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class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Dehydrogenation_of_ethanol"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.2</span> <span>Dehydrogenation of ethanol</span> </div> </a> <ul id="toc-Dehydrogenation_of_ethanol-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydroformylation_of_methanol" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hydroformylation_of_methanol"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.3</span> <span>Hydroformylation of methanol</span> </div> </a> <ul id="toc-Hydroformylation_of_methanol-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-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 Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Tautomerization_to_vinyl_alcohol" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Tautomerization_to_vinyl_alcohol"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Tautomerization to vinyl alcohol</span> </div> </a> <ul id="toc-Tautomerization_to_vinyl_alcohol-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Addition_and_condensation_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Addition_and_condensation_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Addition and condensation reactions</span> </div> </a> <ul id="toc-Addition_and_condensation_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Polymeric_forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymeric_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Polymeric forms</span> </div> </a> <ul id="toc-Polymeric_forms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acetal_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acetal_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Acetal derivatives</span> </div> </a> <ul id="toc-Acetal_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_vinylphosphonic_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_vinylphosphonic_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Precursor to vinylphosphonic acid</span> </div> </a> <ul id="toc-Precursor_to_vinylphosphonic_acid-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Safety</span> </div> </a> <button aria-controls="toc-Safety-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 Safety subsection</span> </button> <ul id="toc-Safety-sublist" class="vector-toc-list"> <li id="toc-Exposure_limits" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Exposure_limits"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Exposure limits</span> </div> </a> <ul id="toc-Exposure_limits-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dangers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dangers"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Dangers</span> </div> </a> <ul id="toc-Dangers-sublist" class="vector-toc-list"> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.1</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Irritation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Irritation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.2</span> <span>Irritation</span> </div> </a> <ul id="toc-Irritation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carcinogenicity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Carcinogenicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.3</span> <span>Carcinogenicity</span> </div> </a> <ul id="toc-Carcinogenicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-DNA_crosslinks" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#DNA_crosslinks"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.4</span> <span>DNA crosslinks</span> </div> </a> <ul id="toc-DNA_crosslinks-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Aggravating_factors" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aggravating_factors"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Aggravating factors</span> </div> </a> <ul id="toc-Aggravating_factors-sublist" class="vector-toc-list"> <li id="toc-Alzheimer's_disease" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Alzheimer's_disease"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3.1</span> <span>Alzheimer's disease</span> </div> </a> <ul id="toc-Alzheimer's_disease-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Genetic_conditions" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Genetic_conditions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3.2</span> <span>Genetic conditions</span> </div> </a> <ul id="toc-Genetic_conditions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Disulfiram" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Disulfiram"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3.3</span> <span>Disulfiram</span> </div> </a> <ul id="toc-Disulfiram-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Sources_of_exposure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sources_of_exposure"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Sources of exposure</span> </div> </a> <ul id="toc-Sources_of_exposure-sublist" class="vector-toc-list"> <li id="toc-Indoor_air" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Indoor_air"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4.1</span> <span>Indoor air</span> </div> </a> <ul id="toc-Indoor_air-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Outdoor_air" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Outdoor_air"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4.2</span> <span>Outdoor air</span> </div> </a> <ul id="toc-Outdoor_air-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tobacco_smoke" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tobacco_smoke"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4.3</span> <span>Tobacco smoke</span> </div> </a> <ul id="toc-Tobacco_smoke-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cannabis_smoke" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cannabis_smoke"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4.4</span> <span>Cannabis smoke</span> </div> </a> <ul id="toc-Cannabis_smoke-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alcohol_consumption" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Alcohol_consumption"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4.5</span> <span>Alcohol consumption</span> </div> </a> <ul id="toc-Alcohol_consumption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plastics" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Plastics"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4.6</span> <span>Plastics</span> </div> </a> <ul id="toc-Plastics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Candida_overgrowth" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Candida_overgrowth"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4.7</span> <span>Candida overgrowth</span> </div> </a> <ul id="toc-Candida_overgrowth-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</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"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</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" title="Table of Contents" > <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">Acetaldehyde</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 58 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-58" 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">58 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%D8%A7%D9%86%D8%A7%D9%84" title="إيثانال – Arabic" lang="ar" hreflang="ar" data-title="إيثانال" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Asetaldehid" title="Asetaldehid – Azerbaijani" lang="az" hreflang="az" data-title="Asetaldehid" 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%B3%D8%AA%D8%A7%D9%84%D8%AF%D9%87%DB%8C%D8%AF" title="استالدهید – South Azerbaijani" lang="azb" hreflang="azb" data-title="استالدهید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%87%E0%A6%A5%E0%A6%BE%E0%A6%A8%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2" title="ইথান্যাল – Bangla" lang="bn" hreflang="bn" data-title="ইথান্যাল" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D1%86%D1%8D%D1%82%D0%B0%D0%BB%D1%8C%D0%B4%D1%8D%D0%B3%D1%96%D0%B4" title="Ацэтальдэгід – Belarusian" lang="be" hreflang="be" data-title="Ацэтальдэгід" 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%90%D1%86%D1%8D%D1%82%D0%B0%D0%BB%D1%8C%D0%B4%D1%8D%D0%B3%D1%96%D0%B4" title="Ацэтальдэгід – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Ацэтальдэгід" 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%90%D1%86%D0%B5%D1%82%D0%B0%D0%BB%D0%B4%D0%B5%D1%85%D0%B8%D0%B4" title="Ацеталдехид – Bulgarian" lang="bg" hreflang="bg" data-title="Ацеталдехид" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Acetaldehid" title="Acetaldehid – Bosnian" lang="bs" hreflang="bs" data-title="Acetaldehid" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Acetaldehid" title="Acetaldehid – Catalan" lang="ca" hreflang="ca" data-title="Acetaldehid" 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/Acetaldehyd" title="Acetaldehyd – Czech" lang="cs" hreflang="cs" data-title="Acetaldehyd" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Ethanal" title="Ethanal – Danish" lang="da" hreflang="da" data-title="Ethanal" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Acetaldehyd" title="Acetaldehyd – German" lang="de" hreflang="de" data-title="Acetaldehyd" 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/Atseetaldeh%C3%BC%C3%BCd" title="Atseetaldehüüd – Estonian" lang="et" hreflang="et" data-title="Atseetaldehüüd" 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/%CE%91%CE%B9%CE%B8%CE%B1%CE%BD%CE%AC%CE%BB%CE%B7" title="Αιθανάλη – Greek" lang="el" hreflang="el" data-title="Αιθανάλη" 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/Acetaldeh%C3%ADdo" title="Acetaldehído – Spanish" lang="es" hreflang="es" data-title="Acetaldehído" 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/Acetaldehido" title="Acetaldehido – Esperanto" lang="eo" hreflang="eo" data-title="Acetaldehido" 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/Azetaldehido" title="Azetaldehido – Basque" lang="eu" hreflang="eu" data-title="Azetaldehido" 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%B3%D8%AA%D8%A7%D9%84%D8%AF%D9%87%DB%8C%D8%AF" title="استالدهید – Persian" lang="fa" hreflang="fa" data-title="استالدهید" 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/Ac%C3%A9tald%C3%A9hyde" title="Acétaldéhyde – French" lang="fr" hreflang="fr" data-title="Acétaldéhyde" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aic%C3%A9ataild%C3%A9ad" title="Aicéataildéad – Irish" lang="ga" hreflang="ga" data-title="Aicéataildéad" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Acetaldehido" title="Acetaldehido – Galician" lang="gl" hreflang="gl" data-title="Acetaldehido" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%84%B8%ED%8A%B8%EC%95%8C%EB%8D%B0%ED%95%98%EC%9D%B4%EB%93%9C" title="아세트알데하이드 – Korean" lang="ko" hreflang="ko" data-title="아세트알데하이드" 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%B1%D6%81%D5%A5%D5%BF%D5%A1%D5%AC%D5%A4%D5%A5%D5%B0%D5%AB%D5%A4" title="Ացետալդեհիդ – Armenian" lang="hy" hreflang="hy" data-title="Ացետալդեհիդ" 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%B8%E0%A4%BF%E0%A4%9F%E0%A4%B2%E0%A5%8D%E0%A4%A1%E0%A4%BF%E0%A4%B9%E0%A4%BE%E0%A4%87%E0%A4%A1" title="एसिटल्डिहाइड – Hindi" lang="hi" hreflang="hi" data-title="एसिटल्डिहाइड" 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/Acetaldehid" title="Acetaldehid – Croatian" lang="hr" hreflang="hr" data-title="Acetaldehid" 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/Asetaldehida" title="Asetaldehida – Indonesian" lang="id" hreflang="id" data-title="Asetaldehida" 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/Acetaldeide" title="Acetaldeide – Italian" lang="it" hreflang="it" data-title="Acetaldeide" 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%A6%D7%98%D7%90%D7%9C%D7%93%D7%94%D7%99%D7%93" title="אצטאלדהיד – Hebrew" lang="he" hreflang="he" data-title="אצטאלדהיד" 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%90%E1%83%AA%E1%83%94%E1%83%A2%E1%83%90%E1%83%9A%E1%83%93%E1%83%94%E1%83%B0%E1%83%98%E1%83%93%E1%83%98" title="აცეტალდეჰიდი – Georgian" lang="ka" hreflang="ka" data-title="აცეტალდეჰიდი" 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%90%D1%86%D0%B5%D1%82%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4" title="Ацетальдегид – Kazakh" lang="kk" hreflang="kk" data-title="Ацетальдегид" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4" title="Ацетальдегид – Kyrgyz" lang="ky" hreflang="ky" data-title="Ацетальдегид" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Ethanal" title="Ethanal – Latin" lang="la" hreflang="la" data-title="Ethanal" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Acetaldeh%C4%ABds" title="Acetaldehīds – Latvian" lang="lv" hreflang="lv" data-title="Acetaldehīds" 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/Acetaldehidas" title="Acetaldehidas – Lithuanian" lang="lt" hreflang="lt" data-title="Acetaldehidas" 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/Acetaldehid" title="Acetaldehid – Hungarian" lang="hu" hreflang="hu" data-title="Acetaldehid" 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%90%D1%86%D0%B5%D1%82%D0%B0%D0%BB%D0%B4%D0%B5%D1%85%D0%B8%D0%B4" title="Ацеталдехид – Macedonian" lang="mk" hreflang="mk" data-title="Ацеталдехид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Aceetaldehyde" title="Aceetaldehyde – Dutch" lang="nl" hreflang="nl" data-title="Aceetaldehyde" 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%A2%E3%82%BB%E3%83%88%E3%82%A2%E3%83%AB%E3%83%87%E3%83%92%E3%83%89" title="アセトアルデヒド – Japanese" lang="ja" hreflang="ja" data-title="アセトアルデヒド" 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/Acetaldehyd" title="Acetaldehyd – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Acetaldehyd" 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-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Acetaldehyd" title="Acetaldehyd – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Acetaldehyd" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Atsetaldegid" title="Atsetaldegid – Uzbek" lang="uz" hreflang="uz" data-title="Atsetaldegid" 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/Aldehyd_octowy" title="Aldehyd octowy – Polish" lang="pl" hreflang="pl" data-title="Aldehyd octowy" 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/Etanal" title="Etanal – Portuguese" lang="pt" hreflang="pt" data-title="Etanal" 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/Acetaldehid%C4%83" title="Acetaldehidă – Romanian" lang="ro" hreflang="ro" data-title="Acetaldehidă" 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%90%D1%86%D0%B5%D1%82%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4" title="Ацетальдегид – Russian" lang="ru" hreflang="ru" data-title="Ацетальдегид" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Acetaldehyd" title="Acetaldehyd – Slovak" lang="sk" hreflang="sk" data-title="Acetaldehyd" 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/Etanal" title="Etanal – Slovenian" lang="sl" hreflang="sl" data-title="Etanal" 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/Acetaldehid" title="Acetaldehid – Serbian" lang="sr" hreflang="sr" data-title="Acetaldehid" 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/Acetaldehid" title="Acetaldehid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Acetaldehid" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Asetaldehydi" title="Asetaldehydi – Finnish" lang="fi" hreflang="fi" data-title="Asetaldehydi" 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/Acetaldehyd" title="Acetaldehyd – Swedish" lang="sv" hreflang="sv" data-title="Acetaldehyd" 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%85%E0%AE%9A%E0%AE%BF%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AE%BE%E0%AE%B2%E0%AF%8D%E0%AE%9F%E0%AE%BF%E0%AE%95%E0%AF%88%E0%AE%9F%E0%AF%81" title="அசிட்டால்டிகைடு – Tamil" lang="ta" hreflang="ta" data-title="அசிட்டால்டிகைடு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%90%D1%82%D1%81%D0%B5%D1%82%D0%B0%D0%BB%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4" title="Атсеталдегид – Tajik" lang="tg" hreflang="tg" data-title="Атсеталдегид" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Asetaldehit" title="Asetaldehit – Turkish" lang="tr" hreflang="tr" data-title="Asetaldehit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%95%D1%82%D0%B0%D0%BD%D0%B0%D0%BB%D1%8C" title="Етаналь – Ukrainian" lang="uk" hreflang="uk" data-title="Етаналь" 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/Acetaldehyde" title="Acetaldehyde – Vietnamese" lang="vi" hreflang="vi" data-title="Acetaldehyde" 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/%E9%86%8B%E9%86%9B" title="醋醛 – Cantonese" lang="yue" hreflang="yue" data-title="醋醛" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B9%99%E9%86%9B" title="乙醛 – Chinese" lang="zh" hreflang="zh" data-title="乙醛" data-language-autonym="中文" data-language-local-name="Chinese" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><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">"Ethanal" redirects here; not to be confused with <a href="/wiki/Ethanol" title="Ethanol">Ethanol</a>.</div><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic chemical compound (CH3CH=O)</div> <p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.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%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Acetaldehyde </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Acetaldehyde-2D-flat.svg" class="mw-file-description" title="Lewis structure of acetaldehyde"><img alt="Lewis structure of acetaldehyde" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Acetaldehyde-2D-flat.svg/120px-Acetaldehyde-2D-flat.svg.png" decoding="async" width="110" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Acetaldehyde-2D-flat.svg/250px-Acetaldehyde-2D-flat.svg.png 1.5x" data-file-width="1100" data-file-height="948" /></a><figcaption>Lewis structure of acetaldehyde</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Acetaldehyde-tall-2D-skeletal.png" class="mw-file-description" title="Skeletal structure of acetaldehyde"><img alt="Skeletal structure of acetaldehyde" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Acetaldehyde-tall-2D-skeletal.png/75px-Acetaldehyde-tall-2D-skeletal.png" decoding="async" width="75" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Acetaldehyde-tall-2D-skeletal.png/113px-Acetaldehyde-tall-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/Acetaldehyde-tall-2D-skeletal.png/150px-Acetaldehyde-tall-2D-skeletal.png 2x" data-file-width="505" data-file-height="798" /></a><figcaption>Skeletal structure of acetaldehyde</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Acetaldehyde-3D-balls.png" class="mw-file-description" title="Ball-and-stick model"><img alt="Ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Acetaldehyde-3D-balls.png/120px-Acetaldehyde-3D-balls.png" decoding="async" width="110" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Acetaldehyde-3D-balls.png/250px-Acetaldehyde-3D-balls.png 1.5x" data-file-width="1100" data-file-height="1057" /></a><figcaption>Ball-and-stick model</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Acetaldehyde-3D-vdW.png" class="mw-file-description" title="Space-filling model"><img alt="Space-filling model" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Acetaldehyde-3D-vdW.png/120px-Acetaldehyde-3D-vdW.png" decoding="async" width="110" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Acetaldehyde-3D-vdW.png/250px-Acetaldehyde-3D-vdW.png 1.5x" data-file-width="1100" data-file-height="1139" /></a><figcaption>Space-filling model</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></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;">Acetaldehyde<sup id="cite_ref-iupac2013_3-0" class="reference"><a href="#cite_note-iupac2013-3"><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;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic 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;">Ethanal<sup id="cite_ref-iupac2013_3-1" class="reference"><a href="#cite_note-iupac2013-3"><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;">Acetic aldehyde<br />Ethyl aldehyde<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 />Acetylaldehyde<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> <th colspan="2" style="background: #f8eaba;color:inherit; 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><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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=75-07-0">75-07-0</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=O%3DCC">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%3DO">Interactive image</a></span></li></ul></div> </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=15343">CHEBI:15343</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/chembl/explore/compound/ChEMBL170365">ChEMBL170365</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.172.html">172</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/100.000.761">100.000.761</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q61457#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>200-836-8</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=6277">6277</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00084">C00084</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;"><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/177">177</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>AB1925000</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/GO1N1ZPR3B">GO1N1ZPR3B</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;"><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/DTXSID5039224">DTXSID5039224</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q61457#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;"><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/C2H4O/c1-2-3/h2H,1H3<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: IKHGUXGNUITLKF-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/C2H4O/c1-2-3/h2H,1H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IKHGUXGNUITLKF-UHFFFAOYAB</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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%;">O=CC</div></li><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%;">CC=O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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>4</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001440530000000000♠"></span>44.053</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colourless gas or liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Ethereal </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.784 g·cm<sup>−3</sup> (20 °C)<sup id="cite_ref-Celanese_4-0" class="reference"><a href="#cite_note-Celanese-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <p>0.7904–0.7928 g·cm<sup>−3</sup> (10 °C)<sup id="cite_ref-Celanese_4-1" class="reference"><a href="#cite_note-Celanese-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−123.37 °C (−190.07 °F; 149.78 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>20.2 °C (68.4 °F; 293.3 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>miscible </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>miscible with <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/Xylene" title="Xylene">xylene</a>, <a href="/wiki/Turpentine" title="Turpentine">turpentine</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a> <br /> slightly soluble in <a href="/wiki/Chloroform" title="Chloroform">chloroform</a> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−0.34 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>740 mmHg (20 °C)<sup id="cite_ref-NIOSH_5-0" class="reference"><a href="#cite_note-NIOSH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>13.57 (25 °C, <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"><a href="/wiki/Water" title="Water">H<sub class="template-chem2-sub">2</sub>O</a></span>)<sup id="cite_ref-CRC97_6-0" class="reference"><a href="#cite_note-CRC97-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−0.5153<sup>−6</sup> cm<sup>3</sup>/g </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.3316 </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>0.21 mPa-s at 20 °C (0.253 mPa-s at 9.5 °C)<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> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td>trigonal planar (sp<sup>2</sup>) at C<sub>1</sub><br />tetrahedral (sp<sup>3</sup>) at C<sub>2</sub> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>2.7 <a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry<sup id="cite_ref-crc_8-0" class="reference"><a