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
ChemSpider 13836520
Jmol interactive 3D Image
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):
10 ppm (45 mg/m3)[1]
TWA 5 ppm (22 mg/m3) ST 10 ppm (44 mg/m3) [skin][1]
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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