Glycol ethers

 ( Commodity Chemicals ) 

Glycol ethers are a class of chemical compounds consisting of alkyl that are based on glycols such as ethylene glycol or propylene glycol. They are commonly used as solvents in and cleaners. They have good solvent properties while having higher boiling points than the lower-molecular-weight ethers and alcohols.

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History The name " Cellosolve" was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corporation (a division History - Union Carbide Company (Year 1920) of Union Carbide Corporation) for "Solvents for Gums, Resins, Cellulose Esters, and the Like". "Ethyl Cellosolve" or simply "Cellosolve" consists mainly of ethylene glycol monoethyl ether and was introduced as a lower-cost solvent alternative to ethyl lactate. "Butyl Cellosolve" (ethylene glycol monobutyl ether) was introduced in 1928, and "Methyl Cellosolve" (ethylene glycol monomethyl ether) in 1929.

H. Benninga (1990). 9780792306252, Kluwer Academic Publishers. ISBN 9780792306252

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.

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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. P-series glycol ethers are marketed as having lower toxicity than the E-series.

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Health impacts Most glycol ethers are water-soluble, biodegradable and only a few are considered toxic.

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 used in the photoresist substances that coat semiconductors.

One study suggests that occupational exposure to glycol ethers is related to low motile Semen analysis, a finding disputed by the chemical industry.

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Subclasses

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Solvents

• Ethylene glycol monomethyl ether (2-methoxyethanol, CH₃ OCH₂CH₂OH)
• Ethylene glycol monoethyl ether (2-ethoxyethanol, CH₃CH₂ OCH₂CH₂OH)
• Ethylene glycol monopropyl ether (2-propoxyethanol, CH₃CH₂CH₂ OCH₂CH₂OH)
• Ethylene glycol monoisopropyl ether (2-isopropoxyethanol, (CH₃)₂CH OCH₂CH₂OH)
• Ethylene glycol monobutyl ether (2-butoxyethanol, CH₃CH₂CH₂CH₂ OCH₂CH₂OH), a widely used solvent in paintings and surface coatings, cleaning products and inks
• Ethylene glycol monophenyl ether (2-phenoxyethanol, C₆H₅ OCH₂CH₂OH)
• Ethylene glycol monobenzyl ether (2-benzyloxyethanol, C₆H₅CH₂ OCH₂CH₂OH)
• Propylene glycol methyl ether, (1-methoxy-2-propanol, CH₃ OCH₂CH(OH)CH₃)
• Diethylene glycol monomethyl ether (2-(2-methoxyethoxy)ethanol, methyl carbitol, CH₃ OCH₂CH₂ OCH₂CH₂OH)
• Diethylene glycol monoethyl ether (2-(2-ethoxyethoxy)ethanol, carbitol cellosolve, CH₃CH₂ OCH₂CH₂ OCH₂CH₂OH)
• Diethylene glycol mono-n-butyl ether (2-(2-butoxyethoxy)ethanol, butyl carbitol, CH₃CH₂CH₂CH₂ OCH₂CH₂ OCH₂CH₂OH)
• Dipropyleneglycol methyl ether
• C12-15 pareth-12 a polyethylene glycol ether used as an emulsifier in cosmetics

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Dialkyl ethers

• Dimethoxyethane (dimethoxyethane, monoglyme, CH₃ OCH₂CH₂ OCH₃), a higher boiling alternative to diethyl ether and tetrahydrofuran, also used as a solvent for polysaccharides, a reagent in organometallic chemistry and in some electrolytes of lithium battery
• Diglyme (1-Methoxy-2-(2-methoxyethoxy)ethane, diglyme, CH₃ OCH₂CH₂ OCH₂CH₂ OCH₃)
• Triethylene glycol dimethyl ether (2,5,8,11-Tetraoxadodecane, triglyme, CH₃ OCH₂CH₂ OCH₂CH₂ OCH₂CH₂ OCH₃)
• Tetraethylene glycol dimethyl ether (2,5,8,11,14-Pentaoxapentadecane, tetraglyme, CH₃ OCH₂CH₂ OCH₂CH₂ OCH₂CH₂ OCH₂CH₂ OCH₃)
• Ethylene glycol diethyl ether (diethoxyethane, CH₃CH₂ OCH₂CH₂ OCH₂CH₃)
• Dibutoxyethane (dibutoxyethane, CH₃CH₂CH₂CH₂ OCH₂CH₂ OCH₂CH₂CH₂CH₃)

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Esters

• Ethylene glycol methyl ether acetate (2-methoxyethyl acetate, CH₃ OCH₂CH₂OCOCH₃)
• Ethylene glycol monoethyl ether acetate (2-ethoxyethyl acetate, CH₃CH₂ OCH₂CH₂OCOCH₃)
• Ethylene glycol monobutyl ether acetate (2-butoxyethyl acetate, CH₃CH₂CH₂CH₂ OCH₂CH₂OCOCH₃)
• Propylene glycol methyl ether acetate (1-methoxy-2-propanol acetate)

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