Glycol Ethers
Encyclopedia
Glycol ethers are a group of solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

s based on alkyl ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...

s of ethylene glycol
Ethylene glycol
Ethylene glycol is an organic compound widely used as an automotive antifreeze and a precursor to polymers. In its pure form, it is an odorless, colorless, syrupy, sweet-tasting liquid...

 commonly used in paint
Paint
Paint is any liquid, liquefiable, or mastic composition which after application to a substrate in a thin layer is converted to an opaque solid film. One may also consider the digital mimicry thereof...

s. These solvents typically have higher boiling point, together with the favorable solvent properties of lower molecular weight of ethers and alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

s. 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", ; the first one was ethyl cellosolve (ethylene glycol monoethyl ether), with the name now generic for glycol ethers.

Glycol ethers can be also derived of diethylene glycol
Diethylene glycol
Diethylene glycol is an organic compound with the formula 2O. It is a colorless, practically odorless, poisonous, and hygroscopic liquid with a sweetish taste. It is miscible in water, alcohol, ether, acetone, and ethylene glycol. DEG is a widely used solvent...

 (carbitols). Acetate
Acetate
An acetate is a derivative of acetic acid. This term includes salts and esters, as well as the anion found in solution. Most of the approximately 5 billion kilograms of acetic acid produced annually in industry are used in the production of acetates, which usually take the form of polymers. In...

s 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
Semen analysis
A semen analysis evaluates certain characteristics of a male's semen and the sperm contained in the semen. It may be done while investigating a couple's infertility or after a vasectomy to verify that the procedure was successful. It is also used for testing donors for sperm donation, in stud...

 in men, but the finding has been disputed by others.

Glycol ether solvents

  • Ethylene glycol monomethyl ether
    2-Methoxyethanol
    2-Methoxyethanol, or methyl cellosolve, is an organic compound that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical...

     (2-methoxyethanol, CH3OCH2CH2OH)

  • Ethylene glycol monoethyl ether
    2-Ethoxyethanol
    2-Ethoxyethanol, also known by the trademark Cellosolve or ethyl cellosolve, is a solvent used widely in commercial and industrial applications...

     (2-ethoxyethanol, CH3CH2OCH2CH2OH)

  • Ethylene glycol monopropyl ether (2-propoxyethanol, CH3CH2CH2OCH2CH2OH)

  • Ethylene glycol monoisopropyl ether (2-isopropoxyethanol, (CH3)2CHOCH2CH2OH)

  • Ethylene glycol monobutyl ether
    2-Butoxyethanol
    2-Butoxyethanol is an organic solvent with the formula BuOC2H4OH . It is a colorless liquid with a sweet, ether-like odour. It is a butyl ether of ethylene glycol...

     (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
    2-ethanol, also known under trade names Carbitol, Carbitol cellosolve, Transcutol, Dioxitol, Poly-solv DE, and Dowanal DE, is an industrial solvent. It is a clear, colorless, hygroscopic liquid. Structurally it is an alcohol and an ether, a triethylene glycol with missing one hydroxyl group with...

     (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
    Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a clear, colorless, aprotic, and liquid ether that is used as a solvent. Dimethoxyethane is miscible with water.Dimethoxyethane is often used as a higher boiling...

     (dimethoxyethane, CH3OCH2CH2OCH3), a higher boiling alternative to diethyl ether
    Diethyl ether
    Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

     and THF
    Tetrahydrofuran
    Tetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. This heterocyclic compound has the chemical formula 4O. As one of the most polar ethers with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor...

    , also used as a solvent for polysaccharides, a reagent in organometallic chemistry and in some electrolytes of lithium batteries
    Lithium battery
    Lithium batteries are disposable batteries that have lithium metal or lithium compounds as an anode. Depending on the design and chemical compounds used, lithium cells can produce voltages from 1.5 V to about 3.7 V, over twice the voltage of an ordinary zinc–carbon battery or alkaline battery...


  • 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)
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