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Glycol ethers
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<h2 id="history">History</h2> <p>The name "Cellosolve" was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corporation (a division<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> of <a href="/facts/Union_Carbide/kCE5YHal"> Union Carbide Corporation</a>) for "Solvents for Gums, Resins, Cellulose Esters, and the Like". "Ethyl Cellosolve" or simply "Cellosolve" consists mainly of <a href="/facts/Ethylene_glycol_monoethyl_ether/qMGX9nl7">ethylene glycol monoethyl ether</a> and was introduced as a lower-cost solvent alternative to <a href="/facts/Ethyl_lactate/JN123yeC">ethyl lactate</a>. "Butyl Cellosolve" (<a href="/facts/Ethylene_glycol_monobutyl_ether/YHX9gXQE">ethylene glycol monobutyl ether</a>) was introduced in 1928, and "Methyl Cellosolve" (<a href="/facts/Ethylene_glycol_monomethyl_ether/eqQpIboH">ethylene glycol monomethyl ether</a>) in 1929.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a><a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> </p> <h2 id="types">Types</h2> <p>Glycol ethers are designated "E-series" or "P-series" for those made from <a href="/facts/Ethylene_oxide/4WDVKX2r">ethylene oxide</a> or <a href="/facts/Propylene_oxide/XWz8SU72">propylene oxide</a>, respectively. Typically, E-series glycol ethers are found in pharmaceuticals, sunscreens, cosmetics, inks, dyes and water-based paints, while P-series glycol ethers are used in degreasers, cleaners, aerosol paints and adhesives. Both E- and P-series glycol ethers can be used as intermediates that undergo further chemical reactions, producing glycol diethers and glycol ether acetates. P-series glycol ethers are marketed as having lower toxicity than the E-series. </p> <h2 id="health-impacts">Health impacts</h2> <p>Most glycol ethers are water-soluble, biodegradable and only a few are considered toxic. </p><p>In the early 1990s, studies found higher than expected rates of miscarriages among women who worked in semiconductor plants, which was traced back to glycol ethers[<i>which?</i>] used in the photoresist substances that coat <a href="/facts/Semiconductors/zFf3mGTE">semiconductors</a>.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p><p>One study suggests that occupational exposure to glycol ethers is related to low motile <a href="/facts/Semen_analysis/orD9znfB">sperm count</a>,<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> a finding disputed by the chemical industry.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p> <h2 id="subclasses">Subclasses</h2> <h3>Solvents</h3> <ul><li><a href="/facts/2-Methoxyethanol/eqQpIboH">Ethylene glycol monomethyl ether</a> (2-methoxyethanol, CH3OCH2CH2OH)</li> <li><a href="/facts/2-Ethoxyethanol/qMGX9nl7">Ethylene glycol monoethyl ether</a> (2-ethoxyethanol, CH3CH2OCH2CH2OH)</li> <li>Ethylene glycol monopropyl ether (2-propoxyethanol, CH3CH2CH2OCH2CH2OH)</li> <li>Ethylene glycol monoisopropyl ether (2-isopropoxyethanol, (CH3)2CHOCH2CH2OH)</li> <li><a href="/facts/2-Butoxyethanol/YHX9gXQE">Ethylene glycol monobutyl ether</a> (2-butoxyethanol, CH3CH2CH2CH2OCH2CH2OH), a widely used solvent in paintings and surface coatings, cleaning products and inks</li> <li><a href="/facts/2-Phenoxyethanol/M8enG3Vh">Ethylene glycol monophenyl ether</a> (2-phenoxyethanol, C6H5OCH2CH2OH)</li> <li>Ethylene glycol monobenzyl ether (2-benzyloxyethanol, C6H5CH2OCH2CH2OH)</li> <li><a href="/facts/Propylene_glycol_methyl_ether/92YAIxs7">Propylene glycol methyl ether</a>, (1-methoxy-2-propanol, CH3OCH2CH(OH)CH3)</li> <li><a href="/facts/2-(2-Methoxyethoxy)ethanol/ys2vGWFK">Diethylene glycol monomethyl ether</a> (2-(2-methoxyethoxy)ethanol, methyl carbitol, CH3OCH2CH2OCH2CH2OH)</li> <li><a href="/facts/2-(2-Ethoxyethoxy)ethanol/TDDX4LSE">Diethylene glycol monoethyl ether</a> (2-(2-ethoxyethoxy)ethanol, carbitol cellosolve, CH3CH2OCH2CH2OCH2CH2OH)</li> <li><a href="/facts/2-(2-Butoxyethoxy)ethanol/r6IyIDmU">Diethylene glycol mono-n-butyl ether</a> (2-(2-butoxyethoxy)ethanol, butyl carbitol, CH3CH2CH2CH2OCH2CH2OCH2CH2OH)</li> <li><a href="/facts/Dipropyleneglycol_methyl_ether/Eev6m2kS">Dipropyleneglycol methyl ether</a></li> <li><a href="/facts/C12-15_pareth-12/2gXb13o9">C12-15 pareth-12</a> a polyethylene glycol