SherbyNet - /page/wikibook/entry.mu

Micron Document

<!DOCTYPE html>

<title>Transesterification</title>

</head>

<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Transesterification</span></span>

</h1>

</header>

</p><p><b>Transesterification</b> is the process of exchanging the organic <a href="Functional_group" title="Functional group">functional group</a> R″ of an <a href="Esters" class="mw-redirect" title="Esters">ester</a> with the organic group R' of an <a href="Alcohols" class="mw-redirect" title="Alcohols">alcohol</a>. These reactions are often <a href="Catalyst" class="mw-redirect" title="Catalyst">catalyzed</a> by the addition of an <a href="Acid" title="Acid">acid</a> or <a href="Base_(chemistry)" title="Base (chemistry)">base</a> catalyst.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Strong acids catalyze the reaction by donating a <a href="Proton" title="Proton">proton</a> to the <a href="Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group, thus making it a more potent <a href="Electrophile" title="Electrophile">electrophile</a>. Bases catalyze the reaction by removing a proton from the alcohol, thus making it more <a href="Nucleophile" title="Nucleophile">nucleophilic</a>. The reaction can also be accomplished with the help of enzymes, particularly <a href="Lipase" title="Lipase">lipases</a> (one example is the lipase E.C.3.1.1.3<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>).

</p>

<p>If the alcohol produced by the reaction can be separated from the reactants by distillation this will drive the <a href="Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> toward the products. This means that esters with larger <a href="Alkoxy_group" title="Alkoxy group">alkoxy groups</a> can be made from methyl or ethyl esters in high purity by heating the mixture of ester, acid/base, and large alcohol.

</p>

<div class="mw-heading mw-heading2"><h2 id="Mechanism">Mechanism</h2></div>

<p>In the transesterification mechanism, the carbonyl carbon of the starting ester reacts to give a <a href="Tetrahedral_molecular_geometry" title="Tetrahedral molecular geometry">tetrahedral</a> intermediate, which either reverts back to the starting material, or proceeds to the transesterified product (RCOOR<sup>2</sup>). The various species exist in equilibrium, and the product distribution depends on the relative energies of the reactant and product. Depending on reaction conditions <a href="Ester_hydrolysis" title="Ester hydrolysis">ester hydrolysis</a> and/or <a href="Esterification" class="mw-redirect" title="Esterification">esterification</a> will also occur, which results in some amount of free carboxylic acid being present.

</p>

<div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Polyester_production">Polyester production</h3></div>

<p>The largest scale application of transesterification is in the synthesis of <a href="Polyester" title="Polyester">polyesters</a>.<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> In this application, diesters undergo transesterification with diols to form macromolecules. For example, <a href="Dimethyl_terephthalate" title="Dimethyl terephthalate">dimethyl terephthalate</a> and <a href="Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a> react to form <a href="Polyethylene_terephthalate" title="Polyethylene terephthalate">polyethylene terephthalate</a> and <a href="Methanol" title="Methanol">methanol</a>, which is evaporated to drive the reaction forward.

</p>

<div class="mw-heading mw-heading3"><h3 id="Methanolysis_and_biodiesel_production">Methanolysis and biodiesel production</h3></div>

<p>The reverse reaction, methanolysis, is also an example of transesterification. This process has been used to recycle polyesters into individual monomers (see <a href="Plastic_recycling" title="Plastic recycling">plastic recycling</a>). It is also used to convert fats (<a href="Triglyceride" title="Triglyceride">triglycerides</a>) into <a href="Biodiesel" title="Biodiesel">biodiesel</a>. This conversion was one of the first uses. Transesterified <a href="Vegetable_oil" title="Vegetable oil">vegetable oil</a> (<a href="Biodiesel" title="Biodiesel">biodiesel</a>) was used to power heavy-duty vehicles in South Africa before <a href="World_War_II" title="World War II">World War II</a>.

</p><p>It was <a href="Patented" class="mw-redirect" title="Patented">patented</a> in the US in the 1950s by <a href="Colgate-Palmolive" title="Colgate-Palmolive">Colgate</a>, though <a href="Biolipid" class="mw-redirect" title="Biolipid">biolipid</a> transesterification may have been discovered much earlier. In the 1940s, researchers were looking for a method to more readily produce <a href="Glycerol" title="Glycerol">glycerol</a>, which was used to produce <a href="Explosives" class="mw-redirect" title="Explosives">explosives</a> for World War II. Many of the methods used today by producers have their origin in the original 1940s research.

