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class="vector-toc-list"> <li id="toc-Industrial_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Industrial routes</span> </div> </a> <ul id="toc-Industrial_routes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biological_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biological_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Biological routes</span> </div> </a> <ul id="toc-Biological_routes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Historical_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Historical_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Historical routes</span> </div> </a> <ul id="toc-Historical_routes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Coolant_and_heat-transfer_agent" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Coolant_and_heat-transfer_agent"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Coolant and heat-transfer agent</span> </div> </a> <ul id="toc-Coolant_and_heat-transfer_agent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anti-freeze" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anti-freeze"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Anti-freeze</span> </div> </a> <ul id="toc-Anti-freeze-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_polymers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_polymers"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Precursor to polymers</span> </div> </a> <ul id="toc-Precursor_to_polymers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Other uses</span> </div> </a> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> <li id="toc-Dehydrating_agent" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Dehydrating_agent"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4.1</span> <span>Dehydrating agent</span> </div> </a> <ul id="toc-Dehydrating_agent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrate_inhibition" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hydrate_inhibition"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4.2</span> <span>Hydrate inhibition</span> </div> </a> <ul id="toc-Hydrate_inhibition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_other_chemicals" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Precursor_to_other_chemicals"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4.3</span> <span>Precursor to other chemicals</span> </div> </a> <ul id="toc-Precursor_to_other_chemicals-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Organic_building_block" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Organic_building_block"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Organic building block</span> </div> </a> <ul id="toc-Organic_building_block-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Miscellaneous_chemical_reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Miscellaneous_chemical_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Miscellaneous chemical reactions</span> </div> </a> <ul id="toc-Miscellaneous_chemical_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environmental_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Environmental_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Environmental effects</span> </div> </a> <ul id="toc-Environmental_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </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" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </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"><span class="mw-page-title-main">Ethylene glycol</span></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 54 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-54" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">54 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D9%8A%D8%AB%D9%8A%D9%84%D9%8A%D9%86_%D8%BA%D9%84%D9%8A%D9%83%D9%88%D9%84" title="إيثيلين غليكول – Arabic" lang="ar" hreflang="ar" data-title="إيثيلين غليكول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Etilenglicol" title="Etilenglicol – Asturian" lang="ast" hreflang="ast" data-title="Etilenglicol" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Etilenqlikol" title="Etilenqlikol – Azerbaijani" lang="az" hreflang="az" data-title="Etilenqlikol" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%AA%DB%8C%D9%84%D9%86_%D9%82%D9%84%DB%8C%DA%A9%D9%88%D9%84" title="اتیلن قلیکول – South Azerbaijani" lang="azb" hreflang="azb" data-title="اتیلن قلیکول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%AD%D1%82%D1%8B%D0%BB%D0%B5%D0%BD%D0%B3%D0%BB%D1%96%D0%BA%D0%BE%D0%BB%D1%8C" title="Этыленгліколь – Belarusian" lang="be" hreflang="be" data-title="Этыленгліколь" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></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%D1%8B%D0%BB%D0%B5%D0%BD%D0%B3%D0%BB%D1%96%D0%BA%D0%BE%D0%BB%D1%8C" title="Этыленгліколь – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Этыленгліколь" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%95%D1%82%D0%B8%D0%BB%D0%B5%D0%BD%D0%B3%D0%BB%D0%B8%D0%BA%D0%BE%D0%BB" title="Етиленгликол – Bulgarian" lang="bg" hreflang="bg" data-title="Етиленгликол" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Etilenglicol" title="Etilenglicol – Catalan" lang="ca" hreflang="ca" data-title="Etilenglicol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ethylenglykol" title="Ethylenglykol – Czech" lang="cs" hreflang="cs" data-title="Ethylenglykol" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ethylenglycol" title="Ethylenglycol – German" lang="de" hreflang="de" data-title="Ethylenglycol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/1,2-etaandiool" title="1,2-etaandiool – Estonian" lang="et" hreflang="et" data-title="1,2-etaandiool" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/1,2-%CE%B1%CE%B9%CE%B8%CE%B1%CE%BD%CE%BF%CE%B4%CE%B9%CF%8C%CE%BB%CE%B7" title="1,2-αιθανοδιόλη – Greek" lang="el" hreflang="el" data-title="1,2-αιθανοδιόλη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Etilenglicol" title="Etilenglicol – Spanish" lang="es" hreflang="es" data-title="Etilenglicol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Etileno-glikolo" title="Etileno-glikolo – Esperanto" lang="eo" hreflang="eo" data-title="Etileno-glikolo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Etilen_glikol" title="Etilen glikol – Basque" lang="eu" hreflang="eu" data-title="Etilen glikol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%AA%DB%8C%D9%84%D9%86_%DA%AF%D9%84%DB%8C%DA%A9%D9%88%D9%84" title="اتیلن گلیکول – Persian" lang="fa" hreflang="fa" data-title="اتیلن گلیکول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89thyl%C3%A8ne_glycol" title="Éthylène glycol – French" lang="fr" hreflang="fr" data-title="Éthylène glycol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%97%90%ED%8B%B8%EB%A0%8C_%EA%B8%80%EB%9D%BC%EC%9D%B4%EC%BD%9C" title="에틸렌 글라이콜 – Korean" lang="ko" hreflang="ko" data-title="에틸렌 글라이콜" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></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%A5%D5%B6%D5%A3%D5%AC%D5%AB%D5%AF%D5%B8%D5%AC" title="Էթիլենգլիկոլ – Armenian" lang="hy" hreflang="hy" data-title="Էթիլենգլիկոլ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%8F%E0%A4%A5%E0%A4%BF%E0%A4%B2%E0%A5%80%E0%A4%A8_%E0%A4%97%E0%A5%8D%E0%A4%B2%E0%A4%BE%E0%A4%87%E0%A4%95%E0%A5%8B%E0%A4%B2" title="एथिलीन ग्लाइकोल – Hindi" lang="hi" hreflang="hi" data-title="एथिलीन ग्लाइकोल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Etilen-glikol" title="Etilen-glikol – Croatian" lang="hr" hreflang="hr" data-title="Etilen-glikol" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Etilena_glikol" title="Etilena glikol – Indonesian" lang="id" hreflang="id" data-title="Etilena glikol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Glicole_etilenico" title="Glicole etilenico – Italian" lang="it" hreflang="it" data-title="Glicole etilenico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%AA%D7%99%D7%9C%D7%9F_%D7%92%D7%9C%D7%99%D7%A7%D7%95%D7%9C" title="אתילן גליקול – Hebrew" lang="he" hreflang="he" data-title="אתילן גליקול" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></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%98%E1%83%9A%E1%83%94%E1%83%9C%E1%83%92%E1%83%9A%E1%83%98%E1%83%99%E1%83%9D%E1%83%9A%E1%83%98" title="ეთილენგლიკოლი – Georgian" lang="ka" hreflang="ka" data-title="ეთილენგლიკოლი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></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%D0%B5%D0%BD%D0%B3%D0%BB%D0%B8%D0%BA%D0%BE%D0%BB%D1%8C" title="Этиленгликоль – Kazakh" lang="kk" hreflang="kk" data-title="Этиленгликоль" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Etil%C4%93nglikols" title="Etilēnglikols – Latvian" lang="lv" hreflang="lv" data-title="Etilēnglikols" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Etilenglikolis" title="Etilenglikolis – Lithuanian" lang="lt" hreflang="lt" data-title="Etilenglikolis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Etil%C3%A9nglikol" title="Etilénglikol – Hungarian" lang="hu" hreflang="hu" data-title="Etilénglikol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%95%D1%82%D0%B8%D0%BB%D0%B5%D0%BD_%D0%B3%D0%BB%D0%B8%D0%BA%D0%BE%D0%BB" title="Етилен гликол – Macedonian" lang="mk" hreflang="mk" data-title="Етилен гликол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Etilena_glikol" title="Etilena glikol – Malay" lang="ms" hreflang="ms" data-title="Etilena glikol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/1,2-ethaandiol" title="1,2-ethaandiol – Dutch" lang="nl" hreflang="nl" data-title="1,2-ethaandiol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%83%81%E3%83%AC%E3%83%B3%E3%82%B0%E3%83%AA%E3%82%B3%E3%83%BC%E3%83%AB" title="エチレングリコール – Japanese" lang="ja" hreflang="ja" data-title="エチレングリコール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Glykol" title="Glykol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Glykol" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Etilenglikol" title="Etilenglikol – Uzbek" lang="uz" hreflang="uz" data-title="Etilenglikol" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Glikol_etylenowy" title="Glikol etylenowy – Polish" lang="pl" hreflang="pl" data-title="Glikol etylenowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Etilenoglicol" title="Etilenoglicol – Portuguese" lang="pt" hreflang="pt" data-title="Etilenoglicol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Etilenglicol" title="Etilenglicol – Romanian" lang="ro" hreflang="ro" data-title="Etilenglicol" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D1%82%D0%B8%D0%BB%D0%B5%D0%BD%D0%B3%D0%BB%D0%B8%D0%BA%D0%BE%D0%BB%D1%8C" title="Этиленгликоль – Russian" lang="ru" hreflang="ru" data-title="Этиленгликоль" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Ethylene_glycol" title="Ethylene glycol – Simple English" lang="en-simple" hreflang="en-simple" data-title="Ethylene glycol" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Etyl%C3%A9nglykol" title="Etylénglykol – Slovak" lang="sk" hreflang="sk" data-title="Etylénglykol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Etilenglikol" title="Etilenglikol – Slovenian" lang="sl" hreflang="sl" data-title="Etilenglikol" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Etilen_glikol" title="Etilen glikol – Serbian" lang="sr" hreflang="sr" data-title="Etilen glikol" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Etilen_glikol" title="Etilen glikol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Etilen glikol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Etilen_glikol" title="Etilen glikol – Sundanese" lang="su" hreflang="su" data-title="Etilen glikol" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Etyleeniglykoli" title="Etyleeniglykoli – Finnish" lang="fi" hreflang="fi" data-title="Etyleeniglykoli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Etandiol" title="Etandiol – Swedish" lang="sv" hreflang="sv" data-title="Etandiol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%8E%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AE%BF%E0%AE%B2%E0%AF%80%E0%AE%A9%E0%AF%8D_%E0%AE%95%E0%AE%BF%E0%AE%B3%E0%AF%88%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AE%BE%E0%AE%B2%E0%AF%8D" title="எத்திலீன் கிளைக்கால் – Tamil" lang="ta" hreflang="ta" data-title="எத்திலீன் கிளைக்கால்" data-language-autonym="தமிழ்" 