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class="mw-page-title-main">Triethanolamine</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 20 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-20" 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">20 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Trietanolamin" title="Trietanolamin – Azerbaijani" lang="az" hreflang="az" data-title="Trietanolamin" 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%AA%D8%B1%DB%8C%E2%80%8C%D8%A7%D8%AA%D8%A7%D9%86%D9%88%D9%84%E2%80%8C%D8%A2%D9%85%DB%8C%D9%86" title="تری‌اتانول‌آمین – South Azerbaijani" lang="azb" hreflang="azb" data-title="تری‌اتانول‌آمین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Triethanolamin" title="Triethanolamin – German" lang="de" hreflang="de" data-title="Triethanolamin" 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/Trietanolamina" title="Trietanolamina – Spanish" lang="es" hreflang="es" data-title="Trietanolamina" 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/Trietanolamino" title="Trietanolamino – Esperanto" lang="eo" hreflang="eo" data-title="Trietanolamino" 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/Trietanolamina" title="Trietanolamina – Basque" lang="eu" hreflang="eu" data-title="Trietanolamina" 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%AA%D8%B1%DB%8C%E2%80%8C%D8%A7%D8%AA%D8%A7%D9%86%D9%88%D9%84%E2%80%8C%D8%A2%D9%85%DB%8C%D9%86" title="تری‌اتانول‌آمین – Persian" lang="fa" hreflang="fa" data-title="تری‌اتانول‌آمین" 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/Tri%C3%A9thanolamine" title="Triéthanolamine – French" lang="fr" hreflang="fr" data-title="Triéthanolamine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Trietanolamina" title="Trietanolamina – Indonesian" lang="id" hreflang="id" data-title="Trietanolamina" 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/Trietanolammina" title="Trietanolammina – Italian" lang="it" hreflang="it" data-title="Trietanolammina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Tri-ethanolamine" title="Tri-ethanolamine – Dutch" lang="nl" hreflang="nl" data-title="Tri-ethanolamine" 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%83%88%E3%83%AA%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="トリエタノールアミン – Japanese" lang="ja" hreflang="ja" data-title="トリエタノールアミン" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Trietanolamina" title="Trietanolamina – Portuguese" lang="pt" hreflang="pt" data-title="Trietanolamina" 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/Trietanolamin%C4%83" title="Trietanolamină – Romanian" lang="ro" hreflang="ro" data-title="Trietanolamină" 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%A2%D1%80%D0%B8%D1%8D%D1%82%D0%B0%D0%BD%D0%BE%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Триэтаноламин – Russian" lang="ru" hreflang="ru" data-title="Триэтаноламин" 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/Trietanolamin" title="Trietanolamin – Serbian" lang="sr" hreflang="sr" data-title="Trietanolamin" 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/Trietanolamin" title="Trietanolamin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Trietanolamin" 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/Trietanoliamiini" title="Trietanoliamiini – Finnish" lang="fi" hreflang="fi" data-title="Trietanoliamiini" 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/Trietanolamin" title="Trietanolamin – Swedish" lang="sv" hreflang="sv" data-title="Trietanolamin" 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%89%E4%B9%99%E9%86%87%E8%83%BA" title="三乙醇胺 – Chinese" lang="zh" hreflang="zh" data-title="三乙醇胺" 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 wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q424314#sitelinks-wikipedia" title="Edit interlanguage links" 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title="Trolamine">Trolamine</a>)</span></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: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">Not to be confused with <a href="/wiki/Triethylamine" title="Triethylamine">Triethylamine</a>.</div> <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>Triethanolamine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Triethanolamine.png" class="mw-file-description"><img alt="Skeletal formula of triethanolamine" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Triethanolamine.png/180px-Triethanolamine.png" decoding="async" width="180" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Triethanolamine.png/270px-Triethanolamine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/68/Triethanolamine.png/360px-Triethanolamine.png 2x" data-file-width="2032" data-file-height="1068" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Triethanolamine_3D_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the triethanolamine molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Triethanolamine_3D_ball.png/160px-Triethanolamine_3D_ball.png" decoding="async" width="160" height="146" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Triethanolamine_3D_ball.png/240px-Triethanolamine_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Triethanolamine_3D_ball.png/320px-Triethanolamine_3D_ball.png 2x" data-file-width="2000" data-file-height="1830" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Sample_of_Triethanolamine.jpg" class="mw-file-description" title="Liquid form"><img alt="Colorless liquid in a stoppered glass bottle" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Sample_of_Triethanolamine.jpg/140px-Sample_of_Triethanolamine.jpg" decoding="async" width="140" height="194" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Sample_of_Triethanolamine.jpg/210px-Sample_of_Triethanolamine.