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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Production</span> </div> </a> <ul id="toc-Production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Acetylation_of_alcohols_and_amines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acetylation_of_alcohols_and_amines"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Acetylation of alcohols and amines</span> </div> </a> <ul id="toc-Acetylation_of_alcohols_and_amines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acetylation_of_aromatic_rings" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acetylation_of_aromatic_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Acetylation of aromatic rings</span> </div> </a> <ul id="toc-Acetylation_of_aromatic_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparation_of_other_acid_anhydrides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Preparation_of_other_acid_anhydrides"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Preparation of other acid anhydrides</span> </div> </a> <ul id="toc-Preparation_of_other_acid_anhydrides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_geminal_diacetates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_geminal_diacetates"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Precursor to geminal diacetates</span> </div> </a> <ul id="toc-Precursor_to_geminal_diacetates-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Hydrolysis</span> </div> </a> <ul id="toc-Hydrolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cinnamic_acid_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cinnamic_acid_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.6</span> <span>Cinnamic acid synthesis</span> </div> </a> <ul id="toc-Cinnamic_acid_synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Legal status</span> </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Acetic anhydride</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 43 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-43" 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">43 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%86%D9%87%D9%8A%D8%AF%D8%B1%D9%8A%D8%AF_%D8%A7%D9%84%D8%A3%D8%B3%D9%8A%D8%AA%D9%8A%D9%83" title="أنهيدريد الأسيتيك – Arabic" lang="ar" hreflang="ar" data-title="أنهيدريد الأسيتيك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Sirk%C9%99_anhidridi" title="Sirkə anhidridi – Azerbaijani" lang="az" hreflang="az" data-title="Sirkə anhidridi" 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%D9%86%DB%8C%D8%AF%D8%B1%DB%8C%D8%AF" title="استیک انیدرید – South Azerbaijani" lang="azb" hreflang="azb" data-title="استیک انیدرید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%92%D0%BE%D1%86%D0%B0%D1%82%D0%BD%D1%8B_%D0%B0%D0%BD%D0%B3%D1%96%D0%B4%D1%80%D1%8B%D0%B4" title="Воцатны ангідрыд – Belarusian" lang="be" hreflang="be" data-title="Воцатны ангідрыд" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Anh%C3%ADdrid_ac%C3%A8tic" title="Anhídrid acètic – Catalan" lang="ca" hreflang="ca" data-title="Anhídrid 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/Acetanhydrid" title="Acetanhydrid – Czech" lang="cs" hreflang="cs" data-title="Acetanhydrid" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Eddikesyreanhydrid" title="Eddikesyreanhydrid – Danish" lang="da" hreflang="da" data-title="Eddikesyreanhydrid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Essigs%C3%A4ureanhydrid" title="Essigsäureanhydrid – German" lang="de" hreflang="de" data-title="Essigsäureanhydrid" 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/Atseetanh%C3%BCdriid" title="Atseetanhüdriid – Estonian" lang="et" hreflang="et" data-title="Atseetanhüdriid" 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%CF%82_%CE%B1%CE%BD%CF%85%CE%B4%CF%81%CE%AF%CF%84%CE%B7%CF%82" title="Οξικός ανυδρίτης – Greek" lang="el" hreflang="el" data-title="Οξικός ανυδρίτης" 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/Anh%C3%ADdrido_ac%C3%A9tico" title="Anhídrido acético – Spanish" lang="es" hreflang="es" data-title="Anhídrido 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_anhidrido" title="Acetata anhidrido – Esperanto" lang="eo" hreflang="eo" data-title="Acetata anhidrido" 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/Anhidrido_azetiko" title="Anhidrido azetiko – Basque" lang="eu" hreflang="eu" data-title="Anhidrido 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%D9%86%DB%8C%D8%AF%D8%B1%DB%8C%D8%AF" title="استیک انیدرید – Persian" lang="fa" hreflang="fa" data-title="استیک انیدرید" 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/Anhydride_ac%C3%A9tique" title="Anhydride acétique – French" lang="fr" hreflang="fr" data-title="Anhydride acétique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%84%B8%ED%8A%B8%EC%82%B0_%EB%AC%B4%EC%88%98%EB%AC%BC" title="아세트산 무수물 – Korean" lang="ko" hreflang="ko" data-title="아세트산 무수물" 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%BE%D5%AB_%D5%A1%D5%B6%D5%B0%D5%AB%D5%A4%D6%80%D5%AB%D5%A4" title="Քացախաթթվի անհիդրիդ – Armenian" lang="hy" hreflang="hy" data-title="Քացախաթթվի անհիդրիդ" 