Catalytic Hydration of Aromatic Alkynes to Ketones over H-MFI Zeolites

doi:10.1007/s40242-021-1209-0

高等学校化学研究 ›› 2022, Vol. 38 ›› Issue (1): 173-180.doi: 10.1007/s40242-021-1209-0

Catalytic Hydration of Aromatic Alkynes to Ketones over H-MFI Zeolites

ZHANG Yunzhe, DAI Weili, WU Guangjun, GUAN Naijia, LI Landong

School of Materials Science and Engineering, Nankai University, Tianjin 300350, P. R. China

收稿日期:2021-05-08 修回日期:2021-05-26 出版日期:2022-02-01 发布日期:2022-01-20
通讯作者: LI Landong E-mail:lild@nankai.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China(No.22025203) and the Municipal Natural Science Fund of Tianjin, China(No.18JCJQJC47400).

Catalytic Hydration of Aromatic Alkynes to Ketones over H-MFI Zeolites

ZHANG Yunzhe, DAI Weili, WU Guangjun, GUAN Naijia, LI Landong

School of Materials Science and Engineering, Nankai University, Tianjin 300350, P. R. China

Received:2021-05-08 Revised:2021-05-26 Online:2022-02-01 Published:2022-01-20
Contact: LI Landong E-mail:lild@nankai.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China(No.22025203) and the Municipal Natural Science Fund of Tianjin, China(No.18JCJQJC47400).

摘要/Abstract

摘要： The hydration of alkyne represents the most straightforward and simplest route toward the synthesis of ketone. Herein, Brønsted acidic zeolites are explored as potential catalysts for the liquid-phase phenylacetylene hydration. The topology structure and Si/Al ratio are disclosed to be key factors controlling the catalytic activity of zeolites. Typically, H-MFI zeolite with a Si/Al molar ratio of 13 exhibits the highest catalytic activity, with turnover frequency of 6.0 h^-1 at 363 K. Besides, H-MFI zeolite shows good catalytic stability and recyclability in the reaction of phenylacetylene hydration, and the substrate scope can be simply extended to other soluble aromatic alkynes. The reaction mechanism of phenylacetylene hydration is investigated by means of kinetic and spectroscopic analyses. The Markovnikov electrophilic addition of phenylacetylene by hydrated protons is established as the rate-determining step, followed by deprotonation and enol isomerization to derive acetophenone product.

关键词: Phenylacetylene, Catalytic hydration, Zeolite, Brønsted acid site, H-MFI

Abstract: The hydration of alkyne represents the most straightforward and simplest route toward the synthesis of ketone. Herein, Brønsted acidic zeolites are explored as potential catalysts for the liquid-phase phenylacetylene hydration. The topology structure and Si/Al ratio are disclosed to be key factors controlling the catalytic activity of zeolites. Typically, H-MFI zeolite with a Si/Al molar ratio of 13 exhibits the highest catalytic activity, with turnover frequency of 6.0 h^-1 at 363 K. Besides, H-MFI zeolite shows good catalytic stability and recyclability in the reaction of phenylacetylene hydration, and the substrate scope can be simply extended to other soluble aromatic alkynes. The reaction mechanism of phenylacetylene hydration is investigated by means of kinetic and spectroscopic analyses. The Markovnikov electrophilic addition of phenylacetylene by hydrated protons is established as the rate-determining step, followed by deprotonation and enol isomerization to derive acetophenone product.

Key words: Phenylacetylene, Catalytic hydration, Zeolite, Brønsted acid site, H-MFI

ZHANG Yunzhe, DAI Weili, WU Guangjun, GUAN Naijia, LI Landong. Catalytic Hydration of Aromatic Alkynes to Ketones over H-MFI Zeolites[J]. 高等学校化学研究, 2022, 38(1): 173-180.

ZHANG Yunzhe, DAI Weili, WU Guangjun, GUAN Naijia, LI Landong. Catalytic Hydration of Aromatic Alkynes to Ketones over H-MFI Zeolites[J]. Chemical Research in Chinese Universities, 2022, 38(1): 173-180.

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Catalytic Hydration of Aromatic Alkynes to Ketones over H-MFI Zeolites

Catalytic Hydration of Aromatic Alkynes to Ketones over H-MFI Zeolites

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