CIEC Promoting Science at the University of York, York, UK

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Basic chemicals Buta-1,3-diene
Buta-1,3-diene

Butadiene is manufactured from fractions obtained from the distillation of oil.  Although by far its major use is in the manufacture of artificial rubbers, some is used to make precursors in the manufacture of polyamides (nylon).

 

Uses of butadiene

By far the greatest use of butadiene is in the manufacture of co-polymers produced from phenylethene (styrene) and butadiene, SBS and propenonitrile (acrylonitrile), butadiene and phenylethene (styrene), ABS.  The next biggest use is in the manufacture of poly(butadiene), a synthetic rubber, which is principally used as one of the components in the rubber used for car tyres:

Other synthetic rubbers made from butadiene include neoprene which is poly(2-chlorobuta-1,3-diene), often known as polychloroprene.  Chloroprene is made from butadiene, by first reacting it with chlorine in the gas phase at ca 500 K to form 3,4-dichlorobut-1-ene and 1,4-dichlorobut-2-ene.  The former, on reaction with sodium hydroxide, yields chloroprene:

On polymerization, neoprene is formed:

Neoprene, in solution, is an excellent adhesive and can also coat aluminium used in food packaging.  It is widely used in cars, as hoses, vibration mounts and shock
absorber seals.  It is also used widely in construction, for example in window seals and in large constructions such as bridges.
After synthetic rubbers, the other major use of butadiene is in the manufacture of 1,6-diaminohexane (hexamethylenediamine), which is then made into a polyamide.

Diaminohexane is made by passing hydrogen cyanide gas into butadiene in the liquid state, under pressure at ca 350 K.

A nickel compound is the catalyst for the reaction. The overall reaction is represented by the equation:

The resulting dinitrile is hydrogenated by passing its vapour and hydrogen over nickel at ca 500 K, under pressure (ca 35 atm):

Annual production of butadiene

World 11.9 million tonnes
Europe 3.7 million tonnes

Manufacture of butadiene

It is mainly manufactured by the

It is also made by the

 

Date last amended: 18th March 2013