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%8F%E0%A4%A8%E0%A4%B9%E0%A4%BE%E0%A4%88%E0%A4%A1%E0%A5%8D%E0%A4%B0%E0%A4%BE%E0%A4%87%E0%A4%A1" title="एसिटिक एनहाईड्राइड – Hindi" lang="hi" hreflang="hi" data-title="एसिटिक एनहाईड्राइड" 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/Acetanhidrid" title="Acetanhidrid – Croatian" lang="hr" hreflang="hr" data-title="Acetanhidrid" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asetat_anhidrida" title="Asetat anhidrida – Indonesian" lang="id" hreflang="id" data-title="Asetat anhidrida" 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-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Ediks%C3%BDruanh%C3%BDdr%C3%AD%C3%B0" title="Ediksýruanhýdríð – Icelandic" lang="is" hreflang="is" data-title="Ediksýruanhýdríð" 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/Anidride_acetica" title="Anidride acetica – Italian" lang="it" hreflang="it" data-title="Anidride acetica" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A0%D7%94%D7%99%D7%93%D7%A8%D7%99%D7%93_%D7%90%D7%A6%D7%98%D7%99" title="אנהידריד אצטי – Hebrew" lang="he" hreflang="he" data-title="אנהידריד אצטי" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%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%E1%83%A1_%E1%83%90%E1%83%9C%E1%83%B0%E1%83%98%E1%83%93%E1%83%A0%E1%83%98%E1%83%93%E1%83%98" title="ძმარმჟავას ანჰიდრიდი – Georgian" lang="ka" hreflang="ka" data-title="ძმარმჟავას ანჰიდრიდი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Acetanhidr%C4%ABds" title="Acetanhidrīds – Latvian" lang="lv" hreflang="lv" data-title="Acetanhidrīds" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ecetsav-anhidrid" title="Ecetsav-anhidrid – Hungarian" lang="hu" hreflang="hu" data-title="Ecetsav-anhidrid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Azijnzuuranhydride" title="Azijnzuuranhydride – Dutch" lang="nl" hreflang="nl" data-title="Azijnzuuranhydride" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E7%84%A1%E6%B0%B4%E9%85%A2%E9%85%B8" title="無水酢酸 – Japanese" lang="ja" hreflang="ja" data-title="無水酢酸" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Bezwodnik_octowy" title="Bezwodnik octowy – Polish" lang="pl" hreflang="pl" data-title="Bezwodnik 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/Anidrido_ac%C3%A9tico" title="Anidrido acético – Portuguese" lang="pt" hreflang="pt" data-title="Anidrido acético" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Anhidrid%C4%83_acetic%C4%83" title="Anhidridă acetică – Romanian" lang="ro" hreflang="ro" data-title="Anhidridă acetică" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A3%D0%BA%D1%81%D1%83%D1%81%D0%BD%D1%8B%D0%B9_%D0%B0%D0%BD%D0%B3%D0%B8%D0%B4%D1%80%D0%B8%D0%B4" title="Уксусный ангидрид – Russian" lang="ru" hreflang="ru" data-title="Уксусный ангидрид" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Acetanhydrid" title="Acetanhydrid – Slovak" lang="sk" hreflang="sk" data-title="Acetanhydrid" 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/Acetanhidrid" title="Acetanhidrid – Slovenian" lang="sl" hreflang="sl" data-title="Acetanhidrid" 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/Anhidrid_sir%C4%87etne_kiseline" title="Anhidrid sirćetne kiseline – Serbian" lang="sr" hreflang="sr" data-title="Anhidrid sirćetne kiseline" 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/Anhidrid_sir%C4%87etne_kiseline" title="Anhidrid sirćetne kiseline – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Anhidrid sirćetne kiseline" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Etikkahappoanhydridi" title="Etikkahappoanhydridi – Finnish" lang="fi" hreflang="fi" data-title="Etikkahappoanhydridi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/%C3%84ttiksyraanhydrid" title="Ättiksyraanhydrid – Swedish" lang="sv" hreflang="sv" data-title="Ättiksyraanhydrid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%9A%E0%AE%BF%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%A8%E0%AF%80%E0%AE%B0%E0%AE%BF%E0%AE%B2%E0%AE%BF" title="அசிட்டிக் நீரிலி – Tamil" lang="ta" 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td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Acetic anhydride </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:Acetic_anhydride2DACS.svg" class="mw-file-description" title="Acetic anhydride"><img alt="Acetic anhydride" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Acetic_anhydride2DACS.svg/150px-Acetic_anhydride2DACS.svg.png" decoding="async" width="150" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Acetic_anhydride2DACS.svg/225px-Acetic_anhydride2DACS.