Preparation of aldoxime through direct ammoximation using titanium silicalite-1 catalyst

doi:10.1016/j.cjche.2021.08.016

Chinese Journal of Chemical Engineering ›› 2022, Vol. 47 ›› Issue (7): 11-17.DOI: 10.1016/j.cjche.2021.08.016

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Preparation of aldoxime through direct ammoximation using titanium silicalite-1 catalyst

Zhigang Xu^1,2, Xiongfei Jin¹, Tao Zhou¹, Qian Zou², Longcheng Liu², zhongbo Wang², Hanbing Sheng², Huasheng Xie³

1. Hunan Provincial Key Laboratory of Efficient and Clean Utilization of Manganese Resources, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China;
2. Kopperchem Industry Corp., LTD, Solvent Extraction Engineering Research Center, Chongqing 401221, China;
3. Cangzhou Dahua Group Co., Ltd., Cangzhou 061000, China

Received:2021-03-23 Revised:2021-08-13 Online:2022-08-19 Published:2022-07-28
Contact: Tao Zhou,E-mail:zhoutao@csu.edu.cn
Supported by:
The authors acknowledge the financial support on this research from the National Natural Science Foundation of China (21376269), the Hunan Provincial Science and Technology Plan, China (2016TP1007) and the independent exploration and innovation project for graduate students of Central South University (2020zzts403).

Preparation of aldoxime through direct ammoximation using titanium silicalite-1 catalyst

Zhigang Xu^1,2, Xiongfei Jin¹, Tao Zhou¹, Qian Zou², Longcheng Liu², zhongbo Wang², Hanbing Sheng², Huasheng Xie³

1. Hunan Provincial Key Laboratory of Efficient and Clean Utilization of Manganese Resources, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China;
2. Kopperchem Industry Corp., LTD, Solvent Extraction Engineering Research Center, Chongqing 401221, China;
3. Cangzhou Dahua Group Co., Ltd., Cangzhou 061000, China

通讯作者: Tao Zhou,E-mail:zhoutao@csu.edu.cn
基金资助:
The authors acknowledge the financial support on this research from the National Natural Science Foundation of China (21376269), the Hunan Provincial Science and Technology Plan, China (2016TP1007) and the independent exploration and innovation project for graduate students of Central South University (2020zzts403).

Abstract

Abstract: The liquid phase direct ammoximation of 5-isooctyl salicylaldehyde with ammonia and hydrogen peroxide was studied using titanium silicalite-1 (TS-1) catalyst. The effect of reaction parameters on the yield of the product was studied, which include reaction temperature, reaction time, molar ratio of ammonia to aldehyde as well as hydrogen peroxide to aldehyde. The influence of the amount of catalyst on the reaction results was also investigated. The maximum 5-isooctyl salicylaldoxime yield of 98.76% was achieved under the following optimal reaction conditions:the molar ratio of 5-isooctylaldehyde to hydrogen peroxide and ammonia of 1:1.4:1.6, the reaction temperature of 70℃, the amount of TS-1 of 17.5 g·mol^-1 (5-isooctyl salicylaldehyde), and the feeding time of 2 h. This method has the mild reaction conditions and avoids the shortcomings of traditional methods. Moreover, useless inorganic salts by-products are avoided, and there is no environmental pollution.

Key words: Titanium silicalite-1, Ammoximation, Aldoxime, Extractant, Process optimization

摘要： The liquid phase direct ammoximation of 5-isooctyl salicylaldehyde with ammonia and hydrogen peroxide was studied using titanium silicalite-1 (TS-1) catalyst. The effect of reaction parameters on the yield of the product was studied, which include reaction temperature, reaction time, molar ratio of ammonia to aldehyde as well as hydrogen peroxide to aldehyde. The influence of the amount of catalyst on the reaction results was also investigated. The maximum 5-isooctyl salicylaldoxime yield of 98.76% was achieved under the following optimal reaction conditions:the molar ratio of 5-isooctylaldehyde to hydrogen peroxide and ammonia of 1:1.4:1.6, the reaction temperature of 70℃, the amount of TS-1 of 17.5 g·mol^-1 (5-isooctyl salicylaldehyde), and the feeding time of 2 h. This method has the mild reaction conditions and avoids the shortcomings of traditional methods. Moreover, useless inorganic salts by-products are avoided, and there is no environmental pollution.

关键词: Titanium silicalite-1, Ammoximation, Aldoxime, Extractant, Process optimization

Zhigang Xu, Xiongfei Jin, Tao Zhou, Qian Zou, Longcheng Liu, zhongbo Wang, Hanbing Sheng, Huasheng Xie. Preparation of aldoxime through direct ammoximation using titanium silicalite-1 catalyst[J]. Chinese Journal of Chemical Engineering, 2022, 47(7): 11-17.

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Preparation of aldoxime through direct ammoximation using titanium silicalite-1 catalyst

Preparation of aldoxime through direct ammoximation using titanium silicalite-1 catalyst

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