Piperylene or 1,3-pentadiene is an organic compound with the formula . It is a volatile, flammable hydrocarbon. It is one of the five positional isomers of pentadiene. It is one of several industrially significant 1,3-dienes, but it has received much less attention than butadiene and isoprene. It consists of two isomers, Z and E, but these are rarely distiguighed.

Synthesis and formation

The dominant route to piperylene is by steam cracking of naphtha. This makes up about 10% of the C5 stream.

Other routes

Piperylene is a product of the decarboxylation of sorbic acid.

Piperylene is obtained as a byproduct of ethylene production from crude oil, combustion of biomass, waste incineration and exhaust gases. It is used as a monomer in the manufacturing of plastics, adhesives and resins.

Reactions

Piperylene behaves as a typical diene. It forms a sulfolene upon treatment with sulfur dioxide. It participates in Ziegler-Natta polymerization. It is converted to 2-Methyltetrahydrofuran by reaction with water. It undergoes hydrocyanation.

Piperylene can be deprotonated using butyl lithium, providing lithium pentadienyl.

See also

• Butadiene

• Cyclopentadiene

• Isoprene

References