Ionic liquid catalyzed solvent-free synthesis of chalcone and its derivatives under mild conditions

doi:10.1016/j.cjche.2020.09.013

Chinese Journal of Chemical Engineering ›› 2021, Vol. 33 ›› Issue (5): 160-166.DOI: 10.1016/j.cjche.2020.09.013

• Catalysis, Kinetics and Reaction Engineering • Previous Articles Next Articles

Ionic liquid catalyzed solvent-free synthesis of chalcone and its derivatives under mild conditions

Qiu Zhao^1,2, Gang Wang^2,3, Fuxia Liao², Yifan Sha¹, Fei Xu², Chunshan Li^2,3, Zengxi Li^2,3, Yijun Cao¹

1 School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou 450001, China;
2 Key Laboratory of Green Process and Engineering, State Key Laboratory of Multiphase Complex Systems, Beijing Key Laboratory of Ionic Liquids Clean Process, Institute of;
Process Engineering, Chinese Academy of Sciences, Beijing 100190, China;
3 School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, China

Received:2020-03-20 Revised:2020-08-30 Online:2021-08-19 Published:2021-05-28
Contact: Yijun Cao
Supported by:
We thank the financial support of Major Program of National Natural Science Foundation of China (21890762), General Program of National Natural Science Foundation of China (21878293), National Natural Science Foundation of China (21676270), Key Research Program of Frontier Sciences, CAS (QYZDY-SSW-JSC011) and the K. C. Wong Education Foundation (GJTD-2018-04).

Ionic liquid catalyzed solvent-free synthesis of chalcone and its derivatives under mild conditions

Qiu Zhao^1,2, Gang Wang^2,3, Fuxia Liao², Yifan Sha¹, Fei Xu², Chunshan Li^2,3, Zengxi Li^2,3, Yijun Cao¹

1 School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou 450001, China;
2 Key Laboratory of Green Process and Engineering, State Key Laboratory of Multiphase Complex Systems, Beijing Key Laboratory of Ionic Liquids Clean Process, Institute of;
Process Engineering, Chinese Academy of Sciences, Beijing 100190, China;
3 School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, China

通讯作者: Yijun Cao
基金资助:
We thank the financial support of Major Program of National Natural Science Foundation of China (21890762), General Program of National Natural Science Foundation of China (21878293), National Natural Science Foundation of China (21676270), Key Research Program of Frontier Sciences, CAS (QYZDY-SSW-JSC011) and the K. C. Wong Education Foundation (GJTD-2018-04).

Abstract

Abstract: An ionic liquid (IL) catalyzed solvent-free process was developed for the direct synthesis of chalcone and its derivatives by using substituted acetophenones and benzaldehydes via aldol reaction under mild conditions. A series of acidic and basic ILs were selected and screened. The influences of cations and reaction conditions on product yield and selectivity were systematically investigated. The [Bmim]OH was identified as the optimal IL, with the highest yield and selectivity reaching up to 96.7% and 100%, respectively. A reaction mechanism-based kinetic model was established and regressed with experimental data, revealing the β-Hydroxylketone dehydrolysis with activation barrier of 37.8 kJ·mol^-1 was observed as the ratecontrolling step.

Key words: Ionic liquid, Chalcone, Aldol reaction, Kinetic model

摘要： An ionic liquid (IL) catalyzed solvent-free process was developed for the direct synthesis of chalcone and its derivatives by using substituted acetophenones and benzaldehydes via aldol reaction under mild conditions. A series of acidic and basic ILs were selected and screened. The influences of cations and reaction conditions on product yield and selectivity were systematically investigated. The [Bmim]OH was identified as the optimal IL, with the highest yield and selectivity reaching up to 96.7% and 100%, respectively. A reaction mechanism-based kinetic model was established and regressed with experimental data, revealing the β-Hydroxylketone dehydrolysis with activation barrier of 37.8 kJ·mol^-1 was observed as the ratecontrolling step.

关键词: Ionic liquid, Chalcone, Aldol reaction, Kinetic model

Qiu Zhao, Gang Wang, Fuxia Liao, Yifan Sha, Fei Xu, Chunshan Li, Zengxi Li, Yijun Cao. Ionic liquid catalyzed solvent-free synthesis of chalcone and its derivatives under mild conditions[J]. Chinese Journal of Chemical Engineering, 2021, 33(5): 160-166.

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Ionic liquid catalyzed solvent-free synthesis of chalcone and its derivatives under mild conditions

Ionic liquid catalyzed solvent-free synthesis of chalcone and its derivatives under mild conditions

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