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href="https://uk.wikipedia.org/wiki/%D0%95%D1%82%D0%B8%D0%BB%D0%B5%D0%BD%D0%B3%D0%BB%D1%96%D0%BA%D0%BE%D0%BB%D1%8C" title="Етиленгліколь – Ukrainian" lang="uk" hreflang="uk" data-title="Етиленгліколь" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Ethylen_glycol" title="Ethylen glycol – Vietnamese" lang="vi" hreflang="vi" data-title="Ethylen glycol" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%94%98%E9%86%87" title="甘醇 – Cantonese" lang="yue" hreflang="yue" data-title="甘醇" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li 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</div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compound ethane-1,2-diol</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">Polyethylene glycol</a>, <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">Diethylene glycol</a>, <a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a>, or <a href="/wiki/Diol" title="Diol">Glycol</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>Ethylene glycol </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Ethylene_glycol.svg" class="mw-file-description" title="Wireframe model of ethylene glycol"><img alt="Wireframe model of ethylene glycol" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Ethylene_glycol.svg/220px-Ethylene_glycol.svg.png" decoding="async" width="220" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Ethylene_glycol.svg/330px-Ethylene_glycol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Ethylene_glycol.svg/440px-Ethylene_glycol.svg.png 2x" data-file-width="92" data-file-height="24" /></a></span> </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:Ethylene-glycol-3D-vdW.png" class="mw-file-description" title="Spacefill model of ethylene glycol"><img alt="Spacefill model of ethylene glycol" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Ethylene-glycol-3D-vdW.png/110px-Ethylene-glycol-3D-vdW.png" decoding="async" width="110" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Ethylene-glycol-3D-vdW.png/165px-Ethylene-glycol-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/16/Ethylene-glycol-3D-vdW.png/220px-Ethylene-glycol-3D-vdW.png 2x" data-file-width="1100" data-file-height="714" /></a><figcaption>Spacefill model of ethylene glycol</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethylene-glycol-3D-balls.png" class="mw-file-description" title="Ball and stick model of ethylene glycol"><img alt="Ball and stick model of ethylene glycol" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Ethylene-glycol-3D-balls.png/110px-Ethylene-glycol-3D-balls.png" decoding="async" width="110" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Ethylene-glycol-3D-balls.png/165px-Ethylene-glycol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Ethylene-glycol-3D-balls.png/220px-Ethylene-glycol-3D-balls.png 2x" data-file-width="1100" data-file-height="618" /></a><figcaption>Ball and stick model of ethylene glycol</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Samlpe_of_Ethylene_glycol.jpg" class="mw-file-description" title="Sample of ethylene glycol"><img alt="Sample of ethylene glycol" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Samlpe_of_Ethylene_glycol.jpg/220px-Samlpe_of_Ethylene_glycol.jpg" decoding="async" width="220" height="325" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Samlpe_of_Ethylene_glycol.jpg/330px-Samlpe_of_Ethylene_glycol.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Samlpe_of_Ethylene_glycol.jpg/440px-Samlpe_of_Ethylene_glycol.jpg 2x" data-file-width="2075" data-file-height="3064" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC names</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Ethylene glycol<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br />Ethane-1,2-diol<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div> </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;">Ethane-1,2-diol<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></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>Ethylene glycol</li><li>1,2-Ethanediol</li><li>Ethylene alcohol</li><li>Hypodicarbonous acid</li><li>Monoethylene glycol</li><li>1,2-Dihydroxyethane</li><li>Glycol solvent</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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=107-21-1">107-21-1</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=OCCO">Interactive image</a></span></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><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00278">B00278</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>MEG </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>505945 </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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30742">CHEBI:30742</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL457299">ChEMBL457299</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.13835235.html">13835235</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.003.159">100.003.159</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q194207#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></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>203-473-3</li></ul></div> </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>943 </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><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01380">C01380</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Ethylene+glycol">Ethylene+glycol</a></span> </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><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/174">174</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>KW2975000</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><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/FC72KVT52F">FC72KVT52F</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>3082 </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> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8020597,">DTXSID4027862 DTXSID8020597, DTXSID4027862</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q194207#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></span></span></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/C2H6O2/c3-1-2-4/h3-4H,1-2H2<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LYCAIKOWRPUZTN-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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/C2H6O2/c3-1-2-4/h3-4H,1-2H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LYCAIKOWRPUZTN-UHFFFAOYAD</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%;">OCCO</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><span title="Carbon">C</span><sub>2</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001620680000000000♠"></span>62.068</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>colorless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Odorless<sup id="cite_ref-PGCH_4-0" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.1132 g/cm<sup>3</sup> (0.04022 lb/cu in) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−12.9 °C (8.8 °F; 260.2 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>197.3 °C (387.1 °F; 470.4 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/Miscible" class="mw-redirect" title="Miscible">Miscible</a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in alcohols, ethyl acetate, THF, and dioxane. Miscible with DCM and slightly miscible with diethyl ether. Not miscible with toluene or hexanes. </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>-1.69<sup id="cite_ref-chemsrc_5-0" class="reference"><a href="#cite_note-chemsrc-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>7.99 Pa (20 °C)<sup id="cite_ref-PGCH_4-1" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>1.61<span style="margin:0 .15em 0 .25em">×</span>10<sup><span class="nowrap"><span data-sort-value="2999800000000000000♠"></span>−2</span></sup> Pa·s<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>149.5 J/(mol·K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>166.9 J/(mol·K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−460 kJ/mol </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;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Harmful, produces poisonous <a href="/wiki/Oxalic_acid" title="Oxalic acid">oxalic acid</a> when ingested, flammable </td></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"><b>GHS</b> 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><span typeof="mw:File"><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></span><span typeof="mw:File"><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></span> </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><b>Warning</b> </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="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H373: May cause damage to organs through prolonged or repeated exposure">H373</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="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.">P301+P312</abbr>, <abbr class="abbr" title="P302: IF ON SKIN:">P302</abbr>, <abbr class="abbr" title="P314: Get Medical advice/attention if you feel unwell.">P314</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></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"><span><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_482e25fdfe95519d" /></span><map name="ImageMap_482e25fdfe95519d"><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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><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"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>111 °C (232 °F; 384 K) closed cup </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>410 °C (770 °F; 683 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>3.2–15.2%<sup id="cite_ref-PGCH_4-2" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </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"><b>NIOSH</b></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>None<sup id="cite_ref-PGCH_4-3" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </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>None established<sup id="cite_ref-PGCH_4-4" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </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>None<sup id="cite_ref-PGCH_4-5" class="reference"><a href="#cite_note-PGCH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="https://www.fishersci.com/msdsproxy%3FproductName%3DE1774%26productDescription%3DETHYLENE%2BGLYCOL%2BLABORATORY%2B4L%26catNo%3DE177-4%2B%26vendorId%3DVN00033897%26storeId%3D10652">External SDS 1</a> <p><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/GB/cs/sds/sial/324558">External SDS 2</a> </p> </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 <a href="/wiki/Diol" title="Diol">diols</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a></li><li><a href="/wiki/Diethylene_glycol" title="Diethylene glycol">Diethylene glycol</a></li><li><a href="/wiki/Triethylene_glycol" title="Triethylene glycol">Triethylene glycol</a></li><li><a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">Polyethylene glycol</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/Ethylene_glycol_(data_page)" title="Ethylene glycol (data page)">Ethylene glycol (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;"><span typeof="mw:File"><span><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" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=457630599&page2=Ethylene+glycol">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><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" /></span></span><span style="display:none">N</span></sup> ?) </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> <p><b>Ethylene glycol</b> (<a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC name</a>: ethane-1,2-diol) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> (a <a href="/wiki/Diol#Vicinal_diols" title="Diol">vicinal diol</a><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>) with the formula <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><span class="chemf nowrap">(CH<sub class="template-chem2-sub">2</sub>OH)<sub class="template-chem2-sub">2</sub></span>. