Cyclohexene
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.Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company.Reactions and uses
Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene. Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.
Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam.
The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxidant, in the presence of a tungsten catalyst.
Cyclohexene is also a precursor to maleic acid, dicyclohexyladipate, and cyclohexene oxide. Furthermore, it is used as a solvent.Structure
Cyclohexene is most stable in a half-chair conformation, unlike the preference for a chair form of cyclohexane. One basis for the cyclohexane conformational preference for a chair is that it allows each bond of the ring to adopt a staggered conformation. For cyclohexene, however, the alkene is planar, equivalent to an eclipsed conformation at that bond.