</p><p>Biolipid transesterification has also been recently shown by Japanese researchers to be possible using a <a href="Supercritical_fluid" title="Supercritical fluid">supercritical</a> methanol methodology, whereby high temperature, high-pressure vessels are used to physically catalyze the biolipid/methanol reaction into fatty-acid methyl esters.<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>

</p>

<div class="mw-heading mw-heading3"><h3 id="Fat_processing">Fat processing</h3></div>

<p><a href="Fat_interesterification" title="Fat interesterification">Fat interesterification</a> is used in the <a href="Food_industry" title="Food industry">food industry</a> to rearrange the <a href="Fatty_acid" title="Fatty acid">fatty acids</a> of <a href="Triglyceride" title="Triglyceride">triglycerides</a> in edible <a href="Fat" title="Fat">fats</a> and <a href="Vegetable_oil" title="Vegetable oil">vegetable oils</a>. For example, a solid fat with mostly saturated fatty acids may be transesterified with a vegetable oil having high unsaturated acid contents, to produce a spreadable semisolid fat whose molecules have a mix both kinds of acids.

</p>

<div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3></div>

<p>Transesterification is used to synthesize <a href="Enol" title="Enol">enol</a> derivatives, which are difficult to prepare by other means. <a href="Vinyl_acetate" title="Vinyl acetate">Vinyl acetate</a>, which is cheaply available, undergoes transesterification, giving access to <a href="Enol_ether" title="Enol ether">vinyl ethers</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><sup id="cite_ref-Ishii_6-0" class="reference"><a href="#cite_note-Ishii-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>

</p>

<dl><dd>ROH + <span class="chemf nowrap">AcOCH=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></span> ⟶ <span class="chemf nowrap">ROCH=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></span> + AcOH</dd></dl>

<p>The reaction can be effected with high enantioselectivity when mediated with a <a href="Lipase" title="Lipase">lipase</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>

</p>

<ul><li><a href="Biodiesel_production" title="Biodiesel production">Biodiesel production</a></li>

<li><a href="Otera's_catalyst" title="Otera's catalyst">Otera's catalyst</a></li>

<li><a href="Transalkylation" title="Transalkylation">Transalkylation</a></li>

<li><a href="Transamidification" title="Transamidification">Transamidification</a></li>

<li><a href="Cocaethylene" title="Cocaethylene">Cocaethylene</a></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

/* start https://en.wikipedia.org/ */

.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}

/* end https://en.wikipedia.org/ */

</style><div class="reflist">

/* start https://en.wikipedia.org/ */

.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("./mw/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("./mw/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("./mw/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("./mw/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}}

/* end https://en.wikipedia.org/ */

</style><cite id="CITEREFOtera1993" class="citation journal cs1">Otera, Junzo. (June 1993). "Transesterification". <i>Chemical Reviews</i>. <b>93</b> (4): <span class="nowrap">1449–</span>1470. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr00020a004">10.1021/cr00020a004</a>.</cite></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"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://enzyme.expasy.org/EC/3.1.1.3">"ENZYME – 3.1.1.3 Triacylglycerol lipase"</a>. <i>enzyme.expasy.org</i>. <a href="Swiss_Institute_of_Bioinformatics" title="Swiss Institute of Bioinformatics">SIB Swiss Institute of Bioinformatics</a><span class="reference-accessdate">. Retrieved <span class="nowrap">17 February</span> 2021</span>.</cite></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">Wilhelm Riemenschneider1 and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a09_565.pub2">10.1002/14356007.a09_565.pub2</a></span>

</li>

<li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><cite id="CITEREFEhimenSunCarrington2010" class="citation journal cs1">Ehimen, E. A.; Sun, Z. F.; Carrington, C. G. (1 March 2010). <span class="id-lock-subscription" title="Paid subscription required"><a rel="nofollow" class="external text" href="https://www.sciencedirect.com/science/article/pii/S0016236109004736">"Variables affecting the in situ transesterification of microalgae lipids"</a></span>. <i>Fuel</i>. <b>89</b> (3): <span class="nowrap">677–</span>684. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2010Fuel...89..677E">2010Fuel...89..677E</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fuel.2009.10.011">10.1016/j.fuel.2009.10.011</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0016-2361">0016-2361</a>.</cite></span>

</li>

<li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><cite id="CITEREFTomotaka_HirabayashiSatoshi_SakaguchiYasutaka_Ishii2005" class="citation journal cs1">Tomotaka Hirabayashi; Satoshi Sakaguchi; Yasutaka Ishii (2005). <a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.082.0055">"Iridium-catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate"</a>. <i>Org. Synth</i>. <b>82</b>: 55. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.082.0055">10.15227/orgsyn.082.0055</a></span>.</cite></span>

</li>

<li id="cite_note-Ishii-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ishii_6-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFYasushi_OboraYasutaka_Ishii2012" class="citation journal cs1">Yasushi Obora; Yasutaka Ishii (2012). "Discussion Addendum: Iridium-catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate". <i>Org. Synth</i>. <b>89</b>: 307. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.089.0307">10.15227/orgsyn.089.0307</a>.</cite></span>

