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class="vector-toc-numb">2.2</span> <span>Solvent</span> </div> </a> <ul id="toc-Solvent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intermediate_in_polycarbonate_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intermediate_in_polycarbonate_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Intermediate in polycarbonate synthesis</span> </div> </a> <ul id="toc-Intermediate_in_polycarbonate_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alternative_fuel_additive" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alternative_fuel_additive"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Alternative fuel additive</span> </div> </a> <ul id="toc-Alternative_fuel_additive-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_lithium-ion_and_lithium-metal_batteries" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_lithium-ion_and_lithium-metal_batteries"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>In lithium-ion and lithium-metal batteries</span> </div> </a> <ul id="toc-In_lithium-ion_and_lithium-metal_batteries-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label 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class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Kohlens%C3%A4uredimethylester" title="Kohlensäuredimethylester – German" lang="de" hreflang="de" data-title="Kohlensäuredimethylester" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Dumetila_karbonato" title="Dumetila karbonato – Esperanto" lang="eo" hreflang="eo" data-title="Dumetila karbonato" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AF%DB%8C%E2%80%8C%D9%85%D8%AA%DB%8C%D9%84_%DA%A9%D8%B1%D8%A8%D9%86%D8%A7%D8%AA" title="دی‌متیل کربنات – Persian" lang="fa" hreflang="fa" data-title="دی‌متیل کربنات" 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/Carbonate_de_dim%C3%A9thyle" title="Carbonate de diméthyle – French" lang="fr" hreflang="fr" data-title="Carbonate de diméthyle" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Dimetilcarbonato" title="Dimetilcarbonato – Italian" lang="it" hreflang="it" data-title="Dimetilcarbonato" 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/Dimethylcarbonaat" title="Dimethylcarbonaat – Dutch" lang="nl" hreflang="nl" data-title="Dimethylcarbonaat" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E7%82%AD%E9%85%B8%E3%82%B8%E3%83%A1%E3%83%81%E3%83%AB" title="炭酸ジメチル – Japanese" lang="ja" hreflang="ja" data-title="炭酸ジメチル" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/W%C4%99glan_dimetylu" title="Węglan dimetylu – Polish" lang="pl" hreflang="pl" data-title="Węglan dimetylu" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D0%B8%D0%BC%D0%B5%D1%82%D0%B8%D0%BB%D0%BA%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%B0%D1%82" title="Диметилкарбонат – Russian" lang="ru" hreflang="ru" data-title="Диметилкарбонат" 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/Dimetil_karbonat" title="Dimetil karbonat – Serbian" lang="sr" hreflang="sr" data-title="Dimetil karbonat" 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/Dimetil_karbonat" title="Dimetil karbonat – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Dimetil karbonat" 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/Dimetyylikarbonaatti" title="Dimetyylikarbonaatti – Finnish" lang="fi" hreflang="fi" data-title="Dimetyylikarbonaatti" 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/Dimetylkarbonat" title="Dimetylkarbonat – Swedish" lang="sv" hreflang="sv" data-title="Dimetylkarbonat" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%87%E0%AE%B0%E0%AF%81%E0%AE%AE%E0%AF%86%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AE%BF%E0%AE%B2%E0%AF%8D_%E0%AE%95%E0%AE%BE%E0%AE%B0%E0%AF%8D%E0%AE%AA%E0%AE%A9%E0%AF%87%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%81" title="இருமெத்தில் கார்பனேட்டு – Tamil" lang="ta" hreflang="ta" data-title="இருமெத்தில் கார்பனேட்டு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%94%D0%B8%D0%BC%D0%B5%D1%82%D0%B8%D0%BB%D0%BA%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D0%B0%D1%82" title="Диметилкарбонат – Ukrainian" lang="uk" hreflang="uk" data-title="Диметилкарбонат" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A2%B3%E9%85%B8%E4%BA%8C%E7%94%B2%E9%85%AF" title="碳酸二甲酯 – Chinese" lang="zh" hreflang="zh" data-title="碳酸二甲酯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span 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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/Dimethyl_carbate" title="Dimethyl carbate">dimethyl carbate</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.