Glycidol
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 | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.008.300 |
KEGG | |
PubChem CID
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UNII | |
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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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[edit]
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]
- Alkylation of 2-methylquinazolin-4(3H)-one with glycidol affords diproqualone.
- Dyphylline was made by the alkylation of theophylline with glycidol.
- Diproxadol
Safety[edit]
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]
See also[edit]
References[edit]
- ^ 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).
- ^ Guenter Sienel, Robert Rieth, Kenneth T. Rowbottom "Epoxides" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a09_531
- ^ 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
- ^ Cheng, Wei-wei; Liu, Guo-qin; Wang, Li-qing; Liu, Zeng-she (2017). "Glycidyl Fatty Acid Esters in Refined Edible Oils: A Review on Formation, Occurrence, Analysis, and Elimination Methods". Comprehensive Reviews in Food Science and Food Safety. 16 (2): 263–281. doi:10.1111/1541-4337.12251. ISSN 1541-4337. PMID 33371535.