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O. V. Morozova, M. E. Khlupova, I. S. Vasil’eva, G. P. Shumakovich, E. A. Zaitseva, A. I. Yaropolov

Study of N,N,N′,N′-tetramethyl-p-phenylenediamine oxidation for clarification of biocatalytic and chemical aniline polymerization mechanism

Abstract

The chemical and enzymatic polymerization of aniline has significant differences, which were studied by the oxidation of N, N, N′, N′-tetramethyl-p-phenylenediamine (TMPD) using ammonium peroxide disulfate and the highly redox potential lacase Trametes hirsuta. In contrast to the laccase-catalyzed reaction, the chemical oxidation of TMPD proceeds in two stages. The radical cation formed in the first stage is oxidized by the peroxydisulfate ion to quinoiddiimine, which can interact with the original TMPD. The kinetics of the formation of the TMPD∙+ was studied by UV-visible and EPR spectroscopy. The received results enabled us to make an assumption about the difference in the mechanisms of chemical and enzymatic polymerization of aniline.
Key words: biocatalysis, laccase, aniline, polymerization, tetramethyl-p-phenylenediamine, oxidation mechanism.
Moscow University Chemistry Bulletin.
2020, Vol. 61, No. 3, P. 243
   

Copyright (C) Chemistry Dept., Moscow State University, 2002
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