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class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Properties subsection</span> </button> <ul id="toc-Properties-sublist" class="vector-toc-list"> <li id="toc-Acidity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acidity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Acidity</span> </div> </a> <ul id="toc-Acidity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Solvent_properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Solvent_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Solvent properties</span> </div> </a> <ul id="toc-Solvent_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-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 Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Methanol_carbonylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Methanol_carbonylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Methanol carbonylation</span> </div> </a> <ul id="toc-Methanol_carbonylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acetaldehyde_oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acetaldehyde_oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Acetaldehyde oxidation</span> </div> </a> <ul id="toc-Acetaldehyde_oxidation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ethylene_oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ethylene_oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Ethylene oxidation</span> </div> </a> <ul id="toc-Ethylene_oxidation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidative_fermentation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidative_fermentation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Oxidative fermentation</span> </div> </a> <ul id="toc-Oxidative_fermentation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anaerobic_fermentation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anaerobic_fermentation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.5</span> <span>Anaerobic fermentation</span> </div> </a> <ul id="toc-Anaerobic_fermentation-sublist" class="vector-toc-list"> </ul> </li> </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> <button aria-controls="toc-Uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Vinyl_acetate_monomer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vinyl_acetate_monomer"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Vinyl acetate monomer</span> </div> </a> <ul id="toc-Vinyl_acetate_monomer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ester_production" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ester_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Ester production</span> </div> </a> <ul id="toc-Ester_production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acetic_anhydride" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acetic_anhydride"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Acetic anhydride</span> </div> </a> <ul id="toc-Acetic_anhydride-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Use_as_solvent" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Use_as_solvent"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Use as solvent</span> </div> </a> <ul id="toc-Use_as_solvent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Medical_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Medical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Medical use</span> </div> </a> <ul id="toc-Medical_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Foods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Foods"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Foods</span> </div> </a> <ul id="toc-Foods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</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-Organic_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Organic_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Organic chemistry</span> </div> </a> <ul id="toc-Organic_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions_with_inorganic_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactions_with_inorganic_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Reactions with inorganic compounds</span> </div> </a> <ul id="toc-Reactions_with_inorganic_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Other derivatives</span> </div> </a> <ul id="toc-Other_derivatives-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Health_and_safety" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Health_and_safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Health and safety</span> </div> </a> <button aria-controls="toc-Health_and_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 Health and safety subsection</span> </button> <ul id="toc-Health_and_safety-sublist" class="vector-toc-list"> <li id="toc-Vapour" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vapour"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Vapour</span> </div> </a> <ul id="toc-Vapour-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Solution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Solution"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Solution</span> </div> </a> <ul id="toc-Solution-sublist" class="vector-toc-list"> </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">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</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">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Acetic acid</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 91 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-91" 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">91 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Asynsuur" title="Asynsuur – Afrikaans" lang="af" hreflang="af" data-title="Asynsuur" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D8%AE%D9%84%D9%8A%D9%83" title="حمض الخليك – Arabic" lang="ar" hreflang="ar" data-title="حمض الخليك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/%C3%81cidu_ac%C3%A9tico" title="Ácidu acético – Asturian" lang="ast" hreflang="ast" data-title="Ácidu acético" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Sirk%C9%99_tur%C5%9Fusu" title="Sirkə turşusu – Azerbaijani" lang="az" hreflang="az" data-title="Sirkə turşusu" 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%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="استیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="استیک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ban mw-list-item"><a href="https://ban.wikipedia.org/wiki/Asam_as%C3%A9tat" title="Asam asétat – Balinese" lang="ban" hreflang="ban" data-title="Asam asétat" data-language-autonym="Basa Bali" data-language-local-name="Balinese" class="interlanguage-link-target"><span>Basa Bali</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%9F%E0%A6%BF%E0%A6%95_%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%A1" title="অ্যাসিটিক অ্যাসিড – Bangla" lang="bn" hreflang="bn" data-title="অ্যাসিটিক অ্যাসিড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Chh%C3%B2%CD%98-sng" title="Chhò͘-sng – Minnan" lang="nan" hreflang="nan" data-title="Chhò͘-sng" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%92%D0%BE%D1%86%D0%B0%D1%82%D0%BD%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Воцатная кіслата – Belarusian" lang="be" hreflang="be" data-title="Воцатная кіслата" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Asidong_asetiko" title="Asidong asetiko – Central Bikol" lang="bcl" hreflang="bcl" data-title="Asidong asetiko" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://bg.wikipedia.org/wiki/%D0%9E%D1%86%D0%B5%D1%82%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Оцетна киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Оцетна киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bo mw-list-item"><a href="https://bo.wikipedia.org/wiki/%E0%BD%A8%E0%BD%BA%E0%BC%8B%E0%BD%A6%E0%BD%B2%E0%BC%8B%E0%BD%8A%E0%BD%B2%E0%BD%82%E0%BC%8B%E0%BD%A6%E0%BE%90%E0%BE%B1%E0%BD%B4%E0%BD%A2%E0%BC%8B%E0%BD%A2%E0%BE%AB%E0%BD%A6%E0%BC%8D" title="ཨེ་སི་ཊིག་སྐྱུར་རྫས། – Tibetan" lang="bo" hreflang="bo" data-title="ཨེ་སི་ཊིག་སྐྱུར་རྫས།" data-language-autonym="བོད་ཡིག" data-language-local-name="Tibetan" class="interlanguage-link-target"><span>བོད་ཡིག</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Sir%C4%87etna_kiselina" title="Sirćetna kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Sirćetna kiselina" 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/%C3%80cid_ac%C3%A8tic" title="Àcid acètic – Catalan" lang="ca" hreflang="ca" data-title="Àcid acètic" 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/Kyselina_octov%C3%A1" title="Kyselina octová – Czech" lang="cs" hreflang="cs" data-title="Kyselina octová" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Asid_asetig" title="Asid asetig – Welsh" lang="cy" hreflang="cy" data-title="Asid asetig" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da badge-Q17559452 badge-recommendedarticle mw-list-item" title="recommended article"><a href="https://da.wikipedia.org/wiki/Eddikesyre" title="Eddikesyre – Danish" lang="da" hreflang="da" data-title="Eddikesyre" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://de.wikipedia.org/wiki/Essigs%C3%A4ure" title="Essigsäure – German" lang="de" hreflang="de" data-title="Essigsäure" 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/Etaanhape" title="Etaanhape – Estonian" lang="et" hreflang="et" data-title="Etaanhape" 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%9F%CE%BE%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Οξικό οξύ – Greek" lang="el" hreflang="el" data-title="Οξικό οξύ" 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/%C3%81cido_ac%C3%A9tico" title="Ácido acético – Spanish" lang="es" hreflang="es" data-title="Ácido acético" 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/Acetata_acido" title="Acetata acido – Esperanto" lang="eo" hreflang="eo" data-title="Acetata acido" 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/Azido_azetiko" title="Azido azetiko – Basque" lang="eu" hreflang="eu" data-title="Azido azetiko" 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%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="استیک اسید – Persian" lang="fa" hreflang="fa" data-title="استیک اسید" 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/Acide_ac%C3%A9tique" title="Acide acétique – French" lang="fr" hreflang="fr" data-title="Acide acétique" 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/Aig%C3%A9ad_eat%C3%A1n%C3%B3ch" title="Aigéad eatánóch – Irish" lang="ga" hreflang="ga" data-title="Aigéad eatánóch" 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/%C3%81cido_ac%C3%A9tico" title="Ácido acético – Galician" lang="gl" hreflang="gl" data-title="Ácido acético" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-inh mw-list-item"><a href="https://inh.wikipedia.org/wiki/%D0%9A%D1%8A%D0%B0%D0%BD%D0%B7%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Къанза кислота – Ingush" lang="inh" hreflang="inh" data-title="Къанза кислота" data-language-autonym="ГӀалгӀай" data-language-local-name="Ingush" class="interlanguage-link-target"><span>ГӀалгӀай</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%82%B0" title="아세트산 – Korean" lang="ko" hreflang="ko" data-title="아세트산" 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/%D5%94%D5%A1%D6%81%D5%A1%D5%AD%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Քացախաթթու – Armenian" lang="hy" hreflang="hy" data-title="Քացախաթթու" 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%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="एसिटिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="एसिटिक अम्ल" 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/Octena_kiselina" title="Octena kiselina – Croatian" lang="hr" hreflang="hr" data-title="Octena kiselina" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Acetat-acido" title="Acetat-acido – Ido" lang="io" hreflang="io" data-title="Acetat-acido" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_asetat" title="Asam asetat – Indonesian" lang="id" hreflang="id" data-title="Asam asetat" 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-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Acido_acetic" title="Acido acetic – Interlingua" lang="ia" hreflang="ia" data-title="Acido acetic" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Ediks%C3%BDra" title="Ediksýra – Icelandic" lang="is" hreflang="is" data-title="Ediksýra" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_acetico" title="Acido acetico – Italian" lang="it" hreflang="it" data-title="Acido acetico" 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%97%D7%95%D7%9E%D7%A6%D7%94_%D7%90%D7%A6%D7%98%D7%99%D7%AA" title="חומצה אצטית – Hebrew" lang="he" hreflang="he" data-title="חומצה אצטית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asem_asetat" title="Asem asetat – Javanese" lang="jv" hreflang="jv" data-title="Asem asetat" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%85%E0%B2%B8%E0%B2%BF%E0%B2%9F%E0%B2%BF%E0%B2%95%E0%B3%8D_%E0%B2%86%E0%B2%AE%E0%B3%8D%E0%B2%B2" title="ಅಸಿಟಿಕ್ ಆಮ್ಲ – Kannada" lang="kn" hreflang="kn" data-title="ಅಸಿಟಿಕ್ ಆಮ್ಲ" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%AB%E1%83%9B%E1%83%90%E1%83%A0%E1%83%9B%E1%83%9F%E1%83%90%E1%83%95%E1%83%90" title="ძმარმჟავა – Georgian" lang="ka" hreflang="ka" data-title="ძმარმჟავა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-csb mw-list-item"><a href="https://csb.wikipedia.org/wiki/%C3%92ctowi_kwas" title="Òctowi kwas – Kashubian" lang="csb" hreflang="csb" data-title="Òctowi kwas" data-language-autonym="Kaszëbsczi" data-language-local-name="Kashubian" class="interlanguage-link-target"><span>Kaszëbsczi</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A1%D1%96%D1%80%D0%BA%D0%B5_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D1%8B" title="Сірке қышқылы – Kazakh" lang="kk" hreflang="kk" data-title="Сірке қышқылы" 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%A3%D0%BA%D1%81%D1%83%D1%81_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D1%81%D1%8B" title="Уксус кислотасы – Kyrgyz" lang="ky" hreflang="ky" data-title="Уксус кислотасы" 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/Acidum_aceticum" title="Acidum aceticum – Latin" lang="la" hreflang="la" data-title="Acidum aceticum" 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/Eti%C4%B7sk%C4%81be" title="Etiķskābe – Latvian" lang="lv" hreflang="lv" data-title="Etiķskābe" 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/Acto_r%C5%ABg%C5%A1tis" title="Acto rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Acto rūgštis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Aekzoer" title="Aekzoer – Limburgish" lang="li" hreflang="li" data-title="Aekzoer" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target"><span>Limburgs</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ecetsav" title="Ecetsav – Hungarian" lang="hu" hreflang="hu" data-title="Ecetsav" 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%9E%D1%86%D0%B5%D1%82%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Оцетна киселина – Macedonian" lang="mk" hreflang="mk" data-title="Оцетна киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%85%E0%B4%B8%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%85%E0%B4%AE%E0%B5%8D%E0%B4%B2%E0%B4%82" title="അസറ്റിക് അമ്ലം – Malayalam" lang="ml" hreflang="ml" data-title="അസറ്റിക് അമ്ലം" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_asetik" title="Asid asetik – Malay" lang="ms" hreflang="ms" data-title="Asid asetik" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-min mw-list-item"><a href="https://min.wikipedia.org/wiki/Asam_asetat" title="Asam asetat – Minangkabau" lang="min" hreflang="min" data-title="Asam asetat" data-language-autonym="Minangkabau" data-language-local-name="Minangkabau" class="interlanguage-link-target"><span>Minangkabau</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Azijnzuur" title="Azijnzuur – Dutch" lang="nl" hreflang="nl" data-title="Azijnzuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://ja.wikipedia.org/wiki/%E9%85%A2%E9%85%B8" title="酢酸 – Japanese" lang="ja" hreflang="ja" data-title="酢酸" 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-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Eetjs%C3%BCren" title="Eetjsüren – Northern Frisian" lang="frr" hreflang="frr" data-title="Eetjsüren" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Eddiksyre" title="Eddiksyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Eddiksyre" 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/Eddiksyre" title="Eddiksyre – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Eddiksyre" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Acid_acetic" title="Acid acetic – Occitan" lang="oc" hreflang="oc" data-title="Acid acetic" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Asiidii_aseetikii" title="Asiidii aseetikii – Oromo" lang="om" hreflang="om" data-title="Asiidii aseetikii" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Sirka_kislota" title="Sirka kislota – Uzbek" lang="uz" hreflang="uz" data-title="Sirka kislota" 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-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%90%E0%A8%B8%E0%A9%80%E0%A8%9F%E0%A8%BF%E0%A8%95_%E0%A8%A4%E0%A9%87%E0%A8%9C%E0%A8%BC%E0%A8%BE%E0%A8%AC" title="ਐਸੀਟਿਕ ਤੇਜ਼ਾਬ – Punjabi" lang="pa" hreflang="pa" data-title="ਐਸੀਟਿਕ ਤੇਜ਼ਾਬ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_octowy" title="Kwas octowy – Polish" lang="pl" hreflang="pl" data-title="Kwas 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/%C3%81cido_etanoico" title="Ácido