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Sample_of_Triethanolamine.jpg/280px-Sample_of_Triethanolamine.jpg 2x" data-file-width="2215" data-file-height="3075" /></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;">2,2′,2′′-Nitrilotri(ethan-1-ol)<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></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>2,2′,2′′-Nitrilotriethanol</li><li>Tris(2-hydroxyethyl)amine</li><li>Triethylolamine</li><li>2,2′,2′′-Trihydroxytriethylamine</li><li>Trolamine</li><li>TEA</li><li>TELA</li><li>TEOA</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=102-71-6">102-71-6</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=OCCN%28CCO%29CCO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B01049">B01049</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1699263 </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=28621">CHEBI:28621</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/ChEMBL446061">ChEMBL446061</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.13835630.html">13835630</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/100.002.773">100.002.773</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q424314#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>203-049-8</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/D00215">D00215</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Biafine">Biafine</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/7618">7618</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>KL9275000</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/9O3K93S3TK">9O3K93S3TK</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/DTXSID9021392">DTXSID9021392</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q424314#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/C6H15NO3/c8-4-1-7(2-5-9)3-6-10/h8-10H,1-6H2<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: GSEJCLTVZPLZKY-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">OCCN(CCO)CCO</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">N(CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH)<sub class="template-chem2-sub">3</sub></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="7002149190000000000♠"></span>149.190</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colourless, viscous liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Ammoniacal </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.124 g/mL </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>21.60 °C; 70.88 °F; 294.75 K </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>335.40 °C; 635.72 °F; 608.55 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/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−0.988 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>1 Pa (at 20 °C) </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>7.74<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/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λ<sub>max</sub>) </td> <td>280 nm </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>1.485 </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>389 J K<sup>−1</sup> mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−665.7 – −662.7 kJ mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−3.8421 – −3.8391 MJ mol<sup>−1</sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_D03" title="ATC code D03">D03AX12</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D03AX12">WHO</a></span>)  </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-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>Warning</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="H319: Causes serious eye irritation">H319</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="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> </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_482e25fdfe95519d" /></span><map name="ImageMap_482e25fdfe95519d"><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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><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 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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</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>179 °C (354 °F; 452 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>325 °C (617 °F; 598 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>1.3–8.5% </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>2.2 g/kg (oral, guinea pig)</li><li>2.2 g/kg (oral, rabbit)</li><li>5.53 g/kg (oral, rat)</li><li>5.846 g/kg (oral, mouse)</li><li>22.5 g/kg (dermal, rabbit)</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://hazard.com/msds/mf/baker/baker/files/t5291.htm">hazard.com</a> </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 alkanols</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/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li><li><a