ether used as an emulsifier in cosmetics</li></ul> <h3>Dialkyl ethers</h3> <ul><li><a href="/facts/Dimethoxyethane/2AdJp7sr">Ethylene glycol dimethyl ether</a> (dimethoxyethane, monoglyme, CH3OCH2CH2OCH3), a higher boiling alternative to <a href="/facts/Diethyl_ether/Ep20vEdj">diethyl ether</a> and <a href="/facts/Tetrahydrofuran/P5t6SkMK">THF</a>, also used as a solvent for polysaccharides, a reagent in organometallic chemistry and in some electrolytes of <a href="/facts/Lithium_battery/D5yfo8XS">lithium batteries</a></li> <li><a href="/facts/Diglyme/GEAdmlEX">Diethylene glycol dimethyl ether</a> (1-Methoxy-2-(2-methoxyethoxy)ethane, diglyme, CH3OCH2CH2OCH2CH2OCH3)</li> <li><a href="/facts/Triethylene_glycol_dimethyl_ether/yeVCgXA2">Triethylene glycol dimethyl ether</a> (2,5,8,11-Tetraoxadodecane, triglyme, CH3OCH2CH2OCH2CH2OCH2CH2OCH3)</li> <li><a href="/facts/Tetraethylene_glycol_dimethyl_ether/RmPuP2Q9">Tetraethylene glycol dimethyl ether</a> (2,5,8,11,14-Pentaoxapentadecane, tetraglyme, CH3OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3)</li> <li><a href="/facts/Ethylene_glycol_diethyl_ether/4LL9PrnU">Ethylene glycol diethyl ether</a> (diethoxyethane, CH3CH2OCH2CH2OCH2CH3)</li> <li>Ethylene glycol dibutyl ether (dibutoxyethane, CH3CH2CH2CH2OCH2CH2OCH2CH2CH2CH3)</li></ul> <h3>Esters</h3> <ul><li>Ethylene glycol methyl ether acetate (2-methoxyethyl acetate, CH3OCH2CH2OCOCH3)</li> <li><a href="/facts/2-Ethoxyethyl_acetate/WFkPq8fF">Ethylene glycol monoethyl ether acetate</a> (2-ethoxyethyl acetate, CH3CH2OCH2CH2OCOCH3)</li> <li>Ethylene glycol monobutyl ether acetate (2-butoxyethyl acetate, CH3CH2CH2CH2OCH2CH2OCOCH3)</li> <li><a href="/facts/1-methoxy-2-propanol_acetate/sNWx6RNv">Propylene glycol methyl ether acetate</a> (1-methoxy-2-propanol acetate)</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>History - Union Carbide Company (Year 1920) <a href="https://www.unioncarbide.com/history.html#content" target="_blank">https://www.unioncarbide.com/history.html#content</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Benninga, H. (1990). A history of lactic acid making: a chapter in the history of biotechnology. Dordrecht [Netherlands]: Kluwer Academic Publishers. p. 251. ISBN 0-7923-0625-2. OCLC 20852966. <a href="0-7923-0625-2" target="_blank">0-7923-0625-2</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Union Carbide later registered "Cellosolve" as a trademark for "ETHYL SILICATES FOR USE AS BINDERS IN INVESTMENT CASTINGS AND IN ZINC-RICH PRIMERS" (Reg. Number 1019768, September 9, 1975), but allowed it to expire. <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Calma, Justine (Dec 8, 2023). "The fight to clean up the toxic legacy of semiconductors". The Verge. Retrieved 5 January 2024. <a href="https://www.theverge.com/23990525/semiconductor-biden-infrastructure-plan-toxic-chemicals" target="_blank">https://www.theverge.com/23990525/semiconductor-biden-infrastructure-plan-toxic-chemicals</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Nicola Cherry; Harry Moore; Roseanne McNamee; Allan Pacey; Gary Burgess; Julie-Ann Clyma; Martin Dippnall; Helen Baillie; Andrew Povey (2008). "Occupation and male infertility: glycol ethers and other exposures". Occup. Environ. Med. 65 (10): 708–714. doi:10.1136/oem.2007.035824. PMID 18417551. <a href="http://oem.bmj.com/cgi/content/abstract/oem.2007.035824v1?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=&author1=povey&andorexactfulltext=and&searchid=1&FIRSTINDEX=0&sortspec=relevance&resourcetype=HWCIT" target="_blank">http://oem.bmj.com/cgi/content/abstract/oem.2007.035824v1?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=&author1=povey&andorexactfulltext=and&searchid=1&FIRSTINDEX=0&sortspec=relevance&resourcetype=HWCIT</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Peter J Boogaard; Gerard M H Swaen (2008). "Letter to the editor on a recent publication titled "Occupation and male infertility: glycol ethers". Occup. Environ. Med. Archived from the original on 2011-07-24. <a href="https://web.archive.org/web/20110724153320/http://oem.bmj.com/content/65/10/708/reply#oemed_el_591" target="_blank">https://web.archive.org/web/20110724153320/http://oem.bmj.com/content/65/10/708/reply#oemed_el_591</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> </ol>