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%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Dimethyl carbonate </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Dimethyl_carbonate_Structural_Formulae.svg" class="mw-file-description" title="Dimethyl carbonate"><img alt="Dimethyl carbonate" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Dimethyl_carbonate_Structural_Formulae.svg/180px-Dimethyl_carbonate_Structural_Formulae.svg.png" decoding="async" width="180" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Dimethyl_carbonate_Structural_Formulae.svg/270px-Dimethyl_carbonate_Structural_Formulae.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Dimethyl_carbonate_Structural_Formulae.svg/360px-Dimethyl_carbonate_Structural_Formulae.svg.png 2x" data-file-width="218" data-file-height="85" /></a><figcaption>Dimethyl carbonate</figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Dimethyl-carbonate-cis-cis-HF-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of dimethyl carbonate"><img alt="Ball-and-stick model of dimethyl carbonate" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Dimethyl-carbonate-cis-cis-HF-3D-balls.png/150px-Dimethyl-carbonate-cis-cis-HF-3D-balls.png" decoding="async" width="150" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Dimethyl-carbonate-cis-cis-HF-3D-balls.png/225px-Dimethyl-carbonate-cis-cis-HF-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Dimethyl-carbonate-cis-cis-HF-3D-balls.png/300px-Dimethyl-carbonate-cis-cis-HF-3D-balls.png 2x" data-file-width="1100" data-file-height="569" /></a><figcaption>Ball-and-stick model of dimethyl carbonate</figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Dimethyl carbonate</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;">DMC<br />Methyl carbonate, di-</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=616-38-6">616-38-6</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=COC%28%3DO%29OC">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=36596">CHEBI:36596</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.11526.html">11526</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/100.009.527">100.009.527</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q416254#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><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/12021">12021</a></span></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/KE9J097SPN">KE9J097SPN</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/DTXSID9029192">DTXSID9029192</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q416254#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C3H6O3/c1-5-3(4)6-2/h1-2H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IEJIGPNLZYLLBP-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C3H6O3/c1-5-3(4)6-2/h1-2H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IEJIGPNLZYLLBP-UHFFFAOYAC</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">COC(=O)OC</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>3</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001900780000000000♠"></span>90.078</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>colorless liquid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.069-1.073 g/mL </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>2 to 4 °C (36 to 39 °F; 275 to 277 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>90 °C (194 °F; 363 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>13.9 g/100 mL </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Flammable </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>17 °C (63 °F; 290 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476999619&page2=Dimethyl+carbonate">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>Dimethyl carbonate</b> (<b>DMC</b>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> OC(OCH<sub>3</sub>)<sub>2</sub>. It is a colourless, flammable liquid. It is classified as a <a href="/wiki/Carbonate_ester" title="Carbonate ester">carbonate ester</a>. This compound has found use as a <a href="/wiki/Methylating_agent" class="mw-redirect" title="Methylating agent">methylating agent</a> and as a co-solvent in <a href="/wiki/Lithium-ion_batteries" class="mw-redirect" title="Lithium-ion batteries">lithium-ion batteries</a>.<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> Notably, dimethyl carbonate is a weak <a href="/wiki/Methylating_agent" class="mw-redirect" title="Methylating agent">methylating agent</a>, and is not considered as a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>.<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> Instead, dimethyl carbonate is often considered to be a <a href="/wiki/Green_chemistry" title="Green chemistry">green reagent</a>,<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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> and it is exempt from the restrictions placed on most <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile organic compounds</a> (VOCs) in the United States.