Butene

Butene, also known as butylene, is an alkene with the formula C₄H₈. It is a colourless gas that is present in crude oil as a minor constituent in quantities that are too small for viable extraction. It is therefore obtained by catalytic cracking of long chain hydrocarbons left during refining of crude oil. Cracking produces a mixture of products, and the butene is extracted from this by fractional distillation.

Butene can be used as the monomer for polybutene but this polymer is more expensive than alternatives with shorter carbon chains such as polypropylene. Polybutene is therefore commonly used as a co-polymer (mixed with another polymer, either during or after reaction), such as in hot-melt adhesives.

Isomers

Among the molecules which have the chemical formula C₄H₈ four isomers are alkenes. All four of these hydrocarbons have four carbon atoms and one double bond in their molecules, but have different chemical structures. The IUPAC and common names, respectively, of these chemical compounds are:

2-Butene

2-Butene is an acyclic alkene with four carbon atoms. It is the simplest alkene exhibiting cis/trans-isomerism (also known as (E/Z)-isomerism); that is, it exists as two geometric isomers cis-2-butene ((Z)-2-butene) and trans-2-butene ((E)-2-butene).

It is a petrochemical, produced by the catalytic cracking of crude oil or the dimerization of ethylene. Its main uses are in the production of gasoline (petrol) and butadiene, although some 2-butene is also used to produce the solvent butanone via hydration to 2-butanol followed by oxidation.

The two isomers are extremely difficult to separate by distillation because of the proximity of their boiling points (~4 °C for cis and ~1 °C for trans). However, separation is unnecessary in most industrial settings, as both isomers behave similarly in most of the desired reactions. A typical industrial 2-butene mixture is 70% (Z)-2-butene (cis-isomer) and 30% (E)-2-butene (trans-isomer). Butane and 1-butene are common impurities, present at 1% or more in industrial mixtures, which also contain smaller amounts of isobutene, butadiene and butyne.

1-Butene

1-Butene is an organic chemical compound, linear alpha-olefin (alkene), and one of the isomers of butene. The formula is CH₃CH₂CH=CH₂. It is a highly flammable, easily condensed gas.

Reactions

1-Butene is stable in itself but polymerizes readily to polybutene. Its main application is as a comonomer in the production of certain kinds of polyethylene, such as linear low-density polyethylene (LLDPE). It has also been used as a precursor to polypropylene resins, butylene oxide, and butanone.

Manufacturing

1-Butene is produced either by separation from crude C₄ refinery streams or from the dimerization of ethylene. It is distilled to give a very high-purity product. An estimated 12 billion kilograms were produced in 2011, usually as a mixture with isomeric butenes.

See also

References

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