Cyclohexylbenzene
Cyclohexylbenzene is the organic compound with the formula C6H5-C6H11. It is a derivative of benzene with a cyclohexyl substituent (C6H11). A colorless liquid, it is produced by the alkylation of benzene with cyclohexene.[1] It is generated by the hydrodesulfurization of dibenzothiophene.[2]
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| Names | |
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| Preferred IUPAC name
Cyclohexylbenzene | |
| Other names
Phenylcyclohexane | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.011.429 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| 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 pictograms |    |
| GHS Signal word | Danger |
GHS hazard statements |
H302, H304, H315, H319, H400, H410 |
| P264, P270, P273, P280, P301+310, P301+312, P302+352, P305+351+338, P321, P330, P331, P332+313, P337+313, 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 | |
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. Cyclohexanone is an important precursor to some nylons.[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.
- 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.
- Plotkin, Jeffrey S. (2016-03-21). "What's New in Phenol Production?". American Chemical Society. Retrieved 2018-01-02.
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