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for <a href="/wiki/Antifreeze" title="Antifreeze">antifreeze</a> formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste, but is <a href="/wiki/Ethylene_glycol_poisoning" title="Ethylene glycol poisoning">toxic in high concentrations</a>. This molecule has been observed in outer space.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=1" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Industrial_routes">Industrial routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=2" title="Edit section: Industrial routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethylene glycol is produced from <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> (ethene), via the intermediate <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a>. Ethylene oxide reacts with <a href="/wiki/Water" title="Water">water</a> to produce ethylene glycol according to the <a href="/wiki/Chemical_equation" title="Chemical equation">chemical equation</a> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>O + H<sub class="template-chem2-sub">2</sub>O → HO−CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>−OH</span></dd></dl> <p>This <a href="/wiki/Chemical_reaction" title="Chemical reaction">reaction</a> can be <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyzed</a> by either <a href="/wiki/Acid" title="Acid">acids</a> or <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">bases</a>, or can occur at neutral <a href="/wiki/PH" title="PH">pH</a> under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the oligomers <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a>, <a href="/wiki/Triethylene_glycol" title="Triethylene glycol">triethylene glycol</a>, and <a href="/wiki/Tetraethylene_glycol" class="mw-redirect" title="Tetraethylene glycol">tetraethylene glycol</a>. The separation of these oligomers and water is energy-intensive. World production of ethylene glycol was ~20 Mt in 2010.<sup id="cite_ref-YueZhaoMa2012_9-0" class="reference"><a href="#cite_note-YueZhaoMa2012-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>A higher selectivity is achieved by the use of <a href="/wiki/Royal_Dutch_Shell" class="mw-redirect" title="Royal Dutch Shell">Shell</a>'s <a href="/wiki/OMEGA_process" title="OMEGA process">OMEGA process</a>. In the OMEGA process, the ethylene oxide is first converted with <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> (CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub>) to <a href="/wiki/Ethylene_carbonate" title="Ethylene carbonate">ethylene carbonate</a>. This ring is then hydrolyzed with a base catalyst in a second step to produce mono-ethylene glycol in 98% selectivity.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The carbon dioxide is released in this step again and can be fed back into the process circuit. The carbon dioxide comes in part from ethylene oxide production, where a part of the ethylene is completely <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a>. </p><p>Ethylene glycol is produced from <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> in countries with large coal reserves and less stringent environmental regulations. The oxidative carbonylation of methanol to <a href="/wiki/Dimethyl_oxalate" title="Dimethyl oxalate">dimethyl oxalate</a> provides a promising approach to the production of <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">1</sub></span></span></span>-based ethylene glycol.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Dimethyl oxalate can be converted into ethylene glycol in high yields (94.7%)<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> by <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> with a copper catalyst:<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:MEG_ex_CO.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/MEG_ex_CO.svg/331px-MEG_ex_CO.svg.png" decoding="async" width="331" height="483" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/MEG_ex_CO.svg/497px-MEG_ex_CO.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/MEG_ex_CO.svg/662px-MEG_ex_CO.svg.png 2x" data-file-width="331" data-file-height="483" /></a><figcaption></figcaption></figure> <p>Because the methanol is recycled, only carbon monoxide, hydrogen, and oxygen are consumed. One plant with a production capacity of <span class="nowrap"><span data-sort-value="7005200000000000000♠"></span>200<span style="margin-left:.25em;">000</span> tons</span> of ethylene glycol per year is in <a href="/wiki/Inner_Mongolia" title="Inner Mongolia">Inner Mongolia</a>, and a second plant in the Chinese province of <a href="/wiki/Henan" title="Henan">Henan</a> with a capacity of <span class="nowrap"><span data-sort-value="7005250000000000000♠"></span>250<span style="margin-left:.25em;">000</span> tons per year</span> was scheduled for 2012.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> As of 2015<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Ethylene_glycol&action=edit">[update]</a></sup>, four plants in China with a capacity of <span class="nowrap"><span data-sort-value="7007196132999999999♠"></span>200<span style="margin-left:.25em;">000</span> t/a</span> each were operating, with at least 17 more to follow.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biological_routes">Biological routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=3" title="Edit section: Biological routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethylene glycol can be produced by recycling its polymeric derivatives such a <a href="/wiki/Polyethylene_terephthalate" title="Polyethylene terephthalate">polyethylene terephthalate</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Historical_routes">Historical routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=4" title="Edit section: Historical routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to most sources, French chemist <a href="/wiki/Charles-Adolphe_Wurtz" class="mw-redirect" title="Charles-Adolphe Wurtz">Charles-Adolphe Wurtz</a> (1817–1884) first prepared ethylene glycol in 1856.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> He first treated "ethylene iodide" (<a href="/wiki/1,2-Diiodoethane" title="1,2-Diiodoethane">1,2-Diiodoethane</a>) with silver acetate and then hydrolyzed the resultant "ethylene diacetate" with <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a>. Wurtz named his new compound "glycol" because it shared qualities with both <a href="/wiki/Ethyl_alcohol" class="mw-redirect" title="Ethyl alcohol">ethyl alcohol</a> (with one hydroxyl group) and <a href="/wiki/Glycerin" class="mw-redirect" title="Glycerin">glycerin</a> (with three hydroxyl groups).<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> In 1859, Wurtz prepared ethylene glycol via the <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a> of <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> There appears to have been no commercial manufacture or application of ethylene glycol prior to <a href="/wiki/World_War_I" title="World War I">World War I</a>, when it was synthesized from <a href="/wiki/Ethylene_dichloride" class="mw-redirect" title="Ethylene dichloride">ethylene dichloride</a> in Germany and used as a substitute for <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> in the <a href="/wiki/Explosives" class="mw-redirect" title="Explosives">explosives</a> industry. </p><p>In the United States, semicommercial production of ethylene glycol via <a href="/wiki/Ethylene_chlorohydrin" class="mw-redirect" title="Ethylene chlorohydrin">ethylene chlorohydrin</a> started in 1917. The first large-scale commercial glycol plant was erected in 1925 at <a href="/wiki/South_Charleston,_West_Virginia" title="South Charleston, West Virginia">South Charleston, West Virginia</a>, by Carbide and Carbon Chemicals Co. (now <a href="/wiki/Union_Carbide" title="Union Carbide">Union Carbide</a> Corp.). By 1929, ethylene glycol was being used by almost all <a href="/wiki/Dynamite" title="Dynamite">dynamite</a> manufacturers. In 1937, Carbide started up the first plant based on Lefort's process for vapor-phase oxidation of ethylene to ethylene oxide. Carbide maintained a monopoly on the direct oxidation process until 1953 when the Scientific Design process was commercialized and offered for licensing. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=5" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Coolant_and_heat-transfer_agent">Coolant and heat-transfer agent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=6" title="Edit section: Coolant and heat-transfer agent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The major use of ethylene glycol is as an antifreeze agent in the <a href="/wiki/Coolant" title="Coolant">coolant</a> in for example, automobiles and <a href="/wiki/Air-conditioning" class="mw-redirect" title="Air-conditioning">air-conditioning</a> systems that either place the <a href="/wiki/Chiller" title="Chiller">chiller</a> or <a href="/wiki/Air_handler" title="Air handler">air handlers</a> outside or must cool below the freezing temperature of water. In <a href="/wiki/Geothermal_heating" title="Geothermal heating">geothermal heating</a>/cooling systems, ethylene glycol is the <a href="/wiki/Fluid" title="Fluid">fluid</a> that transports heat through the use of a <a href="/wiki/Geothermal_heat_pump" class="mw-redirect" title="Geothermal heat pump">geothermal heat pump</a>. The ethylene glycol either gains energy from the source (lake, ocean, <a href="/wiki/Water_well" class="mw-redirect" title="Water well">water well</a>) or dissipates heat to the sink, depending on whether the system is being used for heating or cooling. </p><p>Pure ethylene glycol has a <a href="/wiki/Specific_heat_capacity" title="Specific heat capacity">specific heat capacity</a> about one half that of water. So, while providing freeze protection and an increased boiling point, ethylene glycol lowers the specific heat capacity of water mixtures relative to pure water. A 1:1 mix by mass has a specific heat capacity of about 3140 J/(kg·°C) (0.75 BTU/(lb·°F)), three quarters that of pure water, thus requiring increased flow rates in same-system comparisons with water. </p><p>The mixture of ethylene glycol with water provides additional benefits to coolant and antifreeze solutions, such as preventing corrosion and acid degradation, as well as inhibiting the growth of most microbes and fungi.