href="#cite_note-crc-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </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>89 J·mol<sup>−1</sup>·K<sup>−1</sup> </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>160.2 J·mol<sup>−1</sup>·K<sup>−1</sup> </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>−192.2 kJ·mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gibbs_free_energy#Standard_energy_change_of_formation" title="Gibbs free energy">Gibbs free energy</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>G</i><sup>⦵</sup>)</span></div> </td> <td>−127.6 kJ·mol<sup>−1</sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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/Aldehyde" title="Aldehyde">aldehydes</a></div> </td> <td><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a><br /> <a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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>potential occupational carcinogen<sup id="cite_ref-IDLH_10-0" class="reference"><a href="#cite_note-IDLH-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><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><sup id="cite_ref-sigma_9-0" class="reference"><a href="#cite_note-sigma-9"><span class="cite-bracket">[</span>9<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/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H224: Extremely flammable liquid and vapour">H224</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H351: Suspected of causing cancer">H351</abbr><sup id="cite_ref-sigma_9-1" class="reference"><a href="#cite_note-sigma-9"><span class="cite-bracket">[</span>9<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/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P281: Use personal protective equipment as required.">P281</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr><sup id="cite_ref-sigma_9-2" class="reference"><a href="#cite_note-sigma-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </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_4516129a0d527770" /></span><map name="ImageMap_4516129a0d527770"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" title="Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" /><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 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</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 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" class="notheme mw-no-invert">4</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 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" class="notheme mw-no-invert">3</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−39.00 °C; −38.20 °F; 234.15 K </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>175.00 °C; 347.00 °F; 448.15 K<sup id="cite_ref-NIOSH_5-3" class="reference"><a href="#cite_note-NIOSH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>4.0–60% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>1930 mg/kg (rat, oral) </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>13,000 ppm (rat),<br /> 17,000 ppm (hamster),<br /> 20,000 ppm (rat)<sup id="cite_ref-IDLH_10-2" class="reference"><a href="#cite_note-IDLH-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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>200 ppm (360 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_5-1" class="reference"><a href="#cite_note-NIOSH-5"><span class="cite-bracket">[</span>5<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>2000 ppm<sup id="cite_ref-NIOSH_5-2" class="reference"><a href="#cite_note-NIOSH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IDLH_10-1" class="reference"><a href="#cite_note-IDLH-10"><span class="cite-bracket">[</span>10<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="http://www.hmdb.ca/system/metabolites/msds/000/000/889/original/HMDB00990.pdf?1358893258">HMDB</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Acetaldehyde_(data_page)" title="Acetaldehyde (data page)">Acetaldehyde (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; 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="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477238480&page2=Acetaldehyde">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>Acetaldehyde</b> (IUPAC systematic name <b>ethanal</b>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic chemical compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH=O</span>, sometimes abbreviated as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap"><a href="/wiki/Methyl" class="mw-redirect" title="Methyl">Me</a>CH=O</span>. It is a colorless liquid or gas, boiling near room temperature. It is one of the most important <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a>, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit,<sup id="cite_ref-:2_11-0" class="reference"><a href="#cite_note-:2-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> and is produced by plants. It is also produced by the partial oxidation of <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> by the liver enzyme <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a> and is a contributing cause of <a href="/wiki/Hangover" title="Hangover">hangover</a> after <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a> consumption.<sup id="cite_ref-hsf_12-0" class="reference"><a href="#cite_note-hsf-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke.<sup id="cite_ref-chem_13-0" class="reference"><a href="#cite_note-chem-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Consumption of <a href="/wiki/Disulfiram" title="Disulfiram">disulfiram</a> inhibits <a href="/wiki/Acetaldehyde_dehydrogenase" title="Acetaldehyde dehydrogenase">acetaldehyde dehydrogenase</a>, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body. </p><p><a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">The International Agency for Research on Cancer</a> (IARC) has listed acetaldehyde as a Group 1 <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>.<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> Acetaldehyde is "one of the most frequently found air toxins with cancer risk greater than one in a million".<sup id="cite_ref-:0_15-0" class="reference"><a href="#cite_note-:0-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde was first observed by the Swedish pharmacist/chemist <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a> (1774);<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> it was then investigated by the French chemists <a href="/wiki/Antoine_Fran%C3%A7ois,_comte_de_Fourcroy" class="mw-redirect" title="Antoine François, comte de Fourcroy">Antoine François, comte de Fourcroy</a> and <a href="/wiki/Louis_Nicolas_Vauquelin" title="Louis Nicolas Vauquelin">Louis Nicolas Vauquelin</a> (1800),<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> and the German chemists <a href="/wiki/Johann_Wolfgang_D%C3%B6bereiner" title="Johann Wolfgang Döbereiner">Johann Wolfgang Döbereiner</a> (1821, 1822, 1832)<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> and <a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus von Liebig</a> (1835).<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><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> </p><p>In 1835, Liebig named it "aldehyde",<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> and in the middle of the century the name was altered to "acetaldehyde".<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> <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=Acetaldehyde&action=edit&section=2" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2013, global production was about 438 thousand tons.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Before 1962, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> were the major sources of acetaldehyde. Since then, ethylene is the dominant <a href="/wiki/Raw_material" title="Raw material">feedstock</a>.<sup id="cite_ref-Ull_24-0" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>The main method of production is the oxidation of <a href="/wiki/Ethene" class="mw-redirect" title="Ethene">ethene</a> by the <a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a>, which involves oxidation of ethene using a <a href="/wiki/Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous</a> palladium/copper catalyst system: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">2 CH<sub class="template-chem2-sub">2</sub>=CH<sub class="template-chem2-sub">2</sub> + O<sub class="template-chem2-sub">2</sub> → 2 CH<sub class="template-chem2-sub">3</sub>CH=O</span></dd></dl> <p>In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process exceeded 2 million tonnes annually. </p><p>Smaller quantities can be prepared by the partial <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of ethanol in an exothermic reaction. This process typically is conducted over a silver catalyst at about 500–650 °C (932–1,202 °F).<sup id="cite_ref-Ull_24-1" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">2 CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>OH + O<sub class="template-chem2-sub">2</sub> → 2 CH<sub class="template-chem2-sub">3</sub>CH=O + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>This method is one of the oldest routes for the industrial preparation of acetaldehyde. </p> <div class="mw-heading mw-heading3"><h3 id="Other_methods">Other methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=3" title="Edit section: Other methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Hydration_of_acetylene">Hydration of acetylene</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=4" title="Edit section: Hydration of acetylene"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Prior to the <a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a> and the availability of cheap ethylene, acetaldehyde was produced by the <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a> of <a href="/wiki/Acetylene" title="Acetylene">acetylene</a>.<sup id="cite_ref-Dmitry2007_25-0" class="reference"><a href="#cite_note-Dmitry2007-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> This reaction is catalyzed by <a href="/wiki/Mercury_(element)" title="Mercury (element)">mercury(II)</a> salts: </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">2</sub> + Hg<sup class="template-chem2-sup">2+</sup> + H<sub class="template-chem2-sub">2</sub>O → CH<sub class="template-chem2-sub">3</sub>CH=O + Hg</span></dd></dl> <p>The mechanism involves the intermediacy of <a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">vinyl alcohol</a>, which <a href="/wiki/Tautomer" title="Tautomer">tautomerizes</a> to acetaldehyde. The reaction is conducted at 90–95 °C (194–203 °F), and the acetaldehyde formed is separated from water and mercury and cooled to 25–30 °C (77–86 °F). In the <a href="/wiki/Wet_oxidation" title="Wet oxidation">wet oxidation</a> process, <a href="/wiki/Iron(III)_sulfate" title="Iron(III) sulfate">iron(III) sulfate</a> is used to reoxidize the mercury back to the mercury(II) salt. The resulting <a href="/wiki/Iron(II)_sulfate" title="Iron(II) sulfate">iron(II) sulfate</a> is oxidized in a separate reactor with <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>.<sup id="cite_ref-Ull_24-2" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>The enzyme <a href="/wiki/Acetylene_hydratase" title="Acetylene hydratase">Acetylene hydratase</a> discovered in the strictly anaerobic bacterium <i><a href="/wiki/Pelobacter_acetylenicus" title="Pelobacter acetylenicus">Pelobacter acetylenicus</a></i> can catalyze an analogous reaction without involving any compounds of mercury.