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