Glycidol is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

that contains both

epoxide In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for ...

and

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

s. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

Synthesis and applications

Glycidol is prepared by the epoxidation of

allyl alcohol Allyl alcohol (IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula . Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material ...

.Guenter Sienel, Robert Rieth, Kenneth T. Rowbottom "Epoxides" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. Glycidol is used as a stabilizer for natural oils and vinyl polymers and as a demulsifier. It is used as a chemical intermediate in the synthesis of

glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...

, glycidyl ethers, esters and amines. It is used in surface coatings, chemical synthesis, pharmaceuticals, sanitary chemicals and sterilizing

milk of magnesia Magnesium hydroxide is the inorganic compound with the chemical formula Mg(OH)2. It occurs in nature as the mineral brucite. It is a white solid with low solubility in water (). Magnesium hydroxide is a common component of antacids, such as milk ...

, and as a gelation agent in solid propellants. #Alkylation of 2-methylquinazolin-4(3H)-one with glycidol affords

diproqualone Diproqualone is a quinazolinone class GABAergic and is an analogue of methaqualone developed in the late 1950s by a team at Nogentaise de Produits Chimique. It was marketed primarily in France and some other European countries. It has sedative ...

. #

Dyphylline Diprophylline (International nonproprietary name, INN) or dyphylline (United States Adopted Name, USAN) (trade names Dilor, Lufyllin), is a xanthine Chemical derivative, derivative with bronchodilator and vasodilator effects. It is used in the tre ...

was made by the alkylation of

theophylline Theophylline, also known as 1,3-dimethylxanthine, is a phosphodiesterase inhibiting drug used in therapy for respiratory diseases such as chronic obstructive pulmonary disease (COPD) and asthma under a variety of brand names. As a member of the ...

with glycidol. # Diproxadol

Safety

Glycidol is an irritant of the skin, eyes, mucous membranes, and upper respiratory tract. Exposure to glycidol may also cause

central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all par ...

depression, followed by central nervous system stimulation. It is listed as an IARC Group 2A Agent, meaning that it is "''probably carcinogenic to humans''". In regards to occupational exposures, the

Occupational Safety and Health Administration The Occupational Safety and Health Administration'' (OSHA ) is a large regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. Congress established the agenc ...

has set a

permissible exposure limit The permissible exposure limit (PEL or OSHA PEL) is a legal limit in the United States for exposure of an employee to a chemical substance or physical agent such as high level noise. Permissible exposure limits are established by the Occupational S ...

at 50 ppm over an eight-hour work shift, while the

National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the C ...

recommends a limit at 25 ppm over an eight-hour work shift. Refined edible oils have been shown to contain glycidyl fatty acid esters that are thought to be formed primarily during deodorization;

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

of these compounds in the

digestive tract The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans a ...

releases free glycidol that proved to be carcinogenic in rats.

References

{{Authority control Epoxides Primary alcohols IARC Group 2A carcinogens

Synthesis and applications

Safety

See also

References