Oxidation of benzyl alcohols to ketones and aldehydes by O3 process enhanced using high-gravity technology

doi:10.1016/j.cjche.2020.02.015

中国化学工程学报 ›› 2020, Vol. 28 ›› Issue (3): 808-814.DOI: 10.1016/j.cjche.2020.02.015

• Catalysis, Kinetics and Reaction Engineering • 上一篇下一篇

Oxidation of benzyl alcohols to ketones and aldehydes by O₃ process enhanced using high-gravity technology

Wenqiang Gao^1,2, Lei Du¹, Weizhou Jiao¹, Youzhi Liu¹

1 Shanxi Province Key Laboratory of Higee-Oriented Chemical Engineering, North University of China, Taiyuan 030051, China;
2 Department of Chemistry and Chemical Engineering, Luliang University, Luliang, 033000, China

收稿日期:2019-12-11 修回日期:2020-02-10 出版日期:2020-03-28 发布日期:2020-06-11
通讯作者: Weizhou Jiao
基金资助:
This work was supported by the Specialized Research Fund for Sanjin Scholars Program of Shanxi Province (201707), Key Research & Development Plan of Shanxi Province (201903D321059), Shanxi Scholarship Council of China (2019032) and Shanxi Graduate Education Innovation Project (2019BY106).

Oxidation of benzyl alcohols to ketones and aldehydes by O₃ process enhanced using high-gravity technology

Wenqiang Gao^1,2, Lei Du¹, Weizhou Jiao¹, Youzhi Liu¹

1 Shanxi Province Key Laboratory of Higee-Oriented Chemical Engineering, North University of China, Taiyuan 030051, China;
2 Department of Chemistry and Chemical Engineering, Luliang University, Luliang, 033000, China

Received:2019-12-11 Revised:2020-02-10 Online:2020-03-28 Published:2020-06-11
Contact: Weizhou Jiao
Supported by:
This work was supported by the Specialized Research Fund for Sanjin Scholars Program of Shanxi Province (201707), Key Research & Development Plan of Shanxi Province (201903D321059), Shanxi Scholarship Council of China (2019032) and Shanxi Graduate Education Innovation Project (2019BY106).

摘要/Abstract

摘要： In this study, a practical process for ozonization of benzyl alcohols to ketones and aldehydes in a rotating packed bed (RPB-O₃) reactor has been developed. Using 1-phenylethanol as a model reactant, the performance of RPB-O₃ process in different solvents has been compared with the commonly used stirred tank reactor (STR-O₃). Ethyl acetate was the optimum solvent for the conversion of 1-phenylenthanol to acetophenone in RPB-O₃ process, with 78% yield after 30 min. In a parallel STR-O₃ experiment, the yield of acetophenone was 50%. Other experimental variables, i.e. O₃ concentration, reaction time, high-gravity factor and liquid flow rate were also optimized. The highest yield of acetophenone was obtained using O₃ concentration of 80 mg·L^-1, reaction time of 30 min, high gravity factor of 40 and liquid flow rate of 120 L·h^-1. Under the optimized reaction conditions, a series of structurally diverse primary and secondary alcohols was oxidized with (19%-92%) yield. The ozonization mechanism was studied by Electron Paramagnetic Resonance (EPR) spectroscopy, monitoring the radical species formed upon self-decomposition of O₃. The characteristic quadruple peak with the 1:2:2:1 intensity ratio that corresponds to hydroxyl radicals (·OH) was observed in the electron paramagnetic resonance (EPR) spectrum, indicating an indirect oxidation mechanism of alcohols via ·OH radical.

关键词: Ozone, Benzyl alcohols, Aldehydes and ketones, High-gravity technology

Abstract: In this study, a practical process for ozonization of benzyl alcohols to ketones and aldehydes in a rotating packed bed (RPB-O₃) reactor has been developed. Using 1-phenylethanol as a model reactant, the performance of RPB-O₃ process in different solvents has been compared with the commonly used stirred tank reactor (STR-O₃). Ethyl acetate was the optimum solvent for the conversion of 1-phenylenthanol to acetophenone in RPB-O₃ process, with 78% yield after 30 min. In a parallel STR-O₃ experiment, the yield of acetophenone was 50%. Other experimental variables, i.e. O₃ concentration, reaction time, high-gravity factor and liquid flow rate were also optimized. The highest yield of acetophenone was obtained using O₃ concentration of 80 mg·L^-1, reaction time of 30 min, high gravity factor of 40 and liquid flow rate of 120 L·h^-1. Under the optimized reaction conditions, a series of structurally diverse primary and secondary alcohols was oxidized with (19%-92%) yield. The ozonization mechanism was studied by Electron Paramagnetic Resonance (EPR) spectroscopy, monitoring the radical species formed upon self-decomposition of O₃. The characteristic quadruple peak with the 1:2:2:1 intensity ratio that corresponds to hydroxyl radicals (·OH) was observed in the electron paramagnetic resonance (EPR) spectrum, indicating an indirect oxidation mechanism of alcohols via ·OH radical.

Key words: Ozone, Benzyl alcohols, Aldehydes and ketones, High-gravity technology

Wenqiang Gao, Lei Du, Weizhou Jiao, Youzhi Liu. Oxidation of benzyl alcohols to ketones and aldehydes by O₃ process enhanced using high-gravity technology[J]. 中国化学工程学报, 2020, 28(3): 808-814.

Wenqiang Gao, Lei Du, Weizhou Jiao, Youzhi Liu. Oxidation of benzyl alcohols to ketones and aldehydes by O₃ process enhanced using high-gravity technology[J]. Chinese Journal of Chemical Engineering, 2020, 28(3): 808-814.

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Oxidation of benzyl alcohols to ketones and aldehydes by O₃ process enhanced using high-gravity technology

Oxidation of benzyl alcohols to ketones and aldehydes by O₃ process enhanced using high-gravity technology

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