Berthelot's paper are wrong because chemists at that time used the wrong atomic masses for the elements; e.g., carbon (6 instead of 12), oxygen (8 instead of 16), etc.) </li> <li id="cite_note-siegel-159"><a href="#cite_ref-siegel_159-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSiegel2007" class="citation news cs1">Siegel R (15 February 2007). <a rel="nofollow" class="external text" href="https://www.npr.org/templates/story/story.php?storyId=7426827">"Ethanol, Once Bypassed, Now Surging Ahead"</a>. NPR. Retrieved 22 September 2007.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Ethanol%2C+Once+Bypassed%2C+Now+Surging+Ahead&rft.date=2007-02-15&rft.aulast=Siegel&rft.aufirst=Robert&rft_id=https%3A%2F%2Fwww.npr.org%2Ftemplates%2Fstory%2Fstory.php%3FstoryId%3D7426827&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-dipardo-160"><a href="#cite_ref-dipardo_160-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDiPardo" class="citation web cs1">DiPardo J. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150924050511/http://www.eia.gov/oiaf/analysispaper/pdf/biomass.pdf">"Outlook for Biomass Ethanol Production and Demand"</a> (PDF). United States Department of Energy. Archived from <a rel="nofollow" class="external text" href="http://www.eia.gov/oiaf/analysispaper/pdf/biomass.pdf">the original</a> (PDF) on 24 September 2015. Retrieved 22 September 2007.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Outlook+for+Biomass+Ethanol+Production+and+Demand&rft.pub=United+States+Department+of+Energy&rft.aulast=DiPardo&rft.aufirst=Joseph&rft_id=http%3A%2F%2Fwww.eia.gov%2Foiaf%2Fanalysispaper%2Fpdf%2Fbiomass.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> <li id="cite_note-myers-161"><a href="#cite_ref-myers_161-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMyersMyers2007" class="citation book cs1">Myers RL, Myers RL (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0AnJU-hralEC&pg=PA122">The 100 most important chemical compounds: a reference guide</a>. Westport, CN: Greenwood Press. p. 122. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-313-33758-1" title="Special:BookSources/978-0-313-33758-1"><bdi>978-0-313-33758-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+100+most+important+chemical+compounds%3A+a+reference+guide&rft.place=Westport%2C+CN&rft.pages=122&rft.pub=Greenwood+Press&rft.date=2007&rft.isbn=978-0-313-33758-1&rft.aulast=Myers&rft.aufirst=Richard+L.&rft.au=Myers%2C+Rusty+L.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0AnJU-hralEC%26pg%3DPA122&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=32" title="Edit section: Further reading">edit</a>]</div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1">Boyce JM, Pittet D (2003). <a rel="nofollow" class="external text" href="https://cdc.gov/handhygiene/">"Hand Hygiene in Healthcare Settings"</a>. Atlanta, GA: <a href="/wiki/Centers_for_Disease_Control" class="mw-redirect" title="Centers for Disease Control">Centers for Disease Control</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Hand+Hygiene+in+Healthcare+Settings&rft.place=Atlanta%2C+GA&rft.pub=Centers+for+Disease+Control&rft.date=2003&rft.aulast=Boyce&rft.aufirst=John+M&rft.au=Pittet%2C+Didier&rft_id=http%3A%2F%2Fcdc.gov%2Fhandhygiene%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation conference cs1">Onuki S, Koziel JA, van Leeuwen J, Jenks WS, Grewell D, Cai L (June 2008). <a rel="nofollow" class="external text" href="http://lib.dr.iastate.edu/abe_eng_conf/68/">Ethanol production, purification, and analysis techniques: a review</a>. 2008 ASABE Annual International Meeting. Providence, RI. Retrieved 16 February 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=conference&rft.btitle=Ethanol+production%2C+purification%2C+and+analysis+techniques%3A+a+review&rft.place=Providence%2C+RI&rft.date=2008-06&rft.aulast=Onuki&rft.aufirst=Shinnosuke&rft.au=Koziel%2C+Jacek+A.&rft.au=van+Leeuwen%2C+Johannes&rft.au=Jenks%2C+William+S.&rft.au=Grewell%2C+David&rft.au=Cai%2C+Lingshuang&rft_id=http%3A%2F%2Flib.dr.iastate.edu%2Fabe_eng_conf%2F68%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://sci-toys.com/ingredients/alcohol.html">"Explanation of US denatured alcohol designations"</a>. Sci-toys.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Sci-toys&rft.atitle=Explanation+of+US+denatured+alcohol+designations&rft_id=http%3A%2F%2Fsci-toys.com%2Fingredients%2Falcohol.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1">Lange, Norbert Adolph (1967). John Aurie Dean (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4YlqAAAAMAAJ">Lange's Handbook of Chemistry</a> (10th ed.). McGraw-Hill.