Cyclohexene
| Cyclohexene | |
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Cyclohexene |
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Other names
Tetrahydrobenzene, 1,2,3,4-Tetrahydrobenzene, Benzenetetrahydride, Cyclohex-1-ene, Hexanaphthylene, UN 2256 |
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| Identifiers | |
| CAS number | 110-83-8 |
| PubChem | 8079 |
| ChemSpider | 7788 |
| EC number | 203-807-8 |
| ChEBI | CHEBI:36404 |
| ChEMBL | CHEMBL16396 |
| RTECS number | GW2500000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H10 |
| Molar mass | 82.143 g/mol |
| Appearance | Liquid |
| Density | 0.8110 g/cm3 |
| Melting point |
-103.5 °C, 170 K, -154 °F |
| Boiling point |
82.98 °C, 356 K, 181 °F |
| Solubility in water | 250 mg/L |
| Vapor pressure | 8.93 kPa (20 °C)
11.9 kPa (25 °C) |
| Refractive index (nD) | 1.4465 |
| Hazards | |
| R-phrases | R11, R19, R21/22 |
| S-phrases | S16, S23, S24, S25, S33 |
| NFPA 704 | |
| Flash point | -12 °C (10 °F) |
| Autoignition temperature |
244 °C (471.2 °F) |
| Explosive limits | 1–5 % |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.
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[edit] 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.
[edit] 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)
[edit] See also
[edit] 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
[edit] References
- ^ 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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