<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> <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=Dimethyl_carbonate&action=edit&section=1" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>World production in 1997 was estimated at 1000 barrels a day.<sup id="cite_ref-pachecho_6-0" class="reference"><a href="#cite_note-pachecho-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Production of dimethyl carbonate worldwide is limited to Asia, the Middle East, and Europe. </p><p>Dimethyl carbonate is traditionally prepared by the reaction of <a href="/wiki/Phosgene" title="Phosgene">phosgene</a> and <a href="/wiki/Methanol" title="Methanol">methanol</a>. <a href="/wiki/Methyl_chloroformate" title="Methyl chloroformate">Methyl chloroformate</a> is produced as an intermediate: </p> <dl><dd>COCl<sub>2</sub> + CH<sub>3</sub>OH → CH<sub>3</sub>OCOCl + HCl</dd> <dd>CH<sub>3</sub>OCOCl + CH<sub>3</sub>OH → CH<sub>3</sub>OCO<sub>2</sub>CH<sub>3</sub> + HCl</dd></dl> <p>This synthesis route has been largely replaced by <a href="/wiki/Oxidative_carbonylation" title="Oxidative carbonylation">oxidative carbonylation</a>. In this process, <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> and an oxidizer provide the equivalent of CO<sup>2+</sup>:<sup id="cite_ref-Tundo_7-0" class="reference"><a href="#cite_note-Tundo-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ullmann_8-0" class="reference"><a href="#cite_note-ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><dl><dd>CO + 1/2 O<sub>2</sub> + 2 CH<sub>3</sub>OH → (CH<sub>3</sub>O)<sub>2</sub>CO + H<sub>2</sub>O</dd></dl></dd></dl> <p>It can also be produced industrially by a <a href="/wiki/Transesterification" title="Transesterification">transesterification</a> of <a href="/wiki/Ethylene_carbonate" title="Ethylene carbonate">ethylene carbonate</a> or <a href="/wiki/Propylene_carbonate" title="Propylene carbonate">propylene carbonate</a> and <a href="/wiki/Methanol" title="Methanol">methanol</a>, which also affords respectively ethylene glycol or <a href="/wiki/Propylene_glycol" title="Propylene glycol">propylene glycol</a>. This route is complicated by the methanol-DMC <a href="/wiki/Azeotrope" title="Azeotrope">azeotrope</a>, which requires <a href="/wiki/Azeotropic_distillation" title="Azeotropic distillation">azeotropic distillation</a> or other techniques.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions_and_potential_applications">Reactions and potential applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dimethyl_carbonate&action=edit&section=2" title="Edit section: Reactions and potential applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Methylating_agent">Methylating agent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dimethyl_carbonate&action=edit&section=3" title="Edit section: Methylating agent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dimethyl carbonate methylates <a href="/wiki/Aniline" title="Aniline">anilines</a>, <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>, and <a href="/wiki/Phenols" title="Phenols">phenols</a>, albeit usually slowly.<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><sup id="cite_ref-Shieh2002_11-0" class="reference"><a href="#cite_note-Shieh2002-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><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> Sometimes these reactions require the use of an <a href="/wiki/Autoclave" title="Autoclave">autoclave</a>. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:DMC_Methylation.png" class="mw-file-description" title="Methylation of phenylacetic acid by dimethyl carbonate promoted by DBU"><img alt="Methylation of phenylacetic acid by dimethyl carbonate promoted by DBU" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/DMC_Methylation.png/350px-DMC_Methylation.png" decoding="async" width="350" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/DMC_Methylation.png/525px-DMC_Methylation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/57/DMC_Methylation.png/700px-DMC_Methylation.png 2x" data-file-width="1755" data-file-height="476" /></a></span></dd></dl> <p>Dimethyl carbonate's main benefit over other methylating reagents such as <a href="/wiki/Iodomethane" title="Iodomethane">iodomethane</a> and <a href="/wiki/Dimethyl_sulfate" title="Dimethyl sulfate">dimethyl sulfate</a> is its low toxicity. Additionally, it is biodegradable.<sup id="cite_ref-Tundo_7-1" class="reference"><a href="#cite_note-Tundo-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Unfortunately, it is a relatively weak <a href="/wiki/Methylating_agent" class="mw-redirect" title="Methylating agent">methylating agent</a> compared to these traditional reagents. </p> <div class="mw-heading mw-heading3"><h3 id="Solvent">Solvent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dimethyl_carbonate&action=edit&section=4" title="Edit section: Solvent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the US, dimethyl carbonate was exempted under the definition of <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile organic compounds</a> (VOCs) by the <a href="/wiki/U.S._EPA" class="mw-redirect" title="U.S. EPA">U.S. EPA</a> in 2009.