The Study of the Oxidation of N,N,N',N'-Tetramethyl-p-Phenylenediamine for the Clarification of the Differences in the Mechanisms of Biocatalytic and Chemical Polymerization of Aniline

Abstract

The oxidation of N,N,N',N'-tetramethyl-p-phenylenediamine (TMPD) using ammonium peroxydisulfate and the high redox potential laccase from Trametes hirsuta is studied in order to clarify the significant differences in the chemical and enzymatic polymerization reactions of aniline. As opposed to the laccase-catalyzed reaction, the chemical oxidation of TMPD proceeds in two stages. The radical cation formed at the first stage is oxidized by the peroxydisulfate ion to quinoiddiimine that can interact with the initial TMPD. The kinetics of the formation of the radical cation $${\text{TMP}}{{{\text{D}}}^{{\centerdot + }}}$$ is studied by ultraviolet–visible (UV–Vis) and electron paramagnetic resonance spectroscopy. The obtained data allow making an assumption about the difference in the mechanisms of chemical and enzymatic polymerization of aniline.