Epichlorohydrin

Title: Epichlorohydrin
CAS Registry Number: 106-89-8
CAS Name: Chloromethyloxirane
Additional Names: dl-a-epichlorohydrin; 1-chloro-2,3-epoxypropane; g-chloropropylene oxide
Molecular Formula: C3H5ClO
Molecular Weight: 92.52
Percent Composition: C 38.95%, H 5.45%, Cl 38.32%, O 17.29%
Literature References: Prepn: H. T. Clarke, W. W. Hartman, Org. Synth. coll. vol. I, 233 (2nd ed., 1941); G. Braun, ibid. coll. vol. II, 256 (1943). Manuf: Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 335-338. Toxicity data: H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol. 30, 63 (1948).
Properties: Liquid. d420 1.1812; d425 1.1750; d450 1.1436; d475 1.1101. bp760 117.9°; bp400 98.0°; bp200 79.3°; bp100 62.0°; bp40 42.0°; bp10 16.6°; bp1.0 -16.5°. mp -25.6°. nD11.6 1.44195; nD16 1.43969; nD25 1.43585. Flash pt, open cup: 105°F (40°C). Insol in water. Misc with alcohol, ether, chloroform, trichloroethylene, carbon tetrachloride; immiscible with petr hydrocarbons. LD50 orally in rats: 0.09 g/kg (Smyth, Carpenter).
Melting point: mp -25.6°
Boiling point: bp760 117.9°; bp400 98.0°; bp200 79.3°; bp100 62.0°; bp40 42.0°; bp10 16.6°; bp1.0 -16.5°
Flash point: Flash pt, open cup: 105°F (40°C)
Index of refraction: nD11.6 1.44195; nD16 1.43969; nD25 1.43585
Density: d420 1.1812; d425 1.1750; d450 1.1436; d475 1.1101
Toxicity data: LD50 orally in rats: 0.09 g/kg (Smyth, Carpenter)
CAUTION: Potential symptoms of overexposure are nausea, vomiting; abdominal pain; respiratory distress, coughing; cyanosis; irritation of eyes and skin with deep pain; reproductive effects. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 128. See also Patty's Industrial Hygiene and Toxicology vol. 2A, G. D. Clayton, F. E. Clayton, Eds. (Wiley-Interscience, New York, 3rd ed., 1981) pp 2242-2247. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-113.
Use: Solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels and lacquers, cement for Celluloid. As stabilizer.
Epicholestanol Epicholesterol Epicillin Epimedii Herba Epinastine

(±)-Epichlorohydrin[1]
Epichlorohydrin
Ball-and-stick model of the epichlorohydrin molecule
Identifiers
CAS number 106-89-8 YesY
PubChem 7835
ChemSpider 13837112 YesY
UNII 08OOR508C0 YesY
KEGG C14449 YesY
ChEBI CHEBI:37144 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3H5ClO
Molar mass 92.52 g/mol
Appearance colorless liquid
Odor garlic-like
Density 1.1812 g/cm3
Melting point −25.6 °C; −14.1 °F; 247.6 K
Boiling point 117.9 °C; 244.2 °F; 391.0 K
Solubility in water reacts
Hazards
MSDS External MSDS
EU classification Toxic T
NFPA 704
NFPA 704.svg
3
3
2
Flash point 32 °C; 90 °F; 305 K
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents.[2] Epichlorohydrin is a highly reactive compound and is used in the production of glycerol, plastics, epoxy glues and resins, and elastomers. In contact with water, epichlorohydrin hydrolyzes to 3-MCPD, a carcinogen found in food.