Cyclohexene

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Cyclohexene
Cyclohexene structures.svg
Cyclohexene-conformation-2D-skeletal.png
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 images 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
Hazards
MSDS External MSDS
R-phrases R11, R19, R21/22
S-phrases S16, S23, S24, S25, S33
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −12 °C (10 °F; 261 K)
244 °C (471 °F; 517 K)
Explosive limits 0.8–5 %
1946 mg/kg (oral, rat)
US health exposure limits (NIOSH):
TWA 300 ppm (1015 mg/m3)[1]
TWA 300 ppm (1015 mg/m3)[1]
2000 ppm[1]
Except where noted otherwise, data is 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[edit]

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.[2] Cyclohexene is also a precursor to adipic acid, maleic acid, dicyclohexyladipate, and cyclohexeneoxide. Furthermore, it is used as a solvent.

Laboratory experiments[edit]

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:

Cyclohexensynthese1.svg
Cyclohexensynthese2.svg
  • Critical temperature: 287.2 °C (560.4 K)

See also[edit]

External links[edit]

References[edit]

  1. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0167". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ Michael T. Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a08_217