Glycidol
Names | |
---|---|
Preferred IUPAC name
Oxiranylmethanol | |
Other names
Glycidol
2,3-Epoxy-1-propanol 3-Hydroxypropylene oxide Epoxypropyl alcohol Hydroxymethyl ethylene oxide 2-Hydroxymethyl oxiran | |
Identifiers | |
3D model (
JSmol ) |
|
ChEBI | |
ChemSpider | |
ECHA InfoCard
|
100.008.300 |
KEGG | |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
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)
|
420 mg/kg (oral, rat)[3][4] 1980 mg/kg (dermal, rabbit)[3][5] |
LC50 (median concentration)
|
450 ppm (mouse, 4 hr) 580 ppm (rat, 8 hr)[6] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
|
TWA 50 ppm (150 mg/m3)[2] |
REL (Recommended)
|
TWA 25 ppm (75 mg/m3)[2] |
IDLH (Immediate danger) |
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).
|
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.
Synthesis and applications
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
- Alkylation of 2-methylquinazolin-4(3H)-one with glycidol affords diproqualone.
- Dyphylline was made by the alkylation of theophyllinewith glycidol.
- Diproxadol
Safety
Glycidol is an irritant of the skin, eyes, mucous membranes, and upper respiratory tract. Exposure to glycidol may also cause
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]
See also
References
- ^ a b Merck Index, 11th Edition, 4385
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0303". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- Food and Cosmetics Toxicology. Vol. 19, Pg. 347, 1981
- ^ AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956
- ^ "Glycidol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ Glycidol at chemicalland21.com
- ^ "OSHA guidelines for glycidol". Archived from the original on 2012-09-25. Retrieved 2006-10-20.
- ^ "List of Classifications, Agents classified by the IARC Monographs, Volumes 1–124". IARC Monographs on the Evaluation of Risk to Humans. IARC. July 7, 2019. Retrieved July 14, 2019.
- ^ CDC - NIOSH Pocket Guide to Chemical Hazards
- PMID 33371535.