</li>

<li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><cite id="CITEREFManchand2001" class="citation book cs1">Manchand, Percy S. (2001). "Vinyl Acetate". <i>Encyclopedia of Reagents for Organic Synthesis</i>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F047084289X.rv008">10.1002/047084289X.rv008</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>0-471-93623-5</bdi>.</cite></span>

</li>

</ol></div></div>

/* start https://en.wikipedia.org/ */

.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}

/* end https://en.wikipedia.org/ */

</style><style data-mw-deduplicate="TemplateStyles:r1236075235">

/* start https://en.wikipedia.org/ */

.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}

/* end https://en.wikipedia.org/ */

</style></div><div role="navigation" class="navbox" aria-labelledby="Alcohols540" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><style data-mw-deduplicate="TemplateStyles:r1239400231">

/* start https://en.wikipedia.org/ */

.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}

/* end https://en.wikipedia.org/ */

</style><div id="Alcohols540" style="font-size:114%;margin:0 4em"><a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">By consumption</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Comparison_of_psychoactive_alcohols_in_alcoholic_drinks" title="Comparison of psychoactive alcohols in alcoholic drinks">Alcohols found in<br>alcoholic drinks</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="1-Propanol" title="1-Propanol">1-Propanol</a></li>

<li><a href="2-Methyl-1-butanol" title="2-Methyl-1-butanol">2-Methyl-1-butanol</a></li>

<li><a href="Ethanol" title="Ethanol">Ethanol</a></li>

<li><a href="Isoamyl_alcohol" title="Isoamyl alcohol">Isoamyl alcohol</a></li>

<li><a href="Isobutanol" title="Isobutanol">Isobutanol</a></li>

<li><a href="Phenethyl_alcohol" title="Phenethyl alcohol">Phenethyl alcohol</a></li>

<li><a href="Tert-Amyl_alcohol" title="Tert-Amyl alcohol"><i>tert</i>-Amyl alcohol</a></li>

<li><a href="Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-Butyl alcohol</a></li>

<li><a href="Tryptophol" title="Tryptophol">Tryptophol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Alcohols_(medicine)" title="Alcohols (medicine)">Medical alcohol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li>

<li><a href="Methylpentynol" title="Methylpentynol">Methylpentynol</a></li>

<li>Methanol poisoning

<ul><li><a href="Ethanol" title="Ethanol">Ethanol</a></li></ul></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Toxic_alcohol" class="mw-redirect" title="Toxic alcohol">Toxic alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Isopropyl_alcohol" title="Isopropyl alcohol">Isopropyl alcohol</a></li>

<li><a href="Methanol" title="Methanol">Methanol</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Primary_alcohol" title="Primary alcohol">Primary<br>alcohols</a> (1°)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Methanol" title="Methanol">Methanol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="4-Methylcyclohexanemethanol" title="4-Methylcyclohexanemethanol">4-Methylcyclohexanemethanol</a></li>

<li><a href="Aminomethanol" title="Aminomethanol">Aminomethanol</a></li>

<li><a href="Cyclohexylmethanol" title="Cyclohexylmethanol">Cyclohexylmethanol</a></li>

<li><a href="Methoxymethanol" title="Methoxymethanol">Methoxymethanol</a></li>

<li><a href="Methylazoxymethanol" title="Methylazoxymethanol">Methylazoxymethanol</a></li>

<li><a href="Trifluoromethanol" title="Trifluoromethanol">Trifluoromethanol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Ethanol" title="Ethanol">Ethanol</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="1-Aminoethanol" title="1-Aminoethanol">1-Aminoethanol</a></li>

<li><a href="2%2C2%2C2-Trichloroethanol" title="2,2,2-Trichloroethanol">2,2,2-Trichloroethanol</a></li>

<li><a href="2%2C2%2C2-Trifluoroethanol" title="2,2,2-Trifluoroethanol">2,2,2-Trifluoroethanol</a></li>

<li><a href="2-(2-Ethoxyethoxy)ethanol" title="2-(2-Ethoxyethoxy)ethanol">2-(2-Ethoxyethoxy)ethanol</a></li>

<li><a href="2-(2-Methoxyethoxy)ethanol" title="2-(2-Methoxyethoxy)ethanol">2-(2-Methoxyethoxy)ethanol</a></li>

<li><a href="2-Butoxyethanol" title="2-Butoxyethanol">2-Butoxyethanol</a></li>

<li><a href="2-Chloroethanol" title="2-Chloroethanol">2-Chloroethanol</a></li>

<li><a href="2-Ethoxyethanol" title="2-Ethoxyethanol">2-Ethoxyethanol</a></li>

<li><a href="2-Fluoroethanol" title="2-Fluoroethanol">2-Fluoroethanol</a></li>

<li><a href="2-Mercaptoethanol" title="2-Mercaptoethanol">2-Mercaptoethanol</a></li>

