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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.[2] 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.[3]

Other routes

Piperylene is a product of the decarboxylation of sorbic acid.[4]

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.[5]

Reactions

Piperylene behaves as a typical diene. It forms a sulfolene upon treatment with sulfur dioxide.[6] It participates in Ziegler-Natta polymerization.[7] It is converted to 2-Methyltetrahydrofuran by reaction with water. It undergoes hydrocyanation.[3]

Piperylene can be deprotonated using butyl lithium, providing lithium pentadienyl.[8]

See also

References

  1. ^ Safety (MSDS) data for piperylene Archived 2007-10-11 at the Wayback Machine. Retrieved 2007-11-14.
  2. ^ Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2014). “Hydrocarbons”. Ullmann’s Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN 978-3-527-30673-2.
  3. ^ a b Herrmann, Norman; Vogelsang, Dennis; Behr, Arno; Seidensticker, Thomas (2018). “Homogeneously Catalyzed 1,3-Diene Functionalization – A Success Story from Laboratory to Miniplant Scale”. ChemCatChem. 10 (23): 5342–5365. doi:10.1002/cctc.201801362.
  4. ^ Erich Lück, Martin Jager, Nico Raczek (2000). “Sorbic Acid”. Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_507. ISBN 3527306730.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  5. ^ Piperylene Archived 2009-05-13 at the Wayback Machine at Shell Chemicals. Retrieved 2009-05-19.
  6. ^ Robert L. Frank, Raymond P. Seven (1949). “Isoprene Cyclic Sulfone”. Organic Syntheses. 29: 59. doi:10.15227/orgsyn.029.0059.
  7. ^ Ricci, Giovanni; Pampaloni, Guido; Sommazzi, Anna; Masi, Francesco (2021). “Dienes Polymerization: Where We Are and What Lies Ahead”. Macromolecules. 54 (13): 5879–5914. doi:10.1021/acs.macromol.1c00004.
  8. ^ Seyferth, Dietmar; Pornet, Jacques (1980). “(2,4-Pentadienyl)trimethylsilane: A useful pentadienylation reagent”. The Journal of Organic Chemistry. 45 (9): 1721–1722. doi:10.1021/jo01297a053.