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2-Butene


0.626 g/ml (trans, 0.9 °C) −105.5 °C (trans) (E = 0.8 °C)

  • −42.6·10−6 cm3/mol (cis)
  • −43.3·10−6 cm3/mol (trans) |NFPA-H = 1 |NFPA-F = 4 |NFPA-R = 0 cis-2-Butene trans-2-Butene Isobutene Butyne

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)-but-2-ene) and *trans-*2-butene ((E)-but-2-ene).

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 high-octane gasoline (petrol) on alkylation units and butadiene, although some 2-butene is also used to produce the solvent butanone via hydration reaction 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)-but-2-ene (cis-isomer) and 30% (E)-but-2-ene (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.

References

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. {{GESTIS
  3. {{GESTIS
  4. {{ICSC-ref. 03. 97. (March 1996. {{ICSC-ref). 03. 98. (March 1996.)
  5. {{SIDS-ref. (February 1995.)
  6. [http://www.inchem.org. InChem: Chemical Safety Information from Intergovernmental Organizations] {{webarchive. link. (December 9, 2009)
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