Cyclopentene is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the formula . It is a colorless

liquid Liquid is a state of matter with a definite volume but no fixed shape. Liquids adapt to the shape of their container and are nearly incompressible, maintaining their volume even under pressure. The density of a liquid is usually close to th ...

with a

petrol Gasoline (North American English) or petrol ( Commonwealth English) is a petrochemical product characterized as a transparent, yellowish, and flammable liquid normally used as a fuel for spark-ignited internal combustion engines. When formul ...

-like

odor An odor (American English) or odour ( Commonwealth English; see spelling differences) is a smell or a scent caused by one or more volatilized chemical compounds generally found in low concentrations that humans and many animals can perceive ...

. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%. It is one of the principal

cycloalkene In organic chemistry, a cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed Ring (chemistry), ring of carbon atoms and either one or more double bonds, but has no Aromaticity, aromatic character. Some cycloalkenes, ...

History and synthesis

Cyclopentene was first prepared by Carl Gärtner in 1893 from iodocyclopentane with

potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which utili ...

. He named it pentamethenylene (). Cyclopentene is produced industrially in large amounts by

steam cracking Steam cracking is a petrochemical process in which saturated hydrocarbons are broken down into smaller, often unsaturated, hydrocarbons. It is the principal industrial method for producing the lighter alkenes (or commonly olefins), including ethen ...

naphtha Naphtha (, recorded as less common or nonstandard in all dictionaries: ) is a flammable liquid hydrocarbon mixture. Generally, it is a fraction of crude oil, but it can also be produced from natural-gas condensates, petroleum distillates, and ...

. In the laboratory, it is prepared by dehydration of

cyclopentanol Cyclopentanol or cyclopentyl alcohol is the organic compound with the formula . It is classified as a cyclic alcohol. Synthesis and reactions The bio-derived "platform chemical" furfural can be efficiently converted to cyclopentanol by hydrodeox ...

. Substituted cyclopentenes are the product of the

vinylcyclopropane-cyclopentene rearrangement The vinylcyclopropane rearrangement or vinylcyclopropane-cyclopentene rearrangement is a ring expansion reaction, converting a vinyl-substituted cyclopropane ring into a cyclopentene ring. Cyclopropyl groups adjacent to vinyl groups can undergo rin ...

. It can also be produced by the

catalytic hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...

cyclopentadiene Cyclopentadiene is an organic compound with the chemical formula, formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−. This colorless liquid has a strong and unpleasant odor. At room temperature, ...

.D. Hönicke, R. Födisch, P. Claus, M. Olson: ''Cyclopentadiene and Cyclopentene'', in: '' Ullmanns Enzyklopädie der Technischen Chemie'' 2002, Wiley-VCH, Weinheim. Cyclopentadiene hydrogenation

Reactions

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

Palladium Palladium is a chemical element; it has symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1802 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas (formally 2 Pallas), ...

-catalyzed

hydrocarboxylation In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemis ...

of cyclopentene gives cyclopentanecarboxylic acid: :

References

External links

* {{Authority control Monomers Cycloalkenes