<li><a href="2-Methoxyethanol" title="2-Methoxyethanol">2-Methoxyethanol</a></li>

<li><a href="Aminoethylethanolamine" title="Aminoethylethanolamine">Aminoethylethanolamine</a></li>

<li><a href="Diethylethanolamine" title="Diethylethanolamine">Diethylethanolamine</a></li>

<li><a href="Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li>

<li><a href="Ethanol" title="Ethanol">Ethanol</a></li>

<li><a href="Ethanolamine" title="Ethanolamine">Ethanolamine</a></li>

<li><a href="N%2CN-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol"><i>N</i>,<i>N</i>-Diisopropylaminoethanol</a></li>

<li><a href="N-Methylethanolamine" title="N-Methylethanolamine"><i>N</i>-Methylethanolamine</a></li>

<li><a href="Phenoxyethanol" title="Phenoxyethanol">Phenoxyethanol</a></li>

<li><a href="Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Butanol" title="Butanol">Butanol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="2-Methyl-1-butanol" title="2-Methyl-1-butanol">2-Methyl-1-butanol</a></li>

<li><a href="Isobutanol" title="Isobutanol">Isobutanol</a></li>

<li><a href="N-Butanol" class="mw-redirect" title="N-Butanol"><i>n</i>-Butanol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br>saturated<br>C<sub>1</sub> — C<sub>9</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Methanol" title="Methanol">Methanol</a></li>

<li><a href="Ethanol" title="Ethanol">Ethanol</a></li>

<li><a href="1-Propanol" title="1-Propanol">1-Propanol</a></li>

<li><a href="1-Butanol" title="1-Butanol">1-Butanol</a></li>

<li><a href="1-Pentanol" title="1-Pentanol">1-Pentanol</a></li>

<li><a href="1-Hexanol" title="1-Hexanol">1-Hexanol</a></li>

<li><a href="1-Heptanol" title="1-Heptanol">1-Heptanol</a></li>

<li><a href="1-Octanol" title="1-Octanol">1-Octanol</a> (capryl)</li>

<li><a href="1-Nonanol" title="1-Nonanol">1-Nonanol</a> (pelargonic)</li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br>saturated<br>C<sub>10</sub> — C<sub>19</sub></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="1-Decanol" title="1-Decanol">1-Decanol</a> (capric)</li>

<li><a href="1-Undecanol" class="mw-redirect" title="1-Undecanol">1-Undecanol</a> (hendecyl)</li>

<li><a href="1-Dodecanol" class="mw-redirect" title="1-Dodecanol">1-Dodecanol</a> (lauryl)</li>

<li><a href="1-Tridecanol" title="1-Tridecanol">1-Tridecanol</a></li>

<li><a href="1-Tetradecanol" title="1-Tetradecanol">1-Tetradecanol</a> (myristyl)</li>

<li><a href="1-Pentadecanol" title="1-Pentadecanol">1-Pentadecanol</a></li>

<li><a href="1-Hexadecanol" class="mw-redirect" title="1-Hexadecanol">1-Hexadecanol</a> (cetyl / palmityl)</li>

<li><a href="1-Heptadecanol" title="1-Heptadecanol">1-Heptadecanol</a></li>

<li><a href="1-Octadecanol" class="mw-redirect" title="1-Octadecanol">1-Octadecanol</a> (stearyl)</li>

<li><a href="1-Nonadecanol" title="1-Nonadecanol">1-Nonadecanol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br>saturated<br>C<sub>20</sub> — C<sub>29</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="1-Icosanol" class="mw-redirect" title="1-Icosanol">1-Icosanol</a> (arachidyl)</li>

<li><a href="1-Heneicosanol" title="1-Heneicosanol">1-Heneicosanol</a></li>

<li><a href="1-Docosanol" title="1-Docosanol">1-Docosanol</a> (behenyl)</li>

<li>1-Tricosanol</li>

<li><a href="1-Tetracosanol" title="1-Tetracosanol">1-Tetracosanol</a> (lignoceryl)</li>

<li>1-Pentacosanol</li>

<li><a href="1-Hexacosanol" title="1-Hexacosanol">1-Hexacosanol</a> (ceryl)</li>

<li><a href="1-Heptacosanol" title="1-Heptacosanol">1-Heptacosanol</a></li>

<li><a href="1-Octacosanol" title="1-Octacosanol">1-Octacosanol</a> (cluytyl / montanyl)</li>

<li><a href="1-Nonacosanol" title="1-Nonacosanol">1-Nonacosanol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br>saturated<br>C<sub>30</sub> — C<sub>39</sub></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="1-Triacontanol" title="1-Triacontanol">1-Triacontanol</a> (melissyl / myricyl)</li>

