Allyl glycidyl ether

Allyl glycidyl ether
The skeletal structure of allyl glycidyl ether
Names
IUPAC name
2-(prop-2-enoxymethyl)oxirane
Other names
AGE; 1-Allyloxy-2,3-epoxypropane; Glycidyl allyl ether; [(2-Propenyloxy)methyl] oxirane[1]
Identifiers
106-92-3
3D model (Jmol) Interactive image
ChemSpider 13836520
ECHA InfoCard 100.003.131
PubChem 7838
Properties
C6H10O2
Molar mass 114.2[1]
Appearance Colorless liquid[1]
Odor pleasant[1]
Density 0.97 g/mL (20°C)[1]
Melting point −100 °C; −148 °F; 173 K [1]
Boiling point 154 °C; 309 °F; 427 K [1]
14% (20°C)[1]
Solubility in [[acetone, toluene, octane<ref name=Pubchem/>]] miscible
Vapor pressure 2 mmHg (20°C)[1]
1.4348 (20°C)[2][3]
Hazards
Main hazards poisonous, mild irritant[2]
GHS signal word DANGER
H226, H351, H341, H332, H302, H335, H315, H318, H317, H412
Flash point 57 °C; 135 °F; 330 K [1]
Lethal dose or concentration (LD, LC):
270 ppm (mouse, 4 hr)
670 ppm (rat, 8 hr)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
10 ppm (45 mg/m3)[1]
REL (Recommended)
TWA 5 ppm (22 mg/m3) ST 10 ppm (44 mg/m3) [skin][1]
IDLH (Immediate danger)
50 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Allyl glycidyl ether is a glycidyl ether.

Preparation

Allyl alcohol and epichlorohydrin are the precursors to allyl glycidyl ether. They react in a condensation reaction and the product is subsequently treated with base to produce allyl glycidyl ether.[5]

Uses

Allyl glycidyl ether is used in adhesives and sealants.[2] It is also used in the production of polyvinylcaprolactam.[6]

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 "NIOSH Pocket Guide to Chemical Hazards #0019". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 CID 7838 from PubChem
  3. ↑ Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2199
  4. ↑ "Allyl glycidyl ether". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  5. ↑ Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2197
  6. ↑ Kudyshkin, Mukhitdinova (1999). "Control of the molecular weight of polyvinylcaprolactam". Russian Journal of Applied Chemistry. 72 (10): 1846 – 1848.
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