Glycol ethers
Glycol ethers are a class of chemical compounds consisting of
History
The name "Cellosolve" was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corporation (a division[1] of
Types
Glycol ethers are designated "E-series" or "P-series" for those made from ethylene oxide or propylene oxide, 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.[citation needed] P-series glycol ethers are marketed as having lower toxicity than the E-series.
Health impacts
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Most glycol ethers are water-soluble, biodegradable and only a few are considered toxic.[citation needed]
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[
One study suggests that occupational exposure to glycol ethers is related to low motile sperm count,[5] a finding disputed by the chemical industry.[6]
Subclasses
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)
- Propylene glycol methyl ether, (1-methoxy-2-propanol, CH3OCH2CH(OH)CH3)
- 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, butyl carbitol, CH3CH2CH2CH2OCH2CH2OCH2CH2OH)
- Dipropyleneglycol methyl ether
- C12-15 pareth-12 a polyethylene glycol ether used as an emulsifier in cosmetics
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 monoethyl ether acetate (2-ethoxyethyl acetate, CH3CH2OCH2CH2OCOCH3)
- Ethylene glycol monobutyl ether acetate (2-butoxyethyl acetate, CH3CH2CH2CH2OCH2CH2OCOCH3)
- Propylene glycol methyl ether acetate(1-methoxy-2-propanol acetate)
References
- ^ History - Union Carbide Company (Year 1920)
- OCLC 20852966.
- ^ 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.
- ^ Calma, Justine (Dec 8, 2023). "The fight to clean up the toxic legacy of semiconductors". The Verge. Retrieved 5 January 2024.
- 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. Archived from the original on 2011-07-24.