href="/wiki/Diethylethanolamine" title="Diethylethanolamine">Diethylethanolamine</a></li><li><a href="/wiki/Diethanolamine" title="Diethanolamine">Diethanolamine</a></li><li><a href="/wiki/N,N-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol"><i>N</i>,<i>N</i>-Diisopropylaminoethanol</a></li><li><a href="/wiki/Methyl_diethanolamine" class="mw-redirect" title="Methyl diethanolamine">Methyl diethanolamine</a></li><li><a href="/wiki/Bis-tris_methane" title="Bis-tris methane">Bis-tris methane</a></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Diethylhydroxylamine" title="Diethylhydroxylamine">Diethylhydroxylamine</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="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=470613986&page2=Triethanolamine">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>Triethanolamine</b>, or <b>TEOA</b>, is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N(CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH)<sub class="template-chem2-sub">3</sub></span>. It is a colourless, <a href="/wiki/Viscous" class="mw-redirect" title="Viscous">viscous</a> liquid. It is both a tertiary <a href="/wiki/Amine" title="Amine">amine</a> and a <a href="/wiki/Triol" title="Triol">triol</a>. A triol is a <a href="/wiki/Molecule" title="Molecule">molecule</a> with three <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> <a href="/wiki/Functional_group" title="Functional group">groups</a>. Approximately 150,000 <a href="/wiki/Tonne" title="Tonne">tonnes</a> were produced in 1999.<sup id="cite_ref-Ullmann_3-0" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is a colourless compound although samples may appear yellow because of impurities. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=1" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triethanolamine is produced from the reaction of <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a> with aqueous <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, also produced are <a href="/wiki/Ethanolamine" title="Ethanolamine">ethanolamine</a> and <a href="/wiki/Diethanolamine" title="Diethanolamine">diethanolamine</a>. The ratio of the products can be controlled by changing the <a href="/wiki/Stoichiometry" title="Stoichiometry">stoichiometry</a> of the reactants.<sup id="cite_ref-weissermel_4-0" class="reference"><a href="#cite_note-weissermel-4"><span class="cite-bracket">[</span>4<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/342px-Reaction_of_ethylene_oxide_with_ammonia.png" decoding="async" width="342" height="238" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Reaction_of_ethylene_oxide_with_ammonia.png/513px-Reaction_of_ethylene_oxide_with_ammonia.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Reaction_of_ethylene_oxide_with_ammonia.png/684px-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=Triethanolamine&action=edit&section=2" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triethanolamine is used primarily in making <a href="/wiki/Surfactant" title="Surfactant">surfactants</a>, such as for <a href="/wiki/Emulsifier" class="mw-redirect" title="Emulsifier">emulsifier</a>. It is a common ingredient in formulations used for both industrial and consumer products. The triethanolamine neutralizes <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, adjusts and <a href="/wiki/PH_buffer" class="mw-redirect" title="PH buffer">buffers</a> the <a href="/wiki/PH" title="PH">pH</a>, and solubilizes <a href="/wiki/Oil" title="Oil">oils</a> and other ingredients that are not completely <a href="/wiki/Solubility" title="Solubility">soluble</a> in water. Triethanolammonium salts in some cases are more soluble than salts of <a href="/wiki/Alkali_metals" class="mw-redirect" title="Alkali metals">alkali metals</a> that might be used otherwise, and results in less alkaline products than would from using alkali metal hydroxides to form the salt. Some common products in which triethanolamine is found are <a href="/wiki/Sunscreen_lotion" class="mw-redirect" title="Sunscreen lotion">sunscreen lotions</a>, liquid <a href="/wiki/Laundry_detergent" title="Laundry detergent">laundry detergents</a>, <a href="/wiki/Dishwashing_liquid" title="Dishwashing liquid">dishwashing liquids</a>, general cleaners, <a href="/wiki/Hand_sanitizer" title="Hand sanitizer">hand sanitizers</a>, <a href="/wiki/Polishing" title="Polishing">polishes</a>, <a href="/wiki/Metalworking" title="Metalworking">metalworking</a> fluids, <a href="/wiki/Paint" title="Paint">paints</a>, <a href="/wiki/Shaving_cream" title="Shaving cream">shaving cream</a> and <a href="/wiki/Printing_ink" class="mw-redirect" title="Printing ink">printing inks</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cement_production">Cement production</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=3" title="Edit section: Cement production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triethanolamine is also used as organic additive (0.1 wt%) in the grinding of <a href="/wiki/Clinker_(cement)" class="mw-redirect" title="Clinker (cement)">cement clinker</a>. It facilitates the grinding process by preventing agglomeration and coating of the powder at the surface of balls and mill wall.