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class="vector-toc-numb">3.1</span> <span>Gas stream scrubbing</span> </div> </a> <ul id="toc-Gas_stream_scrubbing-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Other uses</span> </div> </a> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-pH-control_amine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#pH-control_amine"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>pH-control amine</span> </div> </a> <ul id="toc-pH-control_amine-sublist" class="vector-toc-list"> </ul> </li> </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">4</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-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">5</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">6</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" 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mw-first-heading"><span class="mw-page-title-main">Ethanolamine</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 33 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-33" 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">33 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D9%8A%D8%AB%D8%A7%D9%86%D9%88%D9%84%D8%A7%D9%85%D9%8A%D9%86" title="إيثانولامين – Arabic" lang="ar" hreflang="ar" data-title="إيثانولامين" 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/Etanolamin" title="Etanolamin – Azerbaijani" lang="az" hreflang="az" data-title="Etanolamin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%AA%D8%A7%D9%86%D9%88%D9%84%E2%80%8C%D8%A2%D9%85%DB%8C%D9%86" title="اتانول‌آمین – South Azerbaijani" lang="azb" hreflang="azb" data-title="اتانول‌آمین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%95%D1%82%D0%B0%D0%BD%D0%BE%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Етаноламин – Bulgarian" lang="bg" hreflang="bg" data-title="Етаноламин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Etanolamina" title="Etanolamina – Catalan" lang="ca" hreflang="ca" data-title="Etanolamina" 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/Ethanolamin" title="Ethanolamin – Czech" lang="cs" hreflang="cs" data-title="Ethanolamin" 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/Monoethanolamin" title="Monoethanolamin – German" lang="de" hreflang="de" data-title="Monoethanolamin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%B9%CE%B8%CE%B1%CE%BD%CE%BF%CE%BB%CE%B1%CE%BC%CE%AF%CE%BD%CE%B7" title="Αιθανολαμίνη – Greek" lang="el" hreflang="el" data-title="Αιθανολαμίνη" 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/Etanolamina" title="Etanolamina – Spanish" lang="es" hreflang="es" data-title="Etanolamina" 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/Etanolamino" title="Etanolamino – Esperanto" lang="eo" hreflang="eo" data-title="Etanolamino" 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/Etanolamina" title="Etanolamina – Basque" lang="eu" hreflang="eu" data-title="Etanolamina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%AA%D8%A7%D9%86%D9%88%D9%84%E2%80%8C%D8%A2%D9%85%DB%8C%D9%86" title="اتانول‌آمین – Persian" lang="fa" hreflang="fa" data-title="اتانول‌آمین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89thanolamine" title="Éthanolamine – French" lang="fr" hreflang="fr" data-title="Éthanolamine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Etanolamina" title="Etanolamina – Galician" lang="gl" hreflang="gl" data-title="Etanolamina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%97%90%ED%83%84%EC%98%AC%EC%95%84%EB%AF%BC" title="에탄올아민 – Korean" lang="ko" hreflang="ko" data-title="에탄올아민" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Etanolamina" title="Etanolamina – Indonesian" lang="id" hreflang="id" data-title="Etanolamina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Etanolammina" title="Etanolammina – Italian" lang="it" hreflang="it" data-title="Etanolammina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%8E%E0%B2%A5%E0%B3%86%E0%B2%A8%E0%B2%BE%E0%B2%B2%E0%B3%8D_%E0%B2%85%E0%B2%AE%E0%B3%80%E0%B2%A8%E0%B3%81%E0%B2%97%E0%B2%B3%E0%B3%81" title="ಎಥೆನಾಲ್ ಅಮೀನುಗಳು – Kannada" lang="kn" hreflang="kn" data-title="ಎಥೆನಾಲ್ ಅಮೀನುಗಳು" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Etanolamin" title="Etanolamin – Hungarian" lang="hu" hreflang="hu" data-title="Etanolamin" 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/2-amino-ethanol" title="2-amino-ethanol – Dutch" lang="nl" hreflang="nl" data-title="2-amino-ethanol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%82%BF%E3%83%8E%E3%83%BC%E3%83%AB%E3%82%A2%E3%83%9F%E3%83%B3" title="エタノールアミン – Japanese" lang="ja" hreflang="ja" data-title="エタノールアミン" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Etanolaminlar" title="Etanolaminlar – Uzbek" lang="uz" hreflang="uz" data-title="Etanolaminlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Etanoloamina" title="Etanoloamina – Polish" lang="pl" hreflang="pl" data-title="Etanoloamina" 