Cyclopentene
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| Molar mass | 68.11 g/mol |
| Density | 0.771 g/cm3 |
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| Template:Longitem | Cyclopentadiene Cyclobutene |
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Cyclopentene is a chemical compound with the formula Template:Chem2. 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 (Template:Langx).[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]
File:Cyclopentadiene hydrogenation.png
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]
References
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- ↑ Template:Ullmann
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- ↑ D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
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External links
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