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cosmetics_and_medicine">Cosmetics and medicine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=4" title="Edit section: Cosmetics and medicine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Various <a href="/wiki/Ear_infection" class="mw-redirect" title="Ear infection">ear diseases and infections</a> are treated with eardrops containing triethanolamine polypeptide oleate-condensate, such as Cerumenex in the United States. In pharmaceutics, triethanolamine is the active ingredient of some eardrops used to treat impacted <a href="/wiki/Earwax" title="Earwax">earwax</a>. It also serves as a <a href="/wiki/PH" title="PH">pH</a> balancer in many different cosmetic products, ranging from cleansing creams and milks, <a href="/wiki/Skin_lotion" class="mw-redirect" title="Skin lotion">skin lotions</a>, eye gels, <a href="/wiki/Moisturizer" title="Moisturizer">moisturizers</a>, <a href="/wiki/Shampoo" title="Shampoo">shampoos</a>, <a href="/wiki/Shaving_foam" class="mw-redirect" title="Shaving foam">shaving foams</a>, TEOA is a fairly strong base: a 1% solution has a pH of approximately 10, whereas the pH of skin is less than pH 7, approximately 5.5−6.0. Cleansing milk–cream emulsions based on TEOA are particularly good at removing makeup. </p> <div class="mw-heading mw-heading3"><h3 id="Derivatives">Derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=5" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ol><li><a href="/w/index.php?title=Amustaline&action=edit&redlink=1" class="new" title="Amustaline (page does not exist)">Amustaline</a></li> <li><a href="/wiki/Trolnitrate" title="Trolnitrate">Trolnitrate</a></li> <li><a href="/w/index.php?title=Trimustine&action=edit&redlink=1" class="new" title="Trimustine (page does not exist)">Trimustine</a></li></ol> <div class="mw-heading mw-heading3"><h3 id="In_the_laboratory_and_in_amateur_photography">In the laboratory and in amateur photography</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=6" title="Edit section: In the laboratory and in amateur photography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Another common use of TEOA is as a <a href="/wiki/Complexing_agent" class="mw-redirect" title="Complexing agent">complexing agent</a> for <a href="/wiki/Aluminium" title="Aluminium">aluminium</a> ions in aqueous solutions. This reaction is often used to mask such ions before <a href="/wiki/Complexometric_titration" title="Complexometric titration">complexometric titrations</a> with another <a href="/wiki/Chelate" class="mw-redirect" title="Chelate">chelating</a> agent such as <a href="/wiki/EDTA" class="mw-redirect" title="EDTA">EDTA</a>. TEOA has also been used in <a href="/wiki/Photographic_processing" title="Photographic processing">photographic</a> (<a href="/wiki/Silver_halide" title="Silver halide">silver halide</a>) processing. It has been promoted as a useful alkali by amateur photographers. </p> <div class="mw-heading mw-heading3"><h3 id="In_holography">In holography</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=7" title="Edit section: In holography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>TEOA is used to provide a sensitivity boost to silver-halide-based <a href="/wiki/Hologram" class="mw-redirect" title="Hologram">holograms</a>, and also as a swelling agent to color shift holograms. It is possible to get the sensitivity boost without color shift by rinsing out the TEOA before squeegee and drying.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="In_electroless_plating">In electroless plating</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=8" title="Edit section: In electroless plating"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>TEOA is now commonly and very effectively used as a complexing agent in <a href="/wiki/Electroplating#Alternatives_to_electroplating" title="Electroplating">electroless plating</a>. </p> <div class="mw-heading mw-heading3"><h3 id="In_ultrasonic_testing">In ultrasonic testing</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=9" title="Edit section: In ultrasonic testing"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>2-3% in water TEOA is used as an corrosion inhibitor (anti-rust) agent in immersion ultrasonic testing. </p> <div class="mw-heading mw-heading3"><h3 id="In_aluminium_soldering">In aluminium soldering</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=10" title="Edit section: In aluminium soldering"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triethanolamine, <a href="/wiki/Diethanolamine" title="Diethanolamine">diethanolamine</a> and <a href="/wiki/Aminoethylethanolamine" title="Aminoethylethanolamine">aminoethylethanolamine</a> are major components of common liquid organic fluxes for the soldering of aluminium alloys using tin-zinc and other tin or lead-based soft solders.<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><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><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> <div class="mw-heading mw-heading2"><h2 id="Safety_and_regulation">Safety and regulation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=11" title="Edit section: Safety and regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Allergic_reactions">Allergic reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=12" title="Edit section: Allergic reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 1996 study found that triethanolamine (TEOA) occasionally causes contact <a href="/wiki/Allergy" title="Allergy">allergy</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> A 2001 study found TEOA in a <a href="/wiki/Sunscreen" title="Sunscreen">sunscreen</a> caused an allergic contact <a href="/wiki/Dermatitis" title="Dermatitis">dermatitis</a>.