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Available in 18 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-18" 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">18 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D9%8A%D8%AB%D9%8A%D9%84_%D8%A3%D9%83%D8%B1%D9%8A%D9%84%D9%8A%D8%AA" title="إيثيل أكريليت – Arabic" lang="ar" hreflang="ar" data-title="إيثيل أكريليت" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%AA%DB%8C%D9%84_%D8%A7%DA%A9%D8%B1%DB%8C%D9%84%D8%A7%D8%AA" title="اتیل اکریلات – South Azerbaijani" lang="azb" hreflang="azb" data-title="اتیل اکریلات" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ethyl-akryl%C3%A1t" title="Ethyl-akrylát – Czech" lang="cs" hreflang="cs" data-title="Ethyl-akrylát" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Acryls%C3%A4ureethylester" title="Acrylsäureethylester – German" lang="de" hreflang="de" data-title="Acrylsäureethylester" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Acrilato_de_etilo" title="Acrilato de etilo – Spanish" lang="es" hreflang="es" data-title="Acrilato de etilo" 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/Etila_akrilato" title="Etila akrilato – Esperanto" lang="eo" hreflang="eo" data-title="Etila akrilato" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%AA%DB%8C%D9%84_%D8%A7%DA%A9%D8%B1%DB%8C%D9%84%D8%A7%D8%AA" title="اتیل اکریلات – Persian" lang="fa" hreflang="fa" data-title="اتیل اکریلات" 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/Acrylate_d%27%C3%A9thyle" title="Acrylate d'éthyle – French" lang="fr" hreflang="fr" data-title="Acrylate d'éthyle" 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/Aicriligh%C3%A1it_eitile" title="Aicriligháit eitile – Irish" lang="ga" hreflang="ga" data-title="Aicriligháit eitile" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ethylacrylaat" title="Ethylacrylaat – Dutch" lang="nl" hreflang="nl" data-title="Ethylacrylaat" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%82%AF%E3%83%AA%E3%83%AB%E9%85%B8%E3%82%A8%E3%83%81%E3%83%AB" title="アクリル酸エチル – Japanese" lang="ja" hreflang="ja" data-title="アクリル酸エチル" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Acrilato_de_etila" title="Acrilato de etila – Portuguese" lang="pt" hreflang="pt" data-title="Acrilato de etila" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Etilakrilat" title="Etilakrilat – Slovenian" lang="sl" hreflang="sl" data-title="Etilakrilat" 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/Etil_akrilat" title="Etil akrilat – Serbian" lang="sr" hreflang="sr" data-title="Etil akrilat" 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/Etil_akrilat" title="Etil akrilat – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Etil akrilat" 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/Etyyliakrylaatti" title="Etyyliakrylaatti – Finnish" lang="fi" hreflang="fi" data-title="Etyyliakrylaatti" 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/Etylakrylat" title="Etylakrylat – Swedish" lang="sv" hreflang="sv" data-title="Etylakrylat" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B8%99%E7%83%AF%E9%85%B8%E4%B9%99%E9%85%AF" title="丙烯酸乙酯 – Chinese" lang="zh" hreflang="zh" data-title="丙烯酸乙酯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit 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<div id="contentSub"><div id="mw-content-subtitle"><div class="cdx-message cdx-message--block cdx-message--warning mw-revision"><span class="cdx-message__icon"></span><div class="cdx-message__content"><div id="mw-revision-info"><p><b>This is an <a href="/wiki/Help:Page_history" title="Help:Page history">old revision</a> of this page, as edited by <span id="mw-revision-name"><a href="/wiki/Special:Contributions/192.118.27.253" class="mw-userlink mw-anonuserlink" title="Special:Contributions/192.118.27.253" data-mw-revid="927894621"><bdi>192.118.27.253</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:192.118.27.253" class="mw-usertoollinks-talk" title="User talk:192.118.27.253">talk</a>)</span></span> at <span id="mw-revision-date">13:30, 25 November 2019</span><span id="mw-revision-summary"> <span class="comment">(Revert good faith but unconstructive edit by IP 50.64.152.102)</span></span>. The present address (URL) is a <a href="/wiki/Help:Permanent_link" title="Help:Permanent link">permanent link</a> to this revision, which may differ significantly from the <span class="plainlinks"><a class="external text" href="https://en.wikipedia.org/wiki/Ethyl_acrylate">current revision</a></span>.