Piperylene or 1,3-pentadiene is an organic compound with the formula CH3−CH=CH−CH=CH2. 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






