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styrene, liquid hydrocarbon that is important chiefly for its marked tendency to undergo polymerization
(a process in which individual molecules are linked to produce extremely large, multiple-unit molecules).
Styrene is employed in the manufacture of polystyrene, an important plastic, as well as a number of
specialty plastics and synthetic rubbers.

Pure styrene is a clear, colourless, flammable liquid that boils at 145 C (293 F) and freezes at 30.6 C
(23.1 F). Unless treated with inhibitor chemicals, it has a tendency to polymerize spontaneously during
storage. It is slightly toxic to the nervous system if ingested or inhaled, and contact with the skin and
eyes can cause irritation. Although it is suspected of being carcinogenic, studies have not proved it to be
so.

The chemical formula for styrene is C8H8, but its structural formula, CH2=CHC6H5, more clearly reveals
the sources of its commercially useful properties. Styrene is a member of a group of chemical
compounds broadly categorized as vinylsorganic compounds whose molecules contain a double bond
between two carbon atoms. Under the action of chemical catalysts or initiators, this double bond can be
opened, and one of the two resultant single bonds is then able to link to a carbon atom of another
styrene molecule; this link contributes to the formation of polystyrene, in which thousands of styrene
units are linked along a carbon backbone. Hanging from this backbone are phenyl groups (C6H5)large
ring-shaped units that interfere with the spontaneous motion of the chainlike polymer and lend
polystyrene its well-known rigidity. The phenyl group is one of the aromatic ringsso called because
ring-shaped carbon groups of this type are traditionally associated with hydrocarbons that have a
distinct aroma. Styrene, which gives off a penetrating sweetish odour, is therefore one of the aromatic
hydrocarbons.

In the early 19th century, styrene was first isolated from storax, an aromatic balsam obtained from the
flowering shrub Styrax officinalis, after which the compound is named. The liquid, known as styrol, was
first polymerized to a solid form, later called metastyrol, in 1839. However, its industrial manufacture
and utilization were not begun until the late 1930s, after chemists at the Dow Chemical Company in the
United States and IG Farben in Germany devised means for obtaining it in a pure state. Almost all
styrene is now produced by dehydrogenation of ethylbenzene, a compound obtained by reacting
ethylene and benzeneboth of which in turn are derived from petroleum. More than 15 million metric
tons of the liquid are made each year.

More than half of the styrene produced is made into polystyrene, a light, stiff plastic widely used in
injection-molded or foamed articles. Most of the rest is copolymerized with other compoundsfor
example, with acrylonitrile and butadiene to produce acrylonitrile-butadiene-styrene copolymer, a hard,
tough engineering plastic; with butadiene to make styrene-butadiene rubber, a tough synthetic rubber
used in automobile tires; or with acrylonitrile or maleic anhydride to make styrene-acrylonitrile
copolymer or styrene-maleic anhydride copolymer, which have improved heat resistance.