Cyclopentene

From Handwiki
Short description: Organic compound; 5-sided hydrocarbon ring
Cyclopentene
Cyclopentene
Ball-and-stick model of cyclopentene
Space-filling model of cyclopentene
Names
Preferred IUPAC name
Cyclopentene
Identifiers
CAS Number
  • 142-29-0 ☑Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:49155 ☑Y
ChEMBL
  • ChEMBL1797299 ☒N
ChemSpider
  • 8544 ☑Y
PubChem CID
  • 8882
UNII
  • ONM2CKV81Z ☑Y
Properties
Chemical formula
 C
5H
8
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)
Flammability code 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. gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
1
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 ☑Y☒N ?)
Infobox references
Tracking categories (test):
  • SizeSet
  • PairSizeSet

Cyclopentene is a chemical compound with the formula (CH
2)
3(CH)
2. 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][2] 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.[3]

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

Cyclopentadiene hydrogenation.png

Use in mechanistic organic chemistry

Cyclopentene is used in analysing the mechanisms of organic reactions. It can be obtained from vinylcyclopropane in the vinylcyclopropane-cyclopentene rearrangement.[5]

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

References

  1. ↑ Dieter Hönicke; Ringo Födisch; Peter Claus; Michael Olson (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_227. 
  2. ↑ "Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". United States Environmental Protection Agency. 2011. https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100GPED.TXT. 
  3. ↑ B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses 19: 36. doi:10.15227/orgsyn.019.0036. 
  4. ↑ D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
  5. ↑ Baldwin, John E. (2003). "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes". Chemical Reviews 103 (4): 1197–212. doi:10.1021/cr010020z. PMID 12683781. 
  6. ↑ Collins, Scott; Kelly, W. Mark (1992). "The microstructure of poly(cyclopentene) produced by polymerization of cyclopentene with homogeneous Ziegler-Natta catalysts". Macromolecules 25 (1): 233–7. doi:10.1021/ma00027a039. Bibcode: 1992MaMol..25..233C. 

External links



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Cyclopentene&oldid=2204791"

Categories: [Monomers] [Cyclopentenes]

↧ Download as ZWI file | Last modified: 12/02/2022 19:08:54 | 8 views
☰ Source: https://handwiki.org/wiki/Chemistry:Cyclopentene | License: CC BY-SA 3.0

ZWI signed:
  Encycloreader by the Knowledge Standards Foundation (KSF) ✓[what is this?]

ZWI viewer by the EncyclosphereKSF