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lange%27s+Handbook+of+Chemistry&rft.edition=10th&rft.pub=McGraw-Hill&rft.date=1967&rft.aulast=Lange&rft.aufirst=Norbert+Adolph&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4YlqAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanol" class="Z3988"></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Ethanol&action=edit&section=33" title="Edit section: External links">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 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href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Ethanol" class="extiw" title="commons:Ethanol">Ethanol</a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://www.periodicvideos.com/videos/mv_alcohol.htm">Alcohol (Ethanol)</a> at <a href="/wiki/The_Periodic_Table_of_Videos" class="mw-redirect" title="The Periodic Table of Videos">The Periodic Table of Videos</a> (University of Nottingham)</li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0044.htm">International Labour Organization</a> ethanol safety information</li> <li><a rel="nofollow" class="external text" href="http://www.npi.gov.au/substances/ethanol/index.html">National Pollutant Inventory – Ethanol Fact Sheet</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0262.html">CDC – NIOSH Pocket Guide to Chemical Hazards – Ethyl Alcohol</a></li> <li><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?Name=ethanol&Units=SI">National Institute of Standards and Technology</a> chemical data on ethanol</li> <li><a rel="nofollow" class="external text" href="http://www.cmegroup.com/company/cbot.html">Chicago Board of Trade</a> news and market data on ethanol futures</li> <li>Calculation of <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Ethanol">vapor pressure</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Ethanol">liquid density</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Ethanol">dynamic liquid viscosity</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Ethanol">surface tension</a> of ethanol</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20140915061825/http://www.ethanolhistory.com/">Ethanol History</a> A look into the history of ethanol</li> <li><a rel="nofollow" class="external text" href="http://chemsub.online.fr/name/ethyl_alcohol.html">ChemSub Online: Ethyl alcohol</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20170210214845/http://www.inclusive-science-engineering.com/industrial-alcohol-production-from-ethylene-and-sulphuric-acid/industrial-ethyl-alcohol-production-from-ethylene-and-sulphuric-acid/">Industrial ethanol production process flow diagram using ethylene and sulphuric acid</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output 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href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">By consumption</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Comparison_of_psychoactive_alcohols_in_alcoholic_drinks" title="Comparison of psychoactive alcohols in alcoholic drinks">Alcohols found in alcoholic drinks</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Propanol" title="1-Propanol">1-Propanol</a></li> <li><a href="/wiki/2-Methyl-1-butanol" title="2-Methyl-1-butanol">2-Methyl-1-butanol</a></li> <li><a class="mw-selflink selflink">Ethanol</a></li> <li><a href="/wiki/Isoamyl_alcohol" title="Isoamyl alcohol">Isoamyl alcohol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/Phenethyl_alcohol" title="Phenethyl alcohol">Phenethyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">tert-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol">tert-Butyl alcohol</a></li> <li><a href="/wiki/Tryptophol" title="Tryptophol">Tryptophol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohols_(medicine)" title="Alcohols (medicine)">Medical alcohol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li>Methanol poisoning <ul><li><a class="mw-selflink selflink">Ethanol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Toxic_alcohol" class="mw-redirect" title="Toxic alcohol">Toxic alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropyl alcohol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Primary_alcohol" title="Primary alcohol">Primary alcohols</a> (1°)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methanol" title="Methanol">Methanol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Methylcyclohexanemethanol" title="4-Methylcyclohexanemethanol">4-Methylcyclohexanemethanol</a></li> <li><a href="/wiki/Aminomethanol" title="Aminomethanol">Aminomethanol</a></li> <li><a href="/wiki/Cyclohexylmethanol" title="Cyclohexylmethanol">Cyclohexylmethanol</a></li> <li><a href="/wiki/Methoxymethanol" title="Methoxymethanol">Methoxymethanol</a></li> <li><a href="/wiki/Methylazoxymethanol" title="Methylazoxymethanol">Methylazoxymethanol</a></li> <li><a href="/wiki/Trifluoromethanol" title="Trifluoromethanol">Trifluoromethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Ethanol</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Aminoethanol" title="1-Aminoethanol">1-Aminoethanol</a></li> <li><a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">2,2,2-Trichloroethanol</a></li> <li><a href="/wiki/2,2,2-Trifluoroethanol" title="2,2,2-Trifluoroethanol">2,2,2-Trifluoroethanol</a></li> <li><a href="/wiki/2-(2-Ethoxyethoxy)ethanol" title="2-(2-Ethoxyethoxy)ethanol">2-(2-Ethoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-(2-Methoxyethoxy)ethanol" title="2-(2-Methoxyethoxy)ethanol">2-(2-Methoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-(2-Methoxyethoxy)ethanol" title="2-(2-Methoxyethoxy)ethanol">2-(2-Methoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-Butoxyethanol" title="2-Butoxyethanol">2-Butoxyethanol</a></li> <li><a href="/wiki/2-Chloroethanol" title="2-Chloroethanol">2-Chloroethanol</a></li> <li><a href="/wiki/2-Ethoxyethanol" title="2-Ethoxyethanol">2-Ethoxyethanol</a></li> <li><a href="/wiki/2-Fluoroethanol" title="2-Fluoroethanol">2-Fluoroethanol</a></li> <li><a href="/wiki/2-Mercaptoethanol" title="2-Mercaptoethanol">2-Mercaptoethanol</a></li> <li><a href="/wiki/2-Methoxyethanol" title="2-Methoxyethanol">2-Methoxyethanol</a></li> <li><a href="/wiki/Aminoethylethanolamine" title="Aminoethylethanolamine">Aminoethylethanolamine</a></li> <li><a