Cyclohexene

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Cyclohexene
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Names
IUPAC name
Cyclohexene
Other names
Tetrahydrobenzene, 1,2,3,4-Tetrahydrobenzene, Benzenetetrahydride, Cyclohex-1-ene, Hexanaphthylene, UN 2256
Identifiers
110-83-8 YesY
ChEBI CHEBI:36404 YesY
ChEMBL ChEMBL16396 YesY
ChemSpider 7788 YesY
EC Number 203-807-8
Jmol 3D model Interactive image
PubChem 8079
RTECS number GW2500000
Properties
C6H10
Molar mass 82.143 g/mol
Appearance colorless liquid
Odor sweet
Density 0.8110 g/cm3
Melting point −103.5 °C (−154.3 °F; 169.7 K)
Boiling point 82.98 °C (181.36 °F; 356.13 K)
insoluble in water
Solubility miscible with organic solvents
Vapor pressure 8.93 kPa (20 °C)

11.9 kPa (25 °C)

0.022 mol·kg−1·bar−1
1.4465
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms peroxides.

Production and uses

Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by Asahi Chemical Company. It is converted to cyclohexanol, which is dehydrogenated to give cyclohexanone, a precursor to caprolactam.[1] Cyclohexene is also a precursor to adipic acid, maleic acid, dicyclohexyladipate, and cyclohexeneoxide. Furthermore, it is used as a solvent.

Laboratory experiments

A common experiment for beginning organic chemistry students is the acid catalyzed dehydration of cyclohexanol with distillative removal of the resulting cyclohexene from the reaction mixture:

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  • Critical temperature: 287.2 °C (560.4 K)

See also

External links

References

  1. Michael T. Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a08_217