8860. Styrene

Nomenclature

CAS number: 100-42-5
Ethenylbenzene; styrol; styrolene; cinnamene; cinnamol; phenylethylene; vinylbenzene.
C8H8; mol wt 104.15.
C 92.26%, H 7.74%.

Description and references

Isolated from storax, q.v., by Bonastre in 1831. Manuf from benzene and ethylene: Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 779-785. Synthesis starting with 1-phenylethanol and leading to polystyrene: Wilen et al., J. Chem. Educ. 38, 304 (1961). When heated to 200° it is converted into the polymer, polystyrene, which is a clear plastic having excellent insulating properties even at ultra-high radio frequencies. Toxicity data: H. J. Meyer, R. Kretzschmar, Arzneim.-Forsch. 19, 617 (1969). Monograph: W. C. Teach, G. C. Kiessling, Polystyrene (Reinhold, New York, 1960). Reviews of styrene monomer and polymers: Boyer et al., “Styrene Polymers” in Encyclopedia of Polymer Science and Technology vol. 13 (Interscience, New York, 1970) pp 128-447; Coulter et al., “Styrene and Related Monomers” in Vinyl and Diene Monomers (part 2), E. C. Leonard, Ed. (Wiley-Interscience, New York, 1971) pp 479-576. Review of neurotoxicity: R. Pahwa, J. Kalra, Vet. Hum. Toxicol. 35, 516-520 (1993); of toxicology and carcinogenic risk: IARC Sci. Publ. 127, 1-412 (1993); of toxicology and human exposure: Toxicological Profile for Styrene (PB93-110849, 1992) 164 p.

Chemical structure

Properties

Colorless to yellowish, very refractive, oily liq; penetrating odor. On exposure to light and air it slowly undergoes polymerization and oxidation with formation of peroxides, etc. d20 0.9059. mp 30.6°. bp 145-146°. nD20 1.5463. Flash pt, closed cup: 87°F (31°C). Sparingly sol in water; sol in alcohol, ether, methanol, acetone, carbon disulfide. LD50 in mice (mg/kg): 660 ± 44.3 i.p.; 90 ± 5.2 i.v. (Meyer, Kretzschmar).

Derivative

Polystyrene.

Nomenclature

Dylene (Arco); Trycite (Dow).

Properties

Physical properties of unmodified polystyrene: d420 1.04-1.065; nD25 1.60; water-clear solid plastic, begins to soften at ≈85°. Dielectric constant at 100 megacycles: 2.4-2.65.

Caution

Potential symptoms of overexposure are irritation of eyes, nose, respiratory system; headache, fatigue, dizziness, confusion, malaise, drowsiness, weakness and unsteady gait; narcosis; defatting dermatitis; liver injury, reproductive effects. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 286.

Use

Manuf plastics; synthetic rubber; resins; insulator.