Solvent effects on Diels–Alder reaction in ionic liquids: A reaction density functional study

doi:10.1016/j.cjche.2023.10.007

中国化学工程学报 ›› 2024, Vol. 66 ›› Issue (2): 180-188.DOI: 10.1016/j.cjche.2023.10.007

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Solvent effects on Diels–Alder reaction in ionic liquids: A reaction density functional study

Zijiang Dou¹, Weiqiang Tang², Peng Xie¹, Shuangliang Zhao¹

1. Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology and School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;
2. State Key Laboratory of Chemical Engineering and School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China

收稿日期:2023-05-03 修回日期:2023-10-17 出版日期:2024-02-28 发布日期:2024-04-20
通讯作者: Peng Xie,E-mail:xiep@gxu.edu.cn;Shuangliang Zhao,E-mail:szhao@ecust.edu.cn
基金资助:
This work is supported by the National Natural Science Foundation of China (22168002, 22108070, and 21878078), the Natural Science Foundation of Guangxi Province (2020GXNSFAA159119), the Dean Project of Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (2021Z012), the Open Fund of the State Key Laboratory of Molecular Reaction Dynamics in DICP (SKLMRD-K202106) and the Young Elite Scientists Sponsorship Program by CAST (2022QNRC001).

Solvent effects on Diels–Alder reaction in ionic liquids: A reaction density functional study

Zijiang Dou¹, Weiqiang Tang², Peng Xie¹, Shuangliang Zhao¹

1. Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology and School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;
2. State Key Laboratory of Chemical Engineering and School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China

Received:2023-05-03 Revised:2023-10-17 Online:2024-02-28 Published:2024-04-20
Contact: Peng Xie,E-mail:xiep@gxu.edu.cn;Shuangliang Zhao,E-mail:szhao@ecust.edu.cn
Supported by:
This work is supported by the National Natural Science Foundation of China (22168002, 22108070, and 21878078), the Natural Science Foundation of Guangxi Province (2020GXNSFAA159119), the Dean Project of Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (2021Z012), the Open Fund of the State Key Laboratory of Molecular Reaction Dynamics in DICP (SKLMRD-K202106) and the Young Elite Scientists Sponsorship Program by CAST (2022QNRC001).

摘要/Abstract

摘要： Extensive experimental studies have been performed on the Diels–Alder (DA) reactions in ionic liquids (ILs), which demonstrate that the IL environment can significantly influence the reaction rates and selectivity. However, the underlying microscopic mechanism remains ambiguous. In this work, the multiscale reaction density functional theory is applied to explore the effect of 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF₆]) solvent on the reaction of cyclopentadiene (CP) with acrolein, methyl acrylate, or acrylonitrile. By analyzing the free energy landscape during the reaction, it is found that the polarization effect has a relatively small influence, while the solvation effect makes both the activation free energy and reaction free energy decrease. In addition, the rearrangement of local solvent structure shows that the cation spatial distribution responds more evidently to the reaction than the anion, and this indicates that the cation plays a dominant role in the solvation effect and so as to affect the reaction rates and selectivity of the DA reactions.

关键词: Solvent effect, Ionic liquids, Diels–Alder reaction, Reaction density functional theory

Abstract: Extensive experimental studies have been performed on the Diels–Alder (DA) reactions in ionic liquids (ILs), which demonstrate that the IL environment can significantly influence the reaction rates and selectivity. However, the underlying microscopic mechanism remains ambiguous. In this work, the multiscale reaction density functional theory is applied to explore the effect of 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF₆]) solvent on the reaction of cyclopentadiene (CP) with acrolein, methyl acrylate, or acrylonitrile. By analyzing the free energy landscape during the reaction, it is found that the polarization effect has a relatively small influence, while the solvation effect makes both the activation free energy and reaction free energy decrease. In addition, the rearrangement of local solvent structure shows that the cation spatial distribution responds more evidently to the reaction than the anion, and this indicates that the cation plays a dominant role in the solvation effect and so as to affect the reaction rates and selectivity of the DA reactions.

Key words: Solvent effect, Ionic liquids, Diels–Alder reaction, Reaction density functional theory

Zijiang Dou, Weiqiang Tang, Peng Xie, Shuangliang Zhao. Solvent effects on Diels–Alder reaction in ionic liquids: A reaction density functional study[J]. 中国化学工程学报, 2024, 66(2): 180-188.

Zijiang Dou, Weiqiang Tang, Peng Xie, Shuangliang Zhao. Solvent effects on Diels–Alder reaction in ionic liquids: A reaction density functional study[J]. Chinese Journal of Chemical Engineering, 2024, 66(2): 180-188.

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Solvent effects on Diels–Alder reaction in ionic liquids: A reaction density functional study

Solvent effects on Diels–Alder reaction in ionic liquids: A reaction density functional study

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