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/Etanolamina" title="Etanolamina – Portuguese" lang="pt" hreflang="pt" data-title="Etanolamina" 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/Etanolamin%C4%83" title="Etanolamină – Romanian" lang="ro" hreflang="ro" data-title="Etanolamină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D1%82%D0%B0%D0%BD%D0%BE%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Этаноламин – Russian" lang="ru" hreflang="ru" data-title="Этаноламин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Etanolamin" title="Etanolamin – Serbian" lang="sr" hreflang="sr" data-title="Etanolamin" 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/Etanolamin" title="Etanolamin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Etanolamin" 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/2-aminoetanoli" title="2-aminoetanoli – Finnish" lang="fi" hreflang="fi" data-title="2-aminoetanoli" 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/Etanolamin" title="Etanolamin – Swedish" lang="sv" hreflang="sv" data-title="Etanolamin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Etanolamin" title="Etanolamin – Turkish" lang="tr" hreflang="tr" data-title="Etanolamin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%95%D1%82%D0%B0%D0%BD%D0%BE%D0%BB%D0%B0%D0%BC%D1%96%D0%BD" title="Етаноламін – Ukrainian" lang="uk" hreflang="uk" data-title="Етаноламін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B9%99%E9%86%87%E8%83%BA" title="乙醇胺 – Chinese" lang="zh" hreflang="zh" data-title="乙醇胺" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> 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<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>Ethanolamine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Structural_formula_of_monoethanolamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Structural_formula_of_monoethanolamine.svg/220px-Structural_formula_of_monoethanolamine.svg.png" decoding="async" width="220" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Structural_formula_of_monoethanolamine.svg/330px-Structural_formula_of_monoethanolamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Structural_formula_of_monoethanolamine.svg/440px-Structural_formula_of_monoethanolamine.svg.png 2x" data-file-width="214" data-file-height="56" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Ethanolamine_3D_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Ethanolamine_3D_ball.png/220px-Ethanolamine_3D_ball.png" decoding="async" width="220" height="125" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Ethanolamine_3D_ball.png/330px-Ethanolamine_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Ethanolamine_3D_ball.png/440px-Ethanolamine_3D_ball.png 2x" data-file-width="2000" data-file-height="1139" /></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;">2-Aminoethan-1-ol<sup id="cite_ref-iupac2013_1-1" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>2-Aminoethanol</li><li>2-Amino-1-ethanol</li><li>Ethanolamine (not recommended<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>)</li><li>Monoethanolamine</li><li>β-Aminoethanol</li><li>β-hydroxyethylamine</li><li>β-Aminoethyl alcohol</li><li>Glycinol</li><li>Olamine</li><li>MEA</li><li>Ethylolamine</li><li>2-Hydroxyethylamine</li><li>Colamine</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=141-43-5">141-43-5</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=NCCO">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=16000">CHEBI:16000</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL104943">ChEMBL104943</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.13835336.html">13835336</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03994">DB03994</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/100.004.986">100.004.986</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410387#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>205-483-3</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/D05074">D05074</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/700">700</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>KJ5775000</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/5KV86114PT">5KV86114PT</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6022000">DTXSID6022000</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410387#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/C2H7NO/c3-1-2-4/h4H,1-3H2<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: HZAXFHJVJLSVMW-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/C2H7NO/c3-1-2-4/h4H,1-3H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: HZAXFHJVJLSVMW-UHFFFAOYAD</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">NCCO</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>2</sub><span title="Hydrogen">H</span><sub>7</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001610840000000000♠"></span>61.084</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Viscous