Nomenclature
CAS number: 107-13-1
2-Propenenitrile; vinyl cyanide; cyanoethylene; Ventox.
C
3H
3N; mol wt 53.06.
C 67.91%, H 5.70%, N 26.40%.
Description and references
Prepn by dehydration of ethylene cyanohydrin
or acrylamide: Moureu, Ann. Chim. Phys. [7] 2, 186 (1893). Manuf by ammoxidation
of propylene: Faith, Keyes & Clark's
Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds.
(Wiley-Interscience, New York, 4th ed., 1975) pp 46-49. Toxicity:
H. F. Smyth, C. P. Carpenter, J. Ind. Hyg.
Toxicol. 30, 63 (1948). Causes acute and chronic
adrenocortical insufficiency: S. Szabo et al., Lab. Invest. 42, 533 (1980); eidem, J. Appl. Toxicol. 4, 131 (1984). Review of carcinogenic risk: IARC Monographs 19, 73-133 (1979);
of toxicology and human exposure: Toxicological
Profile for Acrylonitrile (PB91-180489, 1990) 136 p.
Comprehensive review: The Chemistry of Acrylonitrile (Am. Cyanamid, New York, 2nd ed., 1959) 272 pp; J. F. Brazdil in Kirk-Othmer Encyclopedia of Chemical Technology vol. 1 (John Wiley & Sons, New York, 4th ed., 1991)
pp 352-369.
Properties
Volatile liquid. Flammable
and combustible. Should be stored and used in closed systems
whenever possible. Work areas should be adequately ventilated, and
should be free from open lights, flames, and equipment that is not
explosion-proof. Handle in hood. May polymerize spontaneously, particularly in the absence of oxygen
or on exposure to visible light. Polymerizes violently in the presence
of concentrated alkali. On standing may slowly develop a yellow color
particularly after excessive exposure to light. bp760 77.3°; bp500 64.7°; bp250 45.5°; bp100 23.6°; bp50 8.7°. mp 83.55°. d420 0.8060; d425 0.8004. nD25 1.3888. Flash pt, open cup: 32°F (0°C). Explosive
mixtures in air at 25°: 3.05% low limit; 17.0% upper limit. At 20°
7.35 parts dissolve in 100 parts water and 3.1 parts water dissolve
in 100 parts acrylonitrile. Miscible with most organic solvents.
LD50 orally in
rats: 0.093 g/kg (Smyth, Carpenter).Caution
Potential symptoms of overexposure
are asphyxia; irritation of eyes and skin; headache; sneezing; nausea,
vomiting; weakness, lightheadedness; skin vesiculation; scaling dermatitis.
See NIOSH Pocket Guide to Chemical
Hazards (DHHS/NIOSH 97-140, 1997) p 8. See also Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins,
Baltimore, 5th ed., 1984) Section II, p 215. This substance is reasonably
anticipated to be a human carcinogen: Report
on Carcinogens, Eleventh Edition (PB2005-104914, 2004)
p III-6.Use
Manufacture of acrylic fibers. In the plastics,
surface coatings, and adhesives industries. As a chemical intermediate
in the synthesis of antioxidants, pharmaceuticals, dyes, surface-active
agents, etc. In organic synthesis to introduce a cyanoethyl group.
As a modifier for natural polymers. As a pesticide fumigant for
stored grain. Experimentally to induce adrenal hemorrhagic necrosis
in rats.