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Concept
Butadiene
Summary
1,3-Butadiene (ˌbjuːtəˈdaɪiːn) is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene.
Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from motor vehicles.
The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. This allene has no industrial significance.
In 1863, French chemist E. Caventou isolated butadiene from the pyrolysis of amyl alcohol. This hydrocarbon was identified as butadiene in 1886, after Henry Edward Armstrong isolated it from among the pyrolysis products of petroleum. In 1910, the Russian chemist Sergei Lebedev polymerized butadiene and obtained a material with rubber-like properties. This polymer was, however, found to be too soft to replace natural rubber in many applications, notably automobile tires.
The butadiene industry originated in the years before World War II. Many of the belligerent nations realized that in the event of war, they could be cut off from rubber plantations controlled by the British Empire, and sought to reduce their dependence on natural rubber. In 1929, Eduard Tschunker and Walter Bock, working for IG Farben in Germany, made a copolymer of styrene and butadiene that could be used in automobile tires. Worldwide production quickly ensued, with butadiene being produced from grain alcohol in the Soviet Union and the United States, and from coal-derived acetylene in Germany.
In the United States, western Europe, and Japan, butadiene is produced as a byproduct of the steam cracking process used to produce ethylene and other alkenes. When mixed with steam and briefly heated to very high temperatures (often over 900 °C), aliphatic hydrocarbons give up hydrogen to produce a complex mixture of unsaturated hydrocarbons, including butadiene.
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