<li>1-Hentriacontanol</li>

<li><a href="1-Dotriacontanol" title="1-Dotriacontanol">1-Dotriacontanol</a> (lacceryl)</li>

<li>1-Tritriacontanol</li>

<li>1-Tetratriacontanol (geddyl)</li>

<li>1-Pentatriacontanol</li>

<li>1-Hexatriacontanol</li>

<li>1-Heptatriacontanol</li>

<li>1-Octatriacontanol</li>

<li>1-Nonatriacontanol</li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br>saturated<br>C<sub>40</sub> — C<sub>49</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li>1-Tetracontanol</li>

<li>1-Hentetracontanol</li>

<li>1-Dotetracontanol</li>

<li>1-Tritetracontanol</li>

<li>1-Tetratetracontanol</li>

<li>1-Pentatetracontanol</li>

<li>1-Hexatetracontanol</li>

<li>1-Heptatetracontanol</li>

<li>1-Octatetracontanol</li>

<li>1-Nonatetracontanol</li></ul>

</div></td></tr></tbody></table><div>

<ul><li><a href="2-Ethylhexanol" title="2-Ethylhexanol">2-Ethylhexanol</a></li>

<li><a href="Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a></li>

<li><a href="Anisyl_alcohol" title="Anisyl alcohol">Anisyl alcohol</a></li>

<li><a href="Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a></li>

<li><a href="Cinnamyl_alcohol" title="Cinnamyl alcohol">Cinnamyl alcohol</a></li>

<li><a href="Crotyl_alcohol" title="Crotyl alcohol">Crotyl alcohol</a></li>

<li><a href="Furfuryl_alcohol" title="Furfuryl alcohol">Furfuryl alcohol</a></li>

<li><a href="Isoamyl_alcohol" title="Isoamyl alcohol">Isoamyl alcohol</a></li>

<li><a href="Neopentyl_alcohol" title="Neopentyl alcohol">Neopentyl alcohol</a></li>

<li><a href="Nicotinyl_alcohol" title="Nicotinyl alcohol">Nicotinyl alcohol</a></li>

<li><a href="Perillyl_alcohol" title="Perillyl alcohol">Perillyl alcohol</a></li>

<li><a href="Phenethyl_alcohol" title="Phenethyl alcohol">Phenethyl alcohol</a></li>

<li><a href="Prenol" title="Prenol">Prenol</a></li>

<li><a href="Propargyl_alcohol" title="Propargyl alcohol">Propargyl alcohol</a></li>

<li><a href="Salicyl_alcohol" title="Salicyl alcohol">Salicyl alcohol</a></li>

<li><a href="Tryptophol" title="Tryptophol">Tryptophol</a></li>

<li><a href="Vanillyl_alcohol" title="Vanillyl alcohol">Vanillyl alcohol</a></li>

<li><a href="Veratrole_alcohol" title="Veratrole alcohol">Veratrole alcohol</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Secondary<br> alcohols (2°)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="1-Phenylethanol" title="1-Phenylethanol">1-Phenylethanol</a></li>

<li><a href="2-Butanol" title="2-Butanol">2-Butanol</a></li>

<li>2-Deoxyerythritol</li>

<li><a href="2-Heptanol" title="2-Heptanol">2-Heptanol</a></li>

<li><a href="3-Heptanol" title="3-Heptanol">3-Heptanol</a></li>

<li><a href="2-Hexanol" title="2-Hexanol">2-Hexanol</a></li>

<li><a href="3-Hexanol" title="3-Hexanol">3-Hexanol</a></li>

<li><a href="3-Methyl-2-butanol" title="3-Methyl-2-butanol">3-Methyl-2-butanol</a></li>

<li><a href="2-Nonanol" title="2-Nonanol">2-Nonanol</a></li>

<li><a href="2-Octanol" title="2-Octanol">2-Octanol</a></li>

<li><a href="2-Pentanol" title="2-Pentanol">2-Pentanol</a></li>

<li><a href="3-Pentanol" title="3-Pentanol">3-Pentanol</a></li>

<li><a href="Cyclohexanol" title="Cyclohexanol">Cyclohexanol</a></li>

<li><a href="Cyclopentanol" title="Cyclopentanol">Cyclopentanol</a></li>

<li><a href="Cyclopropanol" title="Cyclopropanol">Cyclopropanol</a></li>

<li><a href="Diphenylmethanol" title="Diphenylmethanol">Diphenylmethanol</a></li>

<li><a href="Isopropyl_alcohol" title="Isopropyl alcohol">Isopropanol</a></li>

<li><a href="Pinacolyl_alcohol" title="Pinacolyl alcohol">Pinacolyl alcohol</a></li>