href="/wiki/Diethylethanolamine" title="Diethylethanolamine">Diethylethanolamine</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a class="mw-selflink selflink">Ethanol</a></li> <li><a href="/wiki/Ethanolamine" title="Ethanolamine">Ethanolamine</a></li> <li><a href="/wiki/N,N-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol">N,N-Diisopropylaminoethanol</a></li> <li><a href="/wiki/N-Methylethanolamine" title="N-Methylethanolamine">N-Methylethanolamine</a></li> <li><a href="/wiki/Phenoxyethanol" title="Phenoxyethanol">Phenoxyethanol</a></li> <li><a href="/wiki/Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Butanol" title="Butanol">Butanol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methyl-1-butanol" title="2-Methyl-1-butanol">2-Methyl-1-butanol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol">n-Butanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain saturated C1 — C9</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a class="mw-selflink selflink">Ethanol</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">1-Propanol</a></li> <li><a href="/wiki/1-Butanol" title="1-Butanol">1-Butanol</a></li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">1-Pentanol</a></li> <li><a href="/wiki/1-Hexanol" title="1-Hexanol">1-Hexanol</a></li> <li><a href="/wiki/1-Heptanol" title="1-Heptanol">1-Heptanol</a></li> <li><a href="/wiki/1-Octanol" title="1-Octanol">1-Octanol</a> (capryl)</li> <li><a href="/wiki/1-Nonanol" title="1-Nonanol">1-Nonanol</a> (pelargonic)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain saturated C10 — C19</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Decanol" title="1-Decanol">1-Decanol</a> (capric)</li> <li><a href="/wiki/1-Undecanol" class="mw-redirect" title="1-Undecanol">1-Undecanol</a> (hendecyl)</li> <li><a href="/wiki/1-Dodecanol" class="mw-redirect" title="1-Dodecanol">1-Dodecanol</a> (lauryl)</li> <li><a href="/wiki/1-Tridecanol" title="1-Tridecanol">1-Tridecanol</a></li> <li><a href="/wiki/1-Tetradecanol" title="1-Tetradecanol">1-Tetradecanol</a> (myristyl)</li> <li><a href="/wiki/1-Pentadecanol" title="1-Pentadecanol">1-Pentadecanol</a></li> <li><a href="/wiki/1-Hexadecanol" class="mw-redirect" title="1-Hexadecanol">1-Hexadecanol</a> (cetyl / palmityl)</li> <li><a href="/wiki/1-Heptadecanol" class="mw-redirect" title="1-Heptadecanol">1-Heptadecanol</a></li> <li><a href="/wiki/1-Octadecanol" class="mw-redirect" title="1-Octadecanol">1-Octadecanol</a> (stearyl)</li> <li><a href="/wiki/1-Nonadecanol" class="mw-redirect" title="1-Nonadecanol">1-Nonadecanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain saturated C20 — C29</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Icosanol" class="mw-redirect" title="1-Icosanol">1-Icosanol</a> (arachidyl)</li> <li><a href="/wiki/1-Heneicosanol" title="1-Heneicosanol">1-Heneicosanol</a></li> <li><a href="/wiki/1-Docosanol" title="1-Docosanol">1-Docosanol</a> (behenyl)</li> <li><a href="/w/index.php?title=1-Tricosanol&action=edit&redlink=1" class="new" title="1-Tricosanol (page does not exist)">1-Tricosanol</a></li> <li><a href="/wiki/1-Tetracosanol" title="1-Tetracosanol">1-Tetracosanol</a> (lignoceryl)</li> <li><a href="/w/index.php?title=1-Pentacosanol&action=edit&redlink=1" class="new" title="1-Pentacosanol (page does not exist)">1-Pentacosanol</a></li> <li><a href="/wiki/1-Hexacosanol" title="1-Hexacosanol">1-Hexacosanol</a> (ceryl)</li> <li><a href="/wiki/1-Heptacosanol" title="1-Heptacosanol">1-Heptacosanol</a></li> <li><a href="/wiki/1-Octacosanol" title="1-Octacosanol">1-Octacosanol</a> (cluytyl / montanyl)</li> <li><a href="/wiki/1-Nonacosanol" title="1-Nonacosanol">1-Nonacosanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain saturated C30 — C39</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Triacontanol" title="1-Triacontanol">1-Triacontanol</a> (melissyl / myricyl)</li> <li><a href="/w/index.php?title=1-Hentriacontanol&action=edit&redlink=1" class="new" title="1-Hentriacontanol (page does not exist)">1-Hentriacontanol</a></li> <li><a href="/wiki/1-Dotriacontanol" title="1-Dotriacontanol">1-Dotriacontanol</a> (lacceryl)</li> <li><a href="/w/index.php?title=1-Tritriacontanol&action=edit&redlink=1" class="new" title="1-Tritriacontanol (page does not exist)">1-Tritriacontanol</a></li> <li><a href="/w/index.php?title=1-Tetratriacontanol&action=edit&redlink=1" class="new" title="1-Tetratriacontanol (page does not exist)">1-Tetratriacontanol</a> (geddyl)</li> <li><a href="/w/index.php?title=1-Pentatriacontanol&action=edit&redlink=1" class="new" title="1-Pentatriacontanol (page does not exist)">1-Pentatriacontanol</a></li> <li><a href="/w/index.php?title=1-Hexatriacontanol&action=edit&redlink=1" class="new" title="1-Hexatriacontanol (page does not exist)">1-Hexatriacontanol</a></li> <li><a href="/w/index.php?title=1-Heptatriacontanol&action=edit&redlink=1" class="new" title="1-Heptatriacontanol (page does not exist)">1-Heptatriacontanol</a></li> <li><a href="/w/index.php?title=1-Octatriacontanol&action=edit&redlink=1" class="new" title="1-Octatriacontanol (page does not exist)">1-Octatriacontanol</a></li> <li><a href="/w/index.php?title=1-Nonatriacontanol&action=edit&redlink=1" class="new" title="1-Nonatriacontanol (page does not exist)">1-Nonatriacontanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain saturated C40 — C49</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1-Tetracontanol&action=edit&redlink=1" class="new" title="1-Tetracontanol (page does not exist)">1-Tetracontanol</a></li> <li><a href="/w/index.php?title=1-Hentetracontanol&action=edit&redlink=1" class="new" title="1-Hentetracontanol (page does not exist)">1-Hentetracontanol</a></li> <li><a href="/w/index.php?title=1-Dotetracontanol&action=edit&redlink=1" class="new" title="1-Dotetracontanol (page does not exist)">1-Dotetracontanol</a></li> <li><a href="/w/index.php?title=1-Tritetracontanol&action=edit&redlink=1" class="new" title="1-Tritetracontanol (page does not exist)">1-Tritetracontanol</a></li> <li><a href="/w/index.php?title=1-Tetratetracontanol&action=edit&redlink=1" class="new" title="1-Tetratetracontanol (page does not exist)">1-Tetratetracontanol</a></li> <li><a href="/w/index.php?title=1-Pentatetracontanol&action=edit&redlink=1" class="new" title="1-Pentatetracontanol (page does not exist)">1-Pentatetracontanol</a></li> <li><a href="/w/index.php?title=1-Hexatetracontanol&action=edit&redlink=1" class="new" title="1-Hexatetracontanol (page does not exist)">1-Hexatetracontanol</a></li> <li><a href="/w/index.php?title=1-Heptatetracontanol&action=edit&redlink=1" class="new" title="1-Heptatetracontanol (page does not exist)">1-Heptatetracontanol</a></li> <li><a href="/w/index.php?title=1-Octatetracontanol&action=edit&redlink=1" class="new" title="1-Octatetracontanol (page does not exist)">1-Octatetracontanol</a></li> <li><a href="/w/index.php?title=1-Nonatetracontanol&action=edit&redlink=1" class="new" title="1-Nonatetracontanol (page does not exist)">1-Nonatetracontanol</a></li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/2-Ethylhexanol" title="2-Ethylhexanol">2-Ethylhexanol</a></li> <li><a href="/wiki/Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a></li> <li><a href="/wiki/Anisyl_alcohol" title="Anisyl alcohol">Anisyl alcohol</a></li> <li><a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a></li> <li><a href="/wiki/Cinnamyl_alcohol" title="Cinnamyl alcohol">Cinnamyl alcohol</a></li> <li><a href="/wiki/Crotyl_alcohol" title="Crotyl alcohol">Crotyl alcohol</a></li> <li><a href="/wiki/Furfuryl_alcohol" title="Furfuryl alcohol">Furfuryl alcohol</a></li> <li><a href="/wiki/Isoamyl_alcohol" title="Isoamyl alcohol">Isoamyl alcohol</a></li> <li><a href="/wiki/Neopentyl_alcohol" title="Neopentyl alcohol">Neopentyl alcohol</a></li> <li><a href="/wiki/Nicotinyl_alcohol" title="Nicotinyl alcohol">Nicotinyl alcohol</a></li> <li><a href="/wiki/Perillyl_alcohol" title="Perillyl alcohol">Perillyl alcohol</a></li> <li><a href="/wiki/Phenethyl_alcohol" title="Phenethyl alcohol">Phenethyl alcohol</a></li> <li><a href="/wiki/Prenol" title="Prenol">Prenol</a></li> <li><a href="/wiki/Propargyl_alcohol" title="Propargyl alcohol">Propargyl alcohol</a></li> <li><a href="/wiki/Salicyl_alcohol" title="Salicyl alcohol">Salicyl alcohol</a></li> <li><a href="/wiki/Tryptophol" title="Tryptophol">Tryptophol</a></li> <li><a href="/wiki/Vanillyl_alcohol" title="Vanillyl alcohol">Vanillyl alcohol</a></li> <li><a href="/wiki/Veratrole_alcohol" title="Veratrole alcohol">Veratrole alcohol</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Secondary alcohols (2°)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/1-Phenylethanol" title="1-Phenylethanol">1-Phenylethanol</a></li> <li><a href="/wiki/2-Butanol" title="2-Butanol">2-Butanol</a></li> <li><a href="/w/index.php?title=2-Deoxyerythritol&action=edit&redlink=1" class="new" title="2-Deoxyerythritol (page does not exist)">2-Deoxyerythritol</a></li> <li><a href="/wiki/2-Heptanol" title="2-Heptanol">2-Heptanol</a></li> <li><a href="/wiki/3-Heptanol" title="3-Heptanol">3-Heptanol</a></li> <li><a href="/wiki/2-Hexanol" title="2-Hexanol">2-Hexanol</a></li> <li><a href="/wiki/3-Hexanol" title="3-Hexanol">3-Hexanol</a></li> <li><a href="/wiki/3-Methyl-2-butanol" title="3-Methyl-2-butanol">3-Methyl-2-butanol</a></li> <li><a href="/wiki/2-Nonanol" title="2-Nonanol">2-Nonanol</a></li> <li><a href="/wiki/2-Octanol" title="2-Octanol">2-Octanol</a></li> <li><a href="/wiki/2-Pentanol" title="2-Pentanol">2-Pentanol</a></li> <li><a href="/wiki/3-Pentanol" title="3-Pentanol">3-Pentanol</a></li> <li><a href="/wiki/Cyclohexanol" title="Cyclohexanol">Cyclohexanol</a></li> <li><a href="/wiki/Cyclopentanol" title="Cyclopentanol">Cyclopentanol</a></li> <li><a href="/wiki/Cyclopropanol" title="Cyclopropanol">Cyclopropanol</a></li> <li><a href="/wiki/Diphenylmethanol" title="Diphenylmethanol">Diphenylmethanol</a></li> <li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropanol</a></li> <li><a href="/wiki/Pinacolyl_alcohol" title="Pinacolyl alcohol">Pinacolyl alcohol</a></li> <li><a href="/wiki/Pirkle%27s_alcohol" title="Pirkle's alcohol">Pirkle's alcohol</a></li> <li><a href="/wiki/Propylene_glycol_methyl_ether" title="Propylene glycol methyl ether">Propylene glycol methyl ether</a></li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tertiary alcohols (3°)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methyl-2-pentanol" title="2-Methyl-2-pentanol">2-Methyl-2-pentanol</a></li> <li><a href="/w/index.php?title=2-Methylheptan-2-ol&action=edit&redlink=1" class="new" title="2-Methylheptan-2-ol (page does not exist)">2-Methylheptan-2-ol</a></li> <li><a href="/w/index.php?title=2-Methylhexan-2-ol&action=edit&redlink=1" class="new" title="2-Methylhexan-2-ol (page does not exist)">2-Methylhexan-2-ol</a></li> <li><a href="/wiki/3-Methyl-3-pentanol" title="3-Methyl-3-pentanol">3-Methyl-3-pentanol</a></li> <li><a