Cyclohexylbenzene

Cyclohexylbenzene
Names
	Preferred IUPAC name Cyclohexylbenzene
	Other names Phenylcyclohexane
Identifiers
CAS Number	827-52-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3278514;
ChemSpider	12674;
ECHA InfoCard	100.011.429
EC Number	212-572-0;
PubChem CID	13229;
UNII	TRJ2SXT894 ;
CompTox Dashboard (EPA)	DTXSID3061188 ;
	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
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 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.

Formation

Cyclohexylbenzene is produced by the acid-catalyzed alkylation of benzene with cyclohexene.^[1]^[2] The process can proceed using benzene as the exclusive organic precursor. Its partial hydrogenation gives cyclohexene, which alkylates the unhydrogenated benzene.^[3]

It is also generated by the hydrodesulfurization of dibenzothiophene,^[4] and ExxonMobil took a patent in 2009 for a process based on direct hydroalkylation of two benzene molecules.^[5]

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.^[6]^[3]

References

^ Qiao, Kun; Yokoyama, Chiaki (2004). "Novel Acidic Ionic Liquids Catalytic Systems for Friedel–Crafts Alkylation of Aromatic Compounds with Alkenes". Chemistry Letters. 33 (4): 472–473. doi:10.1246/cl.2004.472.
^ B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses. 19: 36. doi:10.15227/orgsyn.019.0036.
^ ^a ^b Weber, Manfred; Weber, Markus; Kleine-Boymann, Michael (2004). "Phenol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_299.pub3. ISBN 978-3527306732.
^ Bai, Jin; Li, Xiang; Wang, Anjie; Prins, Roel; Wang, Yao (2012). "Hydrodesulfurization of Dibenzothiophene and its Hydrogenated Intermediates over Bulk MoP". Journal of Catalysis. 287: 161–169. doi:10.1016/j.jcat.2011.12.018.
^ U.S. patent 8178728B2
^ Plotkin, Jeffrey S. (2016-03-21). "What's New in Phenol Production?". American Chemical Society. Archived from the original on 2019-10-27. Retrieved 2018-01-02.

[1] Qiao, Kun; Yokoyama, Chiaki (2004). "Novel Acidic Ionic Liquids Catalytic Systems for Friedel–Crafts Alkylation of Aromatic Compounds with Alkenes". Chemistry Letters. 33 (4): 472–473. doi:10.1246/cl.2004.472.

[2] B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses. 19: 36. doi:10.15227/orgsyn.019.0036.

[Ullmann-3] Weber, Manfred; Weber, Markus; Kleine-Boymann, Michael (2004). "Phenol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_299.pub3. ISBN 978-3527306732.

[4] Bai, Jin; Li, Xiang; Wang, Anjie; Prins, Roel; Wang, Yao (2012). "Hydrodesulfurization of Dibenzothiophene and its Hydrogenated Intermediates over Bulk MoP". Journal of Catalysis. 287: 161–169. doi:10.1016/j.jcat.2011.12.018.

[5] U.S. patent 8178728B2

[acs_phenol-6] Plotkin, Jeffrey S. (2016-03-21). "What's New in Phenol Production?". American Chemical Society. Archived from the original on 2019-10-27. Retrieved 2018-01-02.

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