etanoico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido etanoico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://ro.wikipedia.org/wiki/Acid_acetic" title="Acid acetic – Romanian" lang="ro" hreflang="ro" data-title="Acid acetic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-qu mw-list-item"><a href="https://qu.wikipedia.org/wiki/Mama_aqha_p%27uchqu" title="Mama aqha p'uchqu – Quechua" lang="qu" hreflang="qu" data-title="Mama aqha p'uchqu" data-language-autonym="Runa Simi" data-language-local-name="Quechua" class="interlanguage-link-target"><span>Runa Simi</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A3%D0%BA%D1%81%D1%83%D1%81%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Уксусная кислота – Russian" lang="ru" hreflang="ru" data-title="Уксусная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Acetic_acid" title="Acetic acid – Scots" lang="sco" hreflang="sco" data-title="Acetic acid" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Acidi_etanoik_ose_acidi_acetik" title="Acidi etanoik ose acidi acetik – Albanian" lang="sq" hreflang="sq" data-title="Acidi etanoik ose acidi acetik" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%87%E0%B7%83%E0%B7%92%E0%B6%A7%E0%B7%92%E0%B6%9A%E0%B7%8A_%E0%B6%85%E0%B6%B8%E0%B7%8A%E0%B6%BD%E0%B6%BA" title="ඇසිටික් අම්ලය – Sinhala" lang="si" hreflang="si" data-title="ඇසිටික් අම්ලය" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Acetic_acid" title="Acetic acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Acetic acid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_octov%C3%A1" title="Kyselina octová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina octová" 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/Etanojska_kislina" title="Etanojska kislina – Slovenian" lang="sl" hreflang="sl" data-title="Etanojska kislina" 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/%D0%A1%D0%B8%D1%80%D1%9B%D0%B5%D1%82%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Сирћетна киселина – Serbian" lang="sr" hreflang="sr" data-title="Сирћетна киселина" 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/Sir%C4%87etna_kiselina" title="Sirćetna kiselina – 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hreflang="tr" data-title="Asetik asit" 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%9E%D1%86%D1%82%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Оцтова кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Оцтова кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A7%DB%8C%D8%B3%DB%8C%D9%B9%DA%A9_%D8%A7%DB%8C%D8%B3%DA%88" title="ایسیٹک ایسڈ – Urdu" lang="ur" hreflang="ur" data-title="ایسیٹک ایسڈ" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_acetic" title="Acid acetic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid acetic" 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-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E4%B9%99%E9%85%B8" title="乙酸 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="乙酸" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Aksido_Asetico" title="Aksido Asetico – Waray" lang="war" hreflang="war" data-title="Aksido Asetico" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a 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Click here for more information."><img alt="Featured article" src="//upload.wikimedia.org/wikipedia/en/thumb/e/e7/Cscr-featured.svg/20px-Cscr-featured.svg.png" decoding="async" width="20" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e7/Cscr-featured.svg/30px-Cscr-featured.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/e/e7/Cscr-featured.svg/40px-Cscr-featured.svg.png 2x" data-file-width="466" data-file-height="443" /></a></span></div></div> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Colorless and faint organic acid found in vinegar</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Acetic" redirects here. Not to be confused with <a href="/wiki/Asceticism" title="Asceticism">Ascetic</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Acetic acid </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" typeof="mw:File"><a href="/wiki/File:Acetic-acid-2D-skeletal.svg" class="mw-file-description" title="Skeletal formula of acetic acid"><img alt="Skeletal formula of acetic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Acetic-acid-2D-skeletal.svg/110px-Acetic-acid-2D-skeletal.svg.png" decoding="async" width="110" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Acetic-acid-2D-skeletal.svg/165px-Acetic-acid-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/08/Acetic-acid-2D-skeletal.svg/220px-Acetic-acid-2D-skeletal.svg.png 2x" data-file-width="454" data-file-height="391" /></a><figcaption>Skeletal formula of acetic acid</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetic-acid-CRC-GED-3D-vdW-B.png" class="mw-file-description" title="Spacefill model of acetic acid"><img alt="Spacefill model of acetic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Acetic-acid-CRC-GED-3D-vdW-B.png/110px-Acetic-acid-CRC-GED-3D-vdW-B.png" decoding="async" width="110" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Acetic-acid-CRC-GED-3D-vdW-B.png/165px-Acetic-acid-CRC-GED-3D-vdW-B.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Acetic-acid-CRC-GED-3D-vdW-B.png/220px-Acetic-acid-CRC-GED-3D-vdW-B.png 2x" data-file-width="1100" data-file-height="975" /></a><figcaption>Spacefill model of acetic acid</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Essigs%C3%A4ure_-_Acetic_acid.svg" class="mw-file-description" title="Skeletal formula of acetic acid with all explicit hydrogens added"><img alt="Skeletal formula of acetic acid with all explicit hydrogens added" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Essigs%C3%A4ure_-_Acetic_acid.svg/110px-Essigs%C3%A4ure_-_Acetic_acid.svg.png" decoding="async" width="110" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Essigs%C3%A4ure_-_Acetic_acid.svg/165px-Essigs%C3%A4ure_-_Acetic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/Essigs%C3%A4ure_-_Acetic_acid.svg/220px-Essigs%C3%A4ure_-_Acetic_acid.svg.png 2x" data-file-width="152" data-file-height="97" /></a><figcaption>Skeletal formula of acetic acid with all explicit hydrogens added</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetic-acid-CRC-GED-3D-balls-B.png" class="mw-file-description" title="Ball and stick model of acetic acid"><img alt="Ball and stick model of acetic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Acetic-acid-CRC-GED-3D-balls-B.png/110px-Acetic-acid-CRC-GED-3D-balls-B.png" decoding="async" width="110" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Acetic-acid-CRC-GED-3D-balls-B.png/165px-Acetic-acid-CRC-GED-3D-balls-B.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Acetic-acid-CRC-GED-3D-balls-B.png/220px-Acetic-acid-CRC-GED-3D-balls-B.png 2x" data-file-width="1100" data-file-height="850" /></a><figcaption>Ball and stick model of acetic acid</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Acetic_acid.jpg" class="mw-file-description" title="Sample of acetic acid in a reagent bottle"><img alt="Sample of acetic acid in a reagent bottle" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Acetic_acid.jpg/244px-Acetic_acid.jpg" decoding="async" width="244" height="402" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Acetic_acid.jpg/366px-Acetic_acid.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Acetic_acid.jpg/488px-Acetic_acid.jpg 2x" data-file-width="598" data-file-height="986" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/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;">Acetic acid<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;">Ethanoic acid</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;">Vinegar (when dilute); Hydrogen acetate; Methanecarboxylic acid; Ethylic acid<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><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; 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=64-19-7">64-19-7</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=CC%28O%29%3DO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00009">B00009</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>AcOH </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>506007 </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=15366">CHEBI:15366</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL539">ChEMBL539</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.171.html">171</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/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03166">DB03166</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/100.000.528">100.000.528</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q47512#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>200-580-7</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E260 <a href="/wiki/E_number#E200–E299" title="E number">(preservatives)</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>1380 </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=1058">1058</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/C00033">C00033</a></span></li><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00010">D00010</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Acetic+acid">Acetic+acid</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/176">176</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>AF1225000</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/Q40Q9N063P">Q40Q9N063P</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>2789 </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/DTXSID5024394">DTXSID5024394</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q47512#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)<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: QTBSBXVTEAMEQO-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></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(O)=O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOH</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="7001600520000000000♠"></span>60.052</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colourless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Heavily vinegar-like </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.049 g/cm<sup>3</sup> (liquid); 1.27 g/cm<sup>3</sup> (solid) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>16 to 17 °C; 61 to 62 °F; 289 to 290 K </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>118 to 119 °C; 244 to 246 °F; 391 to 392 K </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td><a href="/wiki/Miscibility" title="Miscibility">Miscible</a> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−0.28<sup id="cite_ref-chemsrc_4-0" class="reference"><a href="#cite_note-chemsrc-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>1.54653947<span class="nowrap"> </span>kPa (20 °C) <br /> 11.6<span class="nowrap"> </span>mmHg (20 °C)<sup id="cite_ref-lange_5-0" class="reference"><a href="#cite_note-lange-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>4.756 </td></tr> <tr> <td><a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">Conjugate base</a> </td> <td><a href="/wiki/Acetate" title="Acetate">Acetate</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−31.54·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.371 (V<sub>D</sub> = 18.19) </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>1.22 mPa s <br /> 1.22 cP </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>1.74 D </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>123.1 J/(K⋅mol) </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>158.0 J/(K⋅mol) </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>−483.88–483.16 kJ/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−875.50–874.82 kJ/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_G01" title="ATC code G01">G01AD02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G01AD02">WHO</a></span>) <a href="/wiki/ATC_code_S02" title="ATC code S02">S02AA10</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S02AA10">WHO</a></span>) </td></tr> <tr> <td><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_2" title="Standard for the Uniform Scheduling of Medicines and Poisons">S2</a> (Pharmacy medicine) and S6</li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><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-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H226: Flammable liquid and vapour">H226</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</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>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_cac26dcfb9c9c85a" /></span><map name="ImageMap_cac26dcfb9c9c85a"><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 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 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 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>40 °C (104 °F; 313 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>427 °C (801 °F; 700 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>4–16% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><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>3.31 g/kg, oral (rat) </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>5620 ppm (mouse, 1 <a href="/wiki/Hour" title="Hour">h</a>)<br />16000 ppm (rat, 4 h)<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> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 10 ppm (25 mg/m<sup>3</sup>)<sup id="cite_ref-PGCH_6-0" class="reference"><a href="#cite_note-PGCH-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 10 ppm (25 mg/m<sup>3</sup>) ST 15 ppm (37 mg/m<sup>3</sup>)<sup id="cite_ref-PGCH_6-1" class="reference"><a href="#cite_note-PGCH-6"><span class="cite-bracket">[</span>6<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>50 ppm<sup id="cite_ref-PGCH_6-2" class="reference"><a href="#cite_note-PGCH-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a></div> </td> <td><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a><br /><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic acid</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a><br /><a href="/wiki/Acetamide" title="Acetamide">Acetamide</a><br /><a href="/wiki/Acetic_anhydride" title="Acetic anhydride">Acetic anhydride</a><br /><a href="/wiki/Chloroacetic_acid" title="Chloroacetic acid">Chloroacetic acid</a><br /><a href="/wiki/Acetyl_chloride" title="Acetyl chloride">Acetyl chloride</a><br /><a href="/wiki/Glycolic_acid" title="Glycolic acid">Glycolic acid</a><br /><a href="/wiki/Ethyl_acetate" title="Ethyl acetate">Ethyl acetate</a><br /><a href="/wiki/Potassium_acetate" title="Potassium acetate">Potassium acetate</a><br /><a href="/wiki/Sodium_acetate" title="Sodium acetate">Sodium acetate</a><br /><a href="/wiki/Thioacetic_acid" title="Thioacetic acid">Thioacetic acid</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Acetic_acid_(data_page)" title="Acetic acid (data page)">Acetic acid (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477238786&page2=Acetic+acid">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> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Acetic acid">Acetic acid</span></caption><tbody><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/acetic-acid.html">Monograph</a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a></th><td class="infobox-data">E260 <a href="/wiki/E_number#E200–E299" title="E number">(preservatives)</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q47512#P628" 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><th scope="row" class="infobox-label" style="line-height:1.2em;"><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></th><td class="infobox-data"><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/DTXSID5024394">DTXSID5024394</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q47512#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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.528">100.000.528</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q47512#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><th colspan="2" class="infobox-header" style="background:#ddd">Data page</th></tr><tr><td colspan="2" class="infobox-full-data"><a href="/wiki/Acetic_acid_(data_page)" title="Acetic acid (data page)">Acetic acid (data page)</a></td></tr></tbody></table> <p><b>Acetic acid</b> <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ə/: 'a' in 'about'">ə</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'s' in 'sigh'">s</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'t' in 'tie'">t</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'k' in 'kind'">k</span></span>/</a></span></span>, systematically named <b>ethanoic acid</b> <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="/θ/: 'th' in 'thigh'">θ</span><span title="/ə/: 'a' in 'about'">ə</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'n' in 'nigh'">n</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'k' in 'kind'">k</span></span>/</a></span></span>, is an acidic, colourless liquid and <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical 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>COOH</span> (also written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">2</sub></span>, or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HC<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub></span>). <a href="/wiki/Vinegar" title="Vinegar">Vinegar</a> is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC. </p><p>Acetic acid is the second simplest <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> (after <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>). It is an important <a href="/wiki/Reagent" title="Reagent">chemical reagent</a> and industrial chemical across various fields, used primarily in the production of <a href="/wiki/Cellulose_acetate" title="Cellulose acetate">cellulose acetate</a> for <a href="/wiki/Photographic_film" title="Photographic film">photographic film</a>, <a href="/wiki/Polyvinyl_acetate" title="Polyvinyl acetate">polyvinyl acetate</a> for wood <a href="/wiki/Adhesive" title="Adhesive">glue</a>, and synthetic fibres and fabrics. In households, diluted acetic acid is often used in <a href="/wiki/Descaling_agent" title="Descaling agent">descaling agents</a>. In the <a href="/wiki/Food_industry" title="Food industry">food industry</a>, acetic acid is controlled by the <a href="/wiki/E_number" title="E number">food additive code</a> E260 as an <a href="/wiki/Acidity_regulator" title="Acidity regulator">acidity regulator</a> and as a condiment. In <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>, the <a href="/wiki/Acetyl_group" title="Acetyl group">acetyl group</a>, derived from acetic acid, is fundamental to all forms of life. When bound to <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a>, it is central to the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> and <a href="/wiki/Fat" title="Fat">fats</a>. </p><p>The global demand for acetic acid as of 2023 is about 17.88 million <a href="/wiki/Tonne" title="Tonne">metric tonnes</a> per year (t/a). Most of the world's acetic acid is produced via the <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> of <a href="/wiki/Methanol" title="Methanol">methanol</a>. Its production and subsequent industrial use poses health hazards to workers, including incidental skin damage and chronic respiratory injuries from inhalation. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Trivial_name" title="Trivial name">trivial name</a> "acetic acid" is the most commonly used and <a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">preferred IUPAC name</a>. The systematic name "ethanoic acid", a valid <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> name, is constructed according to the substitutive nomenclature.<sup id="cite_ref-BB-prs310305_8-0" class="reference"><a href="#cite_note-BB-prs310305-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The name "acetic acid" derives from the <a href="/wiki/Latin" title="Latin">Latin</a> word for <a href="/wiki/Vinegar" title="Vinegar">vinegar</a>, "<i lang="la"><a href="https://en.wiktionary.org/wiki/acetum#Latin" class="extiw" title="wikt:acetum">acetum</a></i>", which is related to the word "<a href="/wiki/Acid" title="Acid">acid</a>" itself. </p><p>"Glacial acetic acid" is a name for water-free (<a href="/wiki/Anhydrous" title="Anhydrous">anhydrous</a>) acetic acid. Similar to the <a href="/wiki/German_language" title="German language">German</a> name "Eisessig" ("ice vinegar"), the name comes from the solid ice-like crystals that form with agitation, slightly below room temperature at 16.6 °C (61.9 °F). Acetic acid can never be truly water-free in an atmosphere that contains water, so the presence of 0.1% water in glacial acetic acid lowers its melting point by 0.2 °C.<sup id="cite_ref-Purification_of_Laboratory_Chemicals_9-0" class="reference"><a href="#cite_note-Purification_of_Laboratory_Chemicals-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>A common <a href="/wiki/Symbol_(chemistry)" class="mw-redirect" title="Symbol (chemistry)">symbol</a> for acetic acid is AcOH (or HOAc), where Ac is the <a href="/wiki/Pseudoelement_symbol" class="mw-redirect" title="Pseudoelement symbol">pseudoelement symbol</a> representing the <a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">acetyl</a> <a href="/wiki/Functional_group" title="Functional group">group</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−C(=O)−</span>; the <a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate base</a>, <a href="/wiki/Acetate" title="Acetate">acetate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COO<sup class="template-chem2-sup">−</sup></span>), is thus represented as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">AcO<sup class="template-chem2-sup">−</sup></span>.<sup id="cite_ref-Cooper_10-0" class="reference"><a href="#cite_note-Cooper-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Acetate is the <a href="/wiki/Ion" title="Ion">ion</a> resulting from loss of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Proton" title="Proton">H<sup class="template-chem2-sup">+</sup></a></span> from acetic acid. The name "acetate" can also refer to a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> containing this anion, or an <a href="/wiki/Ester" title="Ester">ester</a> of acetic acid.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> (The symbol Ac for the acetyl functional group is not to be confused with the symbol Ac for the element <a href="/wiki/Actinium" title="Actinium">actinium</a>; context prevents confusion among organic chemists). To better reflect its structure, acetic acid is often written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−C(O)OH</span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−C(=O)−OH</span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOH</span>, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span>. In the context of <a href="/wiki/Acid%E2%80%93base_reaction" title="Acid–base reaction">acid–base reactions</a>, the abbreviation HAc is sometimes used,<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> where Ac in this case is a symbol for acetate (rather than acetyl). </p><p>The carboxymethyl functional group derived from removing one hydrogen from the <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> group of acetic acid has the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−C(=O)−OH</span>. </p> <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=Acetic_acid&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Vinegar" title="Vinegar">Vinegar</a> was known early in civilization as the natural result of exposure of <a href="/wiki/Beer" title="Beer">beer</a> and <a href="/wiki/Wine" title="Wine">wine</a> to air because acetic acid-producing bacteria are present globally. The use of acetic acid in <a href="/wiki/Alchemy" title="Alchemy">alchemy</a> extends into the third century BC, when the Greek philosopher <a href="/wiki/Theophrastus" title="Theophrastus">Theophrastus</a> described how vinegar acted on metals to produce <a href="/wiki/Pigment" title="Pigment">pigments</a> useful in art, including <i>white lead</i> (<a href="/wiki/Lead_carbonate" title="Lead carbonate">lead carbonate</a>) and <i><a href="/wiki/Verdigris" title="Verdigris">verdigris</a></i>, a green mixture of <a href="/wiki/Copper" title="Copper">copper</a> salts including <a href="/wiki/Copper(II)_acetate" title="Copper(II) acetate">copper(II) acetate</a>. Ancient <a href="/wiki/Rome" title="Rome">Romans</a> boiled soured wine to produce a highly sweet syrup called <i>sapa</i>. <a href="/wiki/Defrutum" class="mw-redirect" title="Defrutum">Sapa</a> that was produced in lead pots was rich in <a href="/wiki/Lead(II)_acetate" title="Lead(II) acetate">lead acetate</a>, a sweet substance also called <i>sugar of lead</i> or <i>sugar of <a href="/wiki/Saturn_(mythology)" title="Saturn (mythology)">Saturn</a></i>, which contributed to <a href="/wiki/Lead_poisoning" title="Lead poisoning">lead poisoning</a> among the Roman aristocracy.<sup id="cite_ref-martin_13-0" class="reference"><a href="#cite_note-martin-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>In the 16th-century <a href="/wiki/Germany" title="Germany">German</a> alchemist <a href="/wiki/Andreas_Libavius" title="Andreas Libavius">Andreas Libavius</a> described the production of <a href="/wiki/Acetone" title="Acetone">acetone</a> from the <a href="/wiki/Dry_distillation" title="Dry distillation">dry distillation</a> of lead acetate, <a href="/wiki/Ketonic_decarboxylation" title="Ketonic decarboxylation">ketonic decarboxylation</a>. The presence of water in vinegar has such a profound effect on acetic acid's properties that for centuries chemists believed that glacial acetic acid and the acid found in vinegar were two different substances. French chemist <a href="/wiki/Pierre_Adet" title="Pierre Adet">Pierre Adet</a> proved them identical.<sup id="cite_ref-martin_13-1" class="reference"><a href="#cite_note-martin-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><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> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:AceticAcid012.jpg" class="mw-file-description"><img alt="glass beaker of crystallised acetic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/AceticAcid012.jpg/170px-AceticAcid012.jpg" decoding="async" width="170" height="217" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/AceticAcid012.jpg/255px-AceticAcid012.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/AceticAcid012.jpg/340px-AceticAcid012.jpg 2x" data-file-width="583" data-file-height="744" /></a><figcaption>Crystallised acetic acid</figcaption></figure> <p>In 1845 German chemist <a href="/wiki/Hermann_Kolbe" title="Hermann Kolbe">Hermann Kolbe</a> <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesised</a> acetic acid from <a href="/wiki/Inorganic_compound" title="Inorganic compound">inorganic compounds</a> for the first time. This reaction sequence consisted of <a href="/wiki/Chlorination_reaction" class="mw-redirect" title="Chlorination reaction">chlorination</a> of <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">carbon disulfide</a> to <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a>, followed by <a href="/wiki/Pyrolysis" title="Pyrolysis">pyrolysis</a> to <a href="/wiki/Tetrachloroethylene" title="Tetrachloroethylene">tetrachloroethylene</a> and aqueous chlorination to <a href="/wiki/Trichloroacetic_acid" title="Trichloroacetic acid">trichloroacetic acid</a>, and concluded with <a href="/wiki/Electrolysis" title="Electrolysis">electrolytic</a> <a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">reduction</a> to acetic acid.<sup id="cite_ref-goldwhite_15-0" class="reference"><a href="#cite_note-goldwhite-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>By 1910, most glacial acetic acid was obtained from the <a href="/wiki/Pyroligneous_acid" title="Pyroligneous acid">pyroligneous liquor</a>, a product of the distillation of wood. The acetic acid was isolated by treatment with <a href="/wiki/Limewater" class="mw-redirect" title="Limewater">milk of lime</a>, and the resulting <a href="/wiki/Calcium_acetate" title="Calcium acetate">calcium acetate</a> was then acidified with <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> to recover acetic acid. At that time, Germany was producing 10,000 <a href="/wiki/Ton" title="Ton">tons</a> of glacial acetic acid, around 30% of which was used for the manufacture of <a href="/wiki/Indigo_dye" title="Indigo dye">indigo dye</a>.<sup id="cite_ref-martin_13-2" class="reference"><a href="#cite_note-martin-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-schweppe_16-0" class="reference"><a href="#cite_note-schweppe-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Because both <a href="/wiki/Methanol" title="Methanol">methanol</a> and <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> are commodity raw materials, methanol carbonylation long appeared to be attractive precursors to acetic acid. <a href="/wiki/Henri_Dreyfus" title="Henri Dreyfus">Henri Dreyfus</a> at <a href="/wiki/British_Celanese" title="British Celanese">British Celanese</a> developed a methanol carbonylation pilot plant as early as 1925.<sup id="cite_ref-wagner_17-0" class="reference"><a href="#cite_note-wagner-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> However, a lack of practical materials that could contain the corrosive reaction mixture at the high <a href="/wiki/Pressure" title="Pressure">pressures</a> needed (200 <a href="/wiki/Atmosphere_(unit)" class="mw-redirect" title="Atmosphere (unit)">atm</a> or more) discouraged commercialization of these routes. The first commercial methanol carbonylation process, which used a <a href="/wiki/Cobalt" title="Cobalt">cobalt</a> catalyst, was developed by German chemical company <a href="/wiki/BASF" title="BASF">BASF</a> in 1963. In 1968, a <a href="/wiki/Rhodium" title="Rhodium">rhodium</a>-based catalyst (<i>cis</i>−<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Rh(CO)<sub class="template-chem2-sub">2</sub>I<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup></span>) was discovered that could operate efficiently at lower pressure with almost no by-products. US chemical company <a href="/wiki/Monsanto_Company" class="mw-redirect" title="Monsanto Company">Monsanto Company</a> built the first plant using this catalyst in 1970, and rhodium-catalyzed methanol carbonylation became the dominant method of acetic acid production (see <a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto process</a>). In the late 1990s, <a href="/wiki/BP" title="BP">BP</a> Chemicals commercialised the Cativa catalyst (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Ir(CO)<sub class="template-chem2-sub">2</sub>I<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup></span>), which is promoted by <a href="/wiki/Iridium" title="Iridium">iridium</a> for greater efficiency.<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> Known as the <a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a>, the <a href="/wiki/Iridium" title="Iridium">iridium</a>-catalyzed production of glacial acetic acid is <a href="/wiki/Green_chemistry" title="Green chemistry">greener</a>, and has largely supplanted the Monsanto process, often in the same production plants.<sup id="cite_ref-lancaster_19-0" class="reference"><a href="#cite_note-lancaster-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Interstellar_medium">Interstellar medium</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=3" title="Edit section: Interstellar medium"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar</a> acetic acid was discovered in 1996 by a team led by David Mehringer<sup id="cite_ref-Meh_20-0" class="reference"><a href="#cite_note-Meh-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> using the former <a href="/wiki/Berkeley-Illinois-Maryland_Association" title="Berkeley-Illinois-Maryland Association">Berkeley-Illinois-Maryland Association</a> array at the <a href="/wiki/Hat_Creek_Radio_Observatory" title="Hat Creek Radio Observatory">Hat Creek Radio Observatory</a> and the former <a href="/wiki/Millimeter_Array" class="mw-redirect" title="Millimeter Array">Millimeter Array</a> located at the <a href="/wiki/Owens_Valley_Radio_Observatory" title="Owens Valley Radio Observatory">Owens Valley Radio Observatory</a>. It was first detected in the <a href="/wiki/Sagittarius_B2" title="Sagittarius B2">Sagittarius B2</a> North molecular cloud (also known as the Sgr B2 <a href="/wiki/Large_Molecule_Heimat" title="Large Molecule Heimat">Large Molecule Heimat</a> source). Acetic acid has the distinction of being the first molecule discovered in the interstellar medium using solely <a href="/wiki/Radio_telescope#Radio_interferometry" title="Radio telescope">radio interferometers</a>; in all previous ISM molecular discoveries made in the millimetre and centimetre wavelength regimes, single dish radio telescopes were at least partly responsible for the detections.<sup id="cite_ref-Meh_20-1" class="reference"><a href="#cite_note-Meh-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=4" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:AceticAcid010.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/AceticAcid010.png/170px-AceticAcid010.png" decoding="async" width="170" height="230" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/1/19/AceticAcid010.png 1.5x" data-file-width="238" data-file-height="322" /></a><figcaption>Acetic acid crystals</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Acidity">Acidity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=5" title="Edit section: Acidity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The hydrogen centre in the <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl group</a> (−COOH) in carboxylic acids such as acetic acid can separate from the molecule by ionization: </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>COOH ⇌ CH<sub class="template-chem2-sub">3</sub>CO<span class="template-chem2-su"><span>−</span><span>2</span></span> + H<sup class="template-chem2-sup">+</sup></span></dd></dl> <p>Because of this release of the <a href="/wiki/Proton" title="Proton">proton</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sup class="template-chem2-sup">+</sup></span>), acetic acid has acidic character. Acetic acid is a weak <a href="/wiki/Monoprotic_acid" class="mw-redirect" title="Monoprotic acid">monoprotic acid</a>. In aqueous solution, it has a <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pK<sub>a</sub></a> value of 4.76.<sup id="cite_ref-Goldmine_21-0" class="reference"><a href="#cite_note-Goldmine-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Its <a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate base</a> is <a href="/wiki/Acetate" title="Acetate">acetate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COO<sup class="template-chem2-sup">−</sup></span>). A 1.0 <a href="/wiki/Molarity" class="mw-redirect" title="Molarity">M</a> solution (about the concentration of domestic vinegar) has a <a href="/wiki/PH" title="PH">pH</a> of 2.4, indicating that merely 0.4% of the acetic acid molecules are dissociated.