Cyclohexylbenzene

Chemical compound From Wikipedia, the free encyclopedia

Cyclohexylbenzene 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.

Quick facts Names, Identifiers ...
Cyclohexylbenzene
Names
Preferred IUPAC name
Cyclohexylbenzene
Other names
Phenylhexamethylene Phenylcyclohexane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.429 Edit this at Wikidata
EC Number
  • 212-572-0
UNII
  • 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
  • C1CCC(CC1)C2=CC=CC=C2
Properties
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:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H304, H315, H319, H410
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).
Close

History and synthesis

Cyclohexylbenzene was first obtained in 1899 by Markovnikov's student Nikolay Kirsanov (1874–1921).[1] He used a Friedel–Crafts alkylation of benzene with cyclohexyl chloride using a catalyst such as aluminum trichloride:[2]

C6H6 + C6H11Cl → C6H5−C6H11 + HCl

Cyclohexylbenzene is now industrially produced by the acid-catalyzed alkylation of benzene with cyclohexene.[3][4] The process can proceed using benzene as the exclusive organic precursor. Its partial hydrogenation gives cyclohexene, which alkylates the unhydrogenated benzene.[5]

It is also generated by the hydrodesulfurization of dibenzothiophene,[6] and ExxonMobil took a patent in 2009 for a process based on direct hydroalkylation of two benzene molecules.[7]

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.[8][5]

References

Related Articles

Wikiwand AI