<li><a href="Pirkle's_alcohol" title="Pirkle's alcohol">Pirkle's alcohol</a></li>

<li><a href="Propylene_glycol_methyl_ether" title="Propylene glycol methyl ether">Propylene glycol methyl ether</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tertiary<br> alcohols (3°)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="2-Methyl-2-pentanol" title="2-Methyl-2-pentanol">2-Methyl-2-pentanol</a></li>

<li>2-Methylheptan-2-ol</li>

<li>2-Methylhexan-2-ol</li>

<li><a href="3-Methyl-3-pentanol" title="3-Methyl-3-pentanol">3-Methyl-3-pentanol</a></li>

<li>3-Methyloctan-3-ol</li>

<li><a href="Diacetone_alcohol" title="Diacetone alcohol">Diacetone alcohol</a></li>

<li><a href="Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li>

<li><a href="Methylpentynol" title="Methylpentynol">Methylpentynol</a></li>

<li><a href="Nonafluoro-tert-butyl_alcohol" title="Nonafluoro-tert-butyl alcohol">Nonafluoro-<i>tert</i>-butyl alcohol</a></li>

<li><a href="Tert-Amyl_alcohol" title="Tert-Amyl alcohol"><i>tert</i>-Amyl alcohol</a></li>

<li><a href="Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-Butyl alcohol</a></li>

<li><a href="Triphenylethanol" title="Triphenylethanol">Triphenylethanol</a></li>

<li><a href="Triphenylmethanol" title="Triphenylmethanol">Triphenylmethanol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydric alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Monohydric alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Methanol" title="Methanol">Methanol</a> (C<sub>1</sub>)</li>

<li><a href="Ethanol" title="Ethanol">Ethanol</a> (C<sub>2</sub>)</li>

<li><a href="Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a> (C<sub>3</sub>)</li>

<li><a href="1-Butanol" title="1-Butanol">1-Butanol</a> (C<sub>4</sub>)</li>

<li><a href="1-Pentanol" title="1-Pentanol">1-Pentanol</a> (C<sub>5</sub>)</li>

<li><a href="Cetyl_alcohol" title="Cetyl alcohol">Cetyl alcohol</a> (C<sub>16</sub>)</li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Dihydric alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li>

<li><a href="Propylene_glycol" title="Propylene glycol">Propylene glycol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trihydric alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Glycerol" title="Glycerol">Glycerol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Sugar_alcohol" title="Sugar alcohol">Polyhydric alcohols (sugar alcohols)</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Pentaerythritol" title="Pentaerythritol">Pentaerythritol</a></li>

<li><a href="Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> (C<sub>2</sub>)</li>

<li><a href="Glycerol" title="Glycerol">Glycerol</a>, <a href="Propylene_glycol" title="Propylene glycol">Propylene glycol</a> (C<sub>3</sub>)</li>

<li><a href="Erythritol" title="Erythritol">Erythritol</a>, <a href="Threitol" title="Threitol">Threitol</a> (C<sub>4</sub>)</li>

<li><a href="Xylitol" title="Xylitol">Xylitol</a> (C<sub>5</sub>)</li>

<li><a href="Mannitol" title="Mannitol">Mannitol</a>, <a href="Sorbitol" title="Sorbitol">Sorbitol</a> (C<sub>6</sub>)</li>

<li><a href="Volemitol" title="Volemitol">Volemitol</a> (C<sub>7</sub>)</li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Amyl_alcohol" title="Amyl alcohol">Amyl alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="2%2C2-Dimethylpropan-1-ol" class="mw-redirect" title="2,2-Dimethylpropan-1-ol">2,2-Dimethylpropan-1-ol </a></li>

<li><a href="2-Methylbutan-1-ol" class="mw-redirect" title="2-Methylbutan-1-ol">2-Methylbutan-1-ol </a></li>

<li><a href="2-Methylbutan-2-ol" class="mw-redirect" title="2-Methylbutan-2-ol">2-Methylbutan-2-ol </a></li>

<li><a href="3-Methylbutan-1-ol" class="mw-redirect" title="3-Methylbutan-1-ol">3-Methylbutan-1-ol </a></li>

<li><a href="3-Methylbutan-2-ol" class="mw-redirect" title="3-Methylbutan-2-ol">3-Methylbutan-2-ol </a></li>

<li><a href="Pentan-1-ol" class="mw-redirect" title="Pentan-1-ol">Pentan-1-ol </a></li>

<li><a href="Pentan-2-ol" class="mw-redirect" title="Pentan-2-ol">Pentan-2-ol </a></li>

<li><a href="Pentan-3-ol" class="mw-redirect" title="Pentan-3-ol">Pentan-3-ol </a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">Aromatic alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a></li>