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> However, it has thus far not been brought to any large-scale or commercial use. </p> <div class="mw-heading mw-heading4"><h4 id="Dehydrogenation_of_ethanol">Dehydrogenation of ethanol</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=5" title="Edit section: Dehydrogenation of ethanol"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Traditionally, acetaldehyde was produced by the partial <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a> of ethanol: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>OH → CH<sub class="template-chem2-sub">3</sub>CH=O + H<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>In this endothermic process, ethanol vapor is passed at 260–290 °C over a copper-based catalyst. The process was once attractive because of the value of the hydrogen coproduct,<sup id="cite_ref-Ull_24-3" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> but in modern times is not economically viable. </p> <div class="mw-heading mw-heading4"><h4 id="Hydroformylation_of_methanol">Hydroformylation of methanol</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=6" title="Edit section: Hydroformylation of methanol"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> of <a href="/wiki/Methanol" title="Methanol">methanol</a> with catalysts like cobalt, nickel, or iron salts also produces acetaldehyde, although this process is of no industrial importance. Similarly noncompetitive, acetaldehyde arises from <a href="/wiki/Synthesis_gas" class="mw-redirect" title="Synthesis gas">synthesis gas</a> with modest selectivity.<sup id="cite_ref-Ull_24-4" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=7" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Tautomerization_to_vinyl_alcohol">Tautomerization to vinyl alcohol</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=8" title="Edit section: Tautomerization to vinyl alcohol"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Ethanal_Ethenol_Tautomerie.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Ethanal_Ethenol_Tautomerie.svg/330px-Ethanal_Ethenol_Tautomerie.svg.png" decoding="async" width="290" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Ethanal_Ethenol_Tautomerie.svg/435px-Ethanal_Ethenol_Tautomerie.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Ethanal_Ethenol_Tautomerie.svg/580px-Ethanal_Ethenol_Tautomerie.svg.png 2x" data-file-width="393" data-file-height="146" /></a><figcaption>Tautomeric equilibrium between acetaldehyde and vinyl alcohol.</figcaption></figure><div style="clear:left;" class=""></div> <p>Like many other <a href="/wiki/Carbonyl_compound" class="mw-redirect" title="Carbonyl compound">carbonyl compounds</a>, acetaldehyde <a href="/wiki/Tautomer" title="Tautomer">tautomerizes</a> to give an <a href="/wiki/Enol" title="Enol">enol</a> (<a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">vinyl alcohol</a>; IUPAC name: ethenol): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH=O ⇌ CH<sub class="template-chem2-sub">2</sub>=CHOH</span> <span class="nowrap"> </span> <span class="nowrap"> </span> <span class="nowrap"> </span> <span class="nowrap"> </span> <span class="nowrap"> </span> <span class="nowrap"> </span> <span class="nowrap"> </span> <span class="nowrap"> </span> ∆<i>H</i><sub>298,g</sub> = +42.7 kJ/mol</dd></dl> <p>The <a href="/wiki/Equilibrium_constant" title="Equilibrium constant">equilibrium constant</a> is 6<span style="margin:0 .15em 0 .25em">×</span>10<sup>−7</sup> at room temperature, thus that the relative amount of the enol form in a sample of acetaldehyde is very small.<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> At room temperature, acetaldehyde (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH=O</span>) is more stable than <a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">vinyl alcohol</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CHOH</span>) by 42.7 kJ/mol:<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> Overall the keto-enol tautomerization occurs slowly but is catalyzed by acids. </p><p>Photo-induced keto-enol tautomerization is viable under <a href="/wiki/Atmosphere" title="Atmosphere">atmospheric</a> or stratospheric conditions. This photo-tautomerization is relevant to the Earth's atmosphere, because vinyl alcohol is thought to be a precursor to <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> in the atmosphere.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><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> </p> <div class="mw-heading mw-heading3"><h3 id="Addition_and_condensation_reactions">Addition and condensation reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=9" title="Edit section: Addition and condensation reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde is a common electrophile in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>.<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> In <a href="/wiki/Addition_reaction" title="Addition reaction">addition reactions</a> acetaldehyde is <a href="/wiki/Prochiral" class="mw-redirect" title="Prochiral">prochiral</a>. It is used primarily as a source of the "<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C<sup class="template-chem2-sup">+</sup>H(OH)</span>" <a href="/wiki/Synthon" title="Synthon">synthon</a> in <a href="/wiki/Aldol_reaction" title="Aldol reaction">aldol reactions</a> and related <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation reactions</a>.<sup id="cite_ref-Behrens2004_32-0" class="reference"><a href="#cite_note-Behrens2004-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Grignard reagents and <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">organolithium</a> compounds react with MeCHO to give <a href="/wiki/Hydroxyethyl" class="mw-redirect" title="Hydroxyethyl">hydroxyethyl</a> derivatives.<sup id="cite_ref-Walter1955_33-0" class="reference"><a href="#cite_note-Walter1955-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> In one of the more spectacular addition reactions, <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> in the presence of <a href="/wiki/Calcium_hydroxide" title="Calcium hydroxide">calcium hydroxide</a> adds to MeCHO to give <a href="/wiki/Pentaerythritol" title="Pentaerythritol">pentaerythritol</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C(CH<sub class="template-chem2-sub">2</sub>OH)<sub class="template-chem2-sub">4</sub></span> and <a href="/wiki/Formate" title="Formate">formate</a>.<sup id="cite_ref-Schurink1941_34-0" class="reference"><a href="#cite_note-Schurink1941-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>In a <a href="/wiki/Strecker_amino_acid_synthesis" title="Strecker amino acid synthesis">Strecker reaction</a>, acetaldehyde condenses with <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> to give, after <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a>, the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Alanine" title="Alanine">alanine</a>.<sup id="cite_ref-Kendall1941_35-0" class="reference"><a href="#cite_note-Kendall1941-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Acetaldehyde can condense with <a href="/wiki/Amine" title="Amine">amines</a> to yield <a href="/wiki/Imine" title="Imine">imines</a>; for example, with <a href="/wiki/Cyclohexylamine" title="Cyclohexylamine">cyclohexylamine</a> to give <i>N</i>-<a href="/w/index.php?title=Ethylidene&action=edit&redlink=1" class="new" title="Ethylidene (page does not exist)">ethylidenecyclohexylamine</a>. These imines can be used to direct subsequent reactions like an aldol condensation.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>It is also a building block in the synthesis of <a href="/wiki/Heterocyclic_compounds" class="mw-redirect" title="Heterocyclic compounds">heterocyclic compounds</a>. In one example, it converts, upon treatment with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, to <a href="/wiki/5-Ethyl-2-methylpyridine" title="5-Ethyl-2-methylpyridine">5-ethyl-2-methylpyridine</a> ("aldehyde-collidine").<sup id="cite_ref-Frank1963_37-0" class="reference"><a href="#cite_note-Frank1963-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Polymeric_forms">Polymeric forms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=10" title="Edit section: Polymeric forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1273380762/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner span:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent) img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner span:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent) img{background-color:white}}</style><div class="thumb tmulti tleft"><div class="thumbinner multiimageinner" style="width:312px;max-width:312px"><div class="trow"><div class="tsingle" style="width:149px;max-width:149px"><div class="thumbimage" style="height:156px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Paraldehyde_structure.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Paraldehyde_structure.svg/250px-Paraldehyde_structure.svg.png" decoding="async" width="147" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Paraldehyde_structure.svg/330px-Paraldehyde_structure.svg.png 2x" data-file-width="512" data-file-height="546" /></a></span></div></div><div class="tsingle" style="width:159px;max-width:159px"><div class="thumbimage" style="height:156px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Metaldehyde.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Metaldehyde.svg/250px-Metaldehyde.svg.png" decoding="async" width="157" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Metaldehyde.svg/330px-Metaldehyde.svg.png 2x" data-file-width="800" data-file-height="800" /></a></span></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">Cyclic <a href="/wiki/Oligomer" title="Oligomer">oligomers</a> of acetaldehyde (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CHO)<sub class="template-chem2-sub">n</sub></span>: <a href="/wiki/Paraldehyde" title="Paraldehyde">paraldehyde</a> (<i>n</i> = 3, left) and <a href="/wiki/Metaldehyde" title="Metaldehyde">metaldehyde</a> (<i>n</i> = 4, right)</div></div></div></div> <p>Three molecules of acetaldehyde condense to form "<a href="/wiki/Paraldehyde" title="Paraldehyde">paraldehyde</a>", a cyclic trimer containing C-O single bonds. Similarly condensation of four molecules of acetaldehyde give the cyclic molecule <a href="/wiki/Metaldehyde" title="Metaldehyde">metaldehyde</a>. Paraldehyde can be produced in good yields, using a sulfuric acid catalyst. Metaldehyde is only obtained in a few percent yield and with cooling, often using HBr rather than <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>SO<sub class="template-chem2-sub">4</sub></span> as the catalyst. At −40 °C (−40 °F) in the presence of acid catalysts, polyacetaldehyde is produced.<sup id="cite_ref-Ull_24-5" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> There are two <a href="/wiki/Stereomer" class="mw-redirect" title="Stereomer">stereomers</a> of paraldehyde and four of metaldehyde. </p><p>The German chemist Valentin Hermann Weidenbusch (1821–1893) synthesized paraldehyde in 1848 by treating acetaldehyde with acid (either sulfuric or nitric acid) and cooling to 0 °C (32 °F). He found it quite remarkable that when paraldehyde was <i>heated</i> with a trace of the same acid, the reaction went the other way, recreating acetaldehyde.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>Although <a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">vinyl alcohol</a> is a polymeric form of acetaldehyde (<a href="#Tautomerization_to_vinyl_alcohol">§ Tautomerization to vinyl alcohol</a>), <a href="/wiki/Polyvinyl_alcohol" title="Polyvinyl alcohol">polyvinyl alcohol</a> cannot be produced from acetaldehyde. </p> <div class="mw-heading mw-heading3"><h3 id="Acetal_derivatives">Acetal derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=11" title="Edit section: Acetal derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Acetal_formation_2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Acetal_formation_2.png/450px-Acetal_formation_2.png" decoding="async" width="450" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Acetal_formation_2.png/675px-Acetal_formation_2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/e/ef/Acetal_formation_2.png 2x" data-file-width="857" data-file-height="194" /></a><figcaption>Conversion of acetaldehyde to <a href="/wiki/1,1-diethoxyethane" class="mw-redirect" title="1,1-diethoxyethane">1,1-diethoxyethane</a>, R<sup>1</sup>=<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub></span> R<sup>2</sup>=<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub></span></figcaption></figure> <p>Acetaldehyde forms a stable <a href="/wiki/Acetal" title="Acetal">acetal</a> upon reaction with <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> under conditions that favor dehydration. The product, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH(OCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span>, is formally named <a href="/wiki/1,1-diethoxyethane" class="mw-redirect" title="1,1-diethoxyethane">1,1-diethoxyethane</a> but is commonly referred to as "acetal".