Experimental and theoretical study on N-hydroxyphthalimide and its derivatives catalyzed aerobic oxidation of cyclohexylbenzene

doi:10.1016/j.cjche.2021.06.017

Abstract

Abstract: The liquid phase oxidation of cyclohexylbenzene (CHB) is a new green synthetic approach to cyclohexylbenzene-1-hydroperoxide (CHBHP), a key intermediate for preparing phenol and cyclohexanone. In this work, aryl-substituted (Cl and Br) derivatives of N-hydroxyphthalimide (NHPI) were synthesized and their catalytic performances for CHB oxidation were studied. In addition, geometric optimization and transition state search were performed using DFT calculations. Both experimental and theoretical studies have proven that chloro-substitution on NHPI can significantly improve its catalytic effects on the oxidation of CHB by oxygen. Compared with NHPI, CHB conversion and selectivity of CHBHP over Cl₄NHPI were increased by 10.47% and 13.24%. The strategy of aryl -substituting NHPI with halogen atoms proposed in this study would provide a potential way to the development of new NHPI-based catalysts for aerobic oxidation reactions.

Key words: N-hydroxyphthalimide, Aryl-substituted derivative, Cyclohexylbenzene, Oxidation, Radical

摘要： The liquid phase oxidation of cyclohexylbenzene (CHB) is a new green synthetic approach to cyclohexylbenzene-1-hydroperoxide (CHBHP), a key intermediate for preparing phenol and cyclohexanone. In this work, aryl-substituted (Cl and Br) derivatives of N-hydroxyphthalimide (NHPI) were synthesized and their catalytic performances for CHB oxidation were studied. In addition, geometric optimization and transition state search were performed using DFT calculations. Both experimental and theoretical studies have proven that chloro-substitution on NHPI can significantly improve its catalytic effects on the oxidation of CHB by oxygen. Compared with NHPI, CHB conversion and selectivity of CHBHP over Cl₄NHPI were increased by 10.47% and 13.24%. The strategy of aryl -substituting NHPI with halogen atoms proposed in this study would provide a potential way to the development of new NHPI-based catalysts for aerobic oxidation reactions.

关键词: N-hydroxyphthalimide, Aryl-substituted derivative, Cyclohexylbenzene, Oxidation, Radical

Yufei Yang, Jieyi Ma, Junyan Wu, Weixia Zhu, Yadong Zhang. Experimental and theoretical study on N-hydroxyphthalimide and its derivatives catalyzed aerobic oxidation of cyclohexylbenzene[J]. Chinese Journal of Chemical Engineering, 2022, 44(4): 124-130.

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