colourless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Unpleasant <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>-like odour </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.0117<span class="nowrap"> </span>g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>10.3 °C (50.5 °F; 283.4 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>170 °C (338 °F; 443 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Miscible </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>64<span class="nowrap"> </span>Pa (20<span class="nowrap"> </span>°C)<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> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>9.50<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><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>1.4539 (20<span class="nowrap"> </span>°C)<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> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-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="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H312: Harmful in contact with skin">H312</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H332: Harmful if inhaled">H332</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H412: Harmful to aquatic life with long lasting effects">H412</abbr><sup id="cite_ref-sigma_5-1" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</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="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr><sup id="cite_ref-sigma_5-2" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_cac26dcfb9c9c85a" /></span><map name="ImageMap_cac26dcfb9c9c85a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>85 °C (185 °F; 358 K) (closed cup) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>410 °C (770 °F; 683 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>5.5–17% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>3320<span class="nowrap"> </span>mg/kg (rat, oral)</li><li>620<span class="nowrap"> </span>mg/kg (guinea pig, oral)</li><li>2050<span class="nowrap"> </span>mg/kg (rat, oral)</li><li>1475<span class="nowrap"> </span>mg/kg (mouse, oral)</li><li>1000<span class="nowrap"> </span>mg/kg (rabbit, oral)</li><li>700<span class="nowrap"> </span>mg/kg (mouse, oral)</li><li>1720–1970<span class="nowrap"> </span>mg/kg (rat, oral)<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></li></ul></div> </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: 3 ppm (6 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_6-0" class="reference"><a href="#cite_note-NIOSH-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>TWA: 3<span class="nowrap"> </span>ppm (8<span class="nowrap"> </span>mg/m<sup>3</sup>)</li><li>ST: 6<span class="nowrap"> </span>ppm (15<span class="nowrap"> </span>mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_6-1" class="reference"><a href="#cite_note-NIOSH-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li></ul></div> </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>30<span class="nowrap"> </span>ppm<sup id="cite_ref-NIOSH_6-2" class="reference"><a href="#cite_note-NIOSH-6"><span class="cite-bracket">[</span>6<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>Sigma<sup id="cite_ref-sigma_5-0" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/N-Methylethanolamine" title="N-Methylethanolamine"><i>N</i>-Methylethanolamine</a></li><li><a href="/wiki/Diethanolamine" title="Diethanolamine">Diethanolamine</a></li><li><a href="/wiki/Triethanolamine" title="Triethanolamine">Triethanolamine</a></li></ul></div> </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="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=446471897&page2=Ethanolamine">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>Ethanolamine</b> (<b>2-aminoethanol</b>, <b>monoethanolamine</b>, <b>ETA</b>, or <b>MEA</b>) is a naturally occurring <a href="/wiki/Organic_chemical_compound" class="mw-redirect" title="Organic chemical compound">organic chemical compound</a> with the formula <span class="chemf nowrap">HOCH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> or <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span>NO</span>.<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> The molecule is <a href="/wiki/Bifunctional" class="mw-redirect" title="Bifunctional">bifunctional</a>, containing both a <a href="/wiki/Primary_amine" class="mw-redirect" title="Primary amine">primary amine</a> and a <a href="/wiki/Primary_alcohol" title="Primary alcohol">primary alcohol</a>. Ethanolamine is a <a href="/wiki/Color" title="Color">colorless</a>, <a href="/wiki/Viscous" class="mw-redirect" title="Viscous">viscous</a> <a href="/wiki/Liquid" title="Liquid">liquid</a> with an <a href="/wiki/Odor" title="Odor">odor</a> reminiscent of <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>.