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Cyclohexene

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Title: Cyclohexene  
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Subject: Cycloalkene, Alicyclic compound, Alkene, Benzene, Elimination reaction
Collection: Cycloalkenes, Hydrocarbon Solvents
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Cyclohexene

Cyclohexene
Names
IUPAC name
Cyclohexene
Other names
Tetrahydrobenzene, 1,2,3,4-Tetrahydrobenzene, Benzenetetrahydride, Cyclohex-1-ene, Hexanaphthylene, UN 2256
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
EC number 203-807-8
Jmol-3D images Image
PubChem
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
Safety data sheet External MSDS
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)
244 °C (471 °F; 517 K)
Explosive limits 0.8–5 %
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
1946 mg/kg (oral, rat)
13,196 ppm (mouse, 2 hr)[1]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 300 ppm (1015 mg/m3)[2]
REL (Recommended)
TWA 300 ppm (1015 mg/m3)[2]
2000 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Cyclohexene is a peroxides.

Contents

  • Production and uses 1
    • Laboratory experiments 1.1
  • See also 2
  • External links 3
  • References 4

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.[3] 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 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

  • International Chemical Safety Card 1054
  • "NIOSH Pocket Guide to Chemical Hazards #0167".  
  • Material Safety Data Sheet for cyclohexene
  • Safety MSDS data
  • Reaction of Cyclohexene with Bromine and Potassium Permanganate
  • Cyclohexene synthesis
  • Data sheet at inchem.org

References

  1. ^ "Cyclohexene". Immediately Dangerous to Life and Health.  
  2. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0167".  
  3. ^ Michael T. Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a08_217
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