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Acetic_acid_deprotonation.svg" class="mw-file-description" title="Deprotonation equilibrium of acetic acid in water"><img alt="Deprotonation equilibrium of acetic acid in water" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Acetic_acid_deprotonation.svg/375px-Acetic_acid_deprotonation.svg.png" decoding="async" width="375" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Acetic_acid_deprotonation.svg/563px-Acetic_acid_deprotonation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Acetic_acid_deprotonation.svg/750px-Acetic_acid_deprotonation.svg.png 2x" data-file-width="555" data-file-height="100" /></a></span> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Acetic_Acid_Hydrogenbridge_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Acetic_Acid_Hydrogenbridge_V.1.svg/220px-Acetic_Acid_Hydrogenbridge_V.1.svg.png" decoding="async" width="220" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Acetic_Acid_Hydrogenbridge_V.1.svg/330px-Acetic_Acid_Hydrogenbridge_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Acetic_Acid_Hydrogenbridge_V.1.svg/440px-Acetic_Acid_Hydrogenbridge_V.1.svg.png 2x" data-file-width="448" data-file-height="150" /></a><figcaption>Cyclic dimer of acetic acid; dashed <span style="color:green;"><b>green</b></span> lines represent hydrogen bonds</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Structure">Structure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=6" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In solid acetic acid, the molecules form chains of individual molecules interconnected by <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a>.<sup id="cite_ref-jones_23-0" class="reference"><a href="#cite_note-jones-23"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In the vapour phase at 120 °C (248 °F), <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimers</a> can be detected. Dimers also occur in the liquid phase in dilute solutions with non-hydrogen-bonding solvents, and to a certain extent in pure acetic acid,<sup id="cite_ref-briggs_24-0" class="reference"><a href="#cite_note-briggs-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> but are disrupted by hydrogen-bonding solvents. The dissociation <a href="/wiki/Enthalpy" title="Enthalpy">enthalpy</a> of the dimer is estimated at 65.0–66.0 kJ/mol, and the dissociation entropy at 154–157 J mol<sup>−1</sup> K<sup>−1</sup>.<sup id="cite_ref-togeas_25-0" class="reference"><a href="#cite_note-togeas-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Other carboxylic acids engage in similar intermolecular hydrogen bonding interactions.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Solvent_properties">Solvent properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=7" title="Edit section: Solvent properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Liquid" title="Liquid">Liquid</a> acetic acid is a <a href="/wiki/Hydrophile" title="Hydrophile">hydrophilic</a> (<a href="/wiki/Polar_molecule" class="mw-redirect" title="Polar molecule">polar</a>) <a href="/wiki/Protic_solvent" title="Protic solvent">protic solvent</a>, similar to <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and <a href="/wiki/Water" title="Water">water</a>. With a <a href="/wiki/Relative_static_permittivity" class="mw-redirect" title="Relative static permittivity">relative static permittivity</a> (dielectric constant) of 6.2, it dissolves not only polar compounds such as inorganic salts and <a href="/wiki/Sugar" title="Sugar">sugars</a>, but also non-polar compounds such as oils as well as polar solutes. It is miscible with polar and non-polar <a href="/wiki/Solvent" title="Solvent">solvents</a> such as water, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, and <a href="/wiki/Hexane" title="Hexane">hexane</a>. With higher alkanes (starting with <a href="/wiki/Octane" title="Octane">octane</a>), acetic acid is not <a href="/wiki/Miscible" class="mw-redirect" title="Miscible">miscible</a> at all compositions, and solubility of acetic acid in alkanes declines with longer n-alkanes.<sup id="cite_ref-Zieborak_27-0" class="reference"><a href="#cite_note-Zieborak-27"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The solvent and <a href="/wiki/Miscibility" title="Miscibility">miscibility</a> properties of acetic acid make it a useful industrial chemical, for example, as a solvent in the production of <a href="/wiki/Dimethyl_terephthalate" title="Dimethyl terephthalate">dimethyl terephthalate</a>.<sup id="cite_ref-Ullmann_28-0" class="reference"><a href="#cite_note-Ullmann-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biochemistry">Biochemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=8" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>At physiological pHs, acetic acid is usually fully ionised to <a href="/wiki/Acetate" title="Acetate">acetate</a> in aqueous solution.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">acetyl</a> <a href="/wiki/Functional_group" title="Functional group">group</a>, formally derived from acetic acid, is fundamental to all forms of life. Typically, it is bound to <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a> by <a href="/wiki/Acetyl-CoA_synthetase" title="Acetyl-CoA synthetase">acetyl-CoA synthetase</a> enzymes,<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> where it is central to the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> and <a href="/wiki/Fat" title="Fat">fats</a>. Unlike longer-chain carboxylic acids (the <a href="/wiki/Fatty_acids" class="mw-redirect" title="Fatty acids">fatty acids</a>), acetic acid does not occur in natural <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>. Most of the acetate generated in cells for use in <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> is synthesized directly from <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> or <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvate</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> However, the artificial triglyceride <a href="/wiki/Triacetin" title="Triacetin">triacetin</a> (glycerine triacetate) is a common food additive and is found in cosmetics and topical medicines; this additive is metabolized to <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> and acetic acid in the body.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Acetic acid is produced and <a href="/wiki/Excretion" title="Excretion">excreted</a> by <a href="/wiki/Acetic_acid_bacteria" title="Acetic acid bacteria">acetic acid bacteria</a>, notably the genus <i><a href="/wiki/Acetobacter" title="Acetobacter">Acetobacter</a></i> and <i><a href="/wiki/Clostridium_acetobutylicum" title="Clostridium acetobutylicum">Clostridium acetobutylicum</a></i>. These bacteria are found universally in <a href="/wiki/Food" title="Food">foodstuffs</a>, <a href="/wiki/Water" title="Water">water</a>, and <a href="/wiki/Soil" title="Soil">soil</a>, and acetic acid is produced naturally as fruits and other foods spoil. Acetic acid is also a component of the <a href="/wiki/Vaginal_lubrication" title="Vaginal lubrication">vaginal lubrication</a> of <a href="/wiki/Human" title="Human">humans</a> and other <a href="/wiki/Primate" title="Primate">primates</a>, where it appears to serve as a mild <a href="/wiki/Antibacterial" class="mw-redirect" title="Antibacterial">antibacterial</a> agent.<sup id="cite_ref-dict_33-0" class="reference"><a href="#cite_note-dict-33"><span class="cite-bracket">[</span>32<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=Acetic_acid&action=edit&section=9" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Acetic_acid_1884_plant.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Acetic_acid_1884_plant.jpg/220px-Acetic_acid_1884_plant.jpg" decoding="async" width="220" height="282" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Acetic_acid_1884_plant.jpg/330px-Acetic_acid_1884_plant.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Acetic_acid_1884_plant.jpg/440px-Acetic_acid_1884_plant.jpg 2x" data-file-width="467" data-file-height="599" /></a><figcaption>Purification and concentration plant for acetic acid in 1884</figcaption></figure> <p>Acetic acid is produced industrially both synthetically and by bacterial <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a>. About 75% of acetic acid made for use in the chemical industry is made by the <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> of <a href="/wiki/Methanol" title="Methanol">methanol</a>, explained below.<sup id="cite_ref-Ullmann_28-1" class="reference"><a href="#cite_note-Ullmann-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The biological route accounts for only about 10% of world production, but it remains important for the production of vinegar because many food purity laws require vinegar used in foods to be of biological origin. Other processes are <a href="/wiki/Methyl_formate" title="Methyl formate">methyl formate</a> isomerization, conversion of <a href="/wiki/Syngas" title="Syngas">syngas</a> to acetic acid, and gas phase oxidation of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>.<sup id="cite_ref-Yoneda_2001_34-0" class="reference"><a href="#cite_note-Yoneda_2001-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Acetic acid can be purified via <a href="/wiki/Fractional_freezing" title="Fractional freezing">fractional freezing</a> using an ice bath. The water and other <a href="/wiki/Impurity" class="mw-redirect" title="Impurity">impurities</a> will remain liquid while the acetic acid will <a href="/wiki/Precipitation_(chemistry)" title="Precipitation (chemistry)">precipitate</a> out. As of 2003–2005, total worldwide production of virgin acetic acid<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>b<span class="cite-bracket">]</span></a></sup> was estimated at 5 Mt/a (million tonnes per year), approximately half of which was produced in the United States. European production was approximately 1 Mt/a and declining, while Japanese production was 0.7 Mt/a. Another 1.5 Mt were recycled each year, bringing the total world market to 6.5 Mt/a.<sup id="cite_ref-suresh_36-0" class="reference"><a href="#cite_note-suresh-36"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Since then, the global production has increased from 10.7 Mt/a in 2010<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> to 17.88 Mt/a in 2023.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The two biggest producers of virgin acetic acid are <a href="/wiki/Celanese" title="Celanese">Celanese</a> and <a href="/wiki/BP" title="BP">BP</a> Chemicals. Other major producers include <a href="/wiki/Millennium_Chemicals" title="Millennium Chemicals">Millennium Chemicals</a>, <a href="/wiki/Sterling_Chemicals" title="Sterling Chemicals">Sterling Chemicals</a>, <a href="/wiki/Samsung" title="Samsung">Samsung</a>, <a href="/wiki/Eastman_Chemical_Company" title="Eastman Chemical Company">Eastman</a>, and <a href="/w/index.php?title=Svensk_Etanolkemi&action=edit&redlink=1" class="new" title="Svensk Etanolkemi (page does not exist)">Svensk Etanolkemi</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://sv.wikipedia.org/wiki/Svensk_Etanolkemi" class="extiw" title="sv:Svensk Etanolkemi">sv</a>]</span>.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Methanol_carbonylation">Methanol carbonylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=10" title="Edit section: Methanol carbonylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most acetic acid is produced by methanol <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a>. In this process, <a href="/wiki/Methanol" title="Methanol">methanol</a> and <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> react to produce acetic acid according to the equation: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Methanol_formylation.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Methanol_formylation.png/250px-Methanol_formylation.png" decoding="async" width="250" height="47" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Methanol_formylation.png/375px-Methanol_formylation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Methanol_formylation.png/500px-Methanol_formylation.png 2x" data-file-width="1950" data-file-height="366" /></a></span></dd></dl> <p>The process involves <a href="/wiki/Iodomethane" title="Iodomethane">iodomethane</a> as an intermediate, and occurs in three steps. A <a href="/wiki/Metal_carbonyl" title="Metal carbonyl">metal carbonyl</a> <a href="/wiki/Catalysis" title="Catalysis">catalyst</a> is needed for the carbonylation (step 2).<sup id="cite_ref-Yoneda_2001_34-1" class="reference"><a href="#cite_note-Yoneda_2001-34"><span class="cite-bracket">[</span>33<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">CH<sub class="template-chem2-sub">3</sub>OH + HI → CH<sub class="template-chem2-sub">3</sub>I + H<sub class="template-chem2-sub">2</sub>O</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>I + CO → CH<sub class="template-chem2-sub">3</sub>COI</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>COI + H<sub class="template-chem2-sub">2</sub>O → CH<sub class="template-chem2-sub">3</sub>COOH + HI</span></li></ol> <p>Two related processes exist for the carbonylation of methanol: the rhodium-catalyzed <a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto process</a>, and the iridium-catalyzed <a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a>. The latter process is <a href="/wiki/Green_chemistry" title="Green chemistry">greener</a> and more efficient and has largely supplanted the former process.<sup id="cite_ref-lancaster_19-1" class="reference"><a href="#cite_note-lancaster-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Catalytic amounts of water are used in both processes, but the Cativa process requires less, so the <a href="/wiki/Water-gas_shift_reaction" class="mw-redirect" title="Water-gas shift reaction">water-gas shift reaction</a> is suppressed, and fewer by-products are formed. </p><p>By altering the process conditions, <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> may also be produced in plants using rhodium catalysis.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Acetaldehyde_oxidation">Acetaldehyde oxidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=11" title="Edit section: Acetaldehyde oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Prior to the commercialization of the Monsanto process, most acetic acid was produced by oxidation of <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>. This remains the second-most-important manufacturing method, although it is usually not competitive with the carbonylation of methanol. The acetaldehyde can be produced by <a href="/wiki/Alkyne_hydration" class="mw-redirect" title="Alkyne hydration">hydration of acetylene</a>. This was the dominant technology in the early 1900s.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>Light <a href="/wiki/Naphtha" title="Naphtha">naphtha</a> components are readily oxidized by oxygen or even air to give <a href="/wiki/Organic_peroxide" class="mw-redirect" title="Organic peroxide">peroxides</a>, which decompose to produce acetic acid according to the <a href="/wiki/Chemical_equation" title="Chemical equation">chemical equation</a>, illustrated with <a href="/wiki/Butane" title="Butane">butane</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">10</sub> + 5 O<sub class="template-chem2-sub">2</sub> → 4 CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Such oxidations require metal catalyst, such as the <a href="/wiki/Naphthenic_acid" title="Naphthenic acid">naphthenate</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> of <a href="/wiki/Manganese" title="Manganese">manganese</a>, <a href="/wiki/Cobalt" title="Cobalt">cobalt</a>, and <a href="/wiki/Chromium" title="Chromium">chromium</a>. </p><p>The typical reaction is conducted at <a href="/wiki/Temperature" title="Temperature">temperatures</a> and pressures designed to be as hot as possible while still keeping the butane a liquid. Typical reaction conditions are 150 °C (302 °F) and 55 atm.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Side-products may also form, including <a href="/wiki/Butanone" title="Butanone">butanone</a>, <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a>, <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>, and <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a>. These side-products are also commercially valuable, and the reaction conditions may be altered to produce more of them where needed. However, the separation of acetic acid from these by-products adds to the cost of the process.<sup id="cite_ref-Sano_1999_44-0" class="reference"><a href="#cite_note-Sano_1999-44"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>Similar conditions and <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a> are used for butane oxidation, the <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> in <a href="/wiki/Earth%27s_atmosphere" class="mw-redirect" title="Earth's atmosphere">air</a> to produce acetic acid can oxidize <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>.