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Mixtures of ethylene glycol and water are sometimes informally referred to in industry as glycol concentrates, compounds, mixtures, or solutions. </p><p>Table of thermal and physical properties of saturated liquid ethylene glycol:<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable mw-collapsible"> <tbody><tr> <th>Temperature (°C) </th> <th>Density (kg/m<sup>3</sup>) </th> <th>Specific heat (kJ/(kg·K)) </th> <th>Kinematic viscosity (m<sup>2</sup>/s) </th> <th>Conductivity (W/(m⋅K)) </th> <th>Thermal diffusivity (m<sup>2</sup>/s) </th> <th>Prandtl Number </th> <th>Thermal expansivity (K<sup>−1</sup>) </th></tr> <tr> <td>0 </td> <td>1130.75 </td> <td>2.294 </td> <td><span class="nowrap"><span data-sort-value="6995753000000000000♠"></span>7.53<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−5</sup></span> </td> <td>0.242 </td> <td><span class="nowrap"><span data-sort-value="6992934000000000000♠"></span>9.34<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−8</sup></span> </td> <td>615 </td> <td><span class="nowrap"><span data-sort-value="6996650000000000000♠"></span>6.50<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr> <tr> <td>20 </td> <td>1116.65 </td> <td>2.382 </td> <td><span class="nowrap"><span data-sort-value="6995192000000000000♠"></span>1.92<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−5</sup></span> </td> <td>0.249 </td> <td><span class="nowrap"><span data-sort-value="6992939000000000000♠"></span>9.39<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−8</sup></span> </td> <td>204 </td> <td><span class="nowrap"><span data-sort-value="6996650000000000000♠"></span>6.50<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr> <tr> <td>40 </td> <td>1101.43 </td> <td>2.474 </td> <td><span class="nowrap"><span data-sort-value="6994869000000000000♠"></span>8.69<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−6</sup></span> </td> <td>0.256 </td> <td><span class="nowrap"><span data-sort-value="6992939000000000000♠"></span>9.39<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−8</sup></span> </td> <td>93 </td> <td><span class="nowrap"><span data-sort-value="6996650000000000000♠"></span>6.50<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr> <tr> <td>60 </td> <td>1087.66 </td> <td>2.562 </td> <td><span class="nowrap"><span data-sort-value="6994474999999999999♠"></span>4.75<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−6</sup></span> </td> <td>0.26 </td> <td><span class="nowrap"><span data-sort-value="6992932000000000000♠"></span>9.32<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−8</sup></span> </td> <td>51 </td> <td><span class="nowrap"><span data-sort-value="6996650000000000000♠"></span>6.50<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr> <tr> <td>80 </td> <td>1077.56 </td> <td>2.65 </td> <td><span class="nowrap"><span data-sort-value="6994298000000000000♠"></span>2.98<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−6</sup></span> </td> <td>0.261 </td> <td><span class="nowrap"><span data-sort-value="6992921000000000000♠"></span>9.21<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−8</sup></span> </td> <td>32.4 </td> <td><span class="nowrap"><span data-sort-value="6996650000000000000♠"></span>6.50<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr> <tr> <td>100 </td> <td>1058.5 </td> <td>2.742 </td> <td><span class="nowrap"><span data-sort-value="6994202999999999999♠"></span>2.03<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−6</sup></span> </td> <td>0.263 </td> <td><span class="nowrap"><span data-sort-value="6992908000000000000♠"></span>9.08<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−8</sup></span> </td> <td>22.4 </td> <td><span class="nowrap"><span data-sort-value="6996650000000000000♠"></span>6.50<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Anti-freeze">Anti-freeze</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=7" title="Edit section: Anti-freeze"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pure ethylene glycol freezes at about −12 °C (10.4 °F) but, when mixed with water, the mixture freezes at a lower temperature. For example, a mixture of 60% ethylene glycol and 40% water freezes at −45 °C (−49 °F).<sup id="cite_ref-Ullmanns_23-0" class="reference"><a href="#cite_note-Ullmanns-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">Diethylene glycol</a> behaves similarly. The freezing point depression of some mixtures can be explained as a <a href="/wiki/Colligative_property" class="mw-redirect" title="Colligative property">colligative property</a> of solutions but, in highly concentrated mixtures such as the example, deviations from ideal solution behavior are expected due to the influence of <a href="/wiki/Intermolecular_forces" class="mw-redirect" title="Intermolecular forces">intermolecular forces</a>. It's important to note that though pure and distilled water will have a greater specific heat capacity than any mixture of antifreeze and water, commercial antifreezes also typically contain an anti-corrosive additive to prevent pure water from corroding coolant passages in the engine block, cylinder head(s), water pump and radiator. </p><p>There is a difference in the mixing ratio, depending on whether it is ethylene glycol or propylene glycol. For ethylene glycol, the mixing ratios are typically 30/70 and 35/65, whereas the propylene glycol mixing ratios are typically 35/65 and 40/60. It is important that the mixture be frost-proof at the lowest operating temperature.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Because of the depressed freezing temperatures, ethylene glycol is used as a <a href="/wiki/De-icing" class="mw-redirect" title="De-icing">de-icing</a> fluid for <a href="/wiki/Windshield" title="Windshield">windshields</a> and aircraft, as an <a href="/wiki/Antifreeze_(coolant)" class="mw-redirect" title="Antifreeze (coolant)">antifreeze</a> in automobile engines, and as a component of <a href="/wiki/Cryopreservation#Vitrification" title="Cryopreservation">vitrification</a> (anticrystallization) mixtures for low-temperature preservation of biological tissues and organs. </p><p>The use of ethylene glycol not only depresses the freezing point of aqueous mixtures, but also elevates their boiling point. This results in the operating temperature range for heat-transfer fluids being broadened on both ends of the temperature scale. The increase in boiling temperature is due to pure ethylene glycol having a much higher boiling point and lower <a href="/wiki/Vapor_pressure" title="Vapor pressure">vapor pressure</a> than pure water. </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_polymers">Precursor to polymers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=8" title="Edit section: Precursor to polymers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:PET.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/PET.svg/170px-PET.svg.png" decoding="async" width="170" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/PET.svg/255px-PET.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/PET.svg/340px-PET.svg.png 2x" data-file-width="238" data-file-height="133" /></a><figcaption>Ethylene glycol is one precursor to <a href="/wiki/Polyethyleneterephthalate" class="mw-redirect" title="Polyethyleneterephthalate">polyethyleneterephthalate</a>, which is produced on the multimillion ton scale annually.</figcaption></figure> <p>In the <a href="/wiki/Plastics_industry" title="Plastics industry">plastic industry</a>, ethylene glycol is an important precursor to <a href="/wiki/Polyester" title="Polyester">polyester</a> fibers and <a href="/wiki/Resin" title="Resin">resins</a>. <a href="/wiki/Polyethylene_terephthalate" title="Polyethylene terephthalate">Polyethylene terephthalate</a>, used to make <a href="/wiki/Plastic_bottle" title="Plastic bottle">plastic bottles</a> for <a href="/wiki/Soft_drink" title="Soft drink">soft drinks</a>, is prepared from ethylene glycol. </p> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=9" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Dehydrating_agent">Dehydrating agent</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=10" title="Edit section: Dehydrating agent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethylene glycol is used in the natural gas industry to remove water vapor from natural gas before further processing, in much the same manner as <a href="/wiki/Triethylene_glycol" title="Triethylene glycol">triethylene glycol</a> (TEG). </p> <div class="mw-heading mw-heading4"><h4 id="Hydrate_inhibition">Hydrate inhibition</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=11" title="Edit section: Hydrate inhibition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of its high boiling point and affinity for water, ethylene glycol is a useful <a href="/wiki/Desiccant" title="Desiccant">desiccant</a>. Ethylene glycol is widely used to inhibit the formation of <a href="/wiki/Methane_clathrate" title="Methane clathrate">natural gas clathrates</a> (hydrates) in long multiphase pipelines that convey natural gas from remote gas fields to a gas processing facility. Ethylene glycol can be recovered from the natural gas and reused as an inhibitor after purification treatment that removes water and inorganic salts. </p><p>Natural gas is dehydrated by ethylene glycol. In this application, ethylene glycol flows down from the top of a tower and meets a rising mixture of water vapor and <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> gases. Dry gas exits from the top of the tower. The glycol and water are separated, and the glycol recycled. Instead of removing water, ethylene glycol can also be used to depress the temperature at which <a href="/wiki/Hydrate" title="Hydrate">hydrates</a> are formed. The purity of glycol used for hydrate suppression (monoethylene glycol) is typically around 80%, whereas the purity of glycol used for dehydration (triethylene glycol) is typically 95 to more than 99%. Moreover, the injection rate for hydrate suppression is much lower than the circulation rate in a <a href="/wiki/Glycol_dehydration" title="Glycol dehydration">glycol dehydration</a> tower. </p> <div class="mw-heading mw-heading4"><h4 id="Precursor_to_other_chemicals">Precursor to other chemicals</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=12" title="Edit section: Precursor to other chemicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Minor uses of ethylene glycol include the manufacture of capacitors, as a chemical intermediate in the manufacture of <a href="/wiki/1,4-Dioxane" title="1,4-Dioxane">1,4-dioxane</a>, as an additive to prevent <a href="/wiki/Corrosion" title="Corrosion">corrosion</a> in liquid cooling systems for <a href="/wiki/Personal_computer" title="Personal computer">personal computers</a>, and inside the lens devices of cathode-ray tube type of rear projection televisions. Ethylene glycol is also used in the manufacture of some <a href="/wiki/Vaccine" title="Vaccine">vaccines</a>, but it is not itself present in these injections. It is used as a minor (1–2%) ingredient in <a href="/wiki/Shoe_polish" title="Shoe polish">shoe polish</a> and also in some inks and dyes. Ethylene glycol has seen some use as a rot and fungal treatment for wood, both as a preventative and a treatment after the fact. It has been used in a few cases to treat partially rotted wooden objects to be displayed in museums. It is one of only a few treatments that are successful in dealing with rot in wooden boats, and is relatively cheap. Ethylene glycol may also be one of the minor ingredients in screen cleaning solutions, along with the main ingredient <a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">isopropyl alcohol</a>. Ethylene glycol is commonly used as a <a href="/wiki/Preservative" title="Preservative">preservative</a> for biological specimens, especially in secondary schools during <a href="/wiki/Dissection" title="Dissection">dissection</a> as a safer alternative to <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a>. It is also used as part of the water-based hydraulic fluid used to control subsea oil and gas production equipment. </p> <div class="mw-heading mw-heading3"><h3 id="Organic_building_block">Organic building block</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=13" title="Edit section: Organic building block"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although dwarfed by its use as a precursor to <a href="/wiki/Polyester" title="Polyester">polyesters</a>, ethylene glycol is useful in more specialized areas of organic chemistry. </p><p>It serves as a <a href="/wiki/Protecting_group" title="Protecting group">protecting group</a> in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> for manipulation of ketones and aldehydes.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-greene_26-0" class="reference"><a href="#cite_note-greene-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> In one example, <a href="/wiki/Isophorone" title="Isophorone">isophorone</a> was protected using ethylene glycol:<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethylene_glycol_protecting_group.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/Ethylene_glycol_protecting_group.png/450px-Ethylene_glycol_protecting_group.png" decoding="async" width="450" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/Ethylene_glycol_protecting_group.png/675px-Ethylene_glycol_protecting_group.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/52/Ethylene_glycol_protecting_group.png/900px-Ethylene_glycol_protecting_group.png 2x" data-file-width="1978" data-file-height="362" /></a><figcaption></figcaption></figure> <p>The glycol-derived <a href="/w/index.php?title=Dioxalane&action=edit&redlink=1" class="new" title="Dioxalane (page does not exist)">dioxalane</a> of <a href="/wiki/Ethyl_acetoacetate" title="Ethyl acetoacetate">ethyl acetoacetate</a> is a commercial fragrance <a href="/wiki/Fructone" title="Fructone">fructone</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Miscellaneous_chemical_reactions">Miscellaneous chemical reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=14" title="Edit section: Miscellaneous chemical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Silicon dioxide dissolves slowly in hot ethylene glycol in the presence of <a href="/wiki/Alkali_metal" title="Alkali metal">alkali metal</a> base to produce silicates.