href="/w/index.php?title=3-Methyloctan-3-ol&action=edit&redlink=1" class="new" title="3-Methyloctan-3-ol (page does not exist)">3-Methyloctan-3-ol</a></li> <li><a href="/wiki/Diacetone_alcohol" title="Diacetone alcohol">Diacetone alcohol</a></li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/Nonafluoro-tert-butyl_alcohol" title="Nonafluoro-tert-butyl alcohol">Nonafluoro-tert-butyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">tert-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol">tert-Butyl alcohol</a></li> <li><a href="/wiki/Triphenylethanol" title="Triphenylethanol">Triphenylethanol</a></li> <li><a href="/wiki/Triphenylmethanol" title="Triphenylmethanol">Triphenylmethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydric alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Monohydric alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methanol" title="Methanol">Methanol</a> (C1)</li> <li><a class="mw-selflink selflink">Ethanol</a> (C2)</li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a> (C3)</li> <li><a href="/wiki/1-Butanol" title="1-Butanol">1-Butanol</a> (C4)</li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">1-Pentanol</a> (C5)</li> <li><a href="/wiki/Cetyl_alcohol" title="Cetyl alcohol">Cetyl alcohol</a> (C16)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Dihydric alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trihydric alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Polyhydric alcohols (sugar alcohols)</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Pentaerythritol" title="Pentaerythritol">Pentaerythritol</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> (C2)</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a>, <a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a> (C3)</li> <li><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a>, <a href="/wiki/Threitol" title="Threitol">Threitol</a> (C4)</li> <li><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> (C5)</li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a>, <a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> (C6)</li> <li><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> (C7)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amyl_alcohol" title="Amyl alcohol">Amyl alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,2-Dimethylpropan-1-ol" class="mw-redirect" title="2,2-Dimethylpropan-1-ol">2,2-Dimethylpropan-1-ol </a></li> <li><a href="/wiki/2-Methylbutan-1-ol" class="mw-redirect" title="2-Methylbutan-1-ol">2-Methylbutan-1-ol </a></li> <li><a href="/wiki/2-Methylbutan-2-ol" class="mw-redirect" title="2-Methylbutan-2-ol">2-Methylbutan-2-ol </a></li> <li><a href="/wiki/3-Methylbutan-1-ol" class="mw-redirect" title="3-Methylbutan-1-ol">3-Methylbutan-1-ol </a></li> <li><a href="/wiki/3-Methylbutan-2-ol" class="mw-redirect" title="3-Methylbutan-2-ol">3-Methylbutan-2-ol </a></li> <li><a href="/wiki/Pentan-1-ol" class="mw-redirect" title="Pentan-1-ol">Pentan-1-ol </a></li> <li><a href="/wiki/Pentan-2-ol" class="mw-redirect" title="Pentan-2-ol">Pentan-2-ol </a></li> <li><a href="/wiki/Pentan-3-ol" class="mw-redirect" title="Pentan-3-ol">Pentan-3-ol </a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Aromatic alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a></li> <li><a href="/wiki/2,4-Dichlorobenzyl_alcohol" title="2,4-Dichlorobenzyl alcohol">2,4-Dichlorobenzyl alcohol</a></li> <li><a href="/wiki/3-Nitrobenzyl_alcohol" title="3-Nitrobenzyl alcohol">3-Nitrobenzyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Saturated <a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cetostearyl_alcohol" title="Cetostearyl alcohol">Cetostearyl alcohol</a></li> <li><a href="/wiki/Decanol" class="mw-redirect" title="Decanol">Decanol</a></li> <li><a href="/wiki/Lauryl_alcohol" class="mw-redirect" title="Lauryl alcohol">Lauryl alcohol</a></li> <li><a href="/wiki/Myristyl_alcohol" class="mw-redirect" title="Myristyl alcohol">Myristyl alcohol</a></li> <li><a href="/wiki/Nonanol_(disambiguation)" class="mw-redirect mw-disambig" title="Nonanol (disambiguation)">Nonanol</a></li> <li><a href="/wiki/Octanol" title="Octanol">Octanol</a></li> <li><a href="/wiki/Tridecanol" class="mw-redirect" title="Tridecanol">Tridecanol</a></li> <li><a href="/wiki/Undecanol" title="Undecanol">Undecanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Branched and unsaturated <a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Methyl-3-pentanol" title="3-Methyl-3-pentanol">3-Methyl-3-pentanol</a></li> <li><a href="/w/index.php?title=Erucyl_alcohol&action=edit&redlink=1" class="new" title="Erucyl alcohol (page does not exist)">Erucyl alcohol</a></li> <li><a href="/w/index.php?title=Linolenyl_alcohol&action=edit&redlink=1" class="new" title="Linolenyl alcohol (page does not exist)">Linolenyl alcohol</a></li> <li><a href="/wiki/Linoleyl_alcohol" title="Linoleyl alcohol">Linoleyl alcohol</a></li> <li><a href="/wiki/Oleyl_alcohol" title="Oleyl alcohol">Oleyl alcohol</a></li> <li><a href="/w/index.php?title=Palmitoleyl_alcohol&action=edit&redlink=1" class="new" title="Palmitoleyl alcohol (page does not exist)">Palmitoleyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">tert-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol">tert-Butyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Sugar alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">C1 — C7</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylene_glycol" class="mw-redirect" title="Methylene glycol">Methylene glycol</a> (C1)</li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> (C2)</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a> (C3)</li> <li><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a> (C4)</li> <li><a href="/wiki/Threitol" title="Threitol">Threitol</a> (C4)</li> <li><a href="/wiki/Arabitol" title="Arabitol">Arabitol</a> (C5)</li> <li><a href="/wiki/Ribitol" title="Ribitol">Ribitol</a> (C5)</li> <li><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> (C5)</li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a> (C6)</li> <li><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> (C6)</li> <li><a href="/wiki/Galactitol" title="Galactitol">Galactitol</a> (C6)</li> <li><a href="/wiki/Iditol" title="Iditol">Iditol</a> (C6)</li> <li><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> (C7)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Deoxy sugar alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fucitol" title="Fucitol">Fucitol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cyclic sugar alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Inositol" title="Inositol">Inositol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycylglycitols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Maltitol" title="Maltitol">Maltitol</a></li> <li><a href="/wiki/Lactitol" title="Lactitol">Lactitol</a></li> <li><a href="/wiki/Isomalt" title="Isomalt">Isomalt</a></li> <li><a href="/w/index.php?title=Maltotriitol&action=edit&redlink=1" class="new" title="Maltotriitol (page does not exist)">Maltotriitol</a></li> <li><a href="/w/index.php?title=Maltotetraitol&action=edit&redlink=1" class="new" title="Maltotetraitol (page does not exist)">Maltotetraitol</a></li> <li><a href="/w/index.php?title=Polyglycitol&action=edit&redlink=1" class="new" title="Polyglycitol (page does not exist)">Polyglycitol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Terpene alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Monoterpene alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Borneol" title="Borneol">Borneol</a></li> <li><a href="/wiki/Citronellol" title="Citronellol">Citronellol</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Nerol" title="Nerol">Nerol</a></li> <li><a href="/wiki/Rhodinol" title="Rhodinol">Rhodinol</a></li> <li><a href="/wiki/Terpineol" title="Terpineol">Terpineol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sesquiterpene alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bisabolol" title="Bisabolol">Bisabolol</a></li> <li><a href="/wiki/Farnesol" title="Farnesol">Farnesol</a></li> <li><a href="/wiki/Nerolidol" title="Nerolidol">Nerolidol</a></li> <li><a href="/wiki/Patchoulol" title="Patchoulol">Patchoulol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Diterpene alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phytol" title="Phytol">Phytol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Dialcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,4-Butanediol" title="1,4-Butanediol">1,4-Butanediol</a></li> <li><a href="/wiki/1,5-Pentanediol" title="1,5-Pentanediol">1,5-Pentanediol</a></li> <li><a href="/wiki/2-Methyl-2-propyl-1,3-propanediol" title="2-Methyl-2-propyl-1,3-propanediol">2-Methyl-2-propyl-1,3-propanediol</a></li> <li><a href="/wiki/Diethylpropanediol" class="mw-redirect" title="Diethylpropanediol">Diethylpropanediol</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trialcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sterols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/wiki/Beta-Sitosterol" class="mw-redirect" title="Beta-Sitosterol">β-Sitosterol</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fluoroalcohol" title="Fluoroalcohol">Fluoroalcohols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,3-Difluoro-2-propanol" title="1,3-Difluoro-2-propanol">1,3-Difluoro-2-propanol</a></li> <li><a href="/wiki/2,2,2-Trifluoroethanol" title="2,2,2-Trifluoroethanol">2,2,2-Trifluoroethanol</a></li> <li><a href="/wiki/2-Fluoroethanol" title="2-Fluoroethanol">2-Fluoroethanol</a></li> <li><a href="/wiki/Nonafluoro-tert-butyl_alcohol" title="Nonafluoro-tert-butyl alcohol">Nonafluoro-tert-butyl alcohol</a></li> <li><a href="/wiki/Trifluoromethanol" title="Trifluoromethanol">Trifluoromethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Substitution_reaction" title="Substitution reaction">Substitution</a> of <a href="/wiki/Haloalkane#Substitution" title="Haloalkane">haloalkane</a></li> <li><a href="/wiki/Carbonyl_reduction" title="Carbonyl reduction">Carbonyl reduction</a></li> <li><a href="/wiki/Ether_cleavage" title="Ether cleavage">Ether cleavage</a></li> <li><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> of <a href="/wiki/Epoxide#Hydrolysis_and_addition_of_nucleophiles" title="Epoxide">epoxide</a></li> <li><a href="/wiki/Hydration_reaction" title="Hydration reaction">Hydration</a> of <a href="/wiki/Alkene#Hydration" title="Alkene">alkene</a></li> <li><a href="/wiki/Ziegler_process" title="Ziegler process">Ziegler process</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deprotonation" title="Deprotonation">Deprotonation</a></li> <li><a href="/wiki/Protonation" title="Protonation">Protonation</a></li> <li><a href="/wiki/Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a> <ul><li><a href="/wiki/Glycol_cleavage" title="Glycol cleavage">Glycol