Citation: 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. doi: 10.6023/cjoc201908001 shu

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

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

Corresponding author: Wang Yingshu, 1187562077@qq.com
Received Date: 1 August 2019
Revised Date: 2 September 2019
Available Online: 18 January 2019
Fund Project: the National Natural Science Foundation of China 21476049the University-Industry Cooperation Project of Fujian Province 2019H6010the Industrial Technology Joint Innovation Special Project of Fujian Province FG-2016005Project 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)the Regional Development Project of Fujian Province 2016H4023the Program for New Century Excellent Talents in University of Fujian Province HG2017-17

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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.
- 2-ethyl-3-methylpyrazine (EMP),
- 2-acetyl-3-methylpyrazine (AMP),
- allylic oxidation,
- reaction mechanism,
- kinetics,
- scale-up
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1.
沈阳化工大学材料科学与工程学院沈阳 110142