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
A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, a ...
with a
petrol
Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic co ...
-like
odor
An odor (American English) or odour (English in the Commonwealth of Nations, Commonwealth English; American and British English spelling differences#-our, -or, see spelling differences) is caused by one or more volatilized chemical compounds ...
. 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
A cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon Atom, atoms and either one or more double bonds, but has no Aromaticity, aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene ...
s.
Production
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 ethe ...
of
naphtha
Naphtha ( or ) is a flammable liquid hydrocarbon mixture.
Mixtures labelled ''naphtha'' have been produced from natural gas condensates, petroleum distillates, and the distillation of coal tar and peat. In different industries and regions ''n ...
. In the laboratory, it is prepared by dehydration of
cyclopentanol
Cyclopentanol or cyclopentyl alcohol is a cyclic alcohol. It is also known as hydroxycyclopentane.
Reactions
The dehydration of cyclopentanol produces cyclopentene
Cyclopentene is a chemical compound with the formula . It is a colorless liqu ...
.
It can also 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 co ...
of
cyclopentadiene
Cyclopentadiene is an organic compound with the chemical formula, formula C5H6.LeRoy H. Scharpen and Victor W. Laurie (1965): "Structure of cyclopentadiene". ''The Journal of Chemical Physics'', volume 43, issue 8, pages 2765-2766. It is often ab ...
.
[D. Hönicke, R. Födisch, P. Claus, M. Olson: ''Cyclopentadiene and Cyclopentene'', in: '' Ullmanns Enzyklopädie der Technischen Chemie'' 2002, Wiley-VCH, Weinheim.]
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 The vinylcyclopropane rearrangement or vinylcyclopropane-cyclopentene rearrangement is a ring expansion reaction, converting a vinyl-substituted cyclopropane ring into a cyclopentene ring.
Intense experimental as well as computational investigati ...
.
The polymerization of cyclopentene by
Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.
References
External links
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Monomers