Cyclohexene

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 Y
PubChem	8079
ChemSpider	7788 Y
EC number	203-807-8
ChEBI	CHEBI:36404 Y
ChEMBL	CHEMBL16396 Y
RTECS number	GW2500000
Jmol-3D images	Image 1
SMILES C1CCC=CC1
InChI InChI=1S/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2 Y Key: HGCIXCUEYOPUTN-UHFFFAOYSA-N Y InChI=1/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2 Key: HGCIXCUEYOPUTN-UHFFFAOYAQ
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	3 1 0
Flash point	-12 °C (10 °F)
Autoignition temperature	244 °C (471.2 °F)
Explosive limits	1–5 %
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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)

• 1,3-Cyclohexadiene
• 1,4-Cyclohexadiene

See also

• Diels-Alder reaction
• Benzene
• Cyclohexane

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