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Synthesis of Phenol Polymers Using Peroxidases

  • Matthias Reihmann
  • Helmut RitterEmail author
Chapter
Part of the Advances in Polymer Science book series (POLYMER, volume 194)

Abstract

This chapter deals with the peroxidase-catalyzed polymerization of phenol and its derivatives. Such a polymerization needs an oxidation reagent, normally hydrogen peroxide. Since this type of polymerization is believed to be a potential environmentally friendly alternative process for the production of phenol--formaldehyde resins, it has been investigated thoroughly by many research groups. Typical research challenges in this field are investigations regarding the polymerization mechanism, the mechanism of enzyme catalysis, the structure of the resulting phenol polymers, and, needless to say, the synthesis of new materials. A comprehensive overview is given that covers the progress made during recent years, starting from the synthesis of simple resins obtained from unsubstituted phenol and leading up to the production of polyaromatic materials having multiple reactive groups in the side chain. One key for successful work in this field is to understand the characteristics of the enzyme. However, it is also important to be familiar with the influences of different solvents and various concentrations of the reactants (monomer, enzyme, hydrogen peroxide) on the yield, molecular weight, and structure of the resulting polymers. In other words, peroxidase-catalyzed polymerization is an interdisciplinary area covering different fields, mainly biochemistry, organic chemistry, and polymer chemistry for the synthesis of phenol polymers, as well as physical chemistry to understand their properties. This chapter tries to emphasize this aspect.

Enzyme catalysis Horseradish peroxidase Green chemistry Phenol polymer Polyphenol 

Abbreviations

AOT

Bis(2-ethylhexyl)sodium sulfosuccinate

BOD

Bilirubin oxidase

BPA

Poly(isopropylidenediphenol) resin

CP/MASS

Cross polarization/magic angle sample spinning

DIMEB

Heptakis(2,6-di-O-methyl)-β-cyclodextrin

FT-IR

Fourier-transform infrared

HEPES

N-(2-Hydroxyethyl)piperazine-N′-(2-ethanesulfonic acid)

HOMO

Highest occupied molecular orbital

HPLC

High-performance liquid chromatography

HRP

Horseradish peroxidase

LUMO

Lowest unoccupied molecular orbital

MALDI-TOF

Matrix-assisted laser desorption/ionization time-of-flight

MMA

Methyl methacrylate

MPL

Laccase from Myceliophthore

PCL

Laccase from Pycnoporus coccineus

PEG

Polyethylene glycol

PPO

Poly(phenylene oxide)

RAMEB

Randomly 2,6-dimethylated β-cyclodextrin

SBP

Soybean peroxidase

TEED

N,N,N′,N′-tetraethylethylenediamine

TVL

Laccase from Trametes versicolor

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Authors and Affiliations

  1. 1.Institute of Organic and Macromolecular Chemistry IIHeinrich-Heine University of DüsseldorfDüsseldorfGermany

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