Glycidol is an organic compound that contains both epoxide and alcohol functional groups. 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.
Names | |
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Preferred IUPAC name
Oxiranylmethanol | |
Other names
Glycidol
2,3-Epoxy-1-propanol 3-Hydroxypropylene oxide Epoxypropyl alcohol Hydroxymethyl ethylene oxide 2-Hydroxymethyl oxiran | |
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ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.008.300 |
KEGG |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C3H6O2 | |
Molar mass | 74.079 g·mol−1 |
Appearance | Viscous liquid |
Density | 1.1143 g/cm3[1] |
Melting point | −54 °C (−65 °F; 219 K)[3] |
Boiling point | 167 °C (333 °F; 440 K) (decomposes)[1] |
miscible[2] | |
Vapor pressure | 0.9 mmHg (25°C)[2] |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 66 °C (151 °F; 339 K)[3] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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420 mg/kg (oral, rat)[3][4] 1980 mg/kg (dermal, rabbit)[3][5] |
LC50 (median concentration)
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450 ppm (mouse, 4 hr) 580 ppm (rat, 8 hr)[6] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 50 ppm (150 mg/m3)[2] |
REL (Recommended)
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TWA 25 ppm (75 mg/m3)[2] |
IDLH (Immediate danger)
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150 ppm[2] |
Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Glycidol is prepared by the epoxidation of allyl alcohol.[7]
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, glycidyl ethers, esters and amines. It is used in surface coatings, chemical synthesis, pharmaceuticals, sanitary chemicals and sterilizing milk of magnesia, and as a gelation agent in solid propellants.[8]
Glycidol is an irritant of the skin, eyes, mucous membranes, and upper respiratory tract. Exposure to glycidol may also cause central nervous system depression, followed by central nervous system stimulation.[9] It is listed as an IARC Group 2A Agent, meaning that it is "probably carcinogenic to humans".[10] In regards to occupational exposures, the Occupational Safety and Health Administration has set a permissible exposure limit at 50 ppm over an eight-hour work shift, while the National Institute for Occupational Safety and Health recommends a limit at 25 ppm over an eight-hour work shift.[11]
Refined edible oils have been shown to contain glycidyl fatty acid esters that are thought to be formed primarily during deodorization; hydrolysis of these compounds in the digestive tract releases free glycidol that proved to be carcinogenic in rats.[12]