STYROLENE, C 6 H 5 CH:CH 2, also known as phenylethylene or vinylbenzene, an aromatic hydrocarbon found to the extent of 1 to 4% in storax; it also occurs with crude xylene in coal tar fractions.
It may be obtained from storax by distillation with water, and synthetically by heating cinnamic acid with lime, by the action of aluminium chloride on a mixture of vinyl bromide and benzene, by removing the elements of hydrobromic acid from bromethylbenzene by means of alcoholic potash, or, best, by treating (-bromhydrocinnamic acid with soda, when it yields styrolene, carbon dioxide and hydrobromic acid.
Styrolene is oxidized by nitric or chromic acids to benzoic acid; reduction gives ethylbenzene; hydrochloric and hydrobromic acids yield a-haloid ethylbenzenes, e.g.
Styrolene gives origin to three series of derivatives, two of which contain the substituents in the side chain, e.g.
The a-halogen compounds are obtained by heating styrolene chloride (or bromide) with lime or alcoholic potash; they are liquids which have a penetrating odour, and yield acetophenone when heated with water to 180°.
Nitrostyrolene results when styrolene is treated with fuming nitric acid.
Related to styrolene is phenylacetylene, C G H 1 C;CH, which results when a-bromstyrolene or acetophenone chloride are heated to 130° with alcoholic potash, or phenylpropiolic acid with water to 120°.
Ethane, when heated to this degree, splits up into ethylene and hydrogen, whilst ethylene decomposes to methane and acetylene, and the acetylene at once polymerizes to benzene, styrolene, retene, &c. A portion also condenses, and at the same time loses some hydrogen, becoming naphthalene; and the compounds so formed by interactions amongst themselves build up the remainder of the hydrocarbons present in the coal tar, whilst the organic substances containing oxygen in the coal break down, and cause the formation of the phenols in the tar.