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Acetic_anhydride2DACS.svg/300px-Acetic_anhydride2DACS.svg.png 2x" data-file-width="733" data-file-height="474" /></a><figcaption>Acetic anhydride</figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Acetic-anhydride-from-xtal-2003-3D-balls.png" class="mw-file-description" title="Acetic anhydride"><img alt="Acetic anhydride" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Acetic-anhydride-from-xtal-2003-3D-balls.png/150px-Acetic-anhydride-from-xtal-2003-3D-balls.png" decoding="async" width="150" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Acetic-anhydride-from-xtal-2003-3D-balls.png/225px-Acetic-anhydride-from-xtal-2003-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Acetic-anhydride-from-xtal-2003-3D-balls.png/300px-Acetic-anhydride-from-xtal-2003-3D-balls.png 2x" data-file-width="3500" data-file-height="2136" /></a><figcaption>Acetic anhydride</figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Acetic anhydride</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 anhydride</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;">Ethanoyl ethanoate<br />Acetic acid anhydride<br />Acetyl acetate<br />Acetyl oxide<br />Acetic oxide</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=108-24-7">108-24-7</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=O%3DC%28OC%28%3DO%29C%29C">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29OC%28%3DO%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=36610">CHEBI:36610</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1305819">ChEMBL1305819</a></span></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.7630.html">7630</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.003.241">100.003.241</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407775#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>203-564-8</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/7918">7918</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>AK1925000</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/2E48G1QI9Q">2E48G1QI9Q</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>1715 </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/DTXSID0024395">DTXSID0024395</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407775#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3<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: WFDIJRYMOXRFFG-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C4H6O3/c1-3(5)7-4(2)6/h1-2H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: WFDIJRYMOXRFFG-UHFFFAOYAH</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(OC(=O)C)C</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(=O)OC(=O)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>4</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002102089000000000♠"></span>102.089</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>colorless liquid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.082 g cm<sup>−3</sup>, liquid </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−73.1 °C (−99.6 °F; 200.1 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>139.8 °C (283.6 °F; 412.9 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>2.6 g/100 mL, reacts (<i>see text</i>) </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>4 mmHg (20 °C)<sup id="cite_ref-NIOSH_1-0" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−52.8·10<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>1.3901 </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry<sup id="cite_ref-crc_2-0" class="reference"><a href="#cite_note-crc-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/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>−624.4 kJ/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></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_6" title="Standard for the Uniform Scheduling of Medicines and Poisons">S6</a> (Poison)</li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_VI_(Precursors)" title="Controlled Drugs and Substances Act">Schedule VI</a></li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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><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></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="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H330: Fatal if inhaled">H330</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.">P301+P312</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P312: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.">P304+P312</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</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>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P403+P235: Store in a well ventilated place. Keep cool.">P403+P235</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_bcfe8a04562d8f4e" /></span><map name="ImageMap_bcfe8a04562d8f4e"><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 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" title="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid" title="Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid" /></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 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-white-text mw-no-invert"><a href="/wiki/NFPA_704#White" title="NFPA 704"><span class="nfpa-704-diamond-white-wors" title="Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid"><span class="nfpa-704-diamond-white-strike">W</span></span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>49 °C (120 °F; 322 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>316 °C (601 °F; 589 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>2.7–10.3% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>1000 