<sup id="cite_ref-Adkins1941_39-0" class="reference"><a href="#cite_note-Adkins1941-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> This can cause confusion as "acetal" is more commonly used to describe compounds with the <a href="/wiki/Functional_group" title="Functional group">functional groups</a> RCH(OR')<sub>2</sub> or RR'C(OR'')<sub>2</sub> rather than referring to this specific compound — in fact, 1,1-diethoxyethane is also described as the diethyl acetal of acetaldehyde. </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_vinylphosphonic_acid">Precursor to vinylphosphonic acid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=12" title="Edit section: Precursor to vinylphosphonic acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde is a precursor to <a href="/wiki/Vinylphosphonic_acid" title="Vinylphosphonic acid">vinylphosphonic acid</a>, which is used to make adhesives and <a href="/wiki/Ion_conductivity" class="mw-redirect" title="Ion conductivity">ion conductive</a> membranes. The synthesis sequence begins with a reaction with <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">phosphorus trichloride</a>:<sup id="cite_ref-Lavinia_40-0" class="reference"><a href="#cite_note-Lavinia-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <ol><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">PCl<sub class="template-chem2-sub">3</sub> + CH<sub class="template-chem2-sub">3</sub>CHO → CH<sub class="template-chem2-sub">3</sub>CH(O<sup class="template-chem2-sup">−</sup>)PCl<span class="template-chem2-su"><span>+</span><span>3</span></span></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH(O<sup class="template-chem2-sup">−</sup>)PCl<span class="template-chem2-su"><span>+</span><span>3</span></span> + 2 CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H → CH<sub class="template-chem2-sub">3</sub>CH(Cl)PO(OH)<sub class="template-chem2-sub">2</sub> + 2 CH<sub class="template-chem2-sub">3</sub>COCl</span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH(Cl)PO(OH)<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">2</sub>=CHPO(OH)<sub class="template-chem2-sub">2</sub> + HCl</span></li></ol> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=13" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the <a href="/wiki/Liver" title="Liver">liver</a>, the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a> oxidizes <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> into acetaldehyde, which is then further oxidized into harmless <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> by <a href="/wiki/Acetaldehyde_dehydrogenase" title="Acetaldehyde dehydrogenase">acetaldehyde dehydrogenase</a>. These two oxidation reactions are coupled with the reduction of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">NAD<sup class="template-chem2-sup">+</sup></span> to <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a>.<sup id="cite_ref-Hipolito,_L._2007_41-0" class="reference"><a href="#cite_note-Hipolito,_L._2007-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> In the brain, the enzyme <a href="/wiki/Catalase" title="Catalase">catalase</a> is primarily responsible for oxidizing ethanol to acetaldehyde, and <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a> plays a minor role.<sup id="cite_ref-Hipolito,_L._2007_41-1" class="reference"><a href="#cite_note-Hipolito,_L._2007-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> The last steps of alcoholic <a href="/wiki/Fermentation_(food)" class="mw-redirect" title="Fermentation (food)">fermentation</a> in bacteria, plants, and <a href="/wiki/Yeast" title="Yeast">yeast</a> involve the conversion of <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> into acetaldehyde and <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> by the enzyme <a href="/wiki/Pyruvate_decarboxylase" title="Pyruvate decarboxylase">pyruvate decarboxylase</a>, followed by the conversion of acetaldehyde into ethanol. The latter reaction is again catalyzed by an alcohol dehydrogenase, now operating in the opposite direction. </p><p>Many <a href="/wiki/East_Asian_people" title="East Asian people">East Asian people</a> have an <a href="/wiki/ALDH2" title="ALDH2">ALDH2</a> mutation which makes them significantly less efficient at oxidizing acetaldehyde. On consuming alcohol, their bodies tend to accumulate excessive amounts of acetaldehyde, causing the so-called <a href="/wiki/Alcohol_flush_reaction" title="Alcohol flush reaction">alcohol flush reaction</a>.<sup id="cite_ref-Kim2014_42-0" class="reference"><a href="#cite_note-Kim2014-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> They develop a characteristic flush on the face and body, along with "nausea, headache and general physical discomfort".<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Ingestion of the drug <a href="/wiki/Disulfiram" title="Disulfiram">disulfiram</a>, which inhibits ALDH2, leads to a similar reaction <style data-mw-deduplicate="TemplateStyles:r1033199720">.mw-parser-output div.crossreference{padding-left:0}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><span role="note" class="hatnote navigation-not-searchable crossreference">(see: <a href="#Aggravating_factors">§ Aggravating factors</a> below)</span>.<sup id="cite_ref-disul-new_44-0" class="reference"><a href="#cite_note-disul-new-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </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=Acetaldehyde&action=edit&section=14" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Traditionally, acetaldehyde was mainly used as a precursor to acetic acid. This application has declined because acetic acid is produced more efficiently from methanol by the <a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto</a> and <a href="/wiki/Cativa_process" title="Cativa process">Cativa processes</a>. Acetaldehyde is an important precursor to <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> derivatives, <a href="/wiki/Pentaerythritol" title="Pentaerythritol">pentaerythritol</a>, and <a href="/wiki/Crotonaldehyde" title="Crotonaldehyde">crotonaldehyde</a>. Urea and acetaldehyde combine to give a useful <a href="/wiki/Resin" title="Resin">resin</a>. <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">Acetic anhydride</a> reacts with acetaldehyde to give <a href="/wiki/Ethylidene_diacetate" title="Ethylidene diacetate">ethylidene diacetate</a>, a precursor to <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a>, which is used to produce <a href="/wiki/Polyvinyl_acetate" title="Polyvinyl acetate">polyvinyl acetate</a>.<sup id="cite_ref-Ull_24-6" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>The global market for acetaldehyde is declining. Demand has been impacted by changes in the production of plasticizer alcohols, which has shifted because <a href="/wiki/Butyraldehyde" title="Butyraldehyde"><i>n</i>-butyraldehyde</a> is less often produced from acetaldehyde, instead being generated by hydroformylation of <a href="/wiki/Propylene" title="Propylene">propylene</a>. Likewise, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, once produced from acetaldehyde, is made predominantly by the lower-cost methanol carbonylation process.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> The impact on demand has led to increase in prices and thus slowdown in the market.<br /> </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Production_of_acetaldehyde.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Production_of_acetaldehyde.JPG/250px-Production_of_acetaldehyde.JPG" decoding="async" width="220" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Production_of_acetaldehyde.JPG/330px-Production_of_acetaldehyde.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Production_of_acetaldehyde.JPG/500px-Production_of_acetaldehyde.JPG 2x" data-file-width="784" data-file-height="483" /></a><figcaption>Production of Acetaldehyde</figcaption></figure> <table class="wikitable"> <caption>Consumption of acetaldehyde (10<sup>3</sup> t) in 2003<sup id="cite_ref-Ull_24-7" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><br />(* Included in others -glyoxal/glyoxalic acid, crotonaldehyde, lactic acid, <i>n</i>-butanol, 2-ethylhexanol) </caption> <tbody><tr> <th>Product</th> <th>USA</th> <th>Mexico</th> <th>W. Europe</th> <th>Japan</th> <th>Total </th></tr> <tr> <td>Acetic Acid/Acetic anhydride</td> <td>-</td> <td>11</td> <td>89</td> <td>47</td> <td>147 </td></tr> <tr> <td>Acetate esters</td> <td>35</td> <td>8</td> <td>54</td> <td>224</td> <td>321 </td></tr> <tr> <td>Pentaerythritol</td> <td>26</td> <td>–</td> <td>43</td> <td>11</td> <td>80 </td></tr> <tr> <td>Pyridine and pyridine bases</td> <td>73</td> <td>–</td> <td>10</td> <td>*</td> <td>83 </td></tr> <tr> <td>Peracetic acid</td> <td>23</td> <td>–</td> <td>–</td> <td>*</td> <td>23 </td></tr> <tr> <td>1,3-Butylene glycol</td> <td>14</td> <td>–</td> <td>–</td> <td>*</td> <td>14 </td></tr> <tr> <td>Others</td> <td>5</td> <td>3</td> <td>10</td> <td>80</td> <td>98 </td></tr> <tr> <td>Total</td> <td>176</td> <td>22</td> <td>206</td> <td>362</td> <td>766 </td></tr></tbody></table> <p><a href="/wiki/China" title="China">China</a> is the largest consumer of acetaldehyde in the world, accounting for almost half of global consumption in 2012. Major use has been the production of acetic acid. Other uses such as <a href="/wiki/Pyridine" title="Pyridine">pyridines</a> and pentaerythritol are expected to grow faster than acetic acid, but the volumes are not large enough to offset the decline in acetic acid. As a consequence, overall acetaldehyde consumption in <a href="/wiki/China" title="China">China</a> may grow slightly at 1.6% per year through 2018. Western Europe is the second-largest consumer of acetaldehyde worldwide, accounting for 20% of world consumption in 2012. As with China, the Western European acetaldehyde market is expected to increase only very slightly at 1% per year during 2012–2018. However, <a href="/wiki/Japan" title="Japan">Japan</a> could emerge as a potential consumer for acetaldehyde in the next five years due to newfound use in commercial production of <a href="/wiki/Butadiene" title="Butadiene">butadiene</a>. The supply of butadiene has been volatile in Japan and the rest of Asia. This should provide the much needed boost to the flat market, as of 2013.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=15" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Exposure_limits">Exposure limits</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=16" title="Edit section: Exposure limits"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Threshold_limit_value" title="Threshold limit value">threshold limit value</a> is 25ppm (STEL/ceiling value) and the MAK (Maximum Workplace Concentration) is 50 ppm. At 50 ppm acetaldehyde, no irritation or local tissue damage in the <a href="/wiki/Nasal_cavity" title="Nasal cavity">nasal</a> <a href="/wiki/Mucous_membrane" title="Mucous membrane">mucosa</a> is observed. When taken up by the organism, acetaldehyde is metabolized rapidly in the liver to acetic acid. Only a small proportion is exhaled unchanged. After <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a> injection, the half-life in the blood is approximately 90 seconds.<sup id="cite_ref-Ull_24-8" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dangers">Dangers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=17" title="Edit section: Dangers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Toxicity">Toxicity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=18" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many serious cases of acute intoxication have been recorded.<sup id="cite_ref-Ull_24-9" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Acetaldehyde naturally breaks down in the human body.<sup id="cite_ref-chem_13-1" class="reference"><a href="#cite_note-chem-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Irritation">Irritation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=19" title="Edit section: Irritation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde is an irritant of the skin, eyes, mucous membranes, throat, and respiratory tract. This occurs at concentrations as low as 1000 ppm. Symptoms of exposure to this compound include <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, and <a href="/wiki/Headache" title="Headache">headache</a>. These symptoms may not happen immediately. The <a href="/wiki/Perception" title="Perception">perception</a> threshold for acetaldehyde in air is in the range between 0.07 and 0.25 ppm.