A Green and Scalable Cobalt(II)-Catalyzed Oxidation of 2-Ethyl-3-methylpyrazine

doi:10.6023/cjoc201908001

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 78-83.DOI: 10.6023/cjoc201908001 Previous Articles Next Articles

钴(II)催化2-乙基-3-甲基吡嗪绿色氧化方法

陈晶晶^a,b, 王莹淑^b, 余珺^b, 成佳佳^c, 郑辉东^b

a 福州大学材料科学与工程学院福州 350108;
b 福州大学石油化工学院福州 350108;
c 福州大学化学学院福州 350108

收稿日期:2019-08-01 修回日期:2019-09-02 发布日期:2019-09-18
通讯作者: 王莹淑 E-mail:1187562077@qq.com
基金资助:
国家自然科学基金（No.21476049）、福建省科技厅区域发展项目（No.2016H4023）、福建省科技厅高校产学合作项目（No.2019H6010）、福建省发改委产业技术联合创新专项（No.FG-2016005）、福建省高等学校新世纪优秀人才支持计划（No.HG2017-17）资助项目.

A Green and Scalable Cobalt(II)-Catalyzed Oxidation of 2-Ethyl-3-methylpyrazine

Chen Jingjing^a,b, Wang Yingshu^b, Yu Jun^b, Cheng Jiajia^c, Zheng Huidong^b

a College of Materials Science and Engineering, Fuzhou University, Fuzhou 350108;
b College of Chemical Engineering, Fuzhou University, Fuzhou 350108;
c College of Chemistry, Fuzhou University, Fuzhou 350108

Received:2019-08-01 Revised:2019-09-02 Published:2019-09-18
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21476049), the Regional Development Project of Fujian Province (No. 2016H4023), the University-Industry Cooperation Project of Fujian Province (No. 2019H6010), the Industrial Technology Joint Innovation Special Project of Fujian Province (No. FG-2016005) and the Program for New Century Excellent Talents in University of Fujian Province (No. HG2017-17).

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Abstract

A green and scalable oxidation of 2-ethyl-3-methylpyrazine (EMP) by tert-butylhydroperoxide was investigated with a catalytic system of cobalt(II) and N-containing ligand. The effects of catalyst, ligand, solvent and temperature were compared, and the catalysis system of cobalt(II) acetylacetonate and 2,2-bipyridine gave the highest selectivity. Mechanistic study of this catalysis system suggested that the oxidation of EMP followed a free radical oxidation pathway, and a homogeneous reaction kinetics model was established to calculate the reaction rate constant and activation energy. The scale-up of the oxidation system was performed to check the scalability of the oxidation reaction, and the temperature control of the system was the key part of the process.

Key words: 2-ethyl-3-methylpyrazine (EMP), 2-acetyl-3-methylpyrazine (AMP), allylic oxidation, reaction mechanism, kinetics, scale-up

Cite this article

Chen Jingjing, Wang Yingshu, Yu Jun, Cheng Jiajia, Zheng Huidong. A Green and Scalable Cobalt(II)-Catalyzed Oxidation of 2-Ethyl-3-methylpyrazine[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 78-83.

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钴(II)催化2-乙基-3-甲基吡嗪绿色氧化方法

A Green and Scalable Cobalt(II)-Catalyzed Oxidation of 2-Ethyl-3-methylpyrazine

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