<li><a href="2%2C4-Dichlorobenzyl_alcohol" title="2,4-Dichlorobenzyl alcohol">2,4-Dichlorobenzyl alcohol</a></li>

<li><a href="3-Nitrobenzyl_alcohol" title="3-Nitrobenzyl alcohol">3-Nitrobenzyl alcohol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Saturated<br><a href="Fatty_alcohol" title="Fatty alcohol">fatty alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Cetostearyl_alcohol" title="Cetostearyl alcohol">Cetostearyl alcohol</a></li>

<li><a href="Decanol" class="mw-redirect" title="Decanol">Decanol</a></li>

<li><a href="Lauryl_alcohol" class="mw-redirect" title="Lauryl alcohol">Lauryl alcohol</a></li>

<li><a href="Myristyl_alcohol" class="mw-redirect" title="Myristyl alcohol">Myristyl alcohol</a></li>

<li><a href="Nonanol_(disambiguation)" class="mw-redirect mw-disambig" title="Nonanol (disambiguation)">Nonanol</a></li>

<li><a href="Octanol" title="Octanol">Octanol</a></li>

<li><a href="Tridecanol" class="mw-redirect" title="Tridecanol">Tridecanol</a></li>

<li><a href="Undecanol" title="Undecanol">Undecanol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Branched and<br>unsaturated<br><a href="Fatty_alcohol" title="Fatty alcohol">fatty alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="3-Methyl-3-pentanol" title="3-Methyl-3-pentanol">3-Methyl-3-pentanol</a></li>

<li>Erucyl alcohol</li>

<li>Linolenyl alcohol</li>

<li><a href="Linoleyl_alcohol" title="Linoleyl alcohol">Linoleyl alcohol</a></li>

<li><a href="Oleyl_alcohol" title="Oleyl alcohol">Oleyl alcohol</a></li>

<li>Palmitoleyl alcohol</li>

<li><a href="Tert-Amyl_alcohol" title="Tert-Amyl alcohol">tert-Amyl alcohol</a></li>

<li><a href="Tert-Butyl_alcohol" title="Tert-Butyl alcohol">tert-Butyl alcohol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Sugar_alcohol" title="Sugar alcohol">Sugar alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>1</sub> — C<sub>7</sub></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Methylene_glycol" class="mw-redirect" title="Methylene glycol">Methylene glycol</a> (C<sub>1</sub>)</li>

<li><a href="Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> (C<sub>2</sub>)</li>

<li><a href="Glycerol" title="Glycerol">Glycerol</a> (C<sub>3</sub>)</li>

<li><a href="Erythritol" title="Erythritol">Erythritol</a> (C<sub>4</sub>)</li>

<li><a href="Threitol" title="Threitol">Threitol</a> (C<sub>4</sub>)</li>

<li><a href="Arabitol" title="Arabitol">Arabitol</a> (C<sub>5</sub>)</li>

<li><a href="Ribitol" title="Ribitol">Ribitol</a> (C<sub>5</sub>)</li>

<li><a href="Xylitol" title="Xylitol">Xylitol</a> (C<sub>5</sub>)</li>

<li><a href="Mannitol" title="Mannitol">Mannitol</a> (C<sub>6</sub>)</li>

<li><a href="Sorbitol" title="Sorbitol">Sorbitol</a> (C<sub>6</sub>)</li>

<li><a href="Galactitol" title="Galactitol">Galactitol</a> (C<sub>6</sub>)</li>

<li><a href="Iditol" title="Iditol">Iditol</a> (C<sub>6</sub>)</li>

<li><a href="Volemitol" title="Volemitol">Volemitol</a> (C<sub>7</sub>)</li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Deoxy sugar<br> alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Fucitol" title="Fucitol">Fucitol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cyclic sugar<br> alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Inositol" title="Inositol">Inositol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycylglycitols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Maltitol" title="Maltitol">Maltitol</a></li>

<li><a href="Lactitol" title="Lactitol">Lactitol</a></li>

<li><a href="Isomalt" title="Isomalt">Isomalt</a></li>

<li>Maltotriitol</li>

<li>Maltotetraitol</li>

<li>Polyglycitol</li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Terpene alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Monoterpene<br> alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Borneol" title="Borneol">Borneol</a></li>

<li><a href="Citronellol" title="Citronellol">Citronellol</a></li>

<li><a href="Geraniol" title="Geraniol">Geraniol</a></li>

<li><a href="Linalool" title="Linalool">Linalool</a></li>

<li><a href="Menthol" title="Menthol">Menthol</a></li>

<li><a href="Nerol" title="Nerol">Nerol</a></li>

<li><a href="Rhodinol" title="Rhodinol">Rhodinol</a></li>

<li><a href="Terpineol" title="Terpineol">Terpineol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sesquiterpene<br> alcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Bisabolol" title="Bisabolol">Bisabolol</a></li>