<sup id="cite_ref-Laine_29-0" class="reference"><a href="#cite_note-Laine-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=15" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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/Ethylene_glycol_poisoning" title="Ethylene glycol poisoning">Ethylene glycol poisoning</a></div> <p>Ethylene glycol has relatively high mammalian toxicity when ingested, roughly on par with <a href="/wiki/Methanol" title="Methanol">methanol</a>, with an oral <a href="/wiki/Lowest_published_lethal_dose" class="mw-redirect" title="Lowest published lethal dose">LD<sub>Lo</sub></a> = 786 mg/kg for humans.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> The major danger is due to its sweet <a href="/wiki/Taste" title="Taste">taste</a>, which can attract children and animals. Upon ingestion, ethylene glycol is oxidized to <a href="/wiki/Glycolic_acid" title="Glycolic acid">glycolic acid</a>, which is, in turn, oxidized to <a href="/wiki/Oxalic_acid" title="Oxalic acid">oxalic acid</a>, which is <a href="/wiki/Toxicity" title="Toxicity">toxic</a>. It and its toxic byproducts first affect the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>, then the heart, and finally the kidneys. Ingestion of sufficient amounts is fatal if untreated.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Several deaths are recorded annually in the U.S. alone.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>Antifreeze products for automotive use containing <a href="/wiki/Propylene_glycol" title="Propylene glycol">propylene glycol</a> in place of ethylene glycol are available. They are generally considered safer to use, as propylene glycol is not as palatable<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup> and is converted in the body to <a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a>, a normal product of metabolism and exercise.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>Australia, the UK, and seventeen US states (as of 2012) require the addition of a bitter flavoring (<a href="/wiki/Denatonium" title="Denatonium">denatonium benzoate</a>) to antifreeze. In December 2012, US antifreeze manufacturers agreed voluntarily to add a bitter flavoring to all antifreeze that is sold in the consumer market of the US.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>In 2022, several hundred children died of acute <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a> in <a href="/wiki/Indonesia" title="Indonesia">Indonesia</a> and <a href="/wiki/The_Gambia" title="The Gambia">The Gambia</a> because the <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> syrup made by <a href="/wiki/New_Delhi" title="New Delhi">New Delhi</a>-based Maiden Pharmaceuticals contained ethylene glycol and <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a>, ingredients that have been linked to child deaths from <a href="/wiki/Acute_kidney_injury" title="Acute kidney injury">acute kidney injury</a> in The Gambia.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> In December 2022, <a href="/wiki/Uzbekistan" title="Uzbekistan">Uzbekistan</a>'s health ministry has said children died as a result of ethylene glycol in <a href="/wiki/Toxic_cough_syrup" title="Toxic cough syrup">cough syrup</a> made by <a href="/w/index.php?title=Marion_Biotech&action=edit&redlink=1" class="new" title="Marion Biotech (page does not exist)">Marion Biotech</a>, which is based at <a href="/wiki/Noida" title="Noida">Noida</a>, near New Delhi.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Environmental_effects">Environmental effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=16" title="Edit section: Environmental effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethylene glycol is a <a href="/wiki/High_production_volume_chemicals" title="High production volume chemicals">high-production-volume chemical</a>. It breaks down in air in about 10 days and in water or soil in a few weeks. It enters the environment through the dispersal of ethylene glycol-containing products, especially at airports, where it is used in <a href="/wiki/De-icing" class="mw-redirect" title="De-icing">de-icing</a> agents for runways and airplanes.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> While prolonged low doses of ethylene glycol show no toxicity, at near lethal doses (≥ 1000 mg/kg per day) ethylene glycol acts as a <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogen</a>. "Based on a rather extensive database, it induces skeletal variations and malformations in rats and mice by all routes of exposure."<sup id="cite_ref-HC_41-0" class="reference"><a href="#cite_note-HC-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=17" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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 .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text">Pure propylene glycol does not taste bitter, and pure propylene glycol is often used as a food additive, for instance in cake icing and shelf-stable whipped cream. Industrial-grade propylene glycol usually has a slightly bitter or acrid taste due to impurities. See the article on <a href="/wiki/Propylene_glycol" title="Propylene glycol">propylene glycol</a> for more information. The relative sweetness of ethylene glycol<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> and propylene glycol<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> is discussed in the Merck Index, and neither compound is described as bitter.</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=18" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30742">"Ethylene glycol (CHEBI:30742)"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ethylene+glycol+%28CHEBI%3A30742%29&rft_id=https%3A%2F%2Fwww.ebi.ac.uk%2Fchebi%2FsearchId.do%3FchebiId%3D30742&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30742">"Ethylene glycol (CHEBI:30742)"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ethylene+glycol+%28CHEBI%3A30742%29&rft_id=https%3A%2F%2Fwww.ebi.ac.uk%2Fchebi%2FsearchId.do%3FchebiId%3D30742&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFInternational_Union_of_Pure_and_Applied_Chemistry2014" class="citation book cs1"><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> (2014). <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013</i>. <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. p. 690. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013&rft.pages=690&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069&rft.isbn=978-0-85404-182-4&rft.au=International+Union+of+Pure+and+Applied+Chemistry&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-PGCH-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-PGCH_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PGCH_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PGCH_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PGCH_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-PGCH_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-PGCH_4-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0272.html">"#0272"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230272&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0272.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-chemsrc-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-chemsrc_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.chemsrc.com/en/cas/107-21-1_329621.html">"Ethylene glycol"</a>. <i>www.chemsrc.com</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.chemsrc.com&rft.atitle=Ethylene+glycol&rft_id=https%3A%2F%2Fwww.chemsrc.com%2Fen%2Fcas%2F107-21-1_329621.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElert" class="citation web cs1">Elert, Glenn. <a rel="nofollow" class="external text" href="http://physics.info/viscosity/">"Viscosity"</a>. <i>The Physics Hypertextbook</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2007-10-02</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+Physics+Hypertextbook&rft.atitle=Viscosity&rft.aulast=Elert&rft.aufirst=Glenn&rft_id=http%3A%2F%2Fphysics.info%2Fviscosity%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><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/Map%3A_Organic_Chemistry_(Wade)/03%3A_Functional_Groups_and_Nomenclature/3.08%3A_3.8_Alcohols_-__Classification_and_Nomenclature">"3.8: 3.8 Alcohols - Classification and Nomenclature"</a>. <i>Chemistry LibreTexts</i>. 2018-10-13<span class="reference-accessdate">. Retrieved <span class="nowrap">2022-04-21</span></span>.</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=3.8%3A+3.8+Alcohols+-+Classification+and+Nomenclature&rft.date=2018-10-13&rft_id=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FMap%253A_Organic_Chemistry_%28Wade%29%2F03%253A_Functional_Groups_and_Nomenclature%2F3.08%253A_3.8_Alcohols_-__Classification_and_Nomenclature&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJ._M._HollisF._J._LovasP._R._JewellL._H._Coudert2002" class="citation journal cs1">J. M. Hollis; F. J. Lovas; P. R. Jewell; L. H. Coudert (2002-05-20). "Interstellar Antifreeze: Ethylene Glycol". <i>The Astrophysical Journal</i>. <b>571</b> (1): L59–L62. <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/2002ApJ...571L..59H">2002ApJ...571L..59H</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F341148">10.1086/341148</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:56198291">56198291</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Astrophysical+Journal&rft.atitle=Interstellar+Antifreeze%3A+Ethylene+Glycol&rft.volume=571&rft.issue=1&rft.pages=L59-L62&rft.date=2002-05-20&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A56198291%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1086%2F341148&rft_id=info%3Abibcode%2F2002ApJ...571L..59H&rft.au=J.+M.+Hollis&rft.au=F.+J.+Lovas&rft.au=P.+R.+Jewell&rft.au=L.+H.+Coudert&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-YueZhaoMa2012-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-YueZhaoMa2012_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYueZhaoMaGong2012" class="citation journal cs1">Yue, Hairong; Zhao, Yujun; Ma, Xinbin; Gong, Jinlong (2012). "Ethylene glycol: properties, synthesis, and applications". <i>Chemical Society Reviews</i>. <b>41</b> (11): 4218. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fc2cs15359a">10.1039/c2cs15359a</a>. <a href="/wiki/EISSN_(identifier)" class="mw-redirect" title="EISSN (identifier)">eISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1460-4744">1460-4744</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/0306-0012">0306-0012</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/22488259">22488259</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Society+Reviews&rft.atitle=Ethylene+glycol%3A+properties%2C+synthesis%2C+and+applications&rft.volume=41&rft.issue=11&rft.pages=4218&rft.date=2012&rft_id=info%3Apmid%2F22488259&rft.issn=0306-0012&rft.eissn=1460-4744&rft_id=info%3Adoi%2F10.1039%2Fc2cs15359a&rft.aulast=Yue&rft.aufirst=Hairong&rft.au=Zhao%2C+Yujun&rft.au=Ma%2C+Xinbin&rft.au=Gong%2C+Jinlong&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text">Scott D. Barnicki, "Synthetic Organic Chemicals", in Handbook of Industrial Chemistry and Biotechnology edited by James A. Kent, New York : Springer, 2012. 12th ed. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4614-4259-2" title="Special:BookSources/978-1-4614-4259-2">978-1-4614-4259-2</a>.</span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><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/20110714135349/http://www.chemsystems.com/reports/search/docs/prospectus/stmc10_coal_meg.pdf">"Coal to MEG, Changing the Rules of the Game"</a> <span class="cs1-format">(PDF)</span>. <i>Nexant/Chemsystems</i>. Archived from <a rel="nofollow" class="external text" href="http://www.chemsystems.com/reports/search/docs/prospectus/stmc10_coal_meg.pdf">the original</a> <span class="cs1-format">(PDF)</span> on July 14, 2011<span class="reference-accessdate">. Retrieved <span class="nowrap">2016-08-08</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Nexant%2FChemsystems&rft.atitle=Coal+to+MEG%2C+Changing+the+Rules+of+the+Game&rft_id=http%3A%2F%2Fwww.chemsystems.com%2Freports%2Fsearch%2Fdocs%2Fprospectus%2Fstmc10_coal_meg.