<sup id="cite_ref-Ullmann_9-0" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from <a href="/wiki/Diethanolamine" title="Diethanolamine">diethanolamine</a> (DEA) and <a href="/wiki/Triethanolamine" title="Triethanolamine">triethanolamine</a> (TEOA). The ethanolamines comprise a group of <a href="/wiki/Amino_alcohols" class="mw-redirect" title="Amino alcohols">amino alcohols</a>. A class of <a href="/wiki/Antihistamines" class="mw-redirect" title="Antihistamines">antihistamines</a> is identified as ethanolamines, which includes <a href="/wiki/Carbinoxamine" title="Carbinoxamine">carbinoxamine</a>, <a href="/wiki/Clemastine" title="Clemastine">clemastine</a>, <a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">dimenhydrinate</a>, <a href="/wiki/Chlorphenoxamine" title="Chlorphenoxamine">chlorphenoxamine</a>, <a href="/wiki/Diphenhydramine" title="Diphenhydramine">diphenhydramine</a> and <a href="/wiki/Doxylamine" title="Doxylamine">doxylamine</a>.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Ethanolamine_in_Nature">Ethanolamine in Nature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethanolamine&action=edit&section=1" title="Edit section: Ethanolamine in Nature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>ETA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. Ethanolamine is the second-most-abundant head group for <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>, substances found in <a href="/wiki/Biological_membrane" title="Biological membrane">biological membranes</a> (particularly those of prokaryotes); e.g., <a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">phosphatidylethanolamine</a>. It is also used in messenger molecules such as <a href="/wiki/Palmitoylethanolamide" title="Palmitoylethanolamide">palmitoylethanolamide</a>, which has an effect on CB1 receptors.<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> </p><p>ETA was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that ETA molecules exist in interstellar space.<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>Ethanolamine is <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesized</a> by decarboxylation of <a href="/wiki/Serine" title="Serine">serine</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> </p> <dl><dd><span class="chemf nowrap">HOCH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>CH(CO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>H)NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> → <span class="chemf nowrap">HOCH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> + CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub></dd></dl> <p>Derivatives of ethanolamine are widespread in nature; e.g., <a href="/wiki/Lipid" title="Lipid">lipids</a>, as <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> of a variety of <a href="/wiki/N-Acylethanolamine" title="N-Acylethanolamine"><i>N</i>-acylethanolamines</a> (NAEs), that modulate several <a href="/wiki/Animal" title="Animal">animal</a> and <a href="/wiki/Plant" title="Plant">plant</a> <a href="/wiki/Physiology" title="Physiology">physiological</a> processes such as seed <a href="/wiki/Germination" title="Germination">germination</a>, plant–pathogen <a href="/wiki/Plant_communication" title="Plant communication">interactions</a>, <a href="/wiki/Chloroplast" title="Chloroplast">chloroplast</a> development and <a href="/wiki/Flowering_plant" title="Flowering plant">flowering</a>,<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> as well as precursor, combined with <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a> <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">20</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">32</sub></span></span>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> 20:<a href="/wiki/Double_bond" title="Double bond">4</a>, <a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">ω-6</a>), to form the endocannabinoid <a href="/wiki/Anandamide" title="Anandamide">anandamide</a> (AEA: <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">22</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">37</sub></span></span>NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>; 20:4, ω-6).<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>ETA is biodegraded by <a href="/wiki/Ethanolamine_ammonia-lyase" title="Ethanolamine ammonia-lyase">ethanolamine ammonia-lyase</a>, a B12-dependent enzyme. It is converted to <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> via initial H-atom abstraction.