<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> A 2007 study found TEOA in <a href="/wiki/Ear_drops" class="mw-redirect" title="Ear drops">ear drops</a> caused a contact allergy.<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> Systemic and respiratory tract (RT) toxicity was analyzed for 28 days in a nose specific inhalation 2008 study in Wistar rats; TEOA seems to be less potent in regard to systemic toxicity and RT irritancy than <a href="/wiki/Diethanolamine" title="Diethanolamine">diethanolamine</a> (DEA). Exposure to TEOA resulted in focal inflammation, starting in single male animals from 20 mg/m<sup>3</sup> concentrations.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>A 2009 study stated that <a href="/wiki/Patch_test" title="Patch test">patch test</a> reactions reveal a slight irritant potential instead of a true allergic response in several cases, and also indicated the risk of skin sensitization to TEOA seems to be very low.<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> <div class="mw-heading mw-heading3"><h3 id="Tumors">Tumors</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=13" title="Edit section: Tumors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reports indicated that TEOA causes an increased incidence of <a href="/wiki/Liver_tumor" title="Liver tumor">tumor growth</a> in the liver in female B6C3F1 mice, but not in male mice or in Fischer 344 rats.<sup id="cite_ref-Stott_WT_16-0" class="reference"><a href="#cite_note-Stott_WT-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> A 2004 study concluded "TEOA may cause liver tumors in mice via a choline-depletion mode of action and that this effect is likely caused by the inhibition of choline uptake by cells."<sup id="cite_ref-Stott_WT_16-1" class="reference"><a href="#cite_note-Stott_WT-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Environmental_toxicity">Environmental toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=14" title="Edit section: Environmental toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2009 study found that TEOA has potential acute, sub-chronic and chronic toxicity properties in respect to aquatic species.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Regulation">Regulation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=15" title="Edit section: Regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>TEOA is listed under <a href="/wiki/List_of_Schedule_3_substances_(CWC)" title="List of Schedule 3 substances (CWC)">Schedule 3, part B</a> of the <a href="/wiki/Chemical_Weapons_Convention" title="Chemical Weapons Convention">Chemical Weapons Convention</a> as it can be used in the manufacture of <a href="/wiki/HN3_(nitrogen_mustard)" title="HN3 (nitrogen mustard)">HN3 nitrogen mustard</a>. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=16" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Complexometric_titration" title="Complexometric titration">Complexometric titration</a></li> <li><a href="/wiki/Ethanolamine" title="Ethanolamine">Ethanolamine</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Trolamine_salicylate" title="Trolamine salicylate">Triethanolamine salicylate</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triethanolamine&action=edit&section=17" 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"><b><a href="#cite_ref-iupac2013_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1">"Front Matter". <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. P001–P004. <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>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Front+Matter&rft.btitle=Nomenclature+of+Organic+Chemistry+%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=P001-P004&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%3ATriethanolamine" 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 id="CITEREFSimond2012" class="citation journal cs1">Simond, M. R. (2012). "Dissociation Constants of Protonated Amines in Water at Temperatures from 293.15 K to 343.15 K". <i>Journal of Solution Chemistry</i>. <b>41</b>: 130. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs10953-011-9790-3">10.1007/s10953-011-9790-3</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:95755026">95755026</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Solution+Chemistry&rft.atitle=Dissociation+Constants+of+Protonated+Amines+in+Water+at+Temperatures+from+293.15+K+to+343.15+K&rft.volume=41&rft.pages=130&rft.date=2012&rft_id=info%3Adoi%2F10.1007%2Fs10953-011-9790-3&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A95755026%23id-name%3DS2CID&rft.aulast=Simond&rft.aufirst=M.+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATriethanolamine" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFrauenkronMelderRuiderRossbacher" class="citation encyclopaedia cs1">Frauenkron, Matthias; Melder, Johann-Peter; Ruider, Günther; Rossbacher, Roland; Höke, Hartmut. 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