<sup id="cite_ref-Sano_1999_44-1" class="reference"><a href="#cite_note-Sano_1999-44"><span class="cite-bracket">[</span>42<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>CHO + O<sub class="template-chem2-sub">2</sub> → 2 CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span></dd></dl> <p>Using modern catalysts, this reaction can have an acetic acid yield greater than 95%. The major side-products are <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a>, <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>, and <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a>, all of which have lower <a href="/wiki/Boiling_point" title="Boiling point">boiling points</a> than acetic acid and are readily separated by <a href="/wiki/Distillation" title="Distillation">distillation</a>.<sup id="cite_ref-Sano_1999_44-2" class="reference"><a href="#cite_note-Sano_1999-44"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Ethylene_oxidation">Ethylene oxidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=12" title="Edit section: Ethylene oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetaldehyde may be prepared from <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> via the <a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a>, and then oxidised as above. </p><p>In more recent times, chemical company <a href="/wiki/Showa_Denko" title="Showa Denko">Showa Denko</a>, which opened an ethylene oxidation plant in <a href="/wiki/%C5%8Cita_Prefecture" title="Ōita Prefecture">Ōita</a>, Japan, in 1997, commercialised a cheaper single-stage conversion of ethylene to acetic acid.<sup id="cite_ref-Sano_1999_44-3" class="reference"><a href="#cite_note-Sano_1999-44"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> The process is catalyzed by a <a href="/wiki/Palladium" title="Palladium">palladium</a> metal catalyst supported on a <a href="/wiki/Heteropoly_acid" class="mw-redirect" title="Heteropoly acid">heteropoly acid</a> such as <a href="/wiki/Silicotungstic_acid" title="Silicotungstic acid">silicotungstic acid</a>. A similar process uses the same metal catalyst on silicotungstic acid and silica:<sup id="cite_ref-Misono_45-0" class="reference"><a href="#cite_note-Misono-45"><span class="cite-bracket">[</span>43<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">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub> + O<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span></dd></dl> <p>It is thought to be competitive with methanol carbonylation for smaller plants (100–250 kt/a), depending on the local price of ethylene. </p> <div class="mw-heading mw-heading3"><h3 id="Oxidative_fermentation">Oxidative fermentation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=13" title="Edit section: Oxidative fermentation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>For most of human history, acetic acid bacteria of the genus <i><a href="/wiki/Acetobacter" title="Acetobacter">Acetobacter</a></i> have made acetic acid, in the form of vinegar. Given sufficient oxygen, these bacteria can produce vinegar from a variety of alcoholic foodstuffs. Commonly used feeds include <a href="/wiki/Cider" title="Cider">apple cider</a>, <a href="/wiki/Wine" title="Wine">wine</a>, and fermented <a href="/wiki/Cereal" title="Cereal">grain</a>, <a href="/wiki/Malt" title="Malt">malt</a>, <a href="/wiki/Rice" title="Rice">rice</a>, or <a href="/wiki/Potato" title="Potato">potato</a> mashes. The overall chemical reaction facilitated by these bacteria is: </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">5</sub>OH + O<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">3</sub>COOH + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>A dilute alcohol solution inoculated with <i>Acetobacter</i> and kept in a warm, airy place will become vinegar over the course of a few months. Industrial vinegar-making methods accelerate this process by improving the supply of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> to the bacteria.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p><p>The first batches of vinegar produced by fermentation probably followed errors in the <a href="/wiki/Winemaking" title="Winemaking">winemaking</a> process. If <a href="/wiki/Must" title="Must">must</a> is fermented at too high a temperature, acetobacter will overwhelm the <a href="/wiki/Yeast_(wine)" class="mw-redirect" title="Yeast (wine)">yeast</a> naturally occurring on the <a href="/wiki/Grapes" class="mw-redirect" title="Grapes">grapes</a>. As the demand for vinegar for culinary, medical, and sanitary purposes increased, vintners quickly learned to use other organic materials to produce vinegar in the hot summer months before the grapes were ripe and ready for processing into wine. This method was slow, however, and not always successful, as the vintners did not understand the process.<sup id="cite_ref-Hromatka_47-0" class="reference"><a href="#cite_note-Hromatka-47"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>One of the first modern commercial processes was the "fast method" or "German method", first practised in Germany in 1823. In this process, fermentation takes place in a tower packed with wood shavings or <a href="/wiki/Charcoal" title="Charcoal">charcoal</a>. The alcohol-containing feed is trickled into the top of the tower, and fresh <a href="/wiki/Earth%27s_atmosphere" class="mw-redirect" title="Earth's atmosphere">air</a> supplied from the bottom by either natural or forced <a href="/wiki/Convection" title="Convection">convection</a>. The improved air supply in this process cut the time to prepare vinegar from months to weeks.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>Nowadays, most vinegar is made in submerged tank <a href="/wiki/Microbiological_culture" title="Microbiological culture">culture</a>, first described in 1949 by Otto Hromatka and Heinrich Ebner.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> In this method, alcohol is fermented to vinegar in a continuously stirred tank, and oxygen is supplied by bubbling air through the solution. Using modern applications of this method, vinegar of 15% acetic acid can be prepared in only 24 hours in batch process, even 20% in 60-hour fed-batch process.<sup id="cite_ref-Hromatka_47-1" class="reference"><a href="#cite_note-Hromatka-47"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Anaerobic_fermentation">Anaerobic fermentation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=14" title="Edit section: Anaerobic fermentation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Species of <a href="/wiki/Anaerobic_bacteria" class="mw-redirect" title="Anaerobic bacteria">anaerobic bacteria</a>, including members of the genus <i><a href="/wiki/Clostridium" title="Clostridium">Clostridium</a></i> or <i><a href="/wiki/Acetobacterium" title="Acetobacterium">Acetobacterium</a></i>, can convert sugars to acetic acid directly without creating ethanol as an intermediate. The overall chemical reaction conducted by these bacteria may be represented as: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6</sub> → 3 CH<sub class="template-chem2-sub">3</sub>COOH</span></dd></dl> <p>These <a href="/wiki/Acetogen" title="Acetogen">acetogenic</a> bacteria produce acetic acid from one-carbon compounds, including methanol, <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>, or a mixture of <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 CO<sub class="template-chem2-sub">2</sub> + 4 H<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">3</sub>COOH + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>This ability of <i>Clostridium</i> to metabolize sugars directly, or to produce acetic acid from less costly inputs, suggests that these bacteria could produce acetic acid more efficiently than ethanol-oxidizers like <i>Acetobacter</i>. However, <i>Clostridium</i> bacteria are less acid-tolerant than <i>Acetobacter</i>. Even the most acid-tolerant <i>Clostridium</i> strains can produce vinegar in concentrations of only a few per cent, compared to <i>Acetobacter</i> strains that can produce vinegar in concentrations up to 20%. At present, it remains more cost-effective to produce vinegar using <i>Acetobacter</i>, rather than using <i>Clostridium</i> and concentrating it. As a result, although acetogenic bacteria have been known since 1940, their industrial use is confined to a few niche applications.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>48<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=Acetic_acid&action=edit&section=15" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetic acid is a chemical <a href="/wiki/Reagent" title="Reagent">reagent</a> for the production of chemical compounds. The largest single use of acetic acid is in the production of vinyl acetate <a href="/wiki/Monomer" title="Monomer">monomer</a>, closely followed by acetic anhydride and ester production. The volume of acetic acid used in vinegar is comparatively small.<sup id="cite_ref-Ullmann_28-2" class="reference"><a href="#cite_note-Ullmann-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-suresh_36-1" class="reference"><a href="#cite_note-suresh-36"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Vinyl_acetate_monomer">Vinyl acetate monomer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=16" title="Edit section: Vinyl acetate monomer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The primary use of acetic acid is the production of <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a> monomer (VAM). In 2008, this application was estimated to consume a third of the world's production of acetic acid.<sup id="cite_ref-Ullmann_28-3" class="reference"><a href="#cite_note-Ullmann-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The reaction consists of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> and acetic acid with <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> over a <a href="/wiki/Palladium" title="Palladium">palladium</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>, conducted in the gas phase.<sup id="cite_ref-vinyl-esters_51-0" class="reference"><a href="#cite_note-vinyl-esters-51"><span class="cite-bracket">[</span>49<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 H<sub class="template-chem2-sub">3</sub>C−COOH + 2 C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub> + O<sub class="template-chem2-sub">2</sub> → 2 H<sub class="template-chem2-sub">3</sub>C−CO−O−CH=CH<sub class="template-chem2-sub">2</sub> + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Vinyl acetate can be polymerised to <a href="/wiki/Polyvinyl_acetate" title="Polyvinyl acetate">polyvinyl acetate</a> or other <a href="/wiki/Polymers" class="mw-redirect" title="Polymers">polymers</a>, which are components in <a href="/wiki/Paint" title="Paint">paints</a> and <a href="/wiki/Adhesive" title="Adhesive">adhesives</a>.<sup id="cite_ref-vinyl-esters_51-1" class="reference"><a href="#cite_note-vinyl-esters-51"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Ester_production">Ester production</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=17" title="Edit section: Ester production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The major <a href="/wiki/Ester" title="Ester">esters</a> of acetic acid are commonly used as solvents for <a href="/wiki/Ink" title="Ink">inks</a>, <a href="/wiki/Paint" title="Paint">paints</a> and <a href="/wiki/Coating" title="Coating">coatings</a>. The esters include <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a>, <i>n</i>-<a href="/wiki/Butyl_acetate" title="Butyl acetate">butyl acetate</a>, <a href="/wiki/Isobutyl_acetate" title="Isobutyl acetate">isobutyl acetate</a>, and <a href="/wiki/Propyl_acetate" title="Propyl acetate">propyl acetate</a>. They are typically produced by <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyzed</a> reaction from acetic acid and the corresponding <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>: </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>COO−H + HO−R → CH<sub class="template-chem2-sub">3</sub>COO−R + H<sub class="template-chem2-sub">2</sub>O</span>, R = general <a href="/wiki/Alkyl_group" title="Alkyl group">alkyl group</a></dd></dl> <p>For example, acetic acid and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> gives <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> and <a href="/wiki/Water" title="Water">water</a>. </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>COO−H + HO−CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub> → CH<sub class="template-chem2-sub">3</sub>COO−CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Most acetate <a href="/wiki/Esters" class="mw-redirect" title="Esters">esters</a>, however, are produced from <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> using the <a href="/wiki/Tishchenko_reaction" title="Tishchenko reaction">Tishchenko reaction</a>. In addition, ether acetates are used as solvents for <a href="/wiki/Nitrocellulose" title="Nitrocellulose">nitrocellulose</a>, <a href="/wiki/Acrylic_lacquer" class="mw-redirect" title="Acrylic lacquer">acrylic lacquers</a>, <a href="/wiki/Varnish" title="Varnish">varnish</a> removers, and wood stains. First, glycol monoethers are produced from <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a> or <a href="/wiki/Propylene_oxide" title="Propylene oxide">propylene oxide</a> with alcohol, which are then esterified with acetic acid. The three major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA, more commonly known as PGMEA in semiconductor manufacturing processes, where it is used as a resist solvent). This application consumes about 15% to 20% of worldwide acetic acid. Ether acetates, for example EEA, have been shown to be harmful to human reproduction.<sup id="cite_ref-suresh_36-2" class="reference"><a href="#cite_note-suresh-36"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Acetic_anhydride">Acetic anhydride</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=18" title="Edit section: Acetic anhydride"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The product of the <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation</a> of two molecules of acetic acid is <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a>. The worldwide production of acetic anhydride is a major application, and uses approximately 25% to 30% of the global production of acetic acid. The main process involves dehydration of acetic acid to give <a href="/wiki/Ethenone" title="Ethenone">ketene</a> at 700–750 °C. Ketene is thereafter reacted with acetic acid to obtain the anhydride:<sup id="cite_ref-acetic-anh_52-0" class="reference"><a href="#cite_note-acetic-anh-52"><span class="cite-bracket">[</span>50<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">CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H → CH<sub class="template-chem2-sub">2</sub>=C=O + H<sub class="template-chem2-sub">2</sub>O</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H + CH<sub class="template-chem2-sub">2</sub>=C=O → (CH<sub class="template-chem2-sub">3</sub>CO)<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Acetic anhydride is an <a href="/wiki/Acetylation" title="Acetylation">acetylation</a> agent. As such, its major application is for <a href="/wiki/Cellulose_acetate" title="Cellulose acetate">cellulose acetate</a>, a synthetic <a href="/wiki/Textile" title="Textile">textile</a> also used for <a href="/wiki/Photographic_film" title="Photographic film">photographic film</a>. Acetic anhydride is also a reagent for the production of <a href="/wiki/Heroin" title="Heroin">heroin</a> and other compounds.<sup id="cite_ref-acetic-anh_52-1" class="reference"><a href="#cite_note-acetic-anh-52"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Use_as_solvent">Use as solvent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=19" title="Edit section: Use as solvent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a polar <a href="/wiki/Protic_solvent" title="Protic solvent">protic solvent</a>, acetic acid is frequently used for <a href="/wiki/Recrystallization_(chemistry)" title="Recrystallization (chemistry)">recrystallization</a> to purify organic compounds. Acetic acid is used as a <a href="/wiki/Solvent" title="Solvent">solvent</a> in the production of <a href="/wiki/Terephthalic_acid" title="Terephthalic acid">terephthalic acid</a> (TPA), the raw material for <a href="/wiki/Polyethylene_terephthalate" title="Polyethylene terephthalate">polyethylene terephthalate</a> (PET). In 2006, about 20% of acetic acid was used for TPA production.<sup id="cite_ref-suresh_36-3" class="reference"><a href="#cite_note-suresh-36"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>Acetic acid is often used as a solvent for reactions involving <a href="/wiki/Carbocation" title="Carbocation">carbocations</a>, such as <a href="/wiki/Friedel-Crafts#Friedel–Crafts_alkylation" class="mw-redirect" title="Friedel-Crafts">Friedel-Crafts alkylation</a>. For example, one stage in the commercial manufacture of synthetic <a href="/wiki/Camphor" title="Camphor">camphor</a> involves a <a href="/wiki/Wagner-Meerwein_rearrangement" class="mw-redirect" title="Wagner-Meerwein rearrangement">Wagner-Meerwein rearrangement</a> of <a href="/wiki/Camphene" title="Camphene">camphene</a> to <a href="/wiki/Isobornyl_acetate" title="Isobornyl acetate">isobornyl acetate</a>; here acetic acid acts both as a solvent and as a <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> to trap the <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearranged</a> carbocation.<sup id="cite_ref-sell_53-0" class="reference"><a href="#cite_note-sell-53"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>Glacial acetic acid is used in analytical chemistry for the estimation of weakly alkaline substances such as organic amides. Glacial acetic acid is a much weaker <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a> than water, so the amide behaves as a strong base in this medium. It then can be titrated using a solution in glacial acetic acid of a very strong acid, such as <a href="/wiki/Perchloric_acid" title="Perchloric acid">perchloric acid</a>.