Chemistry:Cyclopentene
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.
History and synthesis
Cyclopentene was first prepared by Carl Gärtner in 1893 from iodocyclopentane with potassium hydroxide. He named it pentamethenylene (German: Pentamethenylen).[3]
Cyclopentene is produced industrially in large amounts by steam cracking of naphtha. In the laboratory, it is prepared by dehydration of cyclopentanol.[4] Substituted cyclopentenes are the product of the vinylcyclopropane-cyclopentene rearrangement.[5]
It can also be produced by the catalytic hydrogenation of cyclopentadiene.[6]
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Reactions
The polymerization of cyclopentene by Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.[7]
Palladium-catalyzed hydrocarboxylation of cyclopentene gives cyclopentanecarboxylic acid:[8]
- 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.
- ↑ Gärtner, Carl (January 1893). "Das Pentamethenylen und sein Dibromür" (in en). Justus Liebigs Annalen der Chemie 275 (2-3): 331–332. doi:10.1002/jlac.18932750217. ISSN 0075-4617. https://books.google.com/books?id=QpEBhiH9p4QC&pg=PA331.
- ↑ B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses 19: 36. doi:10.15227/orgsyn.019.0036.
- ↑ Baldwin, John E. (2003). "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes". Chemical Reviews 103 (4): 1197–212. doi:10.1021/cr010020z. PMID 12683781.
- ↑ D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
- ↑ 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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