</b></p><div id="revision-info-plain" style="display: none;">Revision as of 13:30, 25 November 2019 by <a href="/wiki/Special:Contributions/192.118.27.253" class="mw-userlink mw-anonuserlink" title="Special:Contributions/192.118.27.253" data-mw-revid="927894621"><bdi>192.118.27.253</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:192.118.27.253" class="mw-usertoollinks-talk" title="User talk:192.118.27.253">talk</a>)</span> <span class="comment">(Revert good faith but unconstructive edit by IP 50.64.152.102)</span></div></div><div id="mw-revision-nav">(<a href="/w/index.php?title=Ethyl_acrylate&diff=prev&oldid=927894621" title="Ethyl acrylate">diff</a>) <a href="/w/index.php?title=Ethyl_acrylate&direction=prev&oldid=927894621" title="Ethyl acrylate">← Previous revision</a> | <a href="/wiki/Ethyl_acrylate" title="Ethyl acrylate">Latest revision</a> (<a href="/w/index.php?title=Ethyl_acrylate&diff=cur&oldid=927894621" title="Ethyl acrylate">diff</a>) | <a href="/w/index.php?title=Ethyl_acrylate&direction=next&oldid=927894621" title="Ethyl acrylate">Newer revision →</a> (<a href="/w/index.php?title=Ethyl_acrylate&diff=next&oldid=927894621" title="Ethyl acrylate">diff</a>)</div></div></div></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Ethyl acrylate<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> </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Ethyl_acrylate.png" class="mw-file-description"><img alt="Skeletal structure of ethyl acrylate" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Ethyl_acrylate.png/160px-Ethyl_acrylate.png" decoding="async" width="160" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Ethyl_acrylate.png/240px-Ethyl_acrylate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Ethyl_acrylate.png/320px-Ethyl_acrylate.png 2x" data-file-width="645" data-file-height="294" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Ethyl_acrylate_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the ethyl acrylate molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Ethyl_acrylate_molecule_ball.png/220px-Ethyl_acrylate_molecule_ball.png" decoding="async" width="220" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Ethyl_acrylate_molecule_ball.png/330px-Ethyl_acrylate_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Ethyl_acrylate_molecule_ball.png/440px-Ethyl_acrylate_molecule_ball.png 2x" data-file-width="2072" data-file-height="1000" /></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;">Ethyl prop-2-enoate</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;">Ethyl propenoate<br />Ethyl acrylate<br />Acrylic acid ethyl ester<br />Ethyl propenoate<br />Ethyl ester of acrylic acid</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=140-88-5">140-88-5</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=CCOC%28%3DO%29C%3DC">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=82327">CHEBI:82327</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/ChEMBL52084">ChEMBL52084</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.8490.html">8490</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/100.004.945">100.004.945</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q343014#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>205-438-8</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/C19238">C19238</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8821">8821</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>AT0700000</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/71E6178C9T">71E6178C9T</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>1917 </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/DTXSID4020583">DTXSID4020583</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q343014#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/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3<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: JIGUQPWFLRLWPJ-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/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: JIGUQPWFLRLWPJ-UHFFFAOYAN</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%;">CCOC(=O)C=C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>5</sub><span title="Hydrogen">H</span><sub>8</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002100117000000000♠"></span>100.117</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Clear liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Acrid<sup id="cite_ref-PGCH_3-0" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.9405 g/mL </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−71 °C (−96 °F; 202 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>99.4 °C (210.9 °F; 372.5 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>1.5 g/100 mL </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>29 mmHg (20°C)<sup id="cite_ref-PGCH_3-1" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Carcinogenic </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 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.