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span> (PDF; 5,4 MB), 2011 Prospectus.</span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation patent" id="CITEREFS._Tahara_et_al."><a rel="nofollow" class="external text" href="https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=EP046">983 EP 046 983</a>, S. Tahara et al., "Process for continuously preparing ethylene glycol",  assigned to Ube Industries</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.number=046 983&rft.cc=EP&rft.title=Process+for+continuously+preparing+ethylene+glycol&rft.inventor=S.+Tahara+et+al.&rft.assignee=Ube+Industries&rft.appldate=1982-03-10"><span style="display: none;"> </span></span> and H. T. Teunissen and C. J. Elsevier, <i>Ruthenium catalyzed hydrogenation of dimethyl oxalate to ethylene glycol</i>, J. Chem. Soc., Chem. Commun., 1997, 667–668), <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FA700862G">10.1039/A700862G</a>.</span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text">S. Zhang et al., <i>Highly-Dispersed Copper-Based Catalysts from Cu–Zn–Al Layered Double Hydroxide Precursor for Gas-Phase Hydrogenation of Dimethyl Oxalate to Ethylene Glycol</i>, Catalysis Letters, Sept. 2012, <b>142</b> (9), 1121–1127, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs10562-012-0871-8">10.1007/s10562-012-0871-8</a>.</span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClay_Boswell2012" class="citation web cs1">Clay Boswell (30 Jan 2012). <a rel="nofollow" class="external text" href="http://www.icis.com/resources/news/2012/01/30/9527520/china-s-coal-based-chemicals-are-a-trade-off/">"China's coal-based chemicals are a trade-off"</a>. <i>Independent Commodity Intelligence Services</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Independent+Commodity+Intelligence+Services&rft.atitle=China%27s+coal-based+chemicals+are+a+trade-off&rft.date=2012-01-30&rft.au=Clay+Boswell&rft_id=http%3A%2F%2Fwww.icis.com%2Fresources%2Fnews%2F2012%2F01%2F30%2F9527520%2Fchina-s-coal-based-chemicals-are-a-trade-off%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGräbner2014" class="citation book cs1">Gräbner, Martin (2014-11-24). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=EPCeBgAAQBAJ&q=meg+china+synthesis+gas&pg=PA15"><i>Industrial Coal Gasification Technologies Covering Baseline and High-Ash Coal</i></a>. John Wiley & Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527336906" title="Special:BookSources/9783527336906"><bdi>9783527336906</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Industrial+Coal+Gasification+Technologies+Covering+Baseline+and+High-Ash+Coal&rft.pub=John+Wiley+%26+Sons&rft.date=2014-11-24&rft.isbn=9783527336906&rft.aulast=Gr%C3%A4bner&rft.aufirst=Martin&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DEPCeBgAAQBAJ%26q%3Dmeg%2Bchina%2Bsynthesis%2Bgas%26pg%3DPA15&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTournierDuquesneGuillamotCramail2023" class="citation journal cs1">Tournier, Vincent; Duquesne, Sophie; Guillamot, Frédérique; Cramail, Henri; Taton, Daniel; Marty, Alain; André, Isabelle (2023). <a rel="nofollow" class="external text" href="https://hal.science/hal-04150645/file/Andre_Chemical_Reviews_HAL.pdf">"Enzymes' Power for Plastics Degradation"</a> <span class="cs1-format">(PDF)</span>. <i>Chemical Reviews</i>. <b>123</b> (9): 5612–5701. <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%2Facs.chemrev.2c00644">10.1021/acs.chemrev.2c00644</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/36916764">36916764</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Enzymes%27+Power+for+Plastics+Degradation&rft.volume=123&rft.issue=9&rft.pages=5612-5701&rft.date=2023&rft_id=info%3Adoi%2F10.1021%2Facs.chemrev.2c00644&rft_id=info%3Apmid%2F36916764&rft.aulast=Tournier&rft.aufirst=Vincent&rft.au=Duquesne%2C+Sophie&rft.au=Guillamot%2C+Fr%C3%A9d%C3%A9rique&rft.au=Cramail%2C+Henri&rft.au=Taton%2C+Daniel&rft.au=Marty%2C+Alain&rft.au=Andr%C3%A9%2C+Isabelle&rft_id=https%3A%2F%2Fhal.science%2Fhal-04150645%2Ffile%2FAndre_Chemical_Reviews_HAL.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAdolphe_Wurtz1856" class="citation journal cs1"><a href="/wiki/Charles-Adolphe_Wurtz" class="mw-redirect" title="Charles-Adolphe Wurtz">Adolphe Wurtz</a> (1856). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k3000k/f203.image">"Sur le glycol ou alcool diatomique"</a> [On glycol or dibasic alcohol]. <i>Comptes Rendus</i>. <b>43</b>: 199–204.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comptes+Rendus&rft.atitle=Sur+le+glycol+ou+alcool+diatomique&rft.volume=43&rft.pages=199-204&rft.date=1856&rft.au=Adolphe+Wurtz&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k3000k%2Ff203.image&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text">Wurtz (1856), page 200: <i>"… je propose de le nommer </i>glycol<i>, parce qu'il se rapproche à la fois, par ses propriétés, de l'alcool proprement dit et de la glycérin, entre lesquels il se trouve placé."</i> ( … I propose to call it <i>glycol</i> because, by its properties, it is simultaneously close to [ethyl] alcohol properly called and glycerin, between which it is placed.)</span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text">Ad. Wurtz (1859) <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k3006f/f815.item.r=.zoom">"Synthèse du glycol avec l'oxyde d'éthylène et l'eau"</a> (Synthesis of glycol from ethylene oxide and water), <i>Comptes rendus</i>, <b>49</b> : 813–815.</span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><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/20210514041855/http://www.hydratechglobal.net/technical/Ethylene+Glycol/58/en">"Hydratech - Specialist Fluid Solutions"</a>. <i>www.hydratechglobal.net</i>. Archived from <a rel="nofollow" class="external text" href="http://www.hydratechglobal.net/technical/Ethylene+Glycol/58/en">the original</a> on 2021-05-14<span class="reference-accessdate">. Retrieved <span class="nowrap">2020-02-24</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.hydratechglobal.net&rft.atitle=Hydratech+-+Specialist+Fluid+Solutions&rft_id=http%3A%2F%2Fwww.hydratechglobal.net%2Ftechnical%2FEthylene%2BGlycol%2F58%2Fen&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHolman2002" class="citation book cs1">Holman, Jack P. (2002). <i>Heat Transfer</i> (9th ed.). New York, NY: McGraw-Hill Companies, Inc. pp. 600–606. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780072406559" title="Special:BookSources/9780072406559"><bdi>9780072406559</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Heat+Transfer&rft.place=New+York%2C+NY&rft.pages=600-606&rft.edition=9th&rft.pub=McGraw-Hill+Companies%2C+Inc&rft.date=2002&rft.isbn=9780072406559&rft.aulast=Holman&rft.aufirst=Jack+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFrank_P._Incropera,_David_P._Dewitt,_heodore_L._Bergman,_Adrienne_S._Lavigne2007" class="citation book cs1">Frank P. Incropera, David P. Dewitt, heodore L. Bergman, Adrienne S. Lavigne (2007). <i>Fundamentals of Heat and Mass Transfer</i> (6th ed.). Hoboken, NJ: John Wiley and Sons, Inc. pp. 941–950. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471457282" title="Special:BookSources/9780471457282"><bdi>9780471457282</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Fundamentals+of+Heat+and+Mass+Transfer&rft.place=Hoboken%2C+NJ&rft.pages=941-950&rft.edition=6th&rft.pub=John+Wiley+and+Sons%2C+Inc.&rft.date=2007&rft.isbn=9780471457282&rft.au=Frank+P.+Incropera%2C+David+P.+Dewitt%2C+heodore+L.+Bergman%2C+Adrienne+S.+Lavigne&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-Ullmanns-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmanns_23-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSiegfried_RebsdatDieter_Mayer" class="citation encyclopaedia cs1">Siegfried Rebsdat; Dieter Mayer. "Ethylene Glycol". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. 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.a10_101">10.1002/14356007.a10_101</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ethylene+Glycol&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a10_101&rft.isbn=978-3527306732&rft.au=Siegfried+Rebsdat&rft.au=Dieter+Mayer&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1 cs1-prop-foreign-lang-source"><a rel="nofollow" class="external text" href="https://lcglad.dk/glycol/">"Glycol til industri og erhverv"</a> [Glycol for industry and business]. <i>LC Glad</i> (in Danish) – via lcglad.dk.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=LC+Glad&rft.atitle=Glycol+til+industri+og+erhverv&rft_id=https%3A%2F%2Flcglad.dk%2Fglycol%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.synarchive.com/protecting-group/Aldehyde_Ketone_Ethylene_glycol_acetal">"Ethylene glycol acetal"</a>. <i>The Organic Synthesis Archive</i>. synarchive.com.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+Organic+Synthesis+Archive&rft.atitle=Ethylene+glycol+acetal&rft_id=http%3A%2F%2Fwww.synarchive.com%2Fprotecting-group%2FAldehyde_Ketone_Ethylene_glycol_acetal&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-greene-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-greene_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTheodora_W._GreenePeter_G._M._Wuts1999" class="citation book cs1">Theodora W. Greene; Peter G. M. Wuts (1999). <i>Protective Groups in Organic Synthesis</i> (Third ed.). John Wiley & Sons. pp. 312–322. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-16019-9" title="Special:BookSources/978-0-471-16019-9"><bdi>978-0-471-16019-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Protective+Groups+in+Organic+Synthesis&rft.pages=312-322&rft.edition=Third&rft.pub=John+Wiley+%26+Sons&rft.date=1999&rft.isbn=978-0-471-16019-9&rft.au=Theodora+W.+Greene&rft.au=Peter+G.+M.+Wuts&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJ._H._BablerN._C._MalekM._J._Coghlan1978" class="citation journal cs1">J. H. Babler; N. C. Malek; M. J. Coghlan (1978). "Selective hydrolysis of α,β- and β,γ-unsaturated ketals: method for deconjugation of β,β-disubstituted α,β-unsaturated ketones". <i><a href="/wiki/J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a></i> <b>43</b> (9): 1821–1823. <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%2Fjo00403a047">10.1021/jo00403a047</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=Selective+hydrolysis+of+%CE%B1%2C%CE%B2-+and+%CE%B2%2C%CE%B3-unsaturated+ketals%3A+method+for+deconjugation+of+%CE%B2%2C%CE%B2-disubstituted+%CE%B1%2C%CE%B2-unsaturated+ketones&rft.volume=43&rft.issue=9&rft.pages=1821-1823&rft.date=1978&rft_id=info%3Adoi%2F10.1021%2Fjo00403a047&rft.au=J.+H.+Babler&rft.au=N.+C.+Malek&rft.au=M.+J.+Coghlan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPantenSurburg2016" class="citation book cs1">Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. pp. 1–45. <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.t11_t02">10.1002/14356007.t11_t02</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=Flavors+and+Fragrances%2C+3.+Aromatic+and+Heterocyclic+Compounds&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pages=1-45&rft.date=2016&rft_id=info%3Adoi%2F10.1002%2F14356007.t11_t02&rft.isbn=978-3-527-30673-2&rft.aulast=Panten&rft.aufirst=Johannes&rft.au=Surburg%2C+Horst&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-Laine-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-Laine_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLaineBlohowiakRobinsonHoppe1991" class="citation journal cs1">Laine, Richard M.; Blohowiak, Kay Youngdahl; Robinson, Timothy R.; Hoppe, Martin L.; Nardi, Paola; Kampf, Jeffrey; Uhm, Jackie (17 October 1991). <a rel="nofollow" class="external text" href="https://deepblue.lib.umich.edu/bitstream/2027.42/62810/1/353642a0.pdf">"Synthesis of pentacoordinate silicon complexes from SiO<sub>2</sub>"</a> <span class="cs1-format">(PDF)</span>. <i>Nature</i>. <b>353</b> (6345): 642–644. <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/1991Natur.353..642L">1991Natur.353..642L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F353642a0">10.1038/353642a0</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/2027.42%2F62810">2027.42/62810</a></span>. <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:4310228">4310228</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Synthesis+of+pentacoordinate+silicon+complexes+from+SiO%3Csub%3E2%3C%2Fsub%3E&rft.volume=353&rft.issue=6345&rft.pages=642-644&rft.date=1991-10-17&rft_id=info%3Ahdl%2F2027.42%2F62810&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4310228%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1038%2F353642a0&rft_id=info%3Abibcode%2F1991Natur.353..642L&rft.aulast=Laine&rft.aufirst=Richard+M.