<sup id="cite_ref-Felgner_54-0" class="reference"><a href="#cite_note-Felgner-54"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Medical_use">Medical use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=20" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Acetic_acid_(medical_use)" title="Acetic acid (medical use)">Acetic acid (medical use)</a></div> <p>Acetic acid injection into a tumor has been used to treat cancer since the 1800s.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p><p>Acetic acid is used as part of <a href="/wiki/Cervical_cancer_screening" class="mw-redirect" title="Cervical cancer screening">cervical cancer screening</a> in many areas in the <a href="/wiki/Developing_world" class="mw-redirect" title="Developing world">developing world</a>.<sup id="cite_ref-Fok2015_57-0" class="reference"><a href="#cite_note-Fok2015-57"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> The acid is applied to the <a href="/wiki/Cervix" title="Cervix">cervix</a> and if an area of white appears after about a minute the test is positive.<sup id="cite_ref-Fok2015_57-1" class="reference"><a href="#cite_note-Fok2015-57"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>Acetic acid is an effective antiseptic when used as a 1% solution, with broad spectrum of activity against streptococci, staphylococci, pseudomonas, enterococci and others.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> It may be used to treat skin infections caused by pseudomonas strains resistant to typical antibiotics.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p><p>While diluted acetic acid is used in <a href="/wiki/Iontophoresis" title="Iontophoresis">iontophoresis</a>, no high quality evidence supports this treatment for rotator cuff disease.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>As a treatment for <a href="/wiki/Otitis_externa" title="Otitis externa">otitis externa</a>, it is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<sup id="cite_ref-WHO21st_64-0" class="reference"><a href="#cite_note-WHO21st-64"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WHO22nd_65-0" class="reference"><a href="#cite_note-WHO22nd-65"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Foods">Foods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=21" title="Edit section: Foods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Vinegar" title="Vinegar">Vinegar</a></div> <p>Acetic acid has 349 kcal (1,460 kJ) per 100 g.<sup id="cite_ref-FAOSouthgate_66-0" class="reference"><a href="#cite_note-FAOSouthgate-66"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Vinegar is typically no less than 4% acetic acid by mass.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Legal limits on acetic acid content vary by jurisdiction. Vinegar is used directly as a <a href="/wiki/Condiment" title="Condiment">condiment</a>, and in the <a href="/wiki/Pickling" title="Pickling">pickling</a> of vegetables and other foods. Table vinegar tends to be more diluted (4% to 8% acetic acid), while commercial food pickling employs solutions that are more concentrated. The proportion of acetic acid used worldwide as vinegar is not as large as industrial uses, but it is by far the oldest and best-known application.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>68<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=Acetic_acid&action=edit&section=22" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Organic_chemistry">Organic chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=23" title="Edit section: Organic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="thumb tnone" style=""><div class="thumbinner" style="width:402px"><div class="thumbimage noresize" style="width:400px;display:flex;"> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Acetyl_chloride" title="Acetyl chloride">acetyl chloride</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Acetyl_chloride.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Acetyl_chloride.svg/80px-Acetyl_chloride.svg.png" decoding="async" width="80" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Acetyl_chloride.svg/120px-Acetyl_chloride.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/35/Acetyl_chloride.svg/160px-Acetyl_chloride.svg.png 2x" data-file-width="453" data-file-height="354" /></a></span></div> </div><div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 30px;"><div style="text-align:center; width:100%;"><a href="/wiki/Thionyl_chloride" title="Thionyl chloride"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SOCl<sub class="template-chem2-sub">2</sub></span></a></div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 12px;"><div style="position: relative; bottom: 24px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reverse_NNNN_horiz_med.svg" class="mw-file-description" title="Leftward reaction arrow"><img alt="Leftward reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Biochem_reaction_arrow_reverse_NNNN_horiz_med.svg/60px-Biochem_reaction_arrow_reverse_NNNN_horiz_med.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Biochem_reaction_arrow_reverse_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reverse_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Biochem_reaction_arrow_reverse_NNNN_horiz_med.svg/120px-Biochem_reaction_arrow_reverse_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 30px;"></div> </div><div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a class="mw-selflink selflink">acetic acid</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Acetic_acid_Structural_Formula_V1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Acetic_acid_Structural_Formula_V1.svg/80px-Acetic_acid_Structural_Formula_V1.svg.png" decoding="async" width="80" height="53" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Acetic_acid_Structural_Formula_V1.svg/120px-Acetic_acid_Structural_Formula_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Acetic_acid_Structural_Formula_V1.svg/160px-Acetic_acid_Structural_Formula_V1.svg.png 2x" data-file-width="170" data-file-height="113" /></a></span></div> </div><div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 30px;"><div style="text-align:center; width:100%;">(i) <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Li[AlH<sub class="template-chem2-sub">4</sub>]</span></a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a></div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 12px;"><div style="position: relative; bottom: 24px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_NNNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow"><img alt="Rightward reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Biochem_reaction_arrow_forward_NNNN_horiz_med.svg/60px-Biochem_reaction_arrow_forward_NNNN_horiz_med.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Biochem_reaction_arrow_forward_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Biochem_reaction_arrow_forward_NNNN_horiz_med.svg/120px-Biochem_reaction_arrow_forward_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 30px;"><div style="text-align:center; width:100%;">(ii) <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup></span></div></div> </div><div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Ethanol" title="Ethanol">ethanol</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Ethanol_Skelett.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Ethanol_Skelett.svg/80px-Ethanol_Skelett.svg.png" decoding="async" width="80" height="26" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Ethanol_Skelett.svg/120px-Ethanol_Skelett.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Ethanol_Skelett.svg/160px-Ethanol_Skelett.svg.png 2x" data-file-width="137" data-file-height="45" /></a></span></div> </div></div><div class="thumbcaption">Two typical organic reactions of acetic acid</div></div></div> <p>Acetic acid undergoes the typical <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reactions</a> of a carboxylic acid. Upon treatment with a standard base, it converts to metal <a href="/wiki/Acetate" title="Acetate">acetate</a> and <a href="/wiki/Water" title="Water">water</a>. With strong bases (e.g., organolithium reagents), it can be doubly deprotonated to give <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">LiCH<sub class="template-chem2-sub">2</sub>COOLi</span>. Reduction of acetic acid gives ethanol. The OH group is the main site of reaction, as illustrated by the conversion of acetic acid to <a href="/wiki/Acetyl_chloride" title="Acetyl chloride">acetyl chloride</a>. Other substitution derivatives include <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a>; this <a href="/wiki/Anhydride" class="mw-redirect" title="Anhydride">anhydride</a> is produced by <a href="/wiki/Condensation_reaction" title="Condensation reaction">loss of water</a> from two molecules of acetic acid. <a href="/wiki/Ester" title="Ester">Esters</a> of acetic acid can likewise be formed via <a href="/wiki/Fischer_esterification" class="mw-redirect" title="Fischer esterification">Fischer esterification</a>, and <a href="/wiki/Amide" title="Amide">amides</a> can be formed. When heated above 440 °C (824 °F), acetic acid decomposes to produce <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and <a href="/wiki/Methane" title="Methane">methane</a>, or to produce <a href="/wiki/Ketene" title="Ketene">ketene</a> and water:<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Duan1995_73-0" class="reference"><a href="#cite_note-Duan1995-73"><span class="cite-bracket">[</span>71<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">CH<sub class="template-chem2-sub">3</sub>COOH → CH<sub class="template-chem2-sub">4</sub> + CO<sub class="template-chem2-sub">2</sub></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOH → CH<sub class="template-chem2-sub">2</sub>=C=O + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Reactions_with_inorganic_compounds">Reactions with inorganic compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=24" title="Edit section: Reactions with inorganic compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetic acid is mildly <a href="/wiki/Corrosion" title="Corrosion">corrosive</a> to <a href="/wiki/Metal" title="Metal">metals</a> including <a href="/wiki/Iron" title="Iron">iron</a>, <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, and <a href="/wiki/Zinc" title="Zinc">zinc</a>, forming <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> gas and salts called <a href="/wiki/Acetate" title="Acetate">acetates</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mg + 2 CH<sub class="template-chem2-sub">3</sub>COOH → (CH<sub class="template-chem2-sub">3</sub>COO)<sub class="template-chem2-sub">2</sub>Mg + H<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>Because <a href="/wiki/Aluminium" title="Aluminium">aluminium</a> forms a <a href="/wiki/Passivation_(chemistry)" title="Passivation (chemistry)">passivating</a> acid-resistant film of <a href="/wiki/Aluminium_oxide" title="Aluminium oxide">aluminium oxide</a>, aluminium tanks are used to transport acetic acid.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> Containers lined with glass, <a href="/wiki/Stainless_steel" title="Stainless steel">stainless steel</a> or <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a> are also used for this purpose.<sup id="cite_ref-Ullmann_28-4" class="reference"><a href="#cite_note-Ullmann-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Metal acetates can also be prepared from acetic acid and an appropriate <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>, as in the popular "<a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">baking soda</a> + vinegar" reaction giving off <a href="/wiki/Sodium_acetate" title="Sodium acetate">sodium acetate</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaHCO<sub class="template-chem2-sub">3</sub> + CH<sub class="template-chem2-sub">3</sub>COOH → CH<sub class="template-chem2-sub">3</sub>COONa + CO<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>A <a href="/wiki/Colour_reaction" class="mw-redirect" title="Colour reaction">colour reaction</a> for salts of acetic acid is <a href="/wiki/Iron(III)_chloride" title="Iron(III) chloride">iron(III) chloride</a> solution, which results in a deeply red colour that disappears after acidification.<sup id="cite_ref-Charlot_75-0" class="reference"><a href="#cite_note-Charlot-75"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> A more sensitive test uses <a href="/wiki/Lanthanum_nitrate" class="mw-redirect" title="Lanthanum nitrate">lanthanum nitrate</a> with iodine and ammonia to give a blue solution.<sup id="cite_ref-Neelakantam_76-0" class="reference"><a href="#cite_note-Neelakantam-76"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> Acetates when heated with <a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">arsenic trioxide</a> form <a href="/wiki/Cacodyl_oxide" title="Cacodyl oxide">cacodyl oxide</a>, which can be detected by its <a href="/wiki/Odour" class="mw-redirect" title="Odour">malodorous</a> vapours.<sup id="cite_ref-Brantley1947_77-0" class="reference"><a href="#cite_note-Brantley1947-77"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_derivatives">Other derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=25" title="Edit section: Other derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organic or inorganic salts are produced from acetic acid. Some commercially significant derivatives: </p> <ul><li><a href="/wiki/Sodium_acetate" title="Sodium acetate">Sodium acetate</a>, used in the <a href="/wiki/Textile" title="Textile">textile</a> industry and as a food <a href="/wiki/Preservative" title="Preservative">preservative</a> (<a href="/wiki/E_number" title="E number">E262</a>).</li> <li><a href="/wiki/Copper(II)_acetate" title="Copper(II) acetate">Copper(II) acetate</a>, used as a <a href="/wiki/Pigment" title="Pigment">pigment</a> and a <a href="/wiki/Fungicide" title="Fungicide">fungicide</a>.</li> <li><a href="/wiki/Aluminium_acetate" title="Aluminium acetate">Aluminium acetate</a> and <a href="/wiki/Iron(II)_acetate" title="Iron(II) acetate">iron(II) acetate</a>—used as <a href="/wiki/Mordant" title="Mordant">mordants</a> for <a href="/wiki/Dye" title="Dye">dyes</a>.</li> <li><a href="/wiki/Palladium(II)_acetate" title="Palladium(II) acetate">Palladium(II) acetate</a>, used as a catalyst for organic coupling reactions such as the <a href="/wiki/Heck_reaction" title="Heck reaction">Heck reaction</a>.</li></ul> <p>Halogenated acetic acids are produced from acetic acid. Some commercially significant derivatives: </p> <ul><li><a href="/wiki/Chloroacetic_acid" title="Chloroacetic acid">Chloroacetic acid</a> (monochloroacetic acid, MCA), dichloroacetic acid (considered a by-product), and <a href="/wiki/Trichloroacetic_acid" title="Trichloroacetic acid">trichloroacetic acid</a>. MCA is used in the manufacture of <a href="/wiki/Indigo_dye" title="Indigo dye">indigo dye</a>.</li> <li><a href="/wiki/Bromoacetic_acid" title="Bromoacetic acid">Bromoacetic acid</a>, which is esterified to produce the reagent <a href="/wiki/Ethyl_bromoacetate" title="Ethyl bromoacetate">ethyl bromoacetate</a>.</li> <li><a href="/wiki/Trifluoroacetic_acid" title="Trifluoroacetic acid">Trifluoroacetic acid</a>, which is a common reagent in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>.</li></ul> <p>Amounts of acetic acid used in these other applications together account for another 5–10% of acetic acid use worldwide.<sup id="cite_ref-suresh_36-4" class="reference"><a href="#cite_note-suresh-36"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Health_and_safety">Health and safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=26" title="Edit section: Health and safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Vapour">Vapour</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=27" title="Edit section: Vapour"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Prolonged inhalation exposure (eight hours) to acetic acid vapours at 10 ppm can produce some irritation of eyes, nose, and throat; at 100 ppm marked lung irritation and possible damage to lungs, eyes, and skin may result. Vapour concentrations of 1,000 ppm cause marked irritation of eyes, nose and upper respiratory tract and cannot be tolerated. These predictions were based on <a href="/wiki/Animal_testing" title="Animal testing">animal experiments</a> and industrial exposure.<sup id="cite_ref-CDC_78-0" class="reference"><a href="#cite_note-CDC-78"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p><p>In 12 workers exposed for two or more years to an airborne average concentration of 51 ppm acetic acid (estimated), symptoms of conjunctive irritation, upper respiratory tract irritation, and hyperkeratotic dermatitis were produced. Exposure to 50 ppm or more is intolerable to most persons and results in intensive <a href="/wiki/Tears" title="Tears">lacrimation</a> and irritation of the eyes, nose, and throat, with pharyngeal oedema and chronic bronchitis. Unacclimatised humans experience extreme eye and nasal irritation at concentrations in excess of 25 ppm, and conjunctivitis from concentrations below 10 ppm has been reported. In a study of five workers exposed for seven to 12 years to concentrations of 80 to 200 ppm at peaks, the principal findings were blackening and hyperkeratosis of the skin of the hands, conjunctivitis (but no corneal damage), bronchitis and pharyngitis, and erosion of the exposed teeth (incisors and canines).