Cyclohexylbenzene

Cyclohexylbenzene

File:Cyclohexylbenzene.svg
Names
Preferred IUPAC name Cyclohexylbenzene
Other names Phenylcyclohexane
Identifiers
CAS Number	827-52-1 checkY
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3278514
ChemSpider	12674
ECHA InfoCard
EC Number	212-572-0
E number
PubChem CID	13229
UNII	TRJ2SXT894 checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C12H16/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1,3-4,7-8,12H,2,5-6,9-10H2 Key: IGARGHRYKHJQSM-UHFFFAOYSA-N
SMILES C1CCC(CC1)C2=CC=CC=C2
Properties
Chemical formula	C12H16
Molar mass	160.260 g·mol−1
Appearance	Colorless liquid
Density	0.982 g/cm3
Melting point	7.3 °C (45.1 °F; 280.4 K)
Boiling point	240.1 °C (464.2 °F; 513.2 K)
Hazards
GHS labelling:
Pictograms	GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word	Danger
Hazard statements	H302, H304, H315, H319, H410
Precautionary statements	P264, P270, P273, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P321, P330, P331, P332+P313, P337+P313, P362, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclohexylbenzene (or phenylhexamethylene, as it was initially called) is the organic compound with the structural formula C₆H₅−C₆H₁₁. It is a derivative of benzene with a cyclohexyl substituent (C₆H₁₁). It is a colorless liquid.

History and synthesis

Cyclohexylbenzene was first obtained in 1899 by Markovnikov's student Nikolay Kirsanov (1874–1921). He used a Friedel–Crafts alkylation of benzene with cyclohexyl chloride using a catalyst such as aluminum trichloride:

C₆H₆ + C₆H₁₁Cl → C₆H₅−C₆H₁₁ + HCl

Cyclohexylbenzene is now industrially produced by the acid-catalyzed alkylation of benzene with cyclohexene. The process can proceed using benzene as the exclusive organic precursor. Its partial hydrogenation gives cyclohexene, which alkylates the unhydrogenated benzene.

It is also generated by the hydrodesulfurization of dibenzothiophene, and ExxonMobil took a patent in 2009 for a process based on direct hydroalkylation of two benzene molecules.

Applications

A route to phenol analogous to the cumene process begins with cyclohexylbenzene, which is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide. Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and cyclohexanone:

C₆H₅−C₆H₁₀OOH → C₆H₅OH + OC₆H₁₀

Cyclohexanone is an important precursor to some nylons.