<li><a href="Farnesol" title="Farnesol">Farnesol</a></li>

<li><a href="Nerolidol" title="Nerolidol">Nerolidol</a></li>

<li><a href="Patchoulol" title="Patchoulol">Patchoulol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Diterpene<br> alcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Phytol" title="Phytol">Phytol</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Dialcohols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="1%2C4-Butanediol" title="1,4-Butanediol">1,4-Butanediol</a></li>

<li><a href="1%2C5-Pentanediol" title="1,5-Pentanediol">1,5-Pentanediol</a></li>

<li><a href="2-Methyl-2-propyl-1%2C3-propanediol" title="2-Methyl-2-propyl-1,3-propanediol">2-Methyl-2-propyl-1,3-propanediol</a></li>

<li><a href="Diethylpropanediol" class="mw-redirect" title="Diethylpropanediol">Diethylpropanediol</a></li>

<li><a href="Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trialcohols</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Glycerol" title="Glycerol">Glycerol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sterols</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Cholesterol" title="Cholesterol">Cholesterol</a></li>

<li><a href="Ergosterol" title="Ergosterol">Ergosterol</a></li>

<li><a href="Lanosterol" title="Lanosterol">Lanosterol</a></li>

<li><a href="Beta-Sitosterol" class="mw-redirect" title="Beta-Sitosterol">β-Sitosterol</a></li>

<li><a href="Stigmasterol" title="Stigmasterol">Stigmasterol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Fluoroalcohol" title="Fluoroalcohol">Fluoroalcohols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="1%2C3-Difluoro-2-propanol" title="1,3-Difluoro-2-propanol">1,3-Difluoro-2-propanol</a></li>

<li><a href="2%2C2%2C2-Trifluoroethanol" title="2,2,2-Trifluoroethanol">2,2,2-Trifluoroethanol</a></li>

<li><a href="2-Fluoroethanol" title="2-Fluoroethanol">2-Fluoroethanol</a></li>

<li><a href="Nonafluoro-tert-butyl_alcohol" title="Nonafluoro-tert-butyl alcohol">Nonafluoro-<i>tert</i>-butyl alcohol</a></li>

<li><a href="Trifluoromethanol" title="Trifluoromethanol">Trifluoromethanol</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Substitution_reaction" title="Substitution reaction">Substitution</a> of <a href="Haloalkane#Substitution" title="Haloalkane">haloalkane</a></li>

<li><a href="Carbonyl_reduction" title="Carbonyl reduction">Carbonyl reduction</a></li>

<li><a href="Ether_cleavage" title="Ether cleavage">Ether cleavage</a></li>

<li><a href="Hydrolysis" title="Hydrolysis">Hydrolysis</a> of <a href="Epoxide#Hydrolysis_and_addition_of_nucleophiles" title="Epoxide">epoxide</a></li>

<li><a href="Hydration_reaction" title="Hydration reaction">Hydration</a> of <a href="Alkene#Hydration" title="Alkene">alkene</a></li>

<li><a href="Ziegler_process" title="Ziegler process">Ziegler process</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Deprotonation" title="Deprotonation">Deprotonation</a></li>

<li><a href="Protonation" title="Protonation">Protonation</a></li>

<li><a href="Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a>

<ul><li><a href="Glycol_cleavage" title="Glycol cleavage">Glycol cleavage</a></li></ul></li>

<li><a href="Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitution</a></li>

<li><a href="Fischer%E2%80%93Speier_esterification" title="Fischer–Speier esterification">Fischer–Speier esterification</a></li>

<li><a href="Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a></li>

<li><a href="Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li>

<li><a href="Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitution</a> of <a href="Carbonyl_group" title="Carbonyl group">carbonyl group</a></li>

<li><a href="Friedel-Crafts_alkylation" class="mw-redirect" title="Friedel-Crafts alkylation">Friedel-Crafts alkylation</a></li>

<li><a href="Nucleophilic_conjugate_addition" title="Nucleophilic conjugate addition">Nucleophilic conjugate addition</a></li>

</ul>

</div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2"><div>

<ul><li><span class="noviewer" typeof="mw:File"><span title="Category"></span></span> Category</li></ul>

</div></td></tr></tbody></table></div>

<div class="navbox-styles"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox390" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Authority control databases: National </th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4222675-2">Germany</a></span></li></ul></div></td></tr></tbody></table></div></div><div><div class="zim-footer">

This article is issued from <a class="external text" title="Last edited on 2025-06-26" href="https://en.wikipedia.org/wiki/?title=Transesterification&oldid=1297470665">Wikipedia</a>. The text is available under <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">Creative Commons Attribution-Share Alike 4.0</a> unless otherwise noted. Additional terms may apply for the media files.

</div>

</div></div>

</div>

</main>

</div>

</body></html>