Cyclopentene

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Cyclopentene
Cyclopentene
Cyclopentene
Ball-and-stick model of cyclopentene
Ball-and-stick model of cyclopentene
Space-filling model of cyclopentene
Names
Preferred IUPAC name
Cyclopentene
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.005.030 Edit this at Wikidata
UNII
  • InChI=1S/C5H8/c1-2-4-5-3-1/h1-2H,3-5H2 checkY
    Key: LPIQUOYDBNQMRZ-UHFFFAOYSA-N checkY
  • InChI=1/C5H8/c1-2-4-5-3-1/h1-2H,3-5H2
    Key: LPIQUOYDBNQMRZ-UHFFFAOYAS
  • C1CC=CC1
Properties
C5H8
Molar mass 68.11 g/mol
Density 0.771 g/cm3
Melting point −135 °C (−211 °F; 138 K)
Boiling point 44 to 46 °C (111 to 115 °F; 317 to 319 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Flash point −29 °C (−20 °F; 244 K)
Related compounds
Related compounds
 Cyclopentadiene
Cyclobutene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Cyclopentene is 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][2] It is one of the principal cycloalkenes
.

Production

Cyclopentene is produced industrially in large amounts by

vinylcyclopropane-cyclopentene rearrangement.[4]

It can also be produced by the

catalytic hydrogenation of cyclopentadiene.[5]

Reactions

The polymerization of cyclopentene by

Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.[6]

hydrocarboxylation of cyclopentene gives cyclopentanecarboxylic acid:[7]

C5H8 + CO + H2O → C5H9CO2H

References

  1. ISBN 978-3527306732
    .
  2. ^ "Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". nepis.epa.gov. United States Environmental Protection Agency. 2011.
  3. doi:10.15227/orgsyn.019.0036
    .
  4. PMID 12683781
    .
  5. ^ D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
  6. doi:10.1021/ma00027a039
    .
  7. S2CID 199466915
    .

External links
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