<sup id="cite_ref-:0_79-0" class="reference"><a href="#cite_note-:0-79"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Solution">Solution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=28" title="Edit section: Solution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Concentrated acetic acid (≥ 25%) is <a href="/wiki/Corrosion" title="Corrosion">corrosive</a> to skin.<sup id="cite_ref-IPCS_card_80-0" class="reference"><a href="#cite_note-IPCS_card-80"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> These burns or blisters may not appear until hours after exposure.<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> The hazardous properties of acetic acid are dependent on the concentration of the (typically <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous</a>) solution, with the most significant increases in hazard levels at thresholds of 25% and 90% acetic acid concentration by weight. The following table summarizes the hazards of acetic acid solutions by concentration:<sup id="cite_ref-ECHA_82-0" class="reference"><a href="#cite_note-ECHA-82"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th><a href="/wiki/Concentration" title="Concentration">Concentration</a><br />by weight </th> <th>Molarity </th> <th><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">GHS pictograms</a> </th> <th><a href="/wiki/List_of_H-phrases" class="mw-redirect" title="List of H-phrases">H-Phrases</a> </th></tr> <tr> <td>10–25% </td> <td>1.67–4.16 mol/L </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr> </td></tr> <tr> <td>25–90% </td> <td>4.16–14.99 mol/L </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td> <td><abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr> </td></tr> <tr> <td>>90% </td> <td>>14.99 mol/L </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-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td> <td><abbr class="abbr" title="H226: Flammable liquid and vapour">H226</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr> </td></tr></tbody></table> <p>Concentrated acetic acid can be ignited only with difficulty at standard temperature and pressure, but becomes a flammable risk in temperatures greater than 39 °C (102 °F), and can form explosive mixtures with air at higher temperatures with <a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">explosive limits</a> of 5.4–16% concentration. </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=Acetic_acid&action=edit&section=29" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Acetic_acid_(data_page)" title="Acetic acid (data page)">Acetic acid (data page)</a></li> <li><a href="/wiki/Acids_in_wine" title="Acids in wine">Acids in wine</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=30" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-lower-alpha" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text">[H<sub>3</sub>O<sup>+</sup>] = 10<sup>−2.4</sup> = 0.4%</span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text">Acetic acid that is manufactured by intent, rather than recovered from processing (such as the production of cellulose acetates, polyvinyl alcohol operations, and numerous acetic anhydride acylations).</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_acid&action=edit&section=31" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist 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"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1"><i>Scientific literature reviews on generally recognised as safe (GRAS) food ingredients</i>. National Technical Information Service. 1974. p. 1.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Scientific+literature+reviews+on+generally+recognised+as+safe+%28GRAS%29+food+ingredients&rft.pages=1&rft.pub=National+Technical+Information+Service&rft.date=1974&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetic+acid" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">"Chemistry", volume 5, Encyclopædia Britannica, 1961, page 374.</span> </li> <li id="cite_note-iupac2013-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_3-0">^</a></b></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>. 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Retrieved <span class="nowrap">19 February</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Standard+Operating+Procedure+Glacial+Acetic+Acid&rft.pub=UCMERCED&rft.date=2012-10-19&rft_id=https%3A%2F%2Fchemistry.ucmerced.edu%2Fsites%2Fchemistry.ucmerced.edu%2Ffiles%2Fpage%2Fdocuments%2Fejm_acetic_acid.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetic+acid" class="Z3988"></span></span> </li> <li id="cite_note-ECHA-82"><span class="mw-cite-backlink"><b><a href="#cite_ref-ECHA_82-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/85625">"C&L Inventory"</a>. <i>echa.europa.eu</i><span class="reference-accessdate">. Retrieved <span class="nowrap">13 December</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=echa.europa.eu&rft.atitle=C%26L+Inventory&rft_id=https%3A%2F%2Fecha.europa.eu%2Finformation-on-chemicals%2Fcl-inventory-database%2F-%2Fdiscli%2Fdetails%2F85625&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetic+acid" 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=Acetic_acid&action=edit&section=32" 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"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/acetic" class="extiw" title="wiktionary:acetic">acetic</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Category:Acetic_acid" class="extiw" title="commons:Category:Acetic acid"><span style="font-style:italic; font-weight:bold;">Acetic acid</span></a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0363&p_version=2">International Chemical Safety Card 0363</a></li> <li><a rel="nofollow" class="external text" href="http://www.npi.gov.au/resource/acetic-acid-ethanoic-acid">National Pollutant Inventory – Acetic acid fact sheet</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0002.html">NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/docs/2003-154/pdfs/1603.pdf">Method for sampling and analysis</a></li> <li><a rel="nofollow" class="external text" href="https://www.osha.gov/laws-regs/regulations/standardnumber/1910/1910.1000TABLEZ1">29 CFR 1910.1000, Table Z-1</a> (US Permissible exposure limits)</li> <li><a rel="nofollow" class="external text" href="http://chemsub.online.fr/name/Acetic_acid.html">ChemSub Online: Acetic acid</a></li> <li>Calculation of <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Acetic+acid">vapor pressure</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Acetic+acid">liquid density</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Acetic+acid">dynamic liquid viscosity</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Acetic+acid">surface tension</a> of acetic acid</li> <li><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=ACT">Acetic acid bound to proteins</a> in the <a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150207065434/http://apps.kemi.se/flodessok/floden/kemamne_eng/attiksyra_eng.htm">Swedish Chemicals Agency. Information sheet – Acetic Acid</a></li> <li>Process Flow sheet of Acetic acid Production by the <a rel="nofollow" class="external text" href="https://web.archive.org/web/20141102121127/http://www.inclusive-science-engineering.com/processes-for-manufacturing-acetic-acid/acetic-acid/">Carbonylation of Methanol</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 .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul 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style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nystatin" title="Nystatin">Nystatin</a></li> <li><a href="/wiki/Natamycin" title="Natamycin">Natamycin</a></li> <li><a href="/wiki/Amphotericin_B" title="Amphotericin B">Amphotericin B</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ciclopirox" title="Ciclopirox">Ciclopirox</a></li> <li><a href="/wiki/Crystal_violet" title="Crystal violet">Methylrosaniline</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Clodantoin" class="mw-redirect" title="Clodantoin">Clodantoin</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Policresulen" title="Policresulen">Policresulen</a></li> <li><a href="/wiki/Nifuratel" title="Nifuratel">Nifuratel</a></li> <li><a href="/wiki/Furazolidone" title="Furazolidone">Furazolidone</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a></li> <li><a href="/wiki/Protiofate" title="Protiofate">Protiofate</a></li> <li><i><a href="/wiki/Lactobacillus_fermentum" class="mw-redirect" title="Lactobacillus fermentum">Lactobacillus fermentum</a></i></li> <li><a href="/wiki/Copper_usnate" title="Copper usnate">Copper usnate</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Drugs_used_for_diseases_of_the_ear_(S02)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Otologicals" title="Template:Otologicals"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Otologicals" title="Template talk:Otologicals"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Otologicals" title="Special:EditPage/Template:Otologicals"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Drugs_used_for_diseases_of_the_ear_(S02)" style="font-size:114%;margin:0 4em">Drugs used for diseases of the <a href="/wiki/Human_ear" class="mw-redirect" title="Human ear">ear</a> (<a href="/wiki/ATC_code_S02" title="ATC code S02">S02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Infection" title="Infection">Infection</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Acetic acid</a></li> <li><a href="/wiki/Aluminium_acetotartrate" title="Aluminium acetotartrate">Aluminium acetotartrate</a></li> <li><a href="/wiki/Aluminium_triacetate" title="Aluminium triacetate">Aluminium triacetate</a> (<a href="/wiki/Burow%27s_solution" title="Burow's solution">Burow's solution</a>)</li> <li><a href="/wiki/Boric_acid" title="Boric acid">Boric acid</a></li> <li><a href="/wiki/Chloramphenicol" title="Chloramphenicol">Chloramphenicol</a></li> <li><a href="/wiki/Chlorhexidine" title="Chlorhexidine">Chlorhexidine</a></li> <li><a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">Ciprofloxacin</a></li> <li><a href="/wiki/Clioquinol" title="Clioquinol">Clioquinol</a></li> <li><a href="/wiki/Gentamicin" title="Gentamicin">Gentamicin</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Neomycin" title="Neomycin">Neomycin</a></li> <li><a href="/wiki/Nitrofurazone" title="Nitrofurazone">Nitrofurazone</a></li> <li><a href="/wiki/Ofloxacin" title="Ofloxacin">Ofloxacin</a></li> <li><a href="/wiki/Polymyxin_B" title="Polymyxin B">Polymyxin B</a></li> <li><a href="/wiki/Rifamycin" title="Rifamycin">Rifamycin</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Betamethasone" title="Betamethasone">Betamethasone</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Fluocinolone_acetonide" title="Fluocinolone acetonide">Fluocinolone acetonide</a></li> <li><a href="/wiki/Hydrocortisone" title="Hydrocortisone">Hydrocortisone</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Analgesic" title="Analgesic">Analgesics</a> and <a href="/wiki/Anesthetic" title="Anesthetic">anesthetics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lidocaine" title="Lidocaine">Lidocaine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Phenazone" title="Phenazone">Phenazone</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Lipids:_fatty_acids" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Fatty_acids" title="Template:Fatty acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Fatty_acids" title="Template talk:Fatty acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Fatty_acids" title="Special:EditPage/Template:Fatty acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Lipids:_fatty_acids" style="font-size:114%;margin:0 4em"><a href="/wiki/Lipid" title="Lipid">Lipids</a>: <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Saturated_fat" title="Saturated fat">Saturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic</a> (C3)</li> <li><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric</a> (C4)</li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric</a> (C5)</li> <li><a href="/wiki/Caproic_acid" title="Caproic acid">Caproic</a> (C6)</li> <li><a href="/wiki/Enanthic_acid" title="Enanthic acid">Enanthic</a> (C7)</li> <li><a href="/wiki/Caprylic_acid" title="Caprylic acid">Caprylic</a> (C8)</li> <li><a href="/wiki/Pelargonic_acid" title="Pelargonic acid">Pelargonic</a> (C9)</li> <li><a href="/wiki/Capric_acid" title="Capric acid">Capric</a> (C10)</li> <li><a href="/wiki/Undecylic_acid" title="Undecylic acid">Undecylic</a> (C11)</li> <li><a href="/wiki/Lauric_acid" title="Lauric acid">Lauric</a> (C12)</li> <li><a href="/wiki/Tridecylic_acid" title="Tridecylic acid">Tridecylic</a> (C13)</li> <li><a href="/wiki/Myristic_acid" title="Myristic acid">Myristic</a> (C14)</li> <li><a href="/wiki/Pentadecylic_acid" title="Pentadecylic acid">Pentadecylic</a> (C15)</li> <li><a href="/wiki/Palmitic_acid" title="Palmitic acid">Palmitic</a> (C16)</li> <li><a href="/wiki/Margaric_acid" title="Margaric acid">Margaric</a> (C17)</li> <li><a href="/wiki/Stearic_acid" title="Stearic acid">Stearic</a> (C18)</li> <li><a href="/wiki/Nonadecylic_acid" title="Nonadecylic acid">Nonadecylic</a> (C19)</li> <li><a href="/wiki/Arachidic_acid" title="Arachidic acid">Arachidic</a> (C20)</li> <li><a href="/wiki/Heneicosylic_acid" title="Heneicosylic acid">Heneicosylic</a> (C21)</li> <li><a href="/wiki/Behenic_acid" title="Behenic acid">Behenic</a> (C22)</li> <li><a href="/wiki/Tricosylic_acid" title="Tricosylic acid">Tricosylic</a> (C23)</li> <li><a href="/wiki/Lignoceric_acid" title="Lignoceric acid">Lignoceric</a> (C24)</li> <li><a href="/wiki/Pentacosylic_acid" title="Pentacosylic acid">Pentacosylic</a> (C25)</li> <li><a href="/wiki/Cerotic_acid" title="Cerotic acid">Cerotic</a> (C26)</li> <li><a href="/wiki/Carboceric_acid" title="Carboceric acid">Carboceric</a> (C27)</li> <li><a href="/wiki/Montanic_acid" title="Montanic acid">Montanic</a> (C28)</li> <li><a href="/wiki/Nonacosylic_acid" title="Nonacosylic acid">Nonacosylic</a> (C29)</li> <li><a href="/wiki/Melissic_acid" title="Melissic acid">Melissic</a> (C30)</li> <li><a href="/wiki/Hentriacontylic_acid" title="Hentriacontylic acid">Hentriacontylic</a> (C31)</li> <li><a href="/wiki/Lacceroic_acid" title="Lacceroic acid">Lacceroic</a> (C32)</li> <li><a href="/wiki/Psyllic_acid" title="Psyllic acid">Psyllic</a> (C33)</li> <li><a href="/wiki/Geddic_acid" title="Geddic acid">Geddic</a> (C34)</li> <li><a href="/wiki/Ceroplastic_acid" title="Ceroplastic acid">Ceroplastic</a> (C35)</li> <li><a href="/wiki/Hexatriacontylic_acid" title="Hexatriacontylic acid">Hexatriacontylic</a> (C36)</li> <li><a href="/wiki/Heptatriacontanoic_acid" title="Heptatriacontanoic acid">Heptatriacontanoic</a> (C37)</li> <li><a href="/w/index.php?title=Octatriacontanoic_acid&action=edit&redlink=1" class="new" title="Octatriacontanoic acid (page does not exist)">Octatriacontanoic</a> (C38)</li> <li><a href="/w/index.php?title=Nonatriacontanoic_acid&action=edit&redlink=1" class="new" title="Nonatriacontanoic acid (page does not exist)">Nonatriacontanoic</a> (C39)</li> <li><a href="/w/index.php?title=Tetracontanoic_acid&action=edit&redlink=1" class="new" title="Tetracontanoic acid (page does not exist)">Tetracontanoic</a> (C40)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">ω−3 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=5-Octenoic_acid&action=edit&redlink=1" class="new" title="5-Octenoic acid (page does not exist)">Octenoic</a> (8:1)</li> <li><a href="/w/index.php?title=7-Decenoic_acid&action=edit&redlink=1" class="new" title="7-Decenoic acid (page does not exist)">Decenoic</a> (10:1)</li> <li><a href="/w/index.php?title=4,7-Decadienoic_acid&action=edit&redlink=1" class="new" title="4,7-Decadienoic acid (page does not exist)">Decadienoic</a> (10:2)</li> <li><a href="/w/index.php?title=9-Dodecenoic_acid&action=edit&redlink=1" class="new" title="9-Dodecenoic acid (page does not exist)">Lauroleic</a> (12:1)</li> <li><a href="/w/index.php?title=6,9-Dodecadienoic_acid&action=edit&redlink=1" class="new" title="6,9-Dodecadienoic acid (page does not exist)">Laurolinoleic</a> (12:2)</li> <li><a href="/w/index.php?title=11-Tetradecenoic_acid&action=edit&redlink=1" class="new" title="11-Tetradecenoic acid (page does not exist)">Myristovaccenic</a> (14:1)</li> <li><a href="/w/index.php?title=8,11-Tetradecadienoic_acid&action=edit&redlink=1" class="new" title="8,11-Tetradecadienoic acid (page does not exist)">Myristolinoleic</a> (14:2)</li> <li><a href="/w/index.php?title=5,8,11-Tetradecatrienoic_acid&action=edit&redlink=1" class="new" title="5,8,11-Tetradecatrienoic acid (page does not exist)">Myristolinolenic</a> (14:3)</li> <li><a href="/w/index.php?title=7,10,13-Hexadecatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Hexadecatrienoic acid (page does not exist)">Palmitolinolenic</a> (16:3)</li> <li><a href="/w/index.php?title=4,7,10,13-Hexadecatetraenoic_acid&action=edit&redlink=1" class="new" title="4,7,10,13-Hexadecatetraenoic acid (page does not exist)">Palmitidonic</a> (16:4)</li> <li><a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic</a> (18:3)</li> <li><a href="/wiki/Stearidonic_acid" title="Stearidonic acid">Stearidonic</a> (18:4)</li> <li><a href="/wiki/%CE%91-Parinaric_acid" title="Α-Parinaric acid">α-Parinaric</a> (18:4)</li> <li><a href="/w/index.php?title=11,14,17-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="11,14,17-Eicosatrienoic acid (page does not exist)">Dihomo-α-linolenic</a> (20:3)</li> <li><a