Volume 9 Issue 1
Feb.  2024
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Article Navigation >  Green Energy&Environment  > 2024  >  9(1): 114-125
Yang Zhou, Qiang Zeng, Hongyan He, Kejia Wu, Fuqiao Liu, Xuehui Li. Role of methoxy and Cα-based substituents in electrochemical oxidation mechanisms and bond cleavage selectivity of β-O-4 lignin model compounds. Green Energy&Environment, 2024, 9(1): 114-125. doi: 10.1016/j.gee.2022.05.006
Citation: Yang Zhou, Qiang Zeng, Hongyan He, Kejia Wu, Fuqiao Liu, Xuehui Li. Role of methoxy and Cα-based substituents in electrochemical oxidation mechanisms and bond cleavage selectivity of β-O-4 lignin model compounds. Green Energy&Environment, 2024, 9(1): 114-125. doi: 10.1016/j.gee.2022.05.006
shu

Role of methoxy and Cα-based substituents in electrochemical oxidation mechanisms and bond cleavage selectivity of β-O-4 lignin model compounds

doi: 10.1016/j.gee.2022.05.006

  • a. School of Chemistry and Chemical Engineering, The Guangdong Provincial Key Laboratory of Green Chemical Product Technology, State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou, Guangdong, 510640, China;

  • b. CAS Key Laboratory of Green Process and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing, 100190, China

Funds:

The authors gratefully acknowledge the financial support of the Natural Science Foundation of China, China (Grant No. 21975082 and 21736003), the Guangdong Basic and Applied Basic Research Foundation (Grant Number: 2019A1515011472 and 2022A1515011341) and the Science and Technology Program of Guangzhou (Grant Number: 202102080479).

  • Received date 26 March 2022, Accepted date 23 May 2022, RevRecd date 19 May 2022, Publish date 07 June 2022,
    Abstract
  • In order to better understand the specific substituent effects on the electrochemical oxidation process of β-O-4 bond, a series of methoxyphenyl type β-O-4 dimer model compounds with different localized methoxyl groups, including 2-(2-methoxyphenoxy)-1-phenylethanone, 2-(2-methoxyphenoxy)-1-phenylethanol, 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethanone, 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethanol, 2-(2,6-dimethoxyphenoxy)-1-(4-methoxyphenyl)ethanone, 2-(2,6-dimethoxyphenoxy)-1-(4-methoxyphenyl)ethanol have been selected and their electrochemical properties have been studied experimentally by cyclic voltammetry, and FT-IR spectroelectrochemistry. Combining with electrolysis products distribution analysis and density functional theory calculations, oxidation mechanisms of all six model dimers have been explored. In particular, a total effect from substituents of both para-methoxy (on the aryl ring closing to C) and C-OH on the oxidation mechanisms has been clearly observed, showing a significant selectivity on the C-C bond cleavage induced by electrochemical oxidations.

     

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