Cyclopentene Explained

Cyclopentene is a chemical compound with the formula . It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%.[1] It is one of the principal cycloalkenes.

Production

Cyclopentene is produced industrially in large amounts by steam cracking of naphtha. In the laboratory, it is prepared by dehydration of cyclopentanol.[2] Substituted cyclopentenes are the product of the vinylcyclopropane-cyclopentene rearrangement.[3]

It can also be produced by the catalytic hydrogenation of cyclopentadiene.[4]

Reactions

The polymerization of cyclopentene by Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.[5]

Palladium-catalyzed hydrocarboxylation of cyclopentene gives cyclopentanecarboxylic acid:[6]

Notes and References

  1. Web site: Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks . nepis.epa.gov . United States Environmental Protection Agency . 2011.
  2. 10.15227/orgsyn.019.0036. Cyclohexylbenzene. Organic Syntheses. 1939. 19. 36. B. B. Corson, V. N. Ipatieff.
  3. 10.1021/cr010020z. Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes. 2003. Baldwin. John E.. Chemical Reviews. 103. 1197–212. 4. 12683781.
  4. D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
  5. The microstructure of poly(cyclopentene) produced by polymerization of cyclopentene with homogeneous Ziegler-Natta catalysts. Collins, Scott. Kelly, W. Mark. Macromolecules. 1992. 25. 1. 233–7. 10.1021/ma00027a039. 1992MaMol..25..233C.
  6. 10.1002/anie.201908451. Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation . 2019 . Sang . Rui . Kucmierczyk . Peter . Dühren . Ricarda . Razzaq . Rauf . Dong . Kaiwu . Liu . Jie . Franke . Robert . Jackstell . Ralf . Beller . Matthias . Angewandte Chemie International Edition . 58 . 40 . 14365–14373 . 31390131 . 199466915 . free .

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