&rft.au=Blohowiak%2C+Kay+Youngdahl&rft.au=Robinson%2C+Timothy+R.&rft.au=Hoppe%2C+Martin+L.&rft.au=Nardi%2C+Paola&rft.au=Kampf%2C+Jeffrey&rft.au=Uhm%2C+Jackie&rft_id=https%3A%2F%2Fdeepblue.lib.umich.edu%2Fbitstream%2F2027.42%2F62810%2F1%2F353642a0.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSafety_Officer_in_Physical_Chemistry2009" class="citation web cs1">Safety Officer in Physical Chemistry (November 23, 2009). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20111214093006/http://msds.chem.ox.ac.uk/ET/ethylene_glycol.html">"Safety (MSDS) data for ethylene glycol"</a>. Oxford University. Archived from <a rel="nofollow" class="external text" href="http://msds.chem.ox.ac.uk/ET/ethylene_glycol.html">the original</a> on December 14, 2011<span class="reference-accessdate">. Retrieved <span class="nowrap">December 30,</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Safety+%28MSDS%29+data+for+ethylene+glycol&rft.pub=Oxford+University&rft.date=2009-11-23&rft.au=Safety+Officer+in+Physical+Chemistry&rft_id=http%3A%2F%2Fmsds.chem.ox.ac.uk%2FET%2Fethylene_glycol.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750031.html">Ethylene glycol</a>. National Institute for Occupational Safety and Health. Emergency Response Database. August 22, 2008. Retrieved December 31, 2008.</span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><i><a rel="nofollow" class="external text" href="https://emedicine.medscape.com/article/814701-overview">Ethylene Glycol Toxicity</a></i> at <a href="/wiki/EMedicine" title="EMedicine">eMedicine</a></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><i>The Merck Index</i> (15th ed.). Royal Society of Chemistry. 2013. pp. M5122.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Merck+Index&rft.pages=M5122&rft.edition=15th&rft.pub=Royal+Society+of+Chemistry&rft.date=2013&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><i>The Merck Index</i> (15th ed.). Royal Society of Chemistry. 2013. pp. M9238.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Merck+Index&rft.pages=M9238&rft.edition=15th&rft.pub=Royal+Society+of+Chemistry&rft.date=2013&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-36">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPieter_Klapwijk2010" class="citation web cs1">Pieter Klapwijk (January 27, 2010). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130126003300/http://www.resteddoginn.ca/antifreeze.php">"Ethylene Glycol Poisoning"</a>. The Rested Dog Inn. Archived from <a rel="nofollow" class="external text" href="http://www.resteddoginn.ca/antifreeze.php">the original</a> on January 26, 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">October 11,</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ethylene+Glycol+Poisoning&rft.pub=The+Rested+Dog+Inn&rft.date=2010-01-27&rft.au=Pieter+Klapwijk&rft_id=http%3A%2F%2Fwww.resteddoginn.ca%2Fantifreeze.php&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><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/20121228225407/http://www.cspa.org/news-media-center/news-releases/2012/12/antifreeze-and-engine-coolant-being-bittered-nationwide">"Antifreeze and Engine Coolant Being Bittered Nationwide"</a>. Consumer Specialty Products Association. 13 December 2012. Archived from <a rel="nofollow" class="external text" href="http://www.cspa.org/category/news-releases/2012/12/antifreeze-and-engine-coolant-being-bittered-nationwide/">the original</a> on 28 December 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">30 June</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Antifreeze+and+Engine+Coolant+Being+Bittered+Nationwide&rft.pub=Consumer+Specialty+Products+Association&rft.date=2012-12-13&rft_id=http%3A%2F%2Fwww.cspa.org%2Fcategory%2Fnews-releases%2F2012%2F12%2Fantifreeze-and-engine-coolant-being-bittered-nationwide%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.aljazeera.com/news/2022/10/22/indonesia-says-child-deaths-from-acute-kidney-injury-rise-to-133">"Indonesia says child deaths from acute kidney injury rise to 133"</a>. <i><a href="/wiki/Al_Jazeera_Arabic" title="Al Jazeera Arabic">Al Jazeera</a></i>. 22 October 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Al+Jazeera&rft.atitle=Indonesia+says+child+deaths+from+acute+kidney+injury+rise+to+133&rft.date=2022-10-22&rft_id=https%3A%2F%2Fwww.aljazeera.com%2Fnews%2F2022%2F10%2F22%2Findonesia-says-child-deaths-from-acute-kidney-injury-rise-to-133&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-39">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.bbc.co.uk/news/world-asia-india-64114240">"Marion Biotech: Uzbekistan links child deaths to India cough syrup"</a>. <i><a href="/wiki/BBC_News" title="BBC News">BBC News</a></i>. 29 December 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BBC+News&rft.atitle=Marion+Biotech%3A+Uzbekistan+links+child+deaths+to+India+cough+syrup&rft.date=2022-12-29&rft_id=https%3A%2F%2Fwww.bbc.co.uk%2Fnews%2Fworld-asia-india-64114240&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-40">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsDetails.aspx?faqid=85&toxid=21">"Ethylene Glycol"</a>. <i>ToxFAQs</i>. CDC. 12 March 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ToxFAQs&rft.atitle=Ethylene+Glycol&rft.date=2015-03-12&rft_id=https%3A%2F%2Fwwwn.cdc.gov%2FTSP%2FToxFAQs%2FToxFAQsDetails.aspx%3Ffaqid%3D85%26toxid%3D21&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-HC-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-HC_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.hc-sc.gc.ca/ewh-semt/pubs/contaminants/psl2-lsp2/ethylene_glycol/index-eng.php#a2436">"Statement of the Science Report for Ethylene Glycol"</a>. <i>3.3.2.2 Non-neoplastic effects</i>. Health Canada www.hc-sc.gc.ca. June 24, 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">27 August</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=3.3.2.2+Non-neoplastic+effects&rft.atitle=Statement+of+the+Science+Report+for+Ethylene+Glycol&rft.date=2013-06-24&rft_id=http%3A%2F%2Fwww.hc-sc.gc.ca%2Fewh-semt%2Fpubs%2Fcontaminants%2Fpsl2-lsp2%2Fethylene_glycol%2Findex-eng.php%23a2436&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethylene_glycol&action=edit&section=19" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C107211">WebBook page for C2H6O2</a></li> <li><a rel="nofollow" class="external text" href="https://www.atsdr.cdc.gov/csem/egpg/index.html">ATSDR - Case Studies in Environmental Medicine: Ethylene Glycol and Propylene Glycol Toxicity</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0272.html">CDC - NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="https://lcglad.dk/glycol/">Antifreeze ratio for Ethylene Glycol and Propylene Glycol</a></li> <li><a rel="nofollow" class="external text" href="http://www.emedicine.com/emerg/topic177.htm">Medical information</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHairong_YueYujun_ZhaoXinbin_MaJinlong_Gong2012" class="citation journal cs1">Hairong Yue; Yujun Zhao; Xinbin Ma; Jinlong Gong (2012). "Ethylene glycol: properties, synthesis, and applications". <i>Chemical Society Reviews</i>. <b>41</b> (11): 4218–4244. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC2CS15359A">10.1039/C2CS15359A</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/22488259">22488259</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Society+Reviews&rft.atitle=Ethylene+glycol%3A+properties%2C+synthesis%2C+and+applications&rft.volume=41&rft.issue=11&rft.pages=4218-4244&rft.date=2012&rft_id=info%3Adoi%2F10.1039%2FC2CS15359A&rft_id=info%3Apmid%2F22488259&rft.au=Hairong+Yue&rft.au=Yujun+Zhao&rft.au=Xinbin+Ma&rft.au=Jinlong+Gong&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+glycol" 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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<br />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 href="/wiki/Ethanol" title="Ethanol">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"><i>tert</i>-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-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 href="/wiki/Ethanol" title="Ethanol">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<br />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 href="/wiki/Ethanol" title="Ethanol">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 href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Ethanolamine" title="Ethanolamine">Ethanolamine</a></li> <li><a href="/wiki/N,N-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol"><i>N</i>,<i>N</i>-Diisopropylaminoethanol</a></li> <li><a href="/wiki/N-Methylethanolamine" title="N-Methylethanolamine"><i>N</i>-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"><i>n</i>-Butanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>1</sub> — C<sub>9</sub></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 href="/wiki/Ethanol" title="Ethanol">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<br />saturated<br />C<sub>10</sub> — C<sub>19</sub></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<br />saturated<br />C<sub>20</sub> — C<sub>29</sub></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<br />saturated<br />C<sub>30</sub> — C<sub>39</sub></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<br />saturated<br />C<sub>40</sub> — C<sub>49</sub></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<br /> 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<br /> 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-<i>tert</i>-butyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol"><i>tert</i>-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-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> (C<sub>1</sub>)</li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/1-Butanol" title="1-Butanol">1-Butanol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">1-Pentanol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Cetyl_alcohol" title="Cetyl alcohol">Cetyl alcohol</a> (C<sub>16</sub>)</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 class="mw-selflink selflink">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 class="mw-selflink selflink">Ethylene glycol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a>, <a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a>, <a href="/wiki/Threitol" title="Threitol">Threitol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a>, <a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> (C<sub>7</sub>)</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<br /><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<br />unsaturated<br /><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%">C<sub>1</sub> — C<sub>7</sub></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> (C<sub>1</sub>)</li> <li><a class="mw-selflink selflink">Ethylene glycol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Threitol" title="Threitol">Threitol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Arabitol" title="Arabitol">Arabitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Ribitol" title="Ribitol">Ribitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Galactitol" title="Galactitol">Galactitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Iditol" title="Iditol">Iditol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> (C<sub>7</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Deoxy sugar<br /> 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<br /> 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<br /> 