High-efficiency and safe synthesis of tonalid via two Friedel-Crafts reactions in continuous-flow microreactors

doi:10.1016/j.cjche.2021.09.028

中国化学工程学报 ›› 2022, Vol. 52 ›› Issue (12): 126-135.DOI: 10.1016/j.cjche.2021.09.028

• Full Length Article • 上一篇下一篇

High-efficiency and safe synthesis of tonalid via two Friedel-Crafts reactions in continuous-flow microreactors

Yang Han, Yuanyuan Liu, Shiwei Wang, Xuehui Ge, Xiaoda Wang, Ting Qiu

Engineering Research Center of Reactive Distillation, Fujian Province Higher Education Institutes, College of Chemical Engineering, Fuzhou University, Fuzhou 350108, China Qingyuan Innovation Laboratory, Quanzhou 362801, China

收稿日期:2021-08-01 修回日期:2021-09-03 出版日期:2022-12-28 发布日期:2023-01-31
通讯作者: Xiaoda Wang,E-mail:xdwang@fzu.edu.cn;Ting Qiu,E-mail:tingqiu@fzu.edu.cn
基金资助:
We acknowledge the financial support for this work from the National Natural Science Foundation of China (No. 21706034), the Natural Science Foundation of Fujian Province (No. 2021J01645), and the Key Program of Qingyuan Innovation Laboratory (No. 00221004).

High-efficiency and safe synthesis of tonalid via two Friedel-Crafts reactions in continuous-flow microreactors

Yang Han, Yuanyuan Liu, Shiwei Wang, Xuehui Ge, Xiaoda Wang, Ting Qiu

Engineering Research Center of Reactive Distillation, Fujian Province Higher Education Institutes, College of Chemical Engineering, Fuzhou University, Fuzhou 350108, China Qingyuan Innovation Laboratory, Quanzhou 362801, China

Received:2021-08-01 Revised:2021-09-03 Online:2022-12-28 Published:2023-01-31
Contact: Xiaoda Wang,E-mail:xdwang@fzu.edu.cn;Ting Qiu,E-mail:tingqiu@fzu.edu.cn
Supported by:
We acknowledge the financial support for this work from the National Natural Science Foundation of China (No. 21706034), the Natural Science Foundation of Fujian Province (No. 2021J01645), and the Key Program of Qingyuan Innovation Laboratory (No. 00221004).

摘要/Abstract

摘要： Tonalid, an important fragrance ingredient with widespread application, was synthesized via two Friedel-Crafts reactions, which were catalyzed by AlCl₃. The traditional tonalid production was conducted in batch stirring tank reactors, suffering from low production capacity and the safety hazard of temperature runaway. To solve these problems, the continuous-flow technologies were developed for the high-efficiency and intrinsically safe synthesis of tonalid in microreactors. Catalyst AlCl₃ was neatly homogenized in proper solvents by forming complex with reactant, which was a necessary step for the continuous synthesis in microreactors. Several reaction conditions, including reactant molar ratio, catalyst concentration, temperature, and microchannel hydrodynamic diameter, were investigated for the two Friedel-Crafts reactions in microreactors. At optimized conditions, the yields of the two Friedel-Crafts reactions were 44.15% and 97.55%, respectively. In comparison with the batch reactors, the reaction times of these two reactions could both be reduced by nearly two thirds in microreactors at the similar yield.

关键词: Microreactor, Continuous synthesis, Process intensification, Tonalid, Friedel-Crafts reaction

Abstract: Tonalid, an important fragrance ingredient with widespread application, was synthesized via two Friedel-Crafts reactions, which were catalyzed by AlCl₃. The traditional tonalid production was conducted in batch stirring tank reactors, suffering from low production capacity and the safety hazard of temperature runaway. To solve these problems, the continuous-flow technologies were developed for the high-efficiency and intrinsically safe synthesis of tonalid in microreactors. Catalyst AlCl₃ was neatly homogenized in proper solvents by forming complex with reactant, which was a necessary step for the continuous synthesis in microreactors. Several reaction conditions, including reactant molar ratio, catalyst concentration, temperature, and microchannel hydrodynamic diameter, were investigated for the two Friedel-Crafts reactions in microreactors. At optimized conditions, the yields of the two Friedel-Crafts reactions were 44.15% and 97.55%, respectively. In comparison with the batch reactors, the reaction times of these two reactions could both be reduced by nearly two thirds in microreactors at the similar yield.

Key words: Microreactor, Continuous synthesis, Process intensification, Tonalid, Friedel-Crafts reaction

Yang Han, Yuanyuan Liu, Shiwei Wang, Xuehui Ge, Xiaoda Wang, Ting Qiu. High-efficiency and safe synthesis of tonalid via two Friedel-Crafts reactions in continuous-flow microreactors[J]. 中国化学工程学报, 2022, 52(12): 126-135.

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High-efficiency and safe synthesis of tonalid via two Friedel-Crafts reactions in continuous-flow microreactors

High-efficiency and safe synthesis of tonalid via two Friedel-Crafts reactions in continuous-flow microreactors

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