Cyclohexylbenzene Explained

Cyclohexylbenzene is the organic compound with the structural formula . 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.

It is also generated by the hydrodesulfurization of dibenzothiophene.^[3]

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:

Cyclohexanone is an important precursor to some nylons.^[4]

References

1. 10.1246/cl.2004.472. Novel Acidic Ionic Liquids Catalytic Systems for Friedel–Crafts Alkylation of Aromatic Compounds with Alkenes. Chemistry Letters. 33. 4. 472–473. 2004. Qiao. Kun. Yokoyama. Chiaki.
2. 10.15227/orgsyn.019.0036. Cyclohexylbenzene . Organic Syntheses . 1939 . 19 . 36. B. B. Corson, V. N. Ipatieff .
3. 10.1016/j.jcat.2011.12.018. Hydrodesulfurization of Dibenzothiophene and its Hydrogenated Intermediates over Bulk MoP. Journal of Catalysis. 287. 161–169. 2012. Bai. Jin. Li. Xiang. Wang. Anjie. Prins. Roel. Wang. Yao.
4. Web site: What's New in Phenol Production? . Plotkin . Jeffrey S. . American Chemical Society . 2016-03-21 . 2018-01-02 . https://web.archive.org/web/20191027122212/https://www.acs.org/content/acs/en/pressroom/cutting-edge-chemistry/what-s-new-in-phenol-production-.html . 2019-10-27 . dead .