Glycidol

Glycidol
Names
IUPAC name
Oxiranylmethanol
Other names
Glycidol
2,3-Epoxy-1-propanol
3-Hydroxypropylene oxide
Epoxypropyl alcohol
Hydroxymethyl ethylene oxide
2-Hydroxymethyl oxiran
Identifiers
556-52-5 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:30966 YesY
ChemSpider 10691 YesY
ECHA InfoCard 100.008.300
KEGG C10920 YesY
PubChem 11164
Properties
C3H6O2
Molar mass 74.08 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
Safety data sheet External MSDS
NFPA 704
Flammability code 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 fuel Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 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., fluorine Special hazards (white): no codeNFPA 704 four-colored diamond
2
4
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]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 50 ppm (150 mg/m3)[3]
REL (Recommended)
 TWA 25 ppm (75 mg/m3)[3]
IDLH (Immediate danger)
 150 ppm[3]
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

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 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]

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 carcinogen, 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]

See also

References

  1. 1 2 Merck Index, 11th Edition, 4385
  2. 1 2 3 4 Record in the GESTIS Substance Database of the IFA
  3. 1 2 3 4 5 "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 and Health. 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
  10. ↑ IARC Monographs - Classifications - Group2A
  11. ↑ CDC - NIOSH Pocket Guide to Chemical Hazards
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