<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> Due to its classification as VOC exempt, dimethyl carbonate has grown in popularity and applications as a replacement for <a href="/wiki/Methyl_ethyl_ketone" class="mw-redirect" title="Methyl ethyl ketone">methyl ethyl ketone</a> (MEK) and <a href="/wiki/Parachlorobenzotrifluoride" title="Parachlorobenzotrifluoride">parachlorobenzotrifluoride</a>, as well as <a href="/wiki/Tert-Butyl_acetate" title="Tert-Butyl acetate"><i>tert</i>-butyl acetate</a> until it too was exempted.<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> Dimethyl carbonate has an ester- or alcohol-like odor, which is more favorable to users than most hydrocarbon solvents it replaces. Dimethyl carbonate has an evaporation rate of 3.22 (butyl acetate = 1.0), which slightly slower than MEK (3.8) and <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> (4.1), and faster than <a href="/wiki/Toluene" title="Toluene">toluene</a> (2.0) and <a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">isopropanol</a> (1.7). Dimethyl carbonate has solubility profile similar to common <a href="/wiki/Glycol_ether" class="mw-redirect" title="Glycol ether">glycol ethers</a>, meaning dimethyl carbonate can dissolve most common coating resins except perhaps rubber based resins. Hildebrand solubility parameter is 20.3 MPa and Hansen solubility parameters are: dispersion = 15.5, polar = 3.9, H bonding = 9.7.<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> Dimethyl carbonate is partially soluble in water up to 13%, however it is hydrolyzed in water-based systems over time to methanol and CO<sub>2</sub> unless properly buffered. Dimethyl carbonate can freeze at same temperatures as water, it can be thawed out with no loss of properties to itself or coatings based on dimethyl carbonate. </p> <div class="mw-heading mw-heading3"><h3 id="Intermediate_in_polycarbonate_synthesis">Intermediate in polycarbonate synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dimethyl_carbonate&action=edit&section=5" title="Edit section: Intermediate in polycarbonate synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A large captive use of dimethyl carbonate is for the production of <a href="/wiki/Diphenyl_carbonate" title="Diphenyl carbonate">diphenyl carbonate</a> through <a href="/wiki/Transesterification" title="Transesterification">transesterification</a> with <a href="/wiki/Phenol" title="Phenol">phenol</a>. Diphenyl carbonate is a widely used raw material for the synthesis of <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol-A</a>-polycarbonate in a melt polycondensation process,<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> the resulting product being recyclable by reversing the process and transesterifying the polycarbonate with phenol to yield diphenyl carbonate and bisphenol A.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Alternative_fuel_additive">Alternative fuel additive</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dimethyl_carbonate&action=edit&section=6" title="Edit section: Alternative fuel additive"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There is also interest in using this compound as a <a href="/wiki/Fuel_oxygenate_additive" class="mw-redirect" title="Fuel oxygenate additive">fuel oxygenate additive</a>.<sup id="cite_ref-pachecho_6-1" class="reference"><a href="#cite_note-pachecho-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="In_lithium-ion_and_lithium-metal_batteries">In lithium-ion and lithium-metal batteries</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dimethyl_carbonate&action=edit&section=7" title="Edit section: In lithium-ion and lithium-metal batteries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Similar to <a href="/wiki/Ethylene_carbonate" title="Ethylene carbonate">ethylene carbonate</a>, dimethyl carbonate forms an electronically-insulating Li<sup>+</sup>-conducting film at negative <a href="/wiki/Electrode_potentials" class="mw-redirect" title="Electrode potentials">electrode potentials</a>. However, the film in dry DMC solutions is not as effective in passivating the negative electrode as the film in wet solutions.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> For this reason dimethyl carbonate is rarely used in lithium batteries without a co-solvent.