<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> <dl><dd><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">H<sub class="template-chem2-sub">2</sub>NCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH → NH<sub class="template-chem2-sub">3</sub> + CH<sub class="template-chem2-sub">3</sub>CHO</span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Industrial_production">Industrial production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethanolamine&action=edit&section=2" title="Edit section: Industrial production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Monoethanolamine is produced by treating <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a> with aqueous <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>; the reaction also produces <a href="/wiki/Diethanolamine" title="Diethanolamine">diethanolamine</a> and <a href="/wiki/Triethanolamine" title="Triethanolamine">triethanolamine</a>. The ratio of the products can be controlled by the <a href="/wiki/Stoichiometry" title="Stoichiometry">stoichiometry</a> of the reactants.<sup id="cite_ref-weissermel_17-0" class="reference"><a href="#cite_note-weissermel-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Reaction_of_ethylene_oxide_with_ammonia.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Reaction_of_ethylene_oxide_with_ammonia.png/400px-Reaction_of_ethylene_oxide_with_ammonia.png" decoding="async" width="400" height="279" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Reaction_of_ethylene_oxide_with_ammonia.png/600px-Reaction_of_ethylene_oxide_with_ammonia.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Reaction_of_ethylene_oxide_with_ammonia.png/800px-Reaction_of_ethylene_oxide_with_ammonia.png 2x" data-file-width="1364" data-file-height="951" /></a></span></dd></dl> <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=Ethanolamine&action=edit&section=3" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>MEA is used as <a href="/wiki/Feedstock" class="mw-redirect" title="Feedstock">feedstock</a> in the production of <a href="/wiki/Detergent" title="Detergent">detergents</a>, <a href="/wiki/Emulsifiers" class="mw-redirect" title="Emulsifiers">emulsifiers</a>, polishes, pharmaceuticals, corrosion inhibitors, and chemical intermediates.<sup id="cite_ref-Ullmann_9-1" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>For example, reacting ethanolamine with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> gives <a href="/wiki/Ethylenediamine" title="Ethylenediamine">ethylenediamine</a>, a precursor of the commonly used <a href="/wiki/Chelating_agent" class="mw-redirect" title="Chelating agent">chelating agent</a>, <a href="/wiki/EDTA" class="mw-redirect" title="EDTA">EDTA</a>.<sup id="cite_ref-weissermel_17-1" class="reference"><a href="#cite_note-weissermel-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:En_from_ethanolamine.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/En_from_ethanolamine.png/400px-En_from_ethanolamine.png" decoding="async" width="400" height="55" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/En_from_ethanolamine.png/600px-En_from_ethanolamine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/En_from_ethanolamine.png/800px-En_from_ethanolamine.png 2x" data-file-width="1556" data-file-height="214" /></a></span> </p> <div class="mw-heading mw-heading3"><h3 id="Gas_stream_scrubbing">Gas stream scrubbing</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethanolamine&action=edit&section=4" title="Edit section: Gas stream scrubbing"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Carbon_dioxide_scrubber" title="Carbon dioxide scrubber">carbon dioxide scrubber</a> and <a href="/wiki/Sour_gas" title="Sour gas">sour gas</a></div> <p>Monoethanolamines can scrub combusted-coal, combusted-methane and combusted-biogas flue emissions of <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> (CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub>) very efficiently. MEA carbon dioxide scrubbing is also used to regenerate the air on submarines. </p><p>Solutions of MEA in <a href="/wiki/Water_(molecule)" class="mw-redirect" title="Water (molecule)">water</a> are used as a gas stream scrubbing <a href="/wiki/Liquid" title="Liquid">liquid</a> in <a href="/wiki/Amine_gas_treating" title="Amine gas treating">amine treaters</a>.<sup id="cite_ref-Chremos2014_18-0" class="reference"><a href="#cite_note-Chremos2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> For example, aqueous MEA is used to remove <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> (CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub>) and <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S</span>) from various gas streams; e.g., <a href="/wiki/Flue_gas" title="Flue gas">flue gas</a> and <a href="/wiki/Sour_natural_gas" class="mw-redirect" title="Sour natural gas">sour natural gas</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The MEA ionizes dissolved <a href="/wiki/Acidic" class="mw-redirect" title="Acidic">acidic</a> compounds, making them <a href="/wiki/Polar_molecule" class="mw-redirect" title="Polar molecule">polar</a> and considerably more <a href="/wiki/Soluble" class="mw-redirect" title="Soluble">soluble</a>. </p><p>MEA scrubbing solutions can be recycled through a regeneration unit. When heated, MEA, being a rather weak base, will release dissolved <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S</span> or CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub> gas resulting in a pure MEA solution.