Glycol ethers
Glycol ethers are a group of solvents based on alkyl ethers of ethylene glycol commonly used in paints. These solvents typically have a higher boiling point, together with the favorable solvent properties of lower-molecular weight ethers and alcohols. The word "Cellosolve" was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corp. (later named Union Carbide Corp.) for "Solvents for Gums, Resins, Cellulose Esters, and the Like",;[1] the first one was ethyl cellosolve (ethylene glycol monoethyl ether), with the name now generic[citation needed] for glycol ethers.
Glycol ethers are either "e-series" or "p-series" glycol ethers, depending on whether they are made from ethylene or propylene, 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. E-series glycol ethers are higher in molecular weights, and can be used as intermediates that undergo further chemical reactions. P-series glycol ethers are generally high performance industrial solvents. Most glycol ethers are relatively water soluble, biodegradable and only a few are considered toxic. Therefore, they are unlikely to pose an adverse risk to the environment.
Recent study suggests that occupational exposure to glycol ethers is related to low motile sperm count in men,[2] but the finding has been disputed by others.[3]
Glycol ether solvents
- Ethylene glycol monomethyl ether (2-methoxyethanol, CH3OCH2CH2OH)
- Ethylene glycol monoethyl ether (2-ethoxyethanol, CH3CH2OCH2CH2OH)
- Ethylene glycol monopropyl ether (2-propoxyethanol, CH3CH2CH2OCH2CH2OH)
- Ethylene glycol monoisopropyl ether (2-isopropoxyethanol, (CH3)2CHOCH2CH2OH)
- Ethylene glycol monobutyl ether (2-butoxyethanol, CH3CH2CH2CH2OCH2CH2OH), a widely used solvent in paintings and surface coatings, cleaning products and inks
- Ethylene glycol monophenyl ether (2-phenoxyethanol, C6H5OCH2CH2OH)
- Ethylene glycol monobenzyl ether (2-benzyloxyethanol, C6H5CH2OCH2CH2OH)
- Diethylene glycol monomethyl ether (2-(2-methoxyethoxy)ethanol, methyl carbitol, CH3OCH2CH2OCH2CH2OH)
- Diethylene glycol monoethyl ether (2-(2-ethoxyethoxy)ethanol, carbitol cellosolve, CH3CH2OCH2CH2OCH2CH2OH)
- Diethylene glycol mono-n-butyl ether (2-(2-butoxyethoxy)ethanol, CH3CH2CH2CH2OCH2CH2OCH2CH2OH)
Dialkyl ethers
- Ethylene glycol dimethyl ether (dimethoxyethane, CH3OCH2CH2OCH3), a higher boiling alternative to diethyl ether and THF, also used as a solvent for polysaccharides, a reagent in organometallic chemistry and in some electrolytes of lithium batteries
- Ethylene glycol diethyl ether (diethoxyethane, CH3CH2OCH2CH2OCH2CH3)
- Ethylene glycol dibutyl ether (dibutoxyethane, CH3CH2CH2CH2OCH2CH2OCH2CH2CH2CH3)
Esters
- Ethylene glycol methyl ether acetate (2-methoxyethyl acetate, CH3OCH2CH2OCOCH3)
- Ethylene glycol monethyl ether acetate (2-ethoxyethyl acetate, CH3CH2OCH2CH2OCOCH3)
- Ethylene glycol monobutyl ether acetate (2-butoxyethyl acetate, CH3CH2CH2CH2OCH2CH2OCOCH3)
References
- ^ Union Carbide also 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 let it expire
- ^ Nicola Cherry, Harry Moore, Roseanne McNamee, Allan Pacey, Gary Burgess, Julie-Ann Clyma, Martin Dippnall, Helen Baillie and 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.
- ^ 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.
