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

doi:10.1016/j.cjche.2021.06.017

中国化学工程学报 ›› 2022, Vol. 44 ›› Issue (4): 124-130.DOI: 10.1016/j.cjche.2021.06.017

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

Yufei Yang¹, Jieyi Ma¹, Junyan Wu¹, Weixia Zhu¹, Yadong Zhang^1,2

1 School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China;
2 Jiyuan Research Institute, Zhengzhou University, Jiyuan 459000, China

收稿日期:2020-09-17 修回日期:2021-05-12 出版日期:2022-04-28 发布日期:2022-06-18
通讯作者: Yadong Zhang,E-mail:zhangyadong2016@163.com
基金资助:
This work was financially supported by the National Natural Science Foundation of China (21706240). We would like to acknowledge all the reviewers for their valuable suggestions and Prof. Fuqiang Zhang of School of Chemistry and Material Science in Shanxi Normal University for DFT calculations.

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

Yufei Yang¹, Jieyi Ma¹, Junyan Wu¹, Weixia Zhu¹, Yadong Zhang^1,2

1 School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China;
2 Jiyuan Research Institute, Zhengzhou University, Jiyuan 459000, China

Received:2020-09-17 Revised:2021-05-12 Online:2022-04-28 Published:2022-06-18
Contact: Yadong Zhang,E-mail:zhangyadong2016@163.com
Supported by:
This work was financially supported by the National Natural Science Foundation of China (21706240). We would like to acknowledge all the reviewers for their valuable suggestions and Prof. Fuqiang Zhang of School of Chemistry and Material Science in Shanxi Normal University for DFT calculations.

摘要/Abstract

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

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

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]. 中国化学工程学报, 2022, 44(4): 124-130.

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

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

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