Progress in synthesis of cyclohexylbenzene and the catalysts

doi:10.16085/j.issn.1000-6613.2018-1232

Abstract

Abstract:

Cyclohexylbenzene can be oxidized to produce phenol and cyclohexanone. Besides, it can be used as an additive in the electrolyte of lithium ion batteries and as a blend to tune the cetane number of diesel oil, and thus it is a fine chemical with high added value and market potential. The progress in the synthesis of cyclohexylbenzene by alkylation of benzene with cyclohexene and the catalysts used are reviewed. The mechanism and reaction path of benzene hydroalkylation are summarized, including the source of hydroalkylation activity, the inference of carbocation intermediates, and the formation of all reaction products. Based on the hydroalkylation mechanism, the design concepts and the development process of hydroalkylation catalyst were reviewed. Finally, it is pointed out that new catalysts, such as B-acid, B-L-acid, and immobilized ionic liquids, can be developed for the alkylation of benzene with cyclohexene. It is suggested that the hydroalkylation mechanism can be improved by means of the latest research methods of carbocation, and hierarchical porous zeolite can be used as the acidic support of hydroalkylation catalyst.

Key words: benzene, catalysts, synthesis, alkylation, hydroalkylation, cyclohexylbenzene

摘要：

环己基苯经过氧化反应可生产苯酚和环己酮，还可以用作锂离子电池电解液的添加剂，也可用作柴油的十六烷值调和组分，是一种高附加值、有市场潜力的精细化学品。本文介绍了国内外通过苯与环己烯烷基化合成环己基苯及所用催化剂的研究进展，总结了苯加氢烷基化反应机理和反应路径的研究成果，包括加氢烷基化活性的来源、中间产物和碳正离子中间体的推断以及各反应产物的形成。通过对加氢烷基化机理的认识，回顾了加氢烷基化催化剂的设计思路和发展历程。最后指出可开发用于苯与环己烯烷基化的B酸型、B-L酸型以及固载化离子液体等新型催化剂。提出可借助最新的碳正离子研究手段对加氢烷基化机理进行补充完善，并认为可利用多级孔沸石作为加氢烷基化催化剂的酸性载体。

关键词: 苯, 催化剂, 合成, 烷基化, 加氢烷基化, 环己基苯

CLC Number:

TQ241.1

Wennian WANG, Gaowei WANG, Huanxin GAO, Weimin YANG. Progress in synthesis of cyclohexylbenzene and the catalysts[J]. Chemical Industry and Engineering Progress, 2019, 38(01): 324-333.

王闻年, 王高伟, 高焕新, 杨为民. 环己基苯的合成及其催化剂研究进展[J]. 化工进展, 2019, 38(01): 324-333.

Figures/Tables 1

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[4]	WANG Weitao, BAO Tingyu, JIANG Xulu, HE Zhenhong, WANG Kuan, YANG Yang, LIU Zhaotie. Oxidation of benzene to phenol over aldehyde-ketone resin based metal-free catalyst [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4706-4715.
[5]	XIANG Yang, HUANG Xun, WEI Zidong. Recent progresses in the activity and selectivity improvement of electrocatalytic organic synthesis [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4005-4014.
[6]	WANG Yaogang, HAN Zishan, GAO Jiachen, WANG Xinyu, LI Siqi, YANG Quanhong, WENG Zhe. Strategies for regulating product selectivity of copper-based catalysts in electrochemical CO₂ reduction [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4043-4057.
[7]	LI Jia, FAN Xing, CHEN Li, LI Jian. Research progress of simultaneous removal of NO _x and N₂O from the tail gas of nitric acid production [J]. Chemical Industry and Engineering Progress, 2023, 42(7): 3770-3779.
[8]	WANG Shuaiqi, WANG Congxin, WANG Xuelin, TIAN Zhijian. Solvent-free rapid synthesis of ZSM-12 zeolite [J]. Chemical Industry and Engineering Progress, 2023, 42(7): 3561-3571.
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[10]	YU Xixi, ZHANG Jinshuai, LEI Wen, LIU Chengguo. Research progress of self-healing photocuring polymeric materials based on dynamic covalent bonds [J]. Chemical Industry and Engineering Progress, 2023, 42(7): 3589-3599.
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[15]	ZHANG Peng, PAN Yuan. Progress of single atom catalysts in electrocatalytic oxygen reduction to hydrogen peroxide [J]. Chemical Industry and Engineering Progress, 2023, 42(6): 2944-2953.