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_4697d705f8b6763d" /></span><map name="ImageMap_4697d705f8b6763d"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" title="Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</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 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" class="notheme mw-no-invert">2</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>15 °C (59 °F; 288 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>1.4%-14%<sup id="cite_ref-PGCH_3-2" class="reference"><a href="#cite_note-PGCH-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;"><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>2180 ppm (rat, 4 hr)<br />3894 ppm (mouse)<sup id="cite_ref-IDLH_4-0" class="reference"><a href="#cite_note-IDLH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>1204 ppm (rabbit, 7 hr)<br /> 1204 ppm (guinea pig, 7 hr)<sup id="cite_ref-IDLH_4-1" class="reference"><a href="#cite_note-IDLH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 25 ppm (100 mg/m<sup>3</sup>) [skin]<sup id="cite_ref-PGCH_3-3" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<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>Carcinogen<sup id="cite_ref-PGCH_3-4" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<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>Ca [300 ppm]<sup id="cite_ref-PGCH_3-5" class="reference"><a href="#cite_note-PGCH-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:#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=415312157&page2=Ethyl+acrylate">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>Ethyl acrylate</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the formula CH<sub>2</sub>CHCO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>. It is the <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> <a href="/wiki/Ester" title="Ester">ester</a> of <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a>. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers.<sup id="cite_ref-Ullmann_5-0" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is also a <a href="/wiki/Reagent" title="Reagent">reagent</a> in the synthesis of various pharmaceutical intermediates. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2></div> <p>Ethyl acrylate is produced by acid-catalysed esterification of acrylic acid, which in turn is produced by oxidation of <a href="/wiki/Propylene" title="Propylene">propylene</a>. It may also be prepared from <a href="/wiki/Acetylene" title="Acetylene">acetylene</a>, <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> and ethanol by a <a href="/wiki/Walter_Reppe#Reppe_chemistry" title="Walter Reppe">Reppe reaction</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Reactions_and_uses">Reactions and uses</h2></div> <p>Ethyl acrylate is used in the production of polymers including resins, plastics, rubber, and denture material.<sup id="cite_ref-NJ_6-0" class="reference"><a href="#cite_note-NJ-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Ethyl acrylate is a reactant for homologous alkyl acrylates (acrylic esters) by transesterification with higher alcohols through acidic or basic catalysis. In that way speciality acrylates are made accessible, e.g. <a href="/wiki/2-Ethylhexyl_acrylate" title="2-Ethylhexyl acrylate">2-ethylhexyl acrylate</a> (from <a href="/wiki/2-Ethylhexanol" title="2-Ethylhexanol">2-ethylhexanol</a>) used for pressure-sensitive adhesives, <a href="/w/index.php?title=Cyclohexyl_acrylate&action=edit&redlink=1" class="new" title="Cyclohexyl acrylate (page does not exist)">cyclohexyl acrylate</a> (from <a href="/wiki/Cyclohexanol" title="Cyclohexanol">cyclohexanol</a>) used for automotive clear lacquers, <a href="/w/index.php?title=2-hydroxyethyl_acrylate&action=edit&redlink=1" class="new" title="2-hydroxyethyl acrylate (page does not exist)">2-hydroxyethyl acrylate</a> (from <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a>) which is crosslinkable with <a href="/wiki/Diisocyanate" class="mw-redirect" title="Diisocyanate">diisocyanates</a> to form gels used with long-chain acrylates (from C18+ alcohols)<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> as comonomer for <a href="/wiki/Comb_polymers" class="mw-redirect" title="Comb polymers">comb polymers</a> for reduction of the <a href="/wiki/Solidiification_point" class="mw-redirect" title="Solidiification point">solidification point</a> of <a href="/wiki/Mineral_oil" title="Mineral oil">paraffin oils</a> and <a href="/wiki/2-Dimethylaminoethyl_acrylate" class="mw-redirect" title="2-Dimethylaminoethyl acrylate">2-dimethylaminoethyl acrylate</a> (from <a href="/wiki/Dimethylaminoethanol" class="mw-redirect" title="Dimethylaminoethanol">dimethylaminoethanol</a><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>) for the preparation of flocculants for sewage clarification and paper production. </p><p>As a reactive monomer, ethyl acrylate is used in homopolymers and copolymers with e.g. <a href="/wiki/Ethylene" title="Ethylene">ethene</a>, <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a> and its salts, <a href="/wiki/Amide" title="Amide">amides</a> and esters, <a href="/wiki/Methacrylate" title="Methacrylate">methacrylates</a>, <a href="/wiki/Acrylonitrile" title="Acrylonitrile">acrylonitrile</a>, <a href="/w/index.php?title=Maleic_ester&action=edit&redlink=1" class="new" title="Maleic ester (page does not exist)">maleic esters</a>, <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a>, <a href="/wiki/Vinyl_chloride" title="Vinyl chloride">vinyl chloride</a>, <a href="/wiki/Vinylidene_chloride" class="mw-redirect" title="Vinylidene chloride">vinylidene chloride</a>, <a href="/wiki/Styrene" title="Styrene">styrene</a>, butadiene and <a href="/wiki/Unsaturated_polyester" class="mw-redirect" title="Unsaturated polyester">unsaturated polyesters</a>.