环己烯可控选择性催化氧化的最新进展

doi:10.1016/S1872-2067(18)63050-5

摘要/Abstract

摘要：

环己烯是一种价格低廉易得的大宗化工原料，通常由苯选择性加氢来合成.该化合物虽然分子结构简单，但却有两个不同的反应位点.随着反应所发生的位点与反应深度的不同，环己烯的氧化反应可生成一系列不同氧化程度与官能团的产物的混合物.环己烯双键的氧化反应，可生成环氧环己烷，而环氧环己烷进一步水解，则生成1，2-环己二醇，其中，随着使用不同催化剂导致的反应机理差异，产物可分别为顺式或反式结构.在强氧化剂作用下，环己烯双键充分氧化，可生成己二酸.环己烯烯丙基C-H键氧化，则可随着反应深度的不同分别生成2-环己烯醇与2-环己烯酮.
上述环己烯氧化产物都是重要的有机化工中间体.其中，环氧环己烷是农药杀螨剂的主要原料，也用作合成表面活性剂、橡胶助剂等有用产品；1，2-环己二醇可用于合成化工中间体邻苯二酚；环己烯醇与环己烯酮是生产除草剂、香水、药物的原料；己二酸则是合成重要产品尼龙-6，6的原料.因此，随着市场需求的变化，对环己烯氧化反应进行选择性控制，提高其中某种产物的选择性，是重要的化工合成技术，有着巨大的应用潜力；从而控制反应历程与深度是有机化工合成工艺研究中最具有挑战性的研究课题之一，有很好的科学意义.
目前，人们对环己烯的选择性控制氧化反应已进行了广泛的研究.该反应可使用金属催化剂，包括铁、钴、镍、锰、铬、钒、钨、铜、钛、金、银、铋、锇、钼、镉等；也可以使用无金属催化剂如磺酸、2，2，2-三氟苯乙酮、类石墨相碳化氮（g-C₃N₄）等.反应可使用化学氧化剂，如间氯过氧苯甲酸、醋酸碘苯、过氧叔丁醇等，也可使用更加清洁的过氧化氢、分子氧.研究表明，催化剂的种类、用量，以及反应溶剂、温度、氧化剂等一系列外在条件，可以影响环己烯氧化反应的选择性.本文以反应所使用的氧化剂归类，总结了该课题的最新研究进展，以期对从事环己烯可控选择性氧化的学术与工业研究人员有所帮助.

关键词: 环己烯, 选择性氧化, 绿色化学, 环氧环己烷, 环己二醇, 己二酸, 环己烯醇, 环己烯酮

Abstract:

Because of multiple potential reaction sites and variable oxidation depths, oxidation of cyclohexene can lead to a mixture of products with different oxidation states and functional groups, such as 7-oxabicyclo[4.1.0]heptane, trans/cis-cyclohexane-1,2-diol, cyclohex-2-en-1-ol, cyclohex-2-en-1-one, and even adipic acid. These products are broadly and abundantly used intermediates in the chemical industry; therefore, controllable oxidation reactions for cyclohexene that can selectively afford the targeted products are synthetically valuable for applications in both the academy and industry, thus becoming the aim of synthetic and catalytic chemists in the field. Many reports on selective oxidation of cyclohexene have recently appeared in the literature because of its significance. This short review summarizes the recent advances on this subject, and the contents are mainly classified based on the chosen oxidants. We hope that this review can provide a useful guide for controllable and selective catalytic oxidation of cyclohexene for interested readers from both the academy and industry.

Key words: Cyclohexene, Selective oxidation, Green chemistry, 7-Oxabicyclo[4.1.0]heptane, Cyclohexane-1,2-diol, Adipic acid, Cyclohex-2-en-1-ol, Cyclohex-2-en-1-one

曹洪恩, 朱柏燃, 杨钰帆, 徐林, 俞磊, 徐清. 环己烯可控选择性催化氧化的最新进展[J]. 催化学报, 2018, 39(5): 899-907.

Hongen Cao, Boran Zhu, Yufan Yang, Lin Xu, Lei Yu, Qing Xu. Recent advances on controllable and selective catalytic oxidation of cyclohexene[J]. Chinese Journal of Catalysis, 2018, 39(5): 899-907.

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