Glycol ethers

Glycol ethers are a group of solvents based on alkyl ethers of ethylene glycol commonly used in paints. These solvents typically have higher boiling point, together with the favorable solvent properties of lower molecular weight of 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 can be also derived of diethylene glycol (carbitols). Acetates of glycols are a similar kind of potent solvents.

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

1. ^ 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
2. ^ 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. 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. 
3. ^ 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.. http://oem.bmj.com/content/65/10/708/reply#oemed_el_591.