Cyclohexene

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Cyclohexene
IUPAC name

Cyclohexene

Other names

Tetrahydrobenzene, 1,2,3,4-Tetrahydrobenzene, Benzenetetrahydride, Cyclohex-1-ene, Hexanaphthylene, UN 2256

Identifiers
CAS number 110-83-8 YesY
PubChem 8079
ChemSpider 7788 YesY
EC number 203-807-8
ChEBI CHEBI:36404 YesY
ChEMBL CHEMBL16396 YesY
RTECS number GW2500000
Jmol-3D images Image 1
Properties
Molecular formula 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
Solubility in water 2.13 g/100 mL
Solubility miscible with organic solvents
Vapor pressure 8.93 kPa (20 °C)

11.9 kPa (25 °C)

kH 0.022 mol·kg−1·bar−1
Refractive index (nD) 1.4465
Hazards
R-phrases R11, R19, R21/22
S-phrases S16, S23, S24, S25, S33
NFPA 704
3
1
0
Flash point −12 °C; 10 °F; 261 K
Autoignition temperature 244 °C; 471 °F; 517 K
Explosive limits 0.8–5 %
LD50 1946 mg/kg (oral, rat)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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:

  • 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
Alkenes
Dienes
Trienes
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