<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> Copolymers of acrylic acid ethyl ester with ethene (EPA/<a href="/w/index.php?title=Ethylene-ethyl_acrylate_copolymer&action=edit&redlink=1" class="new" title="Ethylene-ethyl acrylate copolymer (page does not exist)">ethylene-ethyl acrylate copolymers</a>) are suitable as adhesives and polymer additives, just like ethene vinyl acetate copolymers. <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> Copolymers with acrylic acid increase the cleaning effect of <a href="/wiki/Liquid_detergent" class="mw-redirect" title="Liquid detergent">liquid detergents</a>,<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> copolymers with methacrylic acid are used as gastric juices tablet covers (Eudragit®).<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><p>The large number of possible comonomer units and their combination in copolymers and terpolymers with ethyl acrylate allows the realization of different properties of the acrylate copolymers in a variety of applications in paints and adhesives, paper, textile and leather <a href="/wiki/Auxiliaries" title="Auxiliaries">auxiliaries</a> together with cosmetic and pharmaceutical products. </p><p>Owing to its tendency to polymerize, samples typically contain an inhibitor such as <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a>. </p><p>Ethyl acrylate reacts with amines catalyzed by Lewis acids in a <a href="/wiki/Michael_addition" class="mw-redirect" title="Michael addition">Michael addition</a> to <a href="/wiki/Beta-Alanine" class="mw-redirect" title="Beta-Alanine">β-alanine</a> derivatives in high yields:<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Michael-Addition_von_Amin_an_EA.svg" class="mw-file-description" title="Michael addition of an amine to ethyl acrylate"><img alt="Michael addition of an amine to ethyl acrylate" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Michael-Addition_von_Amin_an_EA.svg/486px-Michael-Addition_von_Amin_an_EA.svg.png" decoding="async" width="486" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Michael-Addition_von_Amin_an_EA.svg/729px-Michael-Addition_von_Amin_an_EA.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Michael-Addition_von_Amin_an_EA.svg/972px-Michael-Addition_von_Amin_an_EA.svg.png 2x" data-file-width="486" data-file-height="82" /></a></span> </p><p>The nucleophilic addition at ethyl acrylate as an α,β-unsaturated carbonyl compound is a frequent strategy in the synthesis of pharmaceutical intermediates. Examples are the <a href="/wiki/Hypnotic" title="Hypnotic">hypnotic</a> <a href="/wiki/Glutethimide" title="Glutethimide">glutethimide</a> or the <a href="/wiki/Vasodilation" title="Vasodilation">vasodilator</a> <a href="/wiki/Vincamine" title="Vincamine">vincamin</a> (obsolete by now)<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> or more recent therapeutics such as the COPD agent <a href="/wiki/Cilomilast" title="Cilomilast">cilomilast</a> or the <a href="/wiki/Nootropic" title="Nootropic">nootropic</a> <a href="/wiki/Leteprinim" title="Leteprinim">leteprinim</a>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>With <a href="/wiki/Diene" title="Diene">dienes</a> ethyl acrylate reacts as a good <a href="/wiki/Dienophile" class="mw-redirect" title="Dienophile">dienophile</a> in <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels-Alder reactions</a> e.g. with <a href="/wiki/1,3-Butadiene" class="mw-redirect" title="1,3-Butadiene">1,3-butadiene</a> in a [4+2] <a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a> reaction to give a cyclohexene carboxylic acid ester in a high yield.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Ethyl acrylate is also used as a flavoring agent. It has been found as a volatile component in <a href="/wiki/Pineapple" title="Pineapple">pineapples</a> and <a href="/wiki/Beaufort_cheese" title="Beaufort cheese">Beaufort cheese</a><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> and is a secondary component in vanilla flavor obtained from heat extraction of vanilla in amounts of up to 1 ppm. In such high concentrations it negatively affects the extracted aroma.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2></div> <p>The <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> stated, "Overall evaluation, ethyl acrylate is possibly carcinogenic to humans (Group 2B)."<sup id="cite_ref-IARC_19-0" class="reference"><a href="#cite_note-IARC-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> (EPA) states, "Human studies on occupational exposure to ethyl acrylate... have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of <a href="/wiki/Squamous_cell_papilloma" title="Squamous cell papilloma">squamous cell papillomas</a> and carcinomas of the forestomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity since humans do not have a forestomach, and removed ethyl acrylate from its list of carcinogens."