Nomenclature
CAS number: 106-99-0
α,γ-Butadiene; bivinyl; divinyl; erythrene; vinylethylene; biethylene; pyrrolylene.
C
4H
6; mol wt 54.09.
C 88.82%, H 11.18%.
Description and references
Manuf as a coproduct of hydrocarbon steam cracking
to produce ethylene. Also produced from ethanol; from petroleum gases,
i.e., by catalytic dehydrogenation of butene or butene-butane mixtures;
by cracking naphtha and light oil. Manuf: Faith, Keyes & Clark's Industrial Chemicals, F. A.
Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed.,
1975) pp 164-172. Toxicity study: Carpenter et al., J. Ind. Hyg. Toxicol. 26, 69 (1944).
Reviews: Norton, Chem. Rev. 31, 319 (1942); Alder, “The Diene Synthesis” in Newer Methods of Preparative Organic Chemistry (Interscience, New York, 1948); Konrad, Angew. Chem. 62, 491 (1950); Hillyer, Stallings, Pet. Refin. 35(12), 157 (1956);
A. S. Onishchenko, Diene Synthesis (New York, 1964); Bailey, “Butadiene” in Vinyl and Diene Monomers (part 2), E. C. Leonard, Ed.
(Interscience, New York, 1971) pp 757-995; H. N. Sun, J. P. Wristers
in Kirk-Othmer Encyclopedia of Chemical Technology vol. 4 (John Wiley & Sons, New York, 4th ed., 1992)
pp 663-690. Review of toxicology: L. S. Birnbaum, Environ. Health Perspect. 101,
Suppl. 6, 161-167 (1993); and human exposure: Toxicological Profile for 1,3-Butadiene (PB93-110690,
1992) 148 pp; of carcinogenic risk: IARC
Sci. Publ. 127, 1-412 (1993).
Properties
Colorless gas. Mild aromatic odor. Flammable and combustible. mp -108.966°: Glasgow et al., Anal. Chem. 22, 1521
(1950). bp760 -4.5°. d4-6 0.650. Freezing pt -108.902°. Densities
from -17.8° to 60°: Ind. Eng. Chem. Anal.
Ed. 16, 7 (1944). nD-6 1.4223. bp (at pressures greater than 1 atm): 2 atm:
15.3°; 5 atm: 47.0°; 10 atm: 76.0°; 20 atm: 114.0°; 30 atm: 139.8°; 40 atm: 160.0°. Critical temperature
161.8°; critical pressure 42.6 atm. Infrared absorption spectrum:
ibid. 422. Stability: Ind. Eng. Chem. 36, 3 (1944).
Stabilization with o-dihydroxybenzene: GB 569412; with
aliphatic mercaptans: US 2373754. Explosion limits in air, vol%: lower 2.0, upper
11.5. Polymerizes and copolymerizes easily, e.g. under the influence
of sodium, thereby forming synthetic rubbers. Sparingly soluble in
water; slightly soluble in methanol, ethanol; soluble in organic solvents
such as diethyl ether, benzene, carbon tetrachloride. Alcohol dissolves
about 40 vols at room temp. LC50 in
rats (4 hr inhalation): 129,000 ppm; in mice (2 hr inhalation): 122,000 ppm (Birnbaum).Caution
Potential symptoms of overexposure
are irritation of eyes, nose and throat; drowsiness, lightheadedness;
teratogenic and reproductive effects; direct contact with liquid may
cause frostbite. See NIOSH Pocket
Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p
34; Patty's Industrial Hygiene and Toxicology vol. 2B, G. D. Clayton, F. E. Clayton, Eds. (John Wiley
& Sons, Inc., New York, 4th ed., 1994) p 1242, 1250-1252. This
substance is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914,
2004) p III-37.Use
As component in the manuf of polymers such as synthetic
rubbers, plastics, resins. As a chemical intermediate for the production
of many industral materials; in the manuf of adiponitrile.