href="/wiki/Eicosatetraenoic_acid" title="Eicosatetraenoic acid">Eicosatetraenoic</a> (20:4)</li> <li><a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">Eicosapentaenoic</a> (20:5)</li> <li><a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">Clupanodonic</a> (22:5)</li> <li><a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">Docosahexaenoic</a> (22:6)</li> <li><a href="/w/index.php?title=9,12,15,18,21-Tetracosapentaenoic_acid&action=edit&redlink=1" class="new" title="9,12,15,18,21-Tetracosapentaenoic acid (page does not exist)">9,12,15,18,21-Tetracosapentaenoic</a> (24:5)</li> <li><a href="/w/index.php?title=6,9,12,15,18,21-Tetracosahexaenoic_acid&action=edit&redlink=1" class="new" title="6,9,12,15,18,21-Tetracosahexaenoic acid (page does not exist)">6,9,12,15,18,21-Tetracosahexaenoic</a> (24:6)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-5_fatty_acid&action=edit&redlink=1" class="new" title="Omega-5 fatty acid (page does not exist)">ω−5 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Myristoleic_acid" title="Myristoleic acid">Myristoleic</a> (14:1)</li> <li><a href="/w/index.php?title=11-Hexadecenoic_acid&action=edit&redlink=1" class="new" title="11-Hexadecenoic acid (page does not exist)">Palmitovaccenic</a> (16:1)</li> <li><a href="/wiki/%CE%91-Eleostearic_acid" title="Α-Eleostearic acid">α-Eleostearic</a> (18:3)</li> <li><a href="/wiki/%CE%92-Eleostearic_acid" title="Β-Eleostearic acid">β-Eleostearic</a> (<i>trans</i>-18:3)</li> <li><a href="/wiki/Punicic_acid" title="Punicic acid">Punicic</a> (18:3)</li> <li><a href="/w/index.php?title=7,10,13-Octadecatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Octadecatrienoic acid (page does not exist)">7,10,13-Octadecatrienoic</a> (18:3)</li> <li><a href="/w/index.php?title=9,12,15-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="9,12,15-Eicosatrienoic acid (page does not exist)">9,12,15-Eicosatrienoic</a> (20:3)</li> <li><a href="/w/index.php?title=6,9,12,15-Eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="6,9,12,15-Eicosatetraenoic acid (page does not exist)">β-Eicosatetraenoic</a> (20:4)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">ω−6 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=8-Tetradecenoic_acid&action=edit&redlink=1" class="new" title="8-Tetradecenoic acid (page does not exist)">8-Tetradecenoic</a> (14:1)</li> <li><a href="/w/index.php?title=12-Octadecenoic_acid&action=edit&redlink=1" class="new" title="12-Octadecenoic acid (page does not exist)">12-Octadecenoic</a> (18:1)</li> <li><a href="/wiki/Linoleic_acid" title="Linoleic acid">Linoleic</a> (18:2)</li> <li><a href="/wiki/Linolelaidic_acid" title="Linolelaidic acid">Linolelaidic</a> (<i>trans</i>-18:2)</li> <li><a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-Linolenic</a> (18:3)</li> <li><a href="/wiki/Calendic_acid" title="Calendic acid">Calendic</a> (18:3)</li> <li><a href="/wiki/Pinolenic_acid" title="Pinolenic acid">Pinolenic</a> (18:3)</li> <li><a href="/w/index.php?title=Dihomo-linoleic_acid&action=edit&redlink=1" class="new" title="Dihomo-linoleic acid (page does not exist)">Dihomo-linoleic</a> (20:2)</li> <li><a href="/wiki/Dihomo-%CE%B3-linolenic_acid" title="Dihomo-γ-linolenic acid">Dihomo-γ-linolenic</a> (20:3)</li> <li><a href="/wiki/Sciadonic_acid" title="Sciadonic acid">Sciadonic</a> (20:3)</li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic</a> (20:4)</li> <li><a href="/wiki/Docosatetraenoic_acid" title="Docosatetraenoic acid">Adrenic</a> (22:4)</li> <li><a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">Osbond</a> (22:5)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-7_fatty_acid" title="Omega-7 fatty acid">ω−7 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Palmitoleic_acid" title="Palmitoleic acid">Palmitoleic</a> (16:1)</li> <li><a href="/wiki/Vaccenic_acid" title="Vaccenic acid">Vaccenic</a> (18:1)</li> <li><a href="/wiki/Rumenic_acid" title="Rumenic acid">Rumenic</a> (18:2)</li> <li><a href="/wiki/Paullinic_acid" title="Paullinic acid">Paullinic</a> (20:1)</li> <li><a href="/w/index.php?title=7,10,13-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Eicosatrienoic acid (page does not exist)">7,10,13-Eicosatrienoic</a> (20:3)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid">ω−9 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oleic_acid" title="Oleic acid">Oleic</a> (18:1)</li> <li><a href="/wiki/Elaidic_acid" title="Elaidic acid">Elaidic</a> (<i>trans</i>-18:1)</li> <li><a href="/wiki/11-Eicosenoic_acid" title="11-Eicosenoic acid">Gondoic</a> (20:1)</li> <li><a href="/wiki/Erucic_acid" title="Erucic acid">Erucic</a> (22:1)</li> <li><a href="/wiki/Nervonic_acid" title="Nervonic acid">Nervonic</a> (24:1)</li> <li><a href="/w/index.php?title=8,11-Eicosadienoic_acid&action=edit&redlink=1" class="new" title="8,11-Eicosadienoic acid (page does not exist)">8,11-Eicosadienoic</a> (20:2)</li> <li><a href="/wiki/Mead_acid" title="Mead acid">Mead</a> (20:3)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-10_fatty_acid&action=edit&redlink=1" class="new" title="Omega-10 fatty acid (page does not exist)">ω−10 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sapienic_acid" title="Sapienic acid">Sapienic</a> (16:1)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-11_fatty_acid&action=edit&redlink=1" class="new" title="Omega-11 fatty acid (page does not exist)">ω−11 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gadoleic_acid" title="Gadoleic acid">Gadoleic</a> (20:1)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-12_fatty_acid&action=edit&redlink=1" class="new" title="Omega-12 fatty acid (page does not exist)">ω−12 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=4-Hexadecenoic_acid&action=edit&redlink=1" class="new" title="4-Hexadecenoic acid (page does not exist)">4-Hexadecenoic</a> (16:1)</li> <li><a href="/wiki/Petroselinic_acid" title="Petroselinic acid">Petroselinic</a> (18:1)</li> <li><a href="/w/index.php?title=8-Eicosenoic_acid&action=edit&redlink=1" class="new" title="8-Eicosenoic acid (page does not exist)">8-Eicosenoic</a> (20:1)</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Molecules_detected_in_outer_space" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Acetic acid</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Astrochemistry" title="Category:Astrochemistry">Category:Astrochemistry</a></b></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/16px-Earth-moon.jpg" decoding="async" width="16" height="13" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/24px-Earth-moon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/32px-Earth-moon.jpg 2x" data-file-width="3000" data-file-height="2400" /></span></span> </span><a href="/wiki/Portal:Outer_space" title="Portal:Outer space">Outer space portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/16px-Crab_Nebula.jpg" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/24px-Crab_Nebula.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/32px-Crab_Nebula.jpg 2x" data-file-width="3864" data-file-height="3864" /></span></span> </span><a href="/wiki/Portal:Astronomy" title="Portal:Astronomy">Astronomy portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/16px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/24px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/32px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> </span><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry portal</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Acetyl_halides_and_salts_of_the_acetate_ion" style="display:table;;padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit;table-layout:fixed;"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Acetates" title="Template:Acetates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Acetates" title="Template talk:Acetates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Acetates" title="Special:EditPage/Template:Acetates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Acetyl_halides_and_salts_of_the_acetate_ion" style="font-size:114%;margin:0 4em">Acetyl halides and salts of the <a href="/wiki/Acetate" title="Acetate">acetate</a> ion</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a class="mw-selflink selflink">AcOH</a> </td> <td style="background-color:white;border:none"> </td> <td style="background-color:white;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Lithium_acetate" title="Lithium acetate">LiOAc</a> </td> <td><a href="/wiki/Beryllium_acetate" class="mw-redirect" title="Beryllium acetate">Be(OAc)<sub>2</sub></a><br /><a href="/wiki/Basic_beryllium_acetate" title="Basic beryllium acetate">Be<sub>4</sub>O(OAc)<sub>6</sub></a> </td> <td><a href="/w/index.php?title=Borontriacetate&action=edit&redlink=1" class="new" title="Borontriacetate (page does not exist)">B(OAc)<sub>3</sub></a><br /><a href="/wiki/Tetraacetyl_diborate" title="Tetraacetyl diborate">B<sub>2</sub>O(OAc)<sub>4</sub></a> </td> <td><a href="/wiki/Acetic_anhydride" title="Acetic anhydride">AcOAc</a><br /><a href="/wiki/Acetate_ester" class="mw-redirect" title="Acetate ester">ROAc</a> </td> <td><a href="/wiki/Ammonium_acetate" title="Ammonium acetate">NH<sub>4</sub>OAc</a> </td> <td><a href="/wiki/Peracetic_acid" title="Peracetic acid">AcOOH</a> </td> <td><a href="/wiki/Acetyl_fluoride" title="Acetyl fluoride">FAc</a><br /><a href="/w/index.php?title=Acetyl_hypofluorite&action=edit&redlink=1" class="new" title="Acetyl hypofluorite (page does not exist)">FOAc</a> </td> <td>Ne </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Sodium_acetate" title="Sodium acetate">NaOAc</a><br /><a href="/wiki/Sodium_diacetate" title="Sodium diacetate">NaH(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Magnesium_acetate" title="Magnesium acetate">Mg(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Aluminium_triacetate" title="Aluminium triacetate">Al(OAc)<sub>3</sub></a><br /><a href="/wiki/Aluminium_acetotartrate" title="Aluminium acetotartrate">ALSOL</a><br /><a href="/wiki/Aluminium_diacetate" title="Aluminium diacetate">Al(OAc)<sub>2</sub>OH</a><br /><a href="/wiki/Aluminium_monoacetate" title="Aluminium monoacetate">Al(OH)<sub>2</sub>OAc</a><br /><a href="/wiki/Aluminium_sulfacetate" title="Aluminium sulfacetate">Al<sub>2</sub>SO<sub>4</sub>(OAc)<sub>4</sub></a> </td> <td>Si </td> <td>P </td> <td>S </td> <td><a href="/wiki/Acetyl_chloride" title="Acetyl chloride">ClAc</a><br /><a href="/wiki/Acetyl_hypochlorite" title="Acetyl hypochlorite">ClOAc</a> </td> <td>Ar </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Potassium_acetate" title="Potassium acetate">KOAc</a> </td> <td><a href="/wiki/Calcium_acetate" title="Calcium acetate">Ca(OAc)<sub>2</sub></a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Scandium_acetate" title="Scandium acetate">Sc(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Titanium(IV)_acetate" title="Titanium(IV) acetate">Ti(OAc)<sub>4</sub></a> </td> <td><a href="/w/index.php?title=Vanadyl_acetate&action=edit&redlink=1" class="new" title="Vanadyl acetate (page does not exist)">VO(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Chromium(II)_acetate" title="Chromium(II) acetate">Cr(OAc)<sub>2</sub></a><br /><a href="/wiki/Chromium(III)_acetate" title="Chromium(III) acetate">Cr(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Manganese(II)_acetate" title="Manganese(II) acetate">Mn(OAc)<sub>2</sub></a><br /><a href="/wiki/Manganese(III)_acetate" title="Manganese(III) acetate">Mn(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Iron(II)_acetate" title="Iron(II) acetate">Fe(OAc)<sub>2</sub></a><br /><a href="/wiki/Iron(III)_acetate" title="Iron(III) acetate">Fe(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Cobalt(II)_acetate" title="Cobalt(II) acetate">Co(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Nickel(II)_acetate" title="Nickel(II) acetate">Ni(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Copper(I)_acetate" title="Copper(I) acetate">CuOAc</a><br /><a href="/wiki/Copper(II)_acetate" title="Copper(II) acetate">Cu(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Zinc_acetate" title="Zinc acetate">Zn(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Gallium_acetate" title="Gallium acetate">Ga(OAc)<sub>3</sub></a> </td> <td>Ge </td> <td><a href="/w/index.php?title=Arsenic_acetate&action=edit&redlink=1" class="new" title="Arsenic acetate (page does not exist)">As(OAc)<sub>3</sub></a> </td> <td>Se </td> <td><a href="/wiki/Acetyl_bromide" title="Acetyl bromide">BrAc</a><br /><a href="/w/index.php?title=Bromine_acetate&action=edit&redlink=1" class="new" title="Bromine acetate (page does not exist)">BrOAc</a> </td> <td>Kr </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Rubidium_acetate" title="Rubidium acetate">RbOAc</a> </td> <td><a href="/wiki/Strontium_acetate" title="Strontium acetate">Sr(OAc)<sub>2</sub></a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Yttrium_acetate" class="mw-redirect" title="Yttrium acetate">Y(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Zirconium(IV)_acetate" title="Zirconium(IV) acetate">Zr(OAc)<sub>4</sub></a> </td> <td>Nb </td> <td><a href="/wiki/Molybdenum(II)_acetate" title="Molybdenum(II) acetate">Mo(OAc)<sub>2</sub></a> </td> <td>Tc </td> <td><a href="/wiki/Diruthenium_tetraacetate_chloride" title="Diruthenium tetraacetate chloride">Ru<sub>2</sub>(OAc)<sub>4</sub>Cl</a><br /><a href="/wiki/Ruthenium(III)_acetate" title="Ruthenium(III) acetate">Ru(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Rhodium(II)_acetate" title="Rhodium(II) acetate">Rh<sub>2</sub>(OAc)<sub>4</sub></a> </td> <td><a href="/wiki/Palladium(II)_acetate" title="Palladium(II) acetate">Pd(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Silver_acetate" title="Silver acetate">AgOAc</a> </td> <td><a href="/wiki/Cadmium_acetate" title="Cadmium acetate">Cd(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Indium_acetate" title="Indium acetate">In(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Tin(II)_acetate" title="Tin(II) acetate">Sn(OAc)<sub>2</sub></a><br /><a href="/wiki/Tin(IV)_acetate" title="Tin(IV) acetate">Sn(OAc)<sub>4</sub></a> </td> <td><a href="/wiki/Antimony(III)_acetate" title="Antimony(III) acetate">Sb(OAc)<sub>3</sub></a> </td> <td>Te </td> <td><a href="/wiki/Acetyl_iodide" title="Acetyl iodide">IAc</a><br /><a href="/w/index.php?title=Iodine(I)_acetate&action=edit&redlink=1" class="new" title="Iodine(I) acetate (page does not exist)">IOAc</a><br /><a href="/w/index.php?title=Iodine(III)_acetate&action=edit&redlink=1" class="new" title="Iodine(III) acetate (page does not exist)">I(OAc)<sub>3</sub></a> </td> <td>Xe </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Caesium_acetate" title="Caesium acetate">CsOAc</a> </td> <td><a href="/wiki/Barium_acetate" title="Barium acetate">Ba(OAc)<sub>2</sub></a> </td> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lutetium(III)_acetate" title="Lutetium(III) acetate">Lu(OAc)<sub>3</sub></a> </td> <td>Hf </td> <td>Ta </td> <td>W </td> <td>Re </td> <td>Os </td> <td>Ir </td> <td><a href="/wiki/Platinum(II)_acetate" title="Platinum(II) acetate">Pt(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Gold(III)_acetate" title="Gold(III) acetate">Au(OAc)<sub>3</sub></a> </td> <td><a href="/w/index.php?title=Mercury(I)_acetate&action=edit&redlink=1" class="new" title="Mercury(I) acetate (page does not exist)">Hg<sub>2</sub>(OAc)<sub>2</sub></a><br /><a href="/wiki/Mercury(II)_acetate" title="Mercury(II) acetate">Hg(OAc)<sub>2</sub></a> </td> <td><a href="/wiki/Thallous_acetate" title="Thallous acetate">TlOAc</a><br /><a href="/wiki/Thallium(III)_acetate" title="Thallium(III) acetate">Tl(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Lead(II)_acetate" title="Lead(II) acetate">Pb(OAc)<sub>2</sub></a><br /><a href="/wiki/Lead(IV)_acetate" title="Lead(IV) acetate">Pb(OAc)<sub>4</sub></a> </td> <td><a href="/wiki/Bismuth(III)_acetate" title="Bismuth(III) acetate">Bi(OAc)<sub>3</sub></a> </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lanthanum_acetate" title="Lanthanum acetate">La(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Cerium(III)_acetate" title="Cerium(III) acetate">Ce(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Praseodymium(III)_acetate" title="Praseodymium(III) acetate">Pr(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Neodymium_acetate" class="mw-redirect" title="Neodymium acetate">Nd(OAc)<sub>3</sub></a> </td> <td>Pm </td> <td><a href="/wiki/Samarium(III)_acetate" title="Samarium(III) acetate">Sm(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Europium(III)_acetate" title="Europium(III) acetate">Eu(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Gadolinium_acetate" title="Gadolinium acetate">Gd(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Terbium_acetate" title="Terbium acetate">Tb(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Dysprosium(III)_acetate" title="Dysprosium(III) acetate">Dy(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Holmium_acetate" title="Holmium acetate">Ho(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Erbium(III)_acetate" title="Erbium(III) acetate">Er(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Thulium(III)_acetate" title="Thulium(III) acetate">Tm(OAc)<sub>3</sub></a> </td> <td><a href="/wiki/Ytterbium(III)_acetate" title="Ytterbium(III) acetate">Yb(OAc)<sub>3</sub></a> </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">** </td> <td><a href="/w/index.php?title=Actinium(III)_acetate&action=edit&redlink=1" class="new" title="Actinium(III) acetate (page does not exist)">Ac(OAc)<sub>3</sub></a> </td> 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