<sup id="cite_ref-EPA_20-0" class="reference"><a href="#cite_note-EPA-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time.) </p><p>It is toxic in large doses, with an <a href="/wiki/LD50" class="mw-redirect" title="LD50">LD50</a> (rats, oral) of 1020 mg/kg, and <a href="/wiki/Threshold_Limit_Value" class="mw-redirect" title="Threshold Limit Value">day to day continuous exposure</a> to 5 ppm is considered safe. As of October 2018, the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a> withdrew authorization for its use as a synthetic flavoring substance in food, without regard to its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>One favorable safety aspect is that ethyl acrylate has good warning properties; the <a href="/wiki/Odor_detection_threshold" title="Odor detection threshold">odor threshold</a> is much lower than any level of health concern. In other words, the bad odor warns people of ethyl acrylate's presence long before the concentration reaches a level capable of creating a serious health risk. Reports of the exact levels vary somewhat, but, for example, the U.S. E.P.A. reports an odor threshold of 0.0012 parts per million (ppm),<sup id="cite_ref-EPA_20-1" class="reference"><a href="#cite_note-EPA-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> but the E.P.A.'s lowest level of health concern, the <a href="/wiki/Acute_Exposure_Guideline_Levels" title="Acute Exposure Guideline Levels">Acute Exposure Guideline Level-1</a> (AEGL-1) is 8.3 ppm,<sup id="cite_ref-EPA_AEGL_22-0" class="reference"><a href="#cite_note-EPA_AEGL-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> which is almost 7000 times the odor threshold. </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><i>Merck Index</i>, 11th Edition, <b>3715</b>.</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"><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0267.htm">Ethyl acrylate</a> Datasheet at Inchem.org</span> </li> <li id="cite_note-PGCH-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-PGCH_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PGCH_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PGCH_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PGCH_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-PGCH_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-PGCH_3-5"><sup><i><b>f</b></i></sup></a></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 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Retrieved <span class="nowrap">2019-04-28</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Acute+Exposure+Guideline+Levels&rft.atitle=Ethyl+acrylate&rft_id=https%3A%2F%2Fwww.epa.gov%2Faegl%2Fethyl-acrylate-results-aegl-program&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthyl+acrylate" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2></div> <ul><li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0261.html">CDC - NIOSH Pocket Guide to Chemical Hazards - Ethyl Acrylate</a></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&useformat=desktop" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Ethyl_acrylate&oldid=927894621">https://en.wikipedia.org/w/index.php?title=Ethyl_acrylate&oldid=927894621</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Monomers" title="Category:Monomers">Monomers</a></li><li><a href="/wiki/Category:Ethyl_esters" title="Category:Ethyl esters">Ethyl esters</a></li><li><a href="/wiki/Category:Lachrymatory_agents" title="Category:Lachrymatory agents">Lachrymatory agents</a></li><li><a href="/wiki/Category:IARC_Group_2B_carcinogens" title="Category:IARC Group 2B carcinogens">IARC Group 2B carcinogens</a></li><li><a href="/wiki/Category:Acrylate_esters" title="Category:Acrylate esters">Acrylate esters</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Webarchive_template_wayback_links" title="Category:Webarchive template wayback links">Webarchive template wayback links</a></li><li><a href="/wiki/Category:Pages_using_cite_patent_with_unknown_parameters" title="Category:Pages using cite patent with unknown parameters">Pages using cite patent with unknown parameters</a></li><li><a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">CS1 maint: multiple names: authors list</a></li><li><a href="/wiki/Category:CS1_German-language_sources_(de)" title="Category:CS1 German-language sources (de)">CS1 German-language sources (de)</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Pages_using_Chembox_with_unknown_parameters" title="Category:Pages using Chembox with unknown parameters">Pages using Chembox with unknown parameters</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 25 November 2019, at 13:30<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright"><span class="nowraplinks">This version of the page has been <a href="/wiki/Help:Page_history" title="Help:Page history">revised</a>. 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