Allyl glycidyl ether

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
CAS Number	106-92-3
ChemSpider	13836520
Jmol interactive 3D	Image
PubChem	7838
InChI InChI=1S/C6H10O2/c1-2-3-7-4-6-5-8-6/h2,6H,1,3-5H2 Key: LSWYGACWGAICNM-UHFFFAOYSA-N InChI=1/C6H10O2/c1-2-3-7-4-6-5-8-6/h2,6H,1,3-5H2 Key: LSWYGACWGAICNM-UHFFFAOYAR
SMILES C=CCOCC1CO1
Properties
Chemical formula	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]
Solubility in water	14% (20°C)[1]
Solubility in [[acetone, toluene, octane<ref name=Pubchem/>]]	miscible
Vapor pressure	2 mmHg (20°C)[1]
Refractive index (nD)	1.4348 (20°C)[2][3]
Hazards
Main hazards	poisonous, mild irritant[2]
GHS signal word	DANGER
GHS hazard statements	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):
LC50 (Median concentration)	270 ppm (mouse, 4 hr) 670 ppm (rat, 8 hr)[4]
US health exposure limits (NIOSH):
PEL (Permissible)	10 ppm (45 mg/m^3)[1]
REL (Recommended)	TWA 5 ppm (22 mg/m^3) ST 10 ppm (44 mg/m^3) [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. "NIOSH Pocket Guide to Chemical Hazards #0019". National Institute for Occupational Safety and Health (NIOSH).
2. 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.