Chemistry:Cyclohexylbenzene
Cyclohexylbenzene (or phenylhexamethylene, as it was initially called) is the organic compound with the structural formula C
6H
5–C
6H
11. 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).[1] He used a Friedel–Crafts alkylation of benzene with cyclohexyl chloride using a catalyst such as aluminum trichloride:[2]
- C
6H
6 + C
6H
11Cl → C
6H
5–C
6H
11 + 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:
- C
6H
5–C
6H
10OOH → C
6H
5OH + OC
6H
10
Cyclohexanone is an important precursor to some nylons.[8][5]
References
- ↑ Быков, Георгий Владимирович (1978) (in ru). История органической химии: Открытие важнейших органических соединений. Наука. pp. 132. https://books.google.com/books?id=76RbAAAAIAAJ&q=%D1%84%D0%B5%D0%BD%D0%B8%D0%BB%D1%86%D0%B8%D0%BA%D0%BB%D0%BE%D0%B3%D0%B5%D0%BA%D1%81%D0%B0%D0%BD.
- ↑ (in ru) Журнал Русского физико-химического общества. Тип-ія Б. Демакова. 1900. pp. 79. https://books.google.com/books?id=Y20MAQAAIAAJ&pg=RA1-PA79.
- ↑ 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.
- ↑ 5.0 5.1 Weber, Manfred; Weber, Markus; Kleine-Boymann, Michael (2004). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_299.pub3.
- ↑ 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 8,178,728B2
- ↑ Plotkin, Jeffrey S. (2016-03-21). "What's New in Phenol Production?". American Chemical Society. https://www.acs.org/content/acs/en/pressroom/cutting-edge-chemistry/what-s-new-in-phenol-production-.html.
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