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dimethyl_carbonate&action=edit&section=8" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DMC is a flammable liquid with a <a href="/wiki/Flash_point" title="Flash point">flash point</a> of 17 °C (63 °F), which limits its use in consumer and indoor applications. DMC is still safer than <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Methyl_acetate" title="Methyl acetate">methyl acetate</a> and methyl ethyl ketone from a flammability point of view. The <a href="/wiki/University_Transportation_Centers_Program" title="University Transportation Centers Program">National Center for Sustainable Transportation</a> recommends limiting exposure by inhalation to less than 100 ppm over an 8-hour work day, which is similar to that of a number of common industrial solvents (<a href="/wiki/Toluene" title="Toluene">toluene</a>, methyl ethyl ketone).<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Workers should wear protective organic vapor respirators when using DMC indoors or in other conditions where concentrations exceed the REL. DMC is metabolized by the body to <a href="/wiki/Methanol" title="Methanol">methanol</a> and carbon dioxide, so accidental ingestion should be treated in the same manner as <a href="/wiki/Methanol_poisoning" class="mw-redirect" title="Methanol poisoning">methanol poisoning</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2023)">citation needed</span></a></i>]</sup> </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=Dimethyl_carbonate&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Dimethyl_dicarbonate" title="Dimethyl dicarbonate">Dimethyl dicarbonate</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=Dimethyl_carbonate&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><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 id="CITEREFKöntjeMemmAxmannWohlfahrt-Mehrens2014" class="citation journal cs1">Köntje, M.; Memm, M.; Axmann, P.; Wohlfahrt-Mehrens, M. (December 2014). "Substituted transition metal phospho olivines LiMM′PO4 (M = Mn, M′ = Fe, Co, Mg): Optimisation routes for LiMnPO4". <i>Progress in Solid State Chemistry</i>. <b>42</b> (4): <span class="nowrap">106–</span>117. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.progsolidstchem.2014.04.005">10.1016/j.progsolidstchem.2014.04.005</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Solid+State+Chemistry&rft.atitle=Substituted+transition+metal+phospho+olivines+LiMM%E2%80%B2PO4+%28M+%3D+Mn%2C+M%E2%80%B2+%3D+Fe%2C+Co%2C+Mg%29%3A+Optimisation+routes+for+LiMnPO4&rft.volume=42&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E106-%3C%2Fspan%3E117&rft.date=2014-12&rft_id=info%3Adoi%2F10.1016%2Fj.progsolidstchem.2014.04.005&rft.aulast=K%C3%B6ntje&rft.aufirst=M.&rft.au=Memm%2C+M.&rft.au=Axmann%2C+P.&rft.au=Wohlfahrt-Mehrens%2C+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" 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"><a rel="nofollow" class="external free" href="https://www.fsc.go.jp/fsciis/attachedFile/download?retrievalId=kya20180111146&fileId=202">https://www.fsc.go.jp/fsciis/attachedFile/download?retrievalId=kya20180111146&fileId=202</a><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (October 2023)">full citation needed</span></a></i>]</sup></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKreutzberger2001" class="citation cs1">Kreutzberger, Charles B. (2001). "Chloroformates and Carbonates". <i>Kirk-Othmer Encyclopedia of Chemical Technology</i>. New York: John Wiley. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0471238961.0301180204011312.a01.pub2">10.1002/0471238961.0301180204011312.a01.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471238966" title="Special:BookSources/9780471238966"><bdi>9780471238966</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chloroformates+and+Carbonates&rft.btitle=Kirk-Othmer+Encyclopedia+of+Chemical+Technology&rft.place=New+York&rft.pub=John+Wiley&rft.date=2001&rft_id=info%3Adoi%2F10.1002%2F0471238961.0301180204011312.a01.pub2&rft.isbn=9780471238966&rft.aulast=Kreutzberger&rft.aufirst=Charles+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSeo2021" class="citation journal cs1">Seo, Dongseok (16 June 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8421751">"Toxicity assessment of dimethyl carbonate following 28 days repeated inhalation exposure"</a>. <i>Environmental Analysis, Health and Toxicology</i>. <b>36</b> (2): e2021012-0. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.5620%2Feaht.2021012">10.5620/eaht.2021012</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8421751">8421751</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/34130377">34130377</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Analysis%2C+Health+and+Toxicology&rft.atitle=Toxicity+assessment+of+dimethyl+carbonate+following+28+days+repeated+inhalation+exposure&rft.volume=36&rft.issue=2&rft.pages=e2021012-0&rft.date=2021-06-16&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8421751%23id-name%3DPMC&rft_id=info%3Apmid%2F34130377&rft_id=info%3Adoi%2F10.5620%2Feaht.2021012&rft.aulast=Seo&rft.aufirst=Dongseok&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8421751&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20210208171107/https://www.paint.org/voc-exempt/">"Update: U.S. EPA Exempt Volatile Organic Compounds"</a>. <i>American Coatings Association</i>. 