ppm (rat, 4 <a href="/wiki/Hour" title="Hour">h</a>)<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 5 ppm (20 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_1-1" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<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>C 5 ppm (20 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_1-2" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<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>200 ppm<sup id="cite_ref-NIOSH_1-3" class="reference"><a href="#cite_note-NIOSH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0209.htm">ICSC 0209</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Acid_anhydride" title="Acid anhydride">acid anhydrides</a></div> </td> <td><a href="/wiki/Propionic_anhydride" title="Propionic anhydride">Propionic anhydride</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/Acetic_acid" title="Acetic acid">Acetic acid</a><br /><a href="/wiki/Acetyl_chloride" title="Acetyl chloride">Acetyl chloride</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477238827&page2=Acetic+anhydride">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Acetic anhydride</b>, or <b>ethanoic anhydride</b>, is the <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>CO)<sub class="template-chem2-sub">2</sub>O</span>. Commonly abbreviated <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">Ac</a><sub class="template-chem2-sub">2</sub>O</span>, it is the simplest isolable <a href="/wiki/Organic_acid_anhydride" title="Organic acid anhydride">anhydride</a> of a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> and is widely used as a <a href="/wiki/Reagent" title="Reagent">reagent</a> in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. It is a colorless liquid that smells strongly of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, which is formed by its reaction with moisture in the air. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_properties">Structure and properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=1" title="Edit section: Structure and properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Acetic_anhydride.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Acetic_anhydride.jpg/220px-Acetic_anhydride.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Acetic_anhydride.jpg/330px-Acetic_anhydride.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/68/Acetic_anhydride.jpg/440px-Acetic_anhydride.jpg 2x" data-file-width="3968" data-file-height="2976" /></a><figcaption>Acetic anhydride in a glass bottle</figcaption></figure> <p>Acetic anhydride, like most organic acid anhydrides, is a flexible molecule with a nonplanar structure.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Pi_bond" title="Pi bond">pi system linkage</a> through the central oxygen offers very weak resonance stabilization compared to the <a href="/wiki/Dipole" title="Dipole">dipole-dipole</a> repulsion between the two <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> oxygens. The energy barriers to bond rotation between each of the optimal aplanar conformations are quite low.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Like most acid anhydrides, the carbonyl carbon atom of acetic anhydride has <a href="/wiki/Electrophile" title="Electrophile">electrophilic character</a>, as the leaving group is <a href="/wiki/Carboxylate" title="Carboxylate">carboxylate</a>. The internal asymmetry may contribute to acetic anhydride's potent electrophilicity as the asymmetric geometry makes one side of a carbonyl carbon atom more reactive than the other, and in doing so tends to consolidate the electropositivity of a carbonyl carbon atom to one side (see electron density diagram). </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_anhydride&action=edit&section=2" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetic anhydride was first synthesized in 1852 by the French chemist <a href="/wiki/Charles_Fr%C3%A9d%C3%A9ric_Gerhardt" title="Charles Frédéric Gerhardt">Charles Frédéric Gerhardt</a> (1816-1856) by heating <a href="/wiki/Potassium_acetate" title="Potassium acetate">potassium acetate</a> with <a href="/wiki/Benzoyl_chloride" title="Benzoyl chloride">benzoyl chloride</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Acetic anhydride is produced by <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> of <a href="/wiki/Methyl_acetate" title="Methyl acetate">methyl acetate</a>:<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </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>CH<sub class="template-chem2-sub">3</sub> + CO → (CH<sub class="template-chem2-sub">3</sub>CO)<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>The <a href="/wiki/Monsanto_process#Tennessee_Eastman_acetic_anhydride_process" title="Monsanto process">Tennessee Eastman acetic anhydride process</a> involves the conversion of methyl acetate to <a href="/wiki/Iodomethane" title="Iodomethane">methyl iodide</a> and an acetate salt. Carbonylation of the methyl iodide in turn produces <a href="/wiki/Acetyl_iodide" title="Acetyl iodide">acetyl iodide</a>, which reacts with acetate salts or acetic acid to give the product. <a href="/wiki/Rhodium_chloride" class="mw-redirect" title="Rhodium chloride">Rhodium chloride</a> in the presence of <a href="/wiki/Lithium_iodide" title="Lithium iodide">lithium iodide</a> is employed as catalysts. Because acetic anhydride is not stable in water, the conversion is conducted under anhydrous conditions. </p><p>To a decreasing extent, acetic anhydride is also prepared by the reaction of ketene (<a href="/wiki/Ethenone" title="Ethenone">ethenone</a>) with acetic acid at 45–55 °C and low pressure (0.05–0.2 bar).