cleavage</a></li></ul></li> <li><a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitution</a></li> <li><a href="/wiki/Fischer%E2%80%93Speier_esterification" title="Fischer–Speier esterification">Fischer–Speier esterification</a></li> <li><a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitution</a> of <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a></li> <li><a href="/wiki/Friedel-Crafts_alkylation" class="mw-redirect" title="Friedel-Crafts alkylation">Friedel-Crafts alkylation</a></li> <li><a href="/wiki/Nucleophilic_conjugate_addition" title="Nucleophilic conjugate addition">Nucleophilic conjugate addition</a></li> <li><a href="/wiki/Transesterification" title="Transesterification">Transesterification</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2"><div> <ul><li><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /> <a href="/wiki/Category:Alcohols" title="Category:Alcohols">Category</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Motor_fuels" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Motor_fuel" title="Template:Motor fuel"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Motor_fuel" title="Template talk:Motor fuel"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Motor_fuel" title="Special:EditPage/Template:Motor fuel"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Motor_fuels" style="font-size:114%;margin:0 4em"><a href="/wiki/Motor_vehicle" title="Motor vehicle">Motor</a> <a href="/wiki/Fuel" title="Fuel">fuels</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fuel types</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gasoline" title="Gasoline">Gasoline/petrol</a></li> <li><a href="/wiki/Diesel_fuel" title="Diesel fuel">Diesel</a></li> <li><a href="/wiki/Biodiesel" title="Biodiesel">Biodiesel</a></li> <li><a href="/wiki/Biogasoline" title="Biogasoline">Biogasoline</a></li> <li><a href="/wiki/Gasoline#Lead_replacement_petrol_(gasoline)" title="Gasoline">Lead Replacement Petrol</a></li> <li><a href="/wiki/Electric_vehicle" title="Electric vehicle">Electricity</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosene</a></li> <li><a href="/wiki/Compressed_natural_gas" title="Compressed natural gas">Compressed natural gas</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a></li> <li><a class="mw-selflink selflink">Ethanol</a></li> <li><a href="/wiki/Butanol_fuel" title="Butanol fuel">Butanol fuel</a></li> <li><a href="/wiki/Tetraethyllead" title="Tetraethyllead">Racing fuel (Tetraethyllead)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_gasoline_additives" title="List of gasoline additives">Fuel additives</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butyl_rubber" title="Butyl rubber">Butyl rubber</a></li> <li><a href="/wiki/Butylated_hydroxytoluene" title="Butylated hydroxytoluene">Butylated hydroxytoluene</a></li> <li><a href="/wiki/1,2-Dibromoethane" title="1,2-Dibromoethane">1,2-Dibromoethane</a></li> <li><a href="/wiki/1,2-Dichloroethane" title="1,2-Dichloroethane">1,2-Dichloroethane</a></li> <li><a href="/wiki/Dimethyl_methylphosphonate" title="Dimethyl methylphosphonate">Dimethyl methylphosphonate</a></li> <li><a href="/wiki/2,4-Dimethyl-6-tert-butylphenol" title="2,4-Dimethyl-6-tert-butylphenol">2,4-Dimethyl-6-tert-butylphenol</a></li> <li><a href="/wiki/Dinonylnaphthylsulfonic_acid" title="Dinonylnaphthylsulfonic acid">Dinonylnaphthylsulfonic acid</a></li> <li><a href="/wiki/2,6-Di-tert-butylphenol" title="2,6-Di-tert-butylphenol">2,6-Di-tert-butylphenol</a></li> <li><a href="/wiki/Ecalene" title="Ecalene">Ecalene</a></li> <li><a href="/wiki/Ethylenediamine" title="Ethylenediamine">Ethylenediamine</a></li> <li><a href="/wiki/Metal_deactivator" title="Metal deactivator">Metal deactivator</a></li> <li><a href="/wiki/Methyl_tert-butyl_ether" title="Methyl tert-butyl ether">Methyl tert-butyl ether</a></li> <li><a href="/wiki/Nitromethane" title="Nitromethane">Nitromethane</a></li> <li><a href="/wiki/Tetraethyllead" title="Tetraethyllead">Tetraethyllead</a></li> <li><a href="/wiki/Tetranitromethane" title="Tetranitromethane">Tetranitromethane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fluids</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Motor_oil" title="Motor oil">Motor oil</a></li> <li><a href="/wiki/Antifreeze" title="Antifreeze">Antifreeze</a></li> <li><a href="/wiki/Automatic_transmission_fluid" title="Automatic transmission fluid">Automatic transmission fluid</a></li> <li><a href="/wiki/Brake_fluid" title="Brake fluid">Brake fluid</a></li> <li><a href="/wiki/Gear_oil" title="Gear oil">Gear oil</a></li> <li><a href="/wiki/Windshield_washer_fluid" title="Windshield washer fluid">Windshield washer fluid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Filling_station" title="Filling station">Retail</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fuel_card" title="Fuel card">Fuel card</a></li> <li><a href="/wiki/MTBE_controversy" title="MTBE controversy">MTBE controversy</a></li> <li><a href="/wiki/Pay_at_the_pump" title="Pay at the pump">Pay at the pump</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Molecules_detected_in_outer_space" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a> <a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a> <a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N2H+</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC4N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a class="mw-selflink