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<br /> 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<br /> 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 class="mw-selflink selflink">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-<i>tert</i>-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><span class="noviewer" typeof="mw:File"><span title="Category"><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" /></span></span> <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="Internal_combustion_engine" 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:Internal_combustion_engine" title="Template:Internal combustion engine"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Internal_combustion_engine" title="Template talk:Internal combustion engine"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Internal_combustion_engine" title="Special:EditPage/Template:Internal combustion engine"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Internal_combustion_engine" style="font-size:114%;margin:0 4em"><a href="/wiki/Internal_combustion_engine" title="Internal combustion engine">Internal combustion engine</a></div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i>Part of the <a href="/wiki/Car" title="Car">Automobile</a> series</i></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Engine_block" title="Engine block">Engine block</a> and<br /> rotating assembly</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/Balance_shaft" title="Balance shaft">Balance shaft</a></li> <li><a href="/wiki/Block_heater" title="Block heater">Block heater</a></li> <li><a href="/wiki/Bore_(engine)" title="Bore (engine)">Bore</a></li> <li><a href="/wiki/Connecting_rod" title="Connecting rod">Connecting rod</a></li> <li><a href="/wiki/Crankcase" title="Crankcase">Crankcase</a></li> <li><a href="/wiki/Crankcase_ventilation_system" title="Crankcase ventilation system">Crankcase ventilation system (PCV valve)</a></li> <li><a href="/wiki/Crankpin" title="Crankpin">Crankpin</a></li> <li><a href="/wiki/Crankshaft" title="Crankshaft">Crankshaft</a></li> <li><a href="/wiki/Core_plug" title="Core plug">Core plug (freeze plug)</a></li> <li><a href="/wiki/Cylinder_(engine)" title="Cylinder (engine)">Cylinder</a> (<a href="/wiki/Cylinder_bank" class="mw-redirect" title="Cylinder bank">bank</a>, <a href="/wiki/Engine_configuration" title="Engine configuration">layout</a>)</li> <li><a href="/wiki/Engine_displacement" title="Engine displacement">Displacement</a></li> <li><a href="/wiki/Flywheel" title="Flywheel">Flywheel</a></li> <li><a href="/wiki/Firing_order" title="Firing order">Firing order</a></li> <li><a href="/wiki/Stroke_(engine)" title="Stroke (engine)">Stroke</a></li> <li><a href="/wiki/Main_bearing" title="Main bearing">Main bearing</a></li> <li><a href="/wiki/Piston" title="Piston">Piston</a></li> <li><a href="/wiki/Piston_ring" title="Piston ring">Piston ring</a></li> <li><a href="/wiki/Starter_ring_gear" title="Starter ring gear">Starter ring gear</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Valvetrain" title="Valvetrain">Valvetrain</a> and<br /> <a href="/wiki/Cylinder_head" title="Cylinder head">Cylinder head</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/Flathead_engine" title="Flathead engine">Flathead layout</a></li> <li><a href="/wiki/Overhead_camshaft_engine" title="Overhead camshaft engine">Overhead camshaft layout</a></li> <li><a href="/wiki/Overhead_valve_engine" title="Overhead valve engine">Overhead valve (pushrod) layout</a></li></ul> <ul><li><a href="/wiki/Tappet" title="Tappet">Tappet / lifter</a></li> <li><a href="/wiki/Camshaft" title="Camshaft">Camshaft</a></li> <li><a href="/wiki/Chest_(mechanical_engineering)" title="Chest (mechanical engineering)">Chest</a></li> <li><a href="/wiki/Combustion_chamber" title="Combustion chamber">Combustion chamber</a></li> <li><a href="/wiki/Compression_ratio" title="Compression ratio">Compression ratio</a></li> <li><a href="/wiki/Head_gasket" title="Head gasket">Head gasket</a></li> <li><a href="/wiki/Rocker_arm" title="Rocker arm">Rocker arm</a></li> <li><a href="/wiki/Timing_belt_(camshaft)" title="Timing belt (camshaft)">Timing belt</a></li> <li><a href="/wiki/Poppet_valve" title="Poppet valve">Valve</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Forced_induction" title="Forced induction">Forced induction</a></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/Blowoff_valve" title="Blowoff valve">Blowoff valve</a></li> <li><a href="/wiki/Boost_controller" title="Boost controller">Boost controller</a></li> <li><a href="/wiki/Intercooler" title="Intercooler">Intercooler</a></li> <li><a href="/wiki/Supercharger" title="Supercharger">Supercharger</a></li> <li><a href="/wiki/Turbocharger" title="Turbocharger">Turbocharger</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fuel system</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/Diesel_engine" title="Diesel engine">Diesel engine</a></li> <li><a href="/wiki/Petrol_engine" title="Petrol engine">Petrol engine</a></li> <li><a href="/wiki/Carburetor" title="Carburetor">Carburetor</a></li> <li><a href="/wiki/Fuel_filter" title="Fuel filter">Fuel filter</a></li> <li><a href="/wiki/Fuel_injection" title="Fuel injection">Fuel injection</a></li> <li><a href="/wiki/Fuel_pump" title="Fuel pump">Fuel pump</a></li> <li><a href="/wiki/Fuel_tank" title="Fuel tank">Fuel tank</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ignition_system" title="Ignition system">Ignition</a></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/Ignition_magneto" title="Ignition magneto">Magneto</a></li> <li><a href="/wiki/Compression_ignition" class="mw-redirect" title="Compression ignition">Compression ignition</a></li> <li><a href="/wiki/Coil-on-plug_ignition" class="mw-redirect" title="Coil-on-plug ignition">Coil-on-plug</a></li> <li><a href="/wiki/Distributor" title="Distributor">Distributor</a></li> <li><a href="/wiki/Glow_plug_(diesel_engine)" class="mw-redirect" title="Glow plug (diesel engine)">Glow plug</a></li> <li><a href="/wiki/Ignition_coil" title="Ignition coil">Ignition coil</a></li> <li><a href="/wiki/Spark_plug" title="Spark plug">Spark plug</a></li> <li><a href="/wiki/Spark_plug_wires" title="Spark plug wires">Spark plug wires</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Engine management</div></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/Engine_control_unit" title="Engine control unit">Engine control unit (ECU)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Electrical system</div></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/Alternator_(automotive)" title="Alternator (automotive)">Alternator</a></li> <li><a href="/wiki/Automotive_battery" title="Automotive battery">Battery</a></li> <li><a href="/wiki/Dynamo" title="Dynamo">Dynamo</a></li> <li><a href="/wiki/Starter_(engine)" title="Starter (engine)">Starter motor</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intake system</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/Airbox" title="Airbox">Airbox</a></li> <li><a href="/wiki/Air_filter#Internal_combustion_engine_air_filters" title="Air filter">Air filter</a></li> <li><a href="/wiki/Idle_air_control_actuator" title="Idle air control actuator">Idle air control actuator</a></li> <li><a href="/wiki/Inlet_manifold" title="Inlet manifold">Inlet manifold</a></li> <li><a href="/wiki/MAP_sensor" title="MAP sensor">MAP sensor</a></li> <li><a href="/wiki/Mass_flow_sensor" title="Mass flow sensor">MAF sensor</a></li> <li><a href="/wiki/Throttle" title="Throttle">Throttle</a></li> <li><a href="/wiki/Throttle_position_sensor" title="Throttle position sensor">Throttle position sensor</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Exhaust_system" title="Exhaust system">Exhaust system</a></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/Catalytic_converter" title="Catalytic converter">Catalytic converter</a></li> <li><a href="/wiki/Diesel_particulate_filter" title="Diesel particulate filter">Diesel particulate filter</a></li> <li><a href="/wiki/Exhaust_gas_temperature_gauge" title="Exhaust gas temperature gauge">EGT sensor</a></li> <li><a href="/wiki/Exhaust_manifold" title="Exhaust manifold">Exhaust manifold</a></li> <li><a href="/wiki/Muffler" title="Muffler">Muffler</a></li> <li><a href="/wiki/Oxygen_sensor#Automotive_applications" title="Oxygen sensor">Oxygen sensor</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Internal_combustion_engine_cooling" title="Internal combustion engine cooling">Cooling system</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/Air_cooling" title="Air cooling">Air cooling</a></li> <li><a href="/wiki/Water_cooling" title="Water cooling">Water cooling</a></li></ul> <ul><li><a href="/wiki/Fan_(machine)" title="Fan (machine)">Electric fan</a></li> <li><a href="/wiki/Radiator_(engine_cooling)" title="Radiator (engine cooling)">Radiator</a></li> <li><a href="/wiki/Thermostat" title="Thermostat">Thermostat</a></li> <li><a href="/wiki/Fan_clutch" title="Fan clutch">Viscous fan (fan clutch)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Lubrication</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">Oil</a></li> <li><a href="/wiki/Oil_filter" title="Oil filter">Oil filter</a></li> <li><a href="/wiki/Oil_pump_(internal_combustion_engine)" title="Oil pump (internal combustion engine)">Oil pump</a></li> <li><a href="/wiki/Sump" title="Sump">Sump</a> (<a href="/wiki/Wet_sump" title="Wet sump">Wet sump</a>, <a href="/wiki/Dry_sump" title="Dry sump">Dry sump</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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/Engine_knocking" title="Engine knocking">Knocking / pinging</a></li> <li><a href="/wiki/Power_band" title="Power band">Power band</a></li> <li><a href="/wiki/Redline" title="Redline">Redline</a></li> <li><a href="/wiki/Stratified_charge_engine" title="Stratified charge engine">Stratified charge</a></li> <li><a href="/wiki/Dead_centre_(engineering)" title="Dead centre (engineering)">Top dead centre</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2" style="font-weight:bold;"><div> <ul><li><a href="/wiki/Portal:Cars" title="Portal:Cars">Portal</a></li> <li><a href="/wiki/Category:Cars" title="Category:Cars">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="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><span typeof="mw:File"><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></span> <br /><br /><br /><br /> <span typeof="mw:File"><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></span> <br /><br /><br /><br /> <span typeof="mw:File"><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></span></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">N<sub>2</sub>H<sup>+</sup></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<br />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<br />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<br />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)">HC<sub>4</sub>N</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<br />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<br />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<br />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 href="/wiki/Ethanol" title="Ethanol">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<br />atoms<br />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> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a class="mw-selflink selflink">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><br />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">N<sub>2</sub>D<sup>+</sup></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> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</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#See_also" title="List of interstellar and circumstellar molecules">Related</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/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a 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 hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><span class="noviewer" typeof="mw:File"><span title="Category"><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" /></span></span> <a 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