Glycidol

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.

Glycidol
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
UNII
  • InChI=1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2 checkY
    Key: CTKINSOISVBQLD-UHFFFAOYSA-N checkY
  • InChI=1/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2
    Key: CTKINSOISVBQLD-UHFFFAOYAN
  • OCC1OC1
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)[2]
Boiling point 167 °C (333 °F; 440 K) (decomposes)[1]
miscible[3]
Vapor pressure 0.9 mmHg (25°C)[3]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
4
2
3
Flash point 66 °C (151 °F; 339 K)[2]
Lethal dose or concentration (LD, LC):
420 mg/kg (oral, rat)[2][4]
1980 mg/kg (dermal, rabbit)[2][5]
450 ppm (mouse, 4 hr)
580 ppm (rat, 8 hr)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 50 ppm (150 mg/m3)[3]
REL (Recommended)
 TWA 25 ppm (75 mg/m3)[3]
IDLH (Immediate danger)
 150 ppm[3]
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

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 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]

  1. Alkylation of 2-methylquinazolin-4(3H)-one with glycidol affords diproqualone.
  2. Dyphylline was made by the alkylation of theophylline with glycidol.
  3. 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 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

References
  1. Merck Index, 11th Edition, 4385
  2. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. NIOSH Pocket Guide to Chemical Hazards. "#0303". National Institute for Occupational Safety and Health (NIOSH).
  4. Food and Cosmetics Toxicology. Vol. 19, Pg. 347, 1981
  5. AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956
  6. "Glycidol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. 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
  8. Glycidol at chemicalland21.com
  9. "OSHA guidelines for glycidol". Archived from the original on 2012-09-25. Retrieved 2006-10-20.
  10. "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.
  11. CDC - NIOSH Pocket Guide to Chemical Hazards
  12. 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.
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