<sup id="cite_ref-Ull_24-10" class="reference"><a href="#cite_note-Ull-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> At such concentrations, the <a href="/wiki/Fruit" title="Fruit">fruity</a> <a href="/wiki/Odor" title="Odor">odor</a> of acetaldehyde is apparent. <a href="/wiki/Conjunctiva" title="Conjunctiva">Conjunctival</a> irritations have been observed after a 15-minute exposure to concentrations of 25 and 50 ppm, but transient conjunctivitis and irritation of the <a href="/wiki/Respiratory_system" title="Respiratory system">respiratory</a> tract have been reported after exposure to 200 ppm acetaldehyde for 15 minutes. </p> <div class="mw-heading mw-heading4"><h4 id="Carcinogenicity">Carcinogenicity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=20" title="Edit section: Carcinogenicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde is <a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a> in humans.<sup id="cite_ref-Chemical_Summary_For_Acetaldehyde_48-0" class="reference"><a href="#cite_note-Chemical_Summary_For_Acetaldehyde-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> In 1988 the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> stated, "There is <i>sufficient</i> evidence for the carcinogenicity of acetaldehyde (the major metabolite of ethanol) in <a href="/wiki/Experimental_animal" class="mw-redirect" title="Experimental animal">experimental animals</a>."<sup id="cite_ref-International1988_50-0" class="reference"><a href="#cite_note-International1988-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> In October 2009 the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> updated the classification of acetaldehyde stating that acetaldehyde included in and generated <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenously</a> from <a href="/wiki/Alcoholic_beverage" title="Alcoholic beverage">alcoholic beverages</a> is a Group I human carcinogen.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> In addition, acetaldehyde is damaging to <a href="/wiki/DNA" title="DNA">DNA</a><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> and causes abnormal muscle development as it binds to proteins.<sup id="cite_ref-Nicholas2004_53-0" class="reference"><a href="#cite_note-Nicholas2004-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="DNA_crosslinks">DNA crosslinks</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=21" title="Edit section: DNA crosslinks"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde induces DNA interstrand crosslinks, a form of DNA damage. These can be repaired by either of two replication-coupled DNA repair pathways.<sup id="cite_ref-Hodskinson2020_54-0" class="reference"><a href="#cite_note-Hodskinson2020-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> The first is referred to as the FA pathway, because it employs gene products defective in <a href="/wiki/Fanconi%27s_anemia" class="mw-redirect" title="Fanconi's anemia">Fanconi's anemia</a> patients. This repair pathway results in increased mutation frequency and altered mutational spectrum.<sup id="cite_ref-Hodskinson2020_54-1" class="reference"><a href="#cite_note-Hodskinson2020-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> The second repair pathway requires replication fork convergence, breakage of the acetaldehyde crosslink, translesion synthesis by a Y-family DNA polymerase and homologous recombination.<sup id="cite_ref-Hodskinson2020_54-2" class="reference"><a href="#cite_note-Hodskinson2020-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Aggravating_factors">Aggravating factors</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=22" title="Edit section: Aggravating factors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Alzheimer's_disease"><span id="Alzheimer.27s_disease"></span>Alzheimer's disease</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=23" title="Edit section: Alzheimer's disease"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>People with a genetic deficiency for the enzyme responsible for the conversion of acetaldehyde into <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> may have a greater risk of <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>. "These results indicate that the <a href="/wiki/ALDH2" title="ALDH2">ALDH2</a> deficiency is a risk factor for LOAD [late-onset Alzheimer's disease] ..."<sup id="cite_ref-ohta_55-0" class="reference"><a href="#cite_note-ohta-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Genetic_conditions">Genetic conditions</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=24" title="Edit section: Genetic conditions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A study of 818 heavy drinkers found that those exposed to more acetaldehyde than normal through a genetic variant of the gene encoding for <a href="/wiki/ADH1C" title="ADH1C">ADH1C</a>, ADH1C*1, are at greater risk of developing cancers of the <a href="/wiki/Upper_gastrointestinal_tract" class="mw-redirect" title="Upper gastrointestinal tract">upper gastrointestinal tract</a> and liver.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Disulfiram">Disulfiram</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=25" title="Edit section: Disulfiram"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The drug <a href="/wiki/Disulfiram" title="Disulfiram">disulfiram</a> (Antabuse) inhibits acetaldehyde dehydrogenase, an enzyme that oxidizes the compound into acetic acid. Metabolism of ethanol forms acetaldehyde before acetaldehyde dehydrogenase forms acetic acid, but with the enzyme inhibited, acetaldehyde accumulates. If one consumes ethanol while taking disulfiram, the hangover effect of ethanol is felt more rapidly and intensely (<a href="/wiki/Disulfiram-alcohol_reaction" title="Disulfiram-alcohol reaction">disulfiram-alcohol reaction</a>). As such, disulfiram is sometimes used as a deterrent for alcoholics wishing to stay sober.<sup id="cite_ref-disul-new_44-1" class="reference"><a href="#cite_note-disul-new-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Sources_of_exposure">Sources of exposure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=26" title="Edit section: Sources of exposure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Indoor_air">Indoor air</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=27" title="Edit section: Indoor air"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde is a potential contaminant in workplace, indoors, and ambient environments. Moreover, the majority of humans spend more than 90% of their time in indoor environments, increasing any exposure and the risk to human health.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p><p>In a study in <a href="/wiki/France" title="France">France</a>, the mean indoor concentration of acetaldehydes measured in 16 homes was approximately seven times higher than the outside acetaldehyde concentration. The <a href="/wiki/Living_room" title="Living room">living room</a> had a mean of 18.1±17.5 μg m<sup>−3</sup> and the <a href="/wiki/Bedroom" title="Bedroom">bedroom</a> was 18.2±16.9 μg m<sup>−3</sup>, whereas the outdoor air had a mean concentration of 2.3±2.6 μg m<sup>−3</sup>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2018)">citation needed</span></a></i>]</sup> </p><p>It has been concluded that <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile organic compounds (VOC)</a> such as benzene, formaldehyde, acetaldehyde, toluene, and <a href="/wiki/Xylene" title="Xylene">xylenes</a> have to be considered priority <a href="/wiki/Pollutant" title="Pollutant">pollutants</a> with respect to their health effects. It has been pointed that in renovated or completely new buildings, the VOCs concentration levels are often several orders of magnitude higher. The main sources of acetaldehydes in homes include building materials, laminate, PVC flooring, varnished wood flooring, and varnished cork/pine flooring (found in the varnish, not the wood). It is also found in plastics, oil-based and water-based paints, in composite wood ceilings, particle-board, plywood, treated pine wood, and laminated chipboard furniture.<sup id="cite_ref-dafni_58-0" class="reference"><a href="#cite_note-dafni-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Outdoor_air">Outdoor air</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=28" title="Edit section: Outdoor air"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The use of acetaldehyde is widespread in different industries, and it may be released into waste water or the air during production, use, transportation and storage. Sources of acetaldehyde include fuel combustion emissions from stationary internal combustion engines and power plants that burn fossil fuels, wood, or trash, oil and gas extraction, refineries, cement kilns, lumber and wood mills and paper mills.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> Acetaldehyde is also present in automobile and <a href="/wiki/Diesel_exhaust" title="Diesel exhaust">diesel exhaust</a>.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> As a result, acetaldehyde is "one of the most frequently found air toxics with cancer risk greater than one in a million".<sup id="cite_ref-:0_15-1" class="reference"><a href="#cite_note-:0-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Tobacco_smoke">Tobacco smoke</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=29" title="Edit section: Tobacco smoke"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Natural tobacco <a href="/wiki/Polysaccharides" class="mw-redirect" title="Polysaccharides">polysaccharides</a>, including <a href="/wiki/Cellulose" title="Cellulose">cellulose</a>, have been shown to be the primary precursors making acetaldehyde a significant constituent of <a href="/wiki/Tobacco_smoke" title="Tobacco smoke">tobacco smoke</a>.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TalhoutSchulz2011_62-0" class="reference"><a href="#cite_note-TalhoutSchulz2011-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> It has been demonstrated to have a <a href="/wiki/Synergy" title="Synergy">synergistic</a> effect with <a href="/wiki/Nicotine" title="Nicotine">nicotine</a> in <a href="/wiki/Animal_testing_on_rodents" title="Animal testing on rodents">rodent studies</a> of <a href="/wiki/Addiction" title="Addiction">addiction</a>.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Acetaldehyde is also the most abundant carcinogen in tobacco smoke; it is dissolved into the <a href="/wiki/Saliva" title="Saliva">saliva</a> while smoking. </p> <div class="mw-heading mw-heading4"><h4 id="Cannabis_smoke">Cannabis smoke</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=30" title="Edit section: Cannabis smoke"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde has been found in <a href="/wiki/Cannabis_smoking" title="Cannabis smoking">cannabis smoke</a>. This finding emerged through the use of new chemical techniques that demonstrated the acetaldehyde present was causing DNA damage in laboratory settings.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Alcohol_consumption">Alcohol consumption</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=31" title="Edit section: Alcohol consumption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many <a href="/wiki/Microbes" class="mw-redirect" title="Microbes">microbes</a> produce acetaldehyde from ethanol, but they have a lower capacity to eliminate the acetaldehyde, which can lead to the accumulation of acetaldehyde in saliva, stomach acid, and intestinal contents. <a href="/wiki/Fermentation" title="Fermentation">Fermented</a> food and many alcoholic beverages can also contain significant amounts of acetaldehyde. Acetaldehyde, derived from mucosal or microbial oxidation of ethanol, tobacco smoke, and diet, appears to act as a cumulative carcinogen in the upper digestive tract of humans.