selflink">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten atoms or more</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C60, C60+, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C70 fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a> molecules</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N2D+</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> 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href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world 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[\"CITEREFHeit,_C.Dong,_H.Chen,_Y.Thompson,_D.C.2013\"] = 1,\n [\"CITEREFHennell1826\"] = 1,\n [\"CITEREFHennell1828\"] = 1,\n [\"CITEREFHolmyard1957\"] = 1,\n [\"CITEREFHornKrupp2009\"] = 1,\n [\"CITEREFImmergut2015\"] = 1,\n [\"CITEREFJeongJeonKoChung2012\"] = 1,\n [\"CITEREFJones2008\"] = 1,\n [\"CITEREFKaveh\"] = 1,\n [\"CITEREFKosaricDuvnjakFarkasSahm2011\"] = 1,\n [\"CITEREFKuettnerBertram1963\"] = 1,\n [\"CITEREFKunkeeAmerine1968\"] = 1,\n [\"CITEREFLeblováSineckáVaníčková1974\"] = 1,\n [\"CITEREFLide2000\"] = 1,\n [\"CITEREFLide2008\"] = 1,\n [\"CITEREFLide2012\"] = 1,\n [\"CITEREFLiebig1834\"] = 1,\n [\"CITEREFLiewHenstraKöpkeWinzer2017\"] = 1,\n [\"CITEREFLodgsdon1991\"] = 1,\n [\"CITEREFLowiCarter1990\"] = 1,\n [\"CITEREFLowitz1796\"] = 1,\n [\"CITEREFMalaquiasNettoFilhoda_Costa2019\"] = 1,\n [\"CITEREFMartínezRusCompaña\"] = 1,\n [\"CITEREFMcDonnellRussell1999\"] = 1,\n [\"CITEREFMillsEcklund1987\"] = 1,\n [\"CITEREFMorrisonBoyd1972\"] = 1,\n [\"CITEREFMulthauf1966\"] = 1,\n [\"CITEREFMyersMyers2007\"] = 1,\n [\"CITEREFNational_Institute_of_Standards_and_Technology\"] = 1,\n [\"CITEREFOttley1826\"] = 1,\n [\"CITEREFPembertonMash1978\"] = 1,\n [\"CITEREFPohoreckyBrick1988\"] = 1,\n [\"CITEREFPowell_MA2004\"] = 1,\n [\"CITEREFPrincipe2013\"] = 1,\n [\"CITEREFRajvanshiPatilMendonca2007\"] = 1,\n [\"CITEREFReel2006\"] = 1,\n [\"CITEREFReinhardKoppMcKusickRöderer2007\"] = 1,\n [\"CITEREFRoach2005\"] = 1,\n [\"CITEREFRobertsCaserio1977\"] = 1,\n [\"CITEREFRossiGalloMattosoBuckeridge2021\"] = 1,\n [\"CITEREFRossini1937\"] = 1,\n [\"CITEREFSasanamiYamadaObaraNakao2020\"] = 1,\n [\"CITEREFScalley2002\"] = 1,\n [\"CITEREFSchnelle1965\"] = 1,\n [\"CITEREFSchriverSchriver-MazzuoliEhrenfreundd\u0026#039;Hendecourt2007\"] = 1,\n [\"CITEREFSiegel2007\"] = 1,\n [\"CITEREFSongPengHensleyBonnesen2016\"] = 1,\n [\"CITEREFSongWalker2023\"] = 1,\n [\"CITEREFStreitwieserHeathcock1976\"] = 1,\n [\"CITEREFSwami2020\"] = 1,\n [\"CITEREFSérullas1828\"] = 1,\n [\"CITEREFTao2010\"] = 1,\n [\"CITEREFThomas2000\"] = 2,\n [\"CITEREFTullo2021\"] = 1,\n [\"CITEREFTurnerSpanelSmith2006\"] = 1,\n [\"CITEREFWindholz1976\"] = 1,\n [\"CITEREFWittcoffReubenPlotkin2004\"] = 1,\n [\"CITEREFZimmermannWalz2008\"] = 1,\n [\"CITEREFZuccottiFabiano2011\"] = 1,\n [\"CITEREFal-Hassan2009\"] = 1,\n [\"CITEREFde_Saussure1807\"] = 1,\n [\"CITEREFde_Saussure1814\"] = 1,\n}\ntemplate_list = table#1 {\n [\"!\"] = 6,\n [\"Alcohols\"] = 1,\n [\"Authority control\"] = 1,\n [\"Block indent\"] = 3,\n [\"Cascite\"] = 1,\n [\"Chem\"] = 10,\n [\"Chem2\"] = 7,\n [\"Chembox\"] = 1,\n [\"Chembox Hazards\"] = 1,\n [\"Chembox Identifiers\"] = 1,\n [\"Chembox Properties\"] = 1,\n [\"Chembox Related\"] = 1,\n [\"Chemspidercite\"] = 1,\n [\"Circa\"] = 4,\n [\"Citation\"] = 1,\n [\"Cite EB1911\"] = 1,\n [\"Cite book\"] = 39,\n [\"Cite conference\"] = 1,\n [\"Cite encyclopedia\"] = 2,\n [\"Cite journal\"] = 50,\n [\"Cite news\"] = 7,\n [\"Cite web\"] = 51,\n [\"Cn\"] = 2,\n [\"Commons\"] = 1,\n [\"Convert\"] = 25,\n [\"Cvt\"] = 1,\n [\"Distinguish\"] = 1,\n [\"Div col\"] = 1,\n [\"Div col end\"] = 1,\n [\"Drugbankcite\"] = 1,\n [\"Ebicite\"] = 2,\n [\"Eqm\"] = 1,\n [\"Fdacite\"] = 1,\n [\"For\"] = 1,\n [\"Further\"] = 5,\n [\"GHS02\"] = 1,\n [\"GHS07\"] = 1,\n [\"GHS08\"] = 1,\n [\"Google books\"] = 20,\n [\"H-phrases\"] = 1,\n [\"Harvnb\"] = 6,\n [\"IPAc-en\"] = 1,\n [\"Legend\"] = 2,\n [\"Legend-line\"] = 1,\n [\"Main\"] = 3,\n [\"Molecules detected in outer space\"] = 1,\n [\"More citations needed section\"] = 4,\n [\"Motor fuel\"] = 1,\n [\"Navboxes\"] = 1,\n [\"Nbsp\"] = 4,\n [\"Nowrap\"] = 5,\n [\"OEtymD\"] = 1,\n [\"P-phrases\"] = 1,\n [\"PGCH\"] = 1,\n [\"Page needed\"] = 3,\n [\"Pp-move-indef\"] = 1,\n [\"Reflist\"] = 1,\n [\"RubberBible92nd\"] = 1,\n [\"See also\"] = 3,\n [\"Short description\"] = 1,\n [\"Stdinchicite\"] = 2,\n [\"Subscription required\"] = 1,\n [\"Sup\"] = 1,\n [\"Transliteration\"] = 2,\n [\"Ubl\"] = 3,\n [\"Use dmy dates\"] = 1,\n [\"Webarchive\"] = 7,\n [\"Wiktionary\"] = 1,\n}\narticle_whitelist = table#1 {\n}\ntable#1 {\n [\"size\"] = \"tiny\",\n}\ntable#1 {\n [\"size\"] = \"tiny\",\n}\ntable#1 {\n [\"size\"] = \"tiny\",\n}\n","limitreport-profile":[["?","360","19.6"],["recursiveClone \u003CmwInit.lua:45\u003E","280","15.2"],["MediaWiki\\Extension\\Scribunto\\Engines\\LuaSandbox\\LuaSandboxCallback::callParserFunction","180","9.8"],["dataWrapper 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type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Ethanol","url":"https:\/\/en.wikipedia.org\/wiki\/Ethanol","sameAs":"http:\/\/www.wikidata.org\/entity\/Q153","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q153","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2001-11-07T07:17:24Z","dateModified":"2024-11-17T17:38:50Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/8\/83\/Sample_of_Absolute_Ethanol.jpg","headline":"chemical compound"}</script> </body> </html>