<sup id="cite_ref-Arpe_8-0" class="reference"><a href="#cite_note-Arpe-8"><span class="cite-bracket">[</span>8<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">H<sub class="template-chem2-sub">2</sub>C=C=O + CH<sub class="template-chem2-sub">3</sub>COOH → (CH<sub class="template-chem2-sub">3</sub>CO)<sub class="template-chem2-sub">2</sub>O</span></dd> <dd>(Δ<i>H</i> = −63 kJ/mol)</dd></dl> <p>The route from acetic acid to acetic anhydride via ketene was developed by <a href="/wiki/Wacker_Chemie" title="Wacker Chemie">Wacker Chemie</a> in 1922,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> when the demand for acetic anhydride increased due to the production of <a href="/wiki/Cellulose_acetate" title="Cellulose acetate">cellulose acetate</a>. </p><p>Due to its low cost, acetic anhydride is usually purchased, not prepared, for use in research laboratories. </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_anhydride&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetic anhydride is a versatile reagent for <a href="/wiki/Acetylation" title="Acetylation">acetylations</a>, the introduction of acetyl groups to organic substrates.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> In these conversions, acetic anhydride is viewed as a source of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO<sup class="template-chem2-sup">+</sup></span>. </p> <div class="mw-heading mw-heading3"><h3 id="Acetylation_of_alcohols_and_amines">Acetylation of alcohols and amines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=4" title="Edit section: Acetylation of alcohols and amines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> and <a href="/wiki/Amine" title="Amine">amines</a> are readily acetylated.<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> For example, the reaction of acetic anhydride with <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> yields <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</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>CO)<sub class="template-chem2-sub">2</sub>O + CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>OH → CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub> + CH<sub class="template-chem2-sub">3</sub>COOH</span></dd></dl> <p>Often a base such as <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> is added to function as catalyst. In specialized applications, <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acidic</a> <a href="/wiki/Scandium" title="Scandium">scandium</a> salts have also proven effective catalysts.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Acetylation_of_aromatic_rings">Acetylation of aromatic rings</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=5" title="Edit section: Acetylation of aromatic rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aromatic rings are acetylated by acetic anhydride. Usually acid catalysts are used to accelerate the reaction. Illustrative are the conversions of <a href="/wiki/Benzene" title="Benzene">benzene</a> to <a href="/wiki/Acetophenone" title="Acetophenone">acetophenone</a><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a> to acetylferrocene:<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> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>Fe + (CH<sub class="template-chem2-sub">3</sub>CO)<sub class="template-chem2-sub">2</sub>O → (C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)Fe(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">4</sub>COCH<sub class="template-chem2-sub">3</sub>) + CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Preparation_of_other_acid_anhydrides">Preparation of other acid anhydrides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=6" title="Edit section: Preparation of other acid anhydrides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dicarboxylic acids are converted to the anhydrides upon treatment with acetic anhydride.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> It is also used for the preparation of mixed anhydrides such as that with nitric acid, <a href="/wiki/Acetyl_nitrate" title="Acetyl nitrate">acetyl nitrate</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_geminal_diacetates">Precursor to geminal diacetates</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=7" title="Edit section: Precursor to geminal diacetates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Aldehyde" title="Aldehyde">Aldehydes</a> react with acetic anhydride in the presence of an acidic <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> to give geminal diacetates.