<sup id="cite_ref-weissermel_17-2" class="reference"><a href="#cite_note-weissermel-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethanolamine&action=edit&section=5" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In pharmaceutical formulations, MEA is used primarily for buffering or preparation of emulsions. MEA can be used as pH regulator in cosmetics.<sup id="cite_ref-Carrasco_21-0" class="reference"><a href="#cite_note-Carrasco-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>It is an injectable <a href="/wiki/Sclerosant" class="mw-redirect" title="Sclerosant">sclerosant</a> as a treatment option of symptomatic hemorrhoids. 2–5 ml of ethanolamine oleate can be injected into the mucosa just above the hemorrhoids to cause ulceration and mucosal fixation thus preventing hemorrhoids from descending out of the anal canal. </p><p>It is also an ingredient in cleaning fluid for automobile <a href="/wiki/Windshield" title="Windshield">windshields</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="pH-control_amine">pH-control amine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethanolamine&action=edit&section=6" title="Edit section: pH-control amine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethanolamine is often used for alkalinization of water in steam cycles of power plants, including nuclear <a href="/wiki/Power_plant" class="mw-redirect" title="Power plant">power plants</a> with <a href="/wiki/Pressurized_water_reactor" title="Pressurized water reactor">pressurized water reactors</a>. This alkalinization is performed to control corrosion of metal components. ETA (or sometimes a similar organic amine; e.g., <a href="/wiki/Morpholine" title="Morpholine">morpholine</a>) is selected because it does not accumulate in steam generators (boilers) and <a href="/wiki/Crevice_corrosion" title="Crevice corrosion">crevices</a> due to its volatility, but rather distributes relatively uniformly throughout the entire steam cycle. In such application, ETA is a key ingredient of so-called "all-volatile treatment" of water (AVT).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2015)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethanolamine&action=edit&section=7" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Upon reaction with <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>, 2 equivalents of ethanolamine react through the intermediacy of <a href="/wiki/Carbonic_acid" title="Carbonic acid">carbonic acid</a> to form a <a href="/wiki/Carbamate" title="Carbamate">carbamate</a> salt,<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> which when heated reforms ethanolamine and carbon dioxide. </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=Ethanolamine&action=edit&section=8" 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-iupac2013-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac2013_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac2013_1-1"><sup><i><b>b</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 .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1"><i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. pp. 649, 717. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069-FP001">10.1039/9781849733069-FP001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>. <q>For example, the name 'ethanolamine', which is still widely used, is badly constructed because of the presence of two suffixes; it is not an alternative to the preferred IUPAC name, '2-aminoethan-1-ol'.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry+%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=649%2C+717&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-FP001&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanolamine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110715032425/http://www.paclp.com/content/documents/MSDS/Ethanolamine.pdf">"Ethanolamine MSDS"</a> <span class="cs1-format">(PDF)</span>. <a href="/w/index.php?title=Acros_Organics&action=edit&redlink=1" class="new" title="Acros Organics (page does not exist)">Acros Organics</a>. 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"Ingredientes Cosméticos". <i>Diccionario de Ingredientes Cosméticos 4ª Ed</i>. www.imagenpersonal.net. p. 306. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-84-613-4979-1" title="Special:BookSources/978-84-613-4979-1"><bdi>978-84-613-4979-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ingredientes+Cosm%C3%A9ticos&rft.btitle=Diccionario+de+Ingredientes+Cosm%C3%A9ticos+4%C2%AA+Ed&rft.pages=306&rft.pub=www.imagenpersonal.net&rft.date=2009&rft.isbn=978-84-613-4979-1&rft.aulast=Carrasco&rft.aufirst=F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthanolamine" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=swgeJm6aAC0C&pg=RA7-PA128"><i>Federal Motor Vehicle Safety Standards</i></a>. 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