2018-01-30. Archived from <a rel="nofollow" class="external text" href="https://www.paint.org/voc-exempt/">the original</a> on 2021-02-08<span class="reference-accessdate">. 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"Review of Dimethyl Carbonate (DMC) Manufacture and Its Characteristics as a Fuel Additive". <i><a href="/wiki/Energy_%26_Fuels" title="Energy & Fuels">Energy & Fuels</a></i>. <b>11</b>: <span class="nowrap">2–</span>29. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fef9600974">10.1021/ef9600974</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Energy+%26+Fuels&rft.atitle=Review+of+Dimethyl+Carbonate+%28DMC%29+Manufacture+and+Its+Characteristics+as+a+Fuel+Additive&rft.volume=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2-%3C%2Fspan%3E29&rft.date=1997&rft_id=info%3Adoi%2F10.1021%2Fef9600974&rft.aulast=Pacheco&rft.aufirst=Michael+A.&rft.au=Marshall%2C+Christopher+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-Tundo-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Tundo_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Tundo_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPietro_TundoMaurizio_Selva2002" class="citation journal cs1">Pietro Tundo & Maurizio Selva (2002). 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Res.</a></i> <b>35</b> (9): <span class="nowrap">706–</span>16. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Far010076f">10.1021/ar010076f</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12234200">12234200</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acc.+Chem.+Res.&rft.atitle=The+Chemistry+of+Dimethyl+Carbonate&rft.volume=35&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E706-%3C%2Fspan%3E16&rft.date=2002&rft_id=info%3Adoi%2F10.1021%2Far010076f&rft_id=info%3Apmid%2F12234200&rft.au=Pietro+Tundo&rft.au=Maurizio+Selva&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-ullmann-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-ullmann_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHans-Josef_Buysch" class="citation encyclopaedia cs1">Hans-Josef Buysch. "Carbonic Esters". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a05_197">10.1002/14356007.a05_197</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Carbonic+Esters&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a05_197&rft.isbn=978-3-527-30673-2&rft.au=Hans-Josef+Buysch&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPatraşcuBîldeaKiss2022" class="citation journal cs1">Patraşcu, Iulian; Bîldea, Costin S.; Kiss, Anton A. (2022-02-01). <a rel="nofollow" class="external text" href="https://doi.org/10.1007/s11705-021-2047-9">"Novel eco-efficient reactive distillation process for dimethyl carbonate production by indirect alcoholysis of urea"</a>. <i>Frontiers of Chemical Science and Engineering</i>. <b>16</b> (2): <span class="nowrap">316–</span>331. <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%2Fs11705-021-2047-9">10.1007/s11705-021-2047-9</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2095-0187">2095-0187</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+of+Chemical+Science+and+Engineering&rft.atitle=Novel+eco-efficient+reactive+distillation+process+for+dimethyl+carbonate+production+by+indirect+alcoholysis+of+urea&rft.volume=16&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E316-%3C%2Fspan%3E331&rft.date=2022-02-01&rft_id=info%3Adoi%2F10.1007%2Fs11705-021-2047-9&rft.issn=2095-0187&rft.aulast=Patra%C5%9Fcu&rft.aufirst=Iulian&rft.au=B%C3%AEldea%2C+Costin+S.&rft.au=Kiss%2C+Anton+A.&rft_id=https%3A%2F%2Fdoi.org%2F10.1007%2Fs11705-021-2047-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLeeShimizu1998" class="citation journal cs1">Lee, Youngmin; Shimizu, Isao (1998). "Convenient O-Methylation of Phenols with Dimethyl Carbonate". <i>Synlett</i>. <b>1998</b> (10): <span class="nowrap">1063–</span>1064. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-1998-1893">10.1055/s-1998-1893</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:196807122">196807122</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Synlett&rft.atitle=Convenient+O-Methylation+of+Phenols+with+Dimethyl+Carbonate&rft.volume=1998&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1063-%3C%2Fspan%3E1064&rft.date=1998&rft_id=info%3Adoi%2F10.1055%2Fs-1998-1893&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A196807122%23id-name%3DS2CID&rft.aulast=Lee&rft.aufirst=Youngmin&rft.au=Shimizu%2C+Isao&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-Shieh2002-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-Shieh2002_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShiehDell,_StephenRepič,_Oljan2002" class="citation journal cs1">Shieh, Wen-Chung; Dell, Stephen; Repič, Oljan (2002). "Nucleophilic Catalysis with 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) for the Esterification of Carboxylic Acids with Dimethyl Carbonate". <i><a href="/wiki/J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a></i> <b>67</b> (7): <span class="nowrap">2188–</span>2191. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo011036s">10.1021/jo011036s</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11925227">11925227</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=Nucleophilic+Catalysis+with+1%2C8-Diazabicyclo%5B5.4.0%5Dundec-7-ene+%28DBU%29+for+the+Esterification+of+Carboxylic+Acids+with+Dimethyl+Carbonate&rft.volume=67&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2188-%3C%2Fspan%3E2191&rft.date=2002&rft_id=info%3Adoi%2F10.1021%2Fjo011036s&rft_id=info%3Apmid%2F11925227&rft.aulast=Shieh&rft.aufirst=Wen-Chung&rft.au=Dell%2C+Stephen&rft.au=Repi%C4%8D%2C+Oljan&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShiehDellRepič2001" class="citation journal cs1">Shieh, Wen-Chung; Dell, Steven; Repič, Oljan (2001). "1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and Microwave-Accelerated Green Chemistry in Methylation of Phenols, Indoles, and Benzimidazoles with Dimethyl Carbonate". <i>Organic Letters</i>. <b>3</b> (26): <span class="nowrap">4279–</span>81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fol016949n">10.1021/ol016949n</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11784197">11784197</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Letters&rft.atitle=1%2C8-Diazabicyclo%5B5.4.0%5Dundec-7-ene+%28DBU%29+and+Microwave-Accelerated+Green+Chemistry+in+Methylation+of+Phenols%2C+Indoles%2C+and+Benzimidazoles+with+Dimethyl+Carbonate&rft.volume=3&rft.issue=26&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4279-%3C%2Fspan%3E81&rft.date=2001&rft_id=info%3Adoi%2F10.1021%2Fol016949n&rft_id=info%3Apmid%2F11784197&rft.aulast=Shieh&rft.aufirst=Wen-Chung&rft.au=Dell%2C+Steven&rft.au=Repi%C4%8D%2C+Oljan&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="http://www.epa.gov/ttn/oarpg/t1/fact_sheets/voc_exemp01011309.pdf">http://www.epa.gov/ttn/oarpg/t1/fact_sheets/voc_exemp01011309.pdf</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210208171047/https://www.epa.gov/technical-air-pollution-resources">Archived</a> 2021-02-08 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (October 2023)">full citation needed</span></a></i>]</sup> Information about the EPA's action on exempting dimethyl carbonate as a VOC and petitioner's background information, public comments and other references are available electronically at <a rel="nofollow" class="external free" href="https://www.regulations.gov">http://www.regulations.gov</a>, EPA's electronic public docket and comment system. The docket number for this action is Docket ID No. EPA-HQ-OAR-2006-0948. See <a rel="nofollow" class="external free" href="http://www.epa.gov/ttn/oarpg/t1pfpr.html">http://www.epa.gov/ttn/oarpg/t1pfpr.html</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120107130412/http://www.epa.gov/ttn/oarpg/t1pfpr.html">Archived</a> 2012-01-07 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (October 2023)">full citation needed</span></a></i>]</sup> and scroll down to Jan 13, 2009 pdf for the rule.</span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.paint.org/voc-exempt/">"Update: U.S. EPA Exempt Volatile Organic Compounds"</a>. <i>American Coatings Association</i>. 2018-01-30. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190320200925/https://www.paint.org/voc-exempt/">Archived</a> from the original on 2019-03-20<span class="reference-accessdate">. Retrieved <span class="nowrap">June 23,</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=American+Coatings+Association&rft.atitle=Update%3A+U.S.+EPA+Exempt+Volatile+Organic+Compounds&rft.date=2018-01-30&rft_id=https%3A%2F%2Fwww.paint.org%2Fvoc-exempt%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKanegsbergKanegsberg2011" class="citation book cs1">Kanegsberg, Barbara; Kanegsberg, Edward (2011-04-04). