Chemistry:Cyclopentene
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| Preferred IUPAC name
Cyclopentene | |||
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3D model (JSmol)
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PubChem CID
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| Properties | |||
| 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) | |||
| Flash point | −29 °C (−20 °F; 244 K) | ||
| Related compounds | |||
Related compounds
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Cyclopentadiene Cyclobutene | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
 verify (what is   ?)
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| Infobox references | |||
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 be produced by the catalytic hydrogenation of cyclopentadiene.[4]
Reactions
Cyclopentene 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]
Palladium-catalyzed hydrocarboxylation of cyclopentene gives cyclopentanecarboxylic acid:[7]
- C
5H
8 + CO + H
2O → C
5H
9CO
2H
References
- ↑ 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.
- ↑ "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.
- ↑ B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses 19: 36. doi:10.15227/orgsyn.019.0036.
- ↑ D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
- ↑ Baldwin, John E. (2003). "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes". Chemical Reviews 103 (4): 1197–212. doi:10.1021/cr010020z. PMID 12683781.
- ↑ 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.
- ↑ Sang, Rui; Kucmierczyk, Peter; Dühren, Ricarda; Razzaq, Rauf; Dong, Kaiwu; Liu, Jie; Franke, Robert; Jackstell, Ralf et al. (2019). "Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation". Angewandte Chemie International Edition 58 (40): 14365–14373. doi:10.1002/anie.201908451. PMID 31390131.
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