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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 1: 78 - 83

DOI: https://doi.org/10.6023/cjoc201908001

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

  • Chen Jingjing ,
  • Wang Yingshu ,
  • Yu Jun ,
  • Cheng Jiajia ,
  • Zheng Huidong
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  • 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 date: 2019-08-01

  Revised date: 2019-09-02

  Online 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 . DOI: 10.6023/cjoc201908001

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