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> A former industrial route to <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a> involved the intermediate <a href="/wiki/Ethylidene_diacetate" title="Ethylidene diacetate">ethylidene diacetate</a>, the geminal diacetate obtained from <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> and acetic anhydride:<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </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>CHO + (CH<sub class="template-chem2-sub">3</sub>CO)<sub class="template-chem2-sub">2</sub>O → (CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub>CHCH<sub class="template-chem2-sub">3</sub></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Hydrolysis">Hydrolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=8" title="Edit section: Hydrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetic anhydride dissolves in water to approximately 2.6% by weight.<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> Aqueous solutions have limited stability because, like most acid anhydrides, acetic anhydride hydrolyses to give carboxylic acids. In this case, acetic acid is formed, this reaction product being fully water miscible:<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </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>O + H<sub class="template-chem2-sub">2</sub>O → 2 CH<sub class="template-chem2-sub">3</sub>COOH</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Cinnamic_acid_synthesis">Cinnamic acid synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=9" title="Edit section: Cinnamic acid synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the last third of the 19th century the main application for the acetic anhydride was the <a href="/wiki/Perkin_reaction" title="Perkin reaction">Perkin reaction</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=10" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As indicated by its organic chemistry, acetic anhydride is mainly used for acetylations leading to commercially significant materials. Its largest application is for the conversion of cellulose to <a href="/wiki/Cellulose_acetate" title="Cellulose acetate">cellulose acetate</a>, which is a component of photographic film and other coated materials, and is used in the manufacture of cigarette filters. Similarly it is used in the production of <a href="/wiki/Aspirin" title="Aspirin">aspirin</a> (acetylsalicylic acid), which is prepared by the acetylation of <a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a>.<sup id="cite_ref-SIDS_21-0" class="reference"><a href="#cite_note-SIDS-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> It is also used as an active modification agent via <a href="/wiki/Autoclave" title="Autoclave">autoclave</a> impregnation and subsequent acetylation to make a durable and long-lasting timber.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>In starch industry, acetic anhydride is a common acetylation compound, used for the production of <a href="/wiki/Modified_starch" title="Modified starch">modified starches</a> (E1414, E1420, E1422) </p> <div class="mw-heading mw-heading2"><h2 id="Legal_status">Legal status</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=11" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of its use for the synthesis of <a href="/wiki/Heroin" title="Heroin">heroin</a> by the diacetylation of <a href="/wiki/Morphine" title="Morphine">morphine</a>, acetic anhydride is listed as a U.S. DEA List II precursor, and restricted in many other countries.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=12" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetic anhydride is an irritant and combustible liquid; it is highly corrosive to skin and any direct contact will result in severe burns. Because of its reactivity toward water and alcohol, foam or carbon dioxide are preferred for fire suppression.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> The vapour of acetic anhydride is harmful.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <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_anhydride&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-NIOSH-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-NIOSH_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NIOSH_1-1"><sup><i><b>b</b></i></sup></a> <a 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.cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0003.html">"#0003"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span 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Retrieved <span class="nowrap">2006-04-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Pocket+Guide+to+Chemical+Hazards&rft.atitle=NIOSH&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0003.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetic+anhydride" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetic_anhydride&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0209.htm">ICSC 0209</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0003.html">NIOSH Pocket Guide to Chemical 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