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/handbookforcriti00kane_413"><i>Handbook for Critical Cleaning: Cleaning Agents and Systems, Second Edition</i></a></span> (Second ed.). CRC Press. p. <a rel="nofollow" class="external text" href="https://archive.org/details/handbookforcriti00kane_413/page/n45">16</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781439828281" title="Special:BookSources/9781439828281"><bdi>9781439828281</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Handbook+for+Critical+Cleaning%3A+Cleaning+Agents+and+Systems%2C+Second+Edition&rft.pages=16&rft.edition=Second&rft.pub=CRC+Press&rft.date=2011-04-04&rft.isbn=9781439828281&rft.aulast=Kanegsberg&rft.aufirst=Barbara&rft.au=Kanegsberg%2C+Edward&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fhandbookforcriti00kane_413&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFukuoka2012" class="citation book cs1">Fukuoka, Shinsuke (2012). <i>Non-Phosgene Polycarbonate from CO<sub>2</sub> - Industrialization of Green Chemical Process</i>. <a href="/wiki/Nova_Science_Publishers" title="Nova Science Publishers">Nova Science Publishers</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781614708773" title="Special:BookSources/9781614708773"><bdi>9781614708773</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Non-Phosgene+Polycarbonate+from+CO%3Csub%3E2%3C%2Fsub%3E+-+Industrialization+of+Green+Chemical+Process&rft.pub=Nova+Science+Publishers&rft.date=2012&rft.isbn=9781614708773&rft.aulast=Fukuoka&rft.aufirst=Shinsuke&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBuysch2000" class="citation encyclopaedia cs1">Buysch, Hans-Josef (2000). "Carbonic Esters". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a05_197">10.1002/14356007.a05_197</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Carbonic+Esters&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a05_197&rft.isbn=978-3-527-30673-2&rft.aulast=Buysch&rft.aufirst=Hans-Josef&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAurbachEin-Eli1995" class="citation journal cs1">Aurbach, Doron; Ein-Eli, Yair (June 1995). "The Study of Li-Graphite Intercalation Processes in Several Electrolyte Systems Using In Situ X-Ray Diffraction". <i>Journal of the Electrochemical Society</i>. <b>142</b> (6): <span class="nowrap">1746–</span>1752. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1995JElS..142.1746A">1995JElS..142.1746A</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1149%2F1.2044188">10.1149/1.2044188</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+the+Electrochemical+Society&rft.atitle=The+Study+of+Li-Graphite+Intercalation+Processes+in+Several+Electrolyte+Systems+Using+In+Situ+X-Ray+Diffraction&rft.volume=142&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1746-%3C%2Fspan%3E1752&rft.date=1995-06&rft_id=info%3Adoi%2F10.1149%2F1.2044188&rft_id=info%3Abibcode%2F1995JElS..142.1746A&rft.aulast=Aurbach&rft.aufirst=Doron&rft.au=Ein-Eli%2C+Yair&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAurbachMarkovskyShechterEin-Eli1996" class="citation journal cs1">Aurbach, D.; Markovsky, B.; Shechter, A.; Ein-Eli, Y.; Cohen, H. (December 1996). "A Comparative Study of Synthetic Graphite and Li Electrodes in Electrolyte Solutions Based on Ethylene Carbonate-Dimethyl Carbonate Mixtures". <i>Journal of the Electrochemical Society</i>. <b>143</b> (12): <span class="nowrap">3809–</span>3820. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1996JElS..143.3809A">1996JElS..143.3809A</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1149%2F1.1837300">10.1149/1.1837300</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+the+Electrochemical+Society&rft.atitle=A+Comparative+Study+of+Synthetic+Graphite+and+Li+Electrodes+in+Electrolyte+Solutions+Based+on+Ethylene+Carbonate-Dimethyl+Carbonate+Mixtures&rft.volume=143&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3809-%3C%2Fspan%3E3820&rft.date=1996-12&rft_id=info%3Adoi%2F10.1149%2F1.1837300&rft_id=info%3Abibcode%2F1996JElS..143.3809A&rft.aulast=Aurbach&rft.aufirst=D.&rft.au=Markovsky%2C+B.&rft.au=Shechter%2C+A.&rft.au=Ein-Eli%2C+Y.&rft.au=Cohen%2C+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDurbinKaravalakisJohnsonCocker2017" class="citation book cs1">Durbin, Thomas D.; Karavalakis, Georgios; Johnson, Kent C.; Cocker, David; Yang, Jiacheng; Jiang, Yu; Kumar, Sachin (June 2017). <a rel="nofollow" class="external text" href="https://rosap.ntl.bts.gov/view/dot/32485"><i>Evaluating the viability of dimethyl carbonate as an alternative fuel for the transportation sector</i></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Evaluating+the+viability+of+dimethyl+carbonate+as+an+alternative+fuel+for+the+transportation+sector&rft.date=2017-06&rft.aulast=Durbin&rft.aufirst=Thomas+D.&rft.au=Karavalakis%2C+Georgios&rft.au=Johnson%2C+Kent+C.&rft.au=Cocker%2C+David&rft.au=Yang%2C+Jiacheng&rft.au=Jiang%2C+Yu&rft.au=Kumar%2C+Sachin&rft_id=https%3A%2F%2Frosap.ntl.bts.gov%2Fview%2Fdot%2F32485&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADimethyl+carbonate" class="Z3988"></span></span> </li> </ol></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; 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