<sup id="cite_ref-SALASPURO_M_2011_66-0" class="reference"><a href="#cite_note-SALASPURO_M_2011-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> According to European Commission's Scientific Committee on Consumer Safety's (SCCS) "Opinion on Acetaldehyde" (2012) the <a href="/wiki/Cosmetics" title="Cosmetics">cosmetic</a> products special risk limit is 5 mg/L and acetaldehyde should not be used in <a href="/wiki/Mouthwash" title="Mouthwash">mouth-washing</a> products.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Plastics">Plastics</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=32" title="Edit section: Plastics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde can be produced by the <a href="/wiki/Photo-oxidation_of_polymers" title="Photo-oxidation of polymers">photo-oxidation</a> of <a href="/wiki/Polyethylene_terephthalate" title="Polyethylene terephthalate">polyethylene terephthalate</a> (PET), via a <a href="/wiki/Norrish_reaction" title="Norrish reaction">Type II Norrish reaction</a>.<sup id="cite_ref-Wiles&DayIII_68-0" class="reference"><a href="#cite_note-Wiles&DayIII-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Poly(ethylene_terephthalate)_-_Type_II_Norrish_to_acetaldehyde.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/Poly%28ethylene_terephthalate%29_-_Type_II_Norrish_to_acetaldehyde.png/600px-Poly%28ethylene_terephthalate%29_-_Type_II_Norrish_to_acetaldehyde.png" decoding="async" width="600" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/Poly%28ethylene_terephthalate%29_-_Type_II_Norrish_to_acetaldehyde.png/900px-Poly%28ethylene_terephthalate%29_-_Type_II_Norrish_to_acetaldehyde.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/50/Poly%28ethylene_terephthalate%29_-_Type_II_Norrish_to_acetaldehyde.png/1200px-Poly%28ethylene_terephthalate%29_-_Type_II_Norrish_to_acetaldehyde.png 2x" data-file-width="2348" data-file-height="308" /></a><figcaption></figcaption></figure> <p>Although the levels produced by this process are minute acetaldehyde has an exceedingly low taste/<a href="/wiki/Odor_threshold" class="mw-redirect" title="Odor threshold">odor threshold</a> of around 20–40 ppb and can cause an off-taste in bottled water.<sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Candida_overgrowth">Candida overgrowth</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=33" title="Edit section: Candida overgrowth"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Candida_albicans" title="Candida albicans">Candida albicans</a> in patients with potentially carcinogenic oral diseases has been shown to produce acetaldehyde in quantities sufficient to cause problems.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetaldehyde&action=edit&section=34" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">Alcohol dehydrogenase</a></li> <li><a href="/wiki/Disulfiram-like_drug" title="Disulfiram-like drug">Disulfiram-like drug</a></li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Wine_fault" title="Wine fault">Wine fault</a></li></ul> <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=Acetaldehyde&action=edit&section=35" title="Edit section: References"><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 reflist-columns references-column-width" style="column-width: 30em;"> <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">SciFinderScholar (accessed 4 November 2009). Acetaldehyde (75-07-0) Substance Detail.</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"><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 id="CITEREFShackelfordAbdelbaqiAlmhannaMeredith2014" class="citation book cs1">Shackelford, R.E.; Abdelbaqi, M.Q.; Almhanna, K.; Meredith, K. (2014). <a rel="nofollow" class="external text" href="https://link.springer.com/chapter/10.1007/978-94-007-7192-5_6">"Molecular Pathology and Diagnostics in Esophago-gastric Cancer"</a>. In Coppola, D. (ed.). <i>Molecular Pathology and Diagnostics of Cancer</i>. Cancer Growth and Progression. Vol. 16. Springer. pp. 177–210 See p. 190. <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%2F978-94-007-7192-5_6">10.1007/978-94-007-7192-5_6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-007-7192-5" title="Special:BookSources/978-94-007-7192-5"><bdi>978-94-007-7192-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Molecular+Pathology+and+Diagnostics+in+Esophago-gastric+Cancer&rft.btitle=Molecular+Pathology+and+Diagnostics+of+Cancer&rft.series=Cancer+Growth+and+Progression&rft.pages=177-210+See+p.+190&rft.pub=Springer&rft.date=2014&rft_id=info%3Adoi%2F10.1007%2F978-94-007-7192-5_6&rft.isbn=978-94-007-7192-5&rft.aulast=Shackelford&rft.aufirst=R.E.&rft.au=Abdelbaqi%2C+M.Q.&rft.au=Almhanna%2C+K.&rft.au=Meredith%2C+K.&rft_id=https%3A%2F%2Flink.springer.com%2Fchapter%2F10.1007%2F978-94-007-7192-5_6&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-iupac2013-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac2013_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac2013_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. p. 908. <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%2F9781849733069-00648">10.1039/9781849733069-00648</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+%28Blue+Book%29&rft.place=Cambridge&rft.pages=908&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-00648&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-Celanese-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Celanese_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Celanese_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.chemvip.com/eurprodbull-acetaldehyde-de.pdf"><i>Stoffdaten Acetaldehyd bei Celanese Chemicals.</i></a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080517053508/http://www.chemvip.com/eurprodbull-acetaldehyde-de.pdf">Archived</a> 17 May 2008 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> as of December 1999.</span> </li> <li id="cite_note-NIOSH-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-NIOSH_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NIOSH_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-NIOSH_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-NIOSH_5-3"><sup><i><b>d</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/npgd0001.html">"#0001"</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=%230001&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%2Fnpgd0001.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-CRC97-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-CRC97_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHaynesLideBruno2016" class="citation book cs1">Haynes, W.M.; Lide, D.R.; Bruno, T.J., eds. 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PubChem.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Acetaldehyde+%28Compound%29&rft.atitle=3.2.17+Viscosity&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2Facetaldehyde%23section%3DViscosity&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-crc-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-crc_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRumbleLideBruno2018" class="citation book cs1">Rumble, J.R.; Lide, D.R.; Bruno, T.J., eds. (2018). <i>CRC Handbook of Chemistry and Physics</i> (99th ed.). 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Retrieved on 2022-02-15.</span> </li> <li id="cite_note-IDLH-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-IDLH_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IDLH_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IDLH_10-2"><sup><i><b>c</b></i></sup></a></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.cdc.gov/niosh/idlh/75070.html">"Acetaldehyde"</a>. NIOSH. 4 December 2014<span class="reference-accessdate">. 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Office of Pollution Prevention and Toxics, United States Environmental Protection Agency. August 1994. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20020817234502/http://www.epa.gov/chemfact/f_acetal.txt">Archived</a> from the original on 17 August 2002<span class="reference-accessdate">. Retrieved <span class="nowrap">22 January</span> 2011</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=epa.gov&rft.atitle=Chemicals+in+the+Environment%3A+Acetaldehyde+%28CAS+NO.+75-07-0%29&rft.date=1994-08&rft_id=http%3A%2F%2Fwww.epa.gov%2Fchemfact%2Ff_acetal.txt&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></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"><a href="/wiki/List_of_IARC_Group_1_carcinogens" class="mw-redirect" title="List of IARC Group 1 carcinogens">List of IARC Group 1 carcinogens</a></span> </li> <li id="cite_note-:0-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_15-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZhouLiHuijbregtsMumtaz2015" class="citation journal cs1">Zhou, Ying; Li, Chaoyang; Huijbregts, Mark A. J.; Mumtaz, M. Moiz (7 October 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4596837">"Carcinogenic Air Toxics Exposure and Their Cancer-Related Health Impacts in the United States"</a>. <i>PLOS ONE</i>. <b>10</b> (10): e0140013. <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/2015PLoSO..1040013Z">2015PLoSO..1040013Z</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1371%2Fjournal.pone.0140013">10.1371/journal.pone.0140013</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4596837">4596837</a></span>. <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/26444872">26444872</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=PLOS+ONE&rft.atitle=Carcinogenic+Air+Toxics+Exposure+and+Their+Cancer-Related+Health+Impacts+in+the+United+States&rft.volume=10&rft.issue=10&rft.pages=e0140013&rft.date=2015-10-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4596837%23id-name%3DPMC&rft_id=info%3Apmid%2F26444872&rft_id=info%3Adoi%2F10.1371%2Fjournal.pone.0140013&rft_id=info%3Abibcode%2F2015PLoSO..1040013Z&rft.aulast=Zhou&rft.aufirst=Ying&rft.au=Li%2C+Chaoyang&rft.au=Huijbregts%2C+Mark+A.+J.&rft.au=Mumtaz%2C+M.+Moiz&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4596837&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" 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">Scheele, C. W. (1774) "Om Brunsten eller Magnesia nigra och dess egenskaper" (On brown-stone or black magnesia [i.e., manganese ore] and its properties), <i>Kungliga Svenska vetenskapsakademiens handlingar</i> (Proceedings of the Royal Swedish Academy of Sciences), <b>35</b> : 89–116; 177–194. On <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5ME4AAAAMAAJ&pg=PA109">pages 109–110</a>, Scheele mentions that refluxing ("digesting") ethanol (<i>Alkohol vini</i>) with manganese dioxide (<i>Brunsten</i>) and either hydrochloric acid (<i>Spirtus salis</i>) or sulfuric acid (<i>Spiritus Vitrioli</i>) produces a smell like <i>"Aether nitri"</i> (ethanol treated with nitric acid). Later investigators realized that Scheele had produced acetaldehyde.</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">Note: <ul><li>Dabit, a pharmacist in Nantes, France, performed a series of experiments and concluded that acetaldehyde was formed when hydrogen in ethanol combined with oxygen in sulfuric acid to form water: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDabit1800" class="citation journal cs1">Dabit (1800). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=PDZQAAAAcAAJ&pg=PA289">"Extrait du mémoire du cit. Dabit sur l'éther"</a> [Extract of the memoir by citizen Dabit on ether]. <i>Annales de Chimie</i>. <b>34</b>: <span class="nowrap">289–</span>305.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie&rft.atitle=Extrait+du+m%C3%A9moire+du+cit.+Dabit+sur+l%27%C3%A9ther&rft.volume=34&rft.pages=%3Cspan+class%3D%22nowrap%22%3E289-%3C%2Fspan%3E305&rft.date=1800&rft.au=Dabit&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DPDZQAAAAcAAJ%26pg%3DPA289&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></li> <li>Fourcroy and Vauquelin stated that sulfuric acid was not consumed in the production of acetaldehyde: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFourcroyVauquelin1800" class="citation journal cs1">Fourcroy; Vauquelin (1800). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=PDZQAAAAcAAJ&pg=PA318">"Sur l'éther préparé à la manière du cit. Dabit"</a> [On the ether prepared in the way of citizen Dabit]. <i>Annales de Chimie</i>. <b>34</b>: <span class="nowrap">318–</span>332.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie&rft.atitle=Sur+l%27%C3%A9ther+pr%C3%A9par%C3%A9+%C3%A0+la+mani%C3%A8re+du+cit.