Glycidol

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(Redirected from 2,3-epoxy-1-propanol)
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 Edit this at Wikidata
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)[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)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
4
2
3
Flash point 66 °C (151 °F; 339 K)[3]
Lethal dose or concentration (LD, LC):
420 mg/kg (oral, rat)[3][4]
1980 mg/kg (dermal, rabbit)[3][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)[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).
checkY verify (what is checkY☒N ?)

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]

  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[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]

  1. ^ a b Merck Index, 11th Edition, 4385
  2. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0303". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  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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