1,4-Dichlorobut-2-ene

[2] Chloroprene is a monomer for the production of synthetic rubbers such as Neoprene.

The first step is the liquid- or vapour-phase chlorination of butadiene to a mixture of 3,4-dichlorobut-1-ene and 1,4-dichlorobut-2-ene (both isomers).

In the second step, the mixture of 1,4-dichlorobut-2-ene and 3,4-dichlorobut-1-ene is isomerized to 3,4-dichlorobut-1-ene by heating to temperatures of 60–120 °C in the presence of a catalyst.

Finally, dehydrochlorination (elimination of hydrogen chloride) of 3,4-dichlorobut-1-ene with dilute sodium hydroxide solution in the presence of polymerization inhibitors gives crude chloroprene.

[4] The (E)-isomer is also one of the starting materials for the poriferic natural product sceptrin.

1,4-Dichlorobut-2-ene molecule