+Dabit&rft.volume=34&rft.pages=%3Cspan+class%3D%22nowrap%22%3E318-%3C%2Fspan%3E332&rft.date=1800&rft.au=Fourcroy&rft.au=Vauquelin&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DPDZQAAAAcAAJ%26pg%3DPA318&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></li></ul> </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">See: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDöbereiner1821" class="citation journal cs1">Döbereiner, J.W. (1821). <a rel="nofollow" class="external text" href="http://babel.hathitrust.org/cgi/pt?q1=D%C3%B6bereiner;id=nyp.33433069069122;view=1up;seq=301;start=1;size=10;page=search;num=270#view=1up;seq=287">"Neue Aether"</a> [New ethers]. <i>Journal für Chemie und Physik</i>. <b>32</b>: <span class="nowrap">269–</span>270.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+Chemie+und+Physik&rft.atitle=Neue+Aether&rft.volume=32&rft.pages=%3Cspan+class%3D%22nowrap%22%3E269-%3C%2Fspan%3E270&rft.date=1821&rft.aulast=D%C3%B6bereiner&rft.aufirst=J.W.&rft_id=http%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fq1%3DD%25C3%25B6bereiner%3Bid%3Dnyp.33433069069122%3Bview%3D1up%3Bseq%3D301%3Bstart%3D1%3Bsize%3D10%3Bpage%3Dsearch%3Bnum%3D270%23view%3D1up%3Bseq%3D287&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span> Döbereiner named the new "ether" <i>"Sauerstoffäther"</i> (oxygen-ether).</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDöbereiner1822" class="citation journal cs1">Döbereiner, J.W. (1822). <a rel="nofollow" class="external text" href="http://babel.hathitrust.org/cgi/pt?num=124&u=1&seq=344&view=1up&size=100&id=nyp.33433069069148&q1=D%C3%B6bereiner#view=1up;seq=140">"Döbereiner's Apparat zur Darstellung des Sauerstoffaethers"</a> [Döbereiner's apparatus for the preparation of oxygen-ether]. <i>Journal für Chemie und Physik</i>. <b>34</b>: <span class="nowrap">124–</span>5.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+Chemie+und+Physik&rft.atitle=D%C3%B6bereiner%27s+Apparat+zur+Darstellung+des+Sauerstoffaethers&rft.volume=34&rft.pages=%3Cspan+class%3D%22nowrap%22%3E124-%3C%2Fspan%3E5&rft.date=1822&rft.aulast=D%C3%B6bereiner&rft.aufirst=J.W.&rft_id=http%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fnum%3D124%26u%3D1%26seq%3D344%26view%3D1up%26size%3D100%26id%3Dnyp.33433069069148%26q1%3DD%25C3%25B6bereiner%23view%3D1up%3Bseq%3D140&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDöbereiner1832" class="citation journal cs1">Döbereiner, J.W. (1832). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mAYAAAAAMAAJ&pg=PA466">"Bildung des Sauerstoff-Aethers durch atmosphärische Oxidation des Alkohols"</a> [Formation of oxy-ether by atmospheric oxidation of alcohol]. <i>Journal für Chemie und Physik</i>. <b>64</b>: <span class="nowrap">466–</span>8.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+Chemie+und+Physik&rft.atitle=Bildung+des+Sauerstoff-Aethers+durch+atmosph%C3%A4rische+Oxidation+des+Alkohols&rft.volume=64&rft.pages=%3Cspan+class%3D%22nowrap%22%3E466-%3C%2Fspan%3E8&rft.date=1832&rft.aulast=D%C3%B6bereiner&rft.aufirst=J.W.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DmAYAAAAAMAAJ%26pg%3DPA466&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span> In this paper, Döbereiner made acetaldehyde by exposing ethanol vapor to air in the presence of platinum black.</li></ul> </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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLiebig1835" class="citation journal cs1">Liebig, Justus (1835). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=uva.x002457901;view=1up;seq=523">"Ueber die Producte der Oxydation des Alkohols"</a> [On the products of oxidation of alcohol [i.e., ethanol]]. <i>Annalen der Chemie</i>. <b>14</b>: <span class="nowrap">133–</span>167.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Chemie&rft.atitle=Ueber+die+Producte+der+Oxydation+des+Alkohols&rft.volume=14&rft.pages=%3Cspan+class%3D%22nowrap%22%3E133-%3C%2Fspan%3E167&rft.date=1835&rft.aulast=Liebig&rft.aufirst=Justus&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Duva.x002457901%3Bview%3D1up%3Bseq%3D523&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></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 id="CITEREFBrock1997" class="citation book cs1">Brock, William H. 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[I will describe it in this memoir by the name of <i>aldehyde</i>; this name is formed from <i>alcohol dehydrogenatus</i>.]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Sur+les+produits+de+l%27oxidation+de+l%27alcool&rft.volume=59&rft.pages=289-327+See+p.+290&rft.date=1835&rft.aulast=Liebig&rft.aufirst=J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D85c5AAAAcAAJ%26pg%3DPA289&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" 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="CITEREFSchlossberger1850" class="citation book cs1 cs1-prop-foreign-lang-source">Schlossberger, Julius Eugen (1850). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NWA3AAAAMAAJ&pg=PA234"><i>Lehrbuch der organischen Chemie mit besonderer Rücksicht auf Physiologie und Pathologie, auf Pharmacie, Technik und Landwirthschaft</i></a> (in German). 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(March 2013). <a rel="nofollow" class="external text" href="https://www.um.edu.mt/library/oar//handle/123456789/16302">"Production of carcinogenic acetaldehyde by <i>Candida albicans</i> from patients with potentially malignant oral mucosal disorders"</a>. <i>Journal of Oral Pathology and Medicine</i>. <b>42</b> (3): <span class="nowrap">243–</span>9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1600-0714.2012.01203.x">10.1111/j.1600-0714.2012.01203.x</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/22909057">22909057</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Oral+Pathology+and+Medicine&rft.atitle=Production+of+carcinogenic+acetaldehyde+by+Candida+albicans+from+patients+with+potentially+malignant+oral+mucosal+disorders&rft.volume=42&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E243-%3C%2Fspan%3E9&rft.date=2013-03&rft_id=info%3Adoi%2F10.1111%2Fj.1600-0714.2012.01203.x&rft_id=info%3Apmid%2F22909057&rft.aulast=Gainza-Cirauqui&rft.aufirst=M.L.&rft.au=Nieminen%2C+M.T.&rft.au=Novak+Frazer%2C+L.&rft.au=Aguirre-Urizar%2C+J.M.&rft.au=Moragues%2C+M.D.&rft.au=Rautemaa%2C+R.&rft_id=https%3A%2F%2Fwww.um.edu.mt%2Flibrary%2Foar%2F%2Fhandle%2F123456789%2F16302&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></span> </li> </ol></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=Acetaldehyde&action=edit&section=36" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/40px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/60px-Commons-logo.svg.png 1.5x" data-file-width="1024" data-file-height="1376" /></a></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Acetaldehyde" class="extiw" title="commons:Category:Acetaldehyde">Acetaldehyde</a></span>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0009.htm">International Chemical Safety Card 0009</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0001.html">NIOSH Pocket Guide to Chemical Hazards</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20081227035621/http://www.cdc.gov/niosh/nmam/pdfs/2018.pdf">"ALIPHATIC ALDEHYDES: METHOD 2018"</a> <span class="cs1-format">(PDF)</span>. <i>NIOSH Manual of Analytical Methods (NMAM)</i> (4th ed.). 15 March 2003. pp. <span class="nowrap">1–</span>10.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=ALIPHATIC+ALDEHYDES%3A+METHOD+2018&rft.btitle=NIOSH+Manual+of+Analytical+Methods+%28NMAM%29&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E10&rft.edition=4th&rft.date=2003-03-15&rft_id=https%3A%2F%2Fweb.archive.org%2Fweb%2F20081227035621%2Fhttp%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnmam%2Fpdfs%2F2018.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://publications.iarc.fr/_publications/media/download/2291/c8544cbda9f596bef663eb54801042da1af73405.pdf">"ACETALDEHYDE"</a> <span class="cs1-format">(PDF)</span>. <a rel="nofollow" class="external text" href="https://publications.iarc.fr/89"><i>Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide</i></a>. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Vol. 71. 1999. pp. <span class="nowrap">319–</span>334. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-832-1271-3" title="Special:BookSources/978-92-832-1271-3"><bdi>978-92-832-1271-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=ACETALDEHYDE&rft.btitle=Re-evaluation+of+Some+Organic+Chemicals%2C+Hydrazine+and+Hydrogen+Peroxide&rft.series=IARC+Monographs+on+the+Evaluation+of+Carcinogenic+Risks+to+Humans&rft.pages=%3Cspan+class%3D%22nowrap%22%3E319-%3C%2Fspan%3E334&rft.date=1999&rft.isbn=978-92-832-1271-3&rft_id=https%3A%2F%2Fpublications.iarc.fr%2F_publications%2Fmedia%2Fdownload%2F2291%2Fc8544cbda9f596bef663eb54801042da1af73405.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetaldehyde" class="Z3988"></span></li> <li>Hal Kibbey, <a rel="nofollow" class="external text" href="http://www.indiana.edu/~rcapub/v17n3/p18.html">Genetic Influences on Alcohol Drinking and Alcoholism</a>, Indiana University Research and Creative Activity, Vol. 17 no. 3.</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20041009142826/http://www.grokfood.com/additives/2.htm">United States Food and Drug Administration (FDA) information for acetaldehyde</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20130601111815/http://www.inclusive-science-engineering.com/acetaldehyde-production-ethylene-oxidation-stage-process/">Acetaldehyde production process flow sheet by ethylene oxidation method</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output 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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/120px-Ethanol-3D-balls.png 1.5x" 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/120px-Buckminsterfullerene-perspective-3D-balls.png 1.5x" 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="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">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/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</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/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</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/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</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/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="/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="/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/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/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</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="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</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/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 class="mw-selflink selflink">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/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</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/Acrolein" title="Acrolein">Acrolein</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/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</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/Ethanethiol" title="Ethanethiol">Ethanethiol</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/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</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/Propionitrile" title="Propionitrile">Propionitrile</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/Butyronitrile" title="Butyronitrile">Butyronitrile</a></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 href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</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> <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/Pyrimidine" title="Pyrimidine">Pyrimidine</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/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</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/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</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/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</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/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 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