Enzymatic oxidative polymerization of 4-hydroxybenzoic acid derivatives to poly(phenylene oxide)s

✍ Scribed by Ikeda, Ryohei; Sugihara, Junji; Uyama, Hiroshi; Kobayashi, Shiro

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 251 KB
• Volume: 47
• Category: Article
• ISSN: 0959-8103
• DOI: 10.1002/(sici)1097-0126(199811)47:3<295::aid-pi7>3.0.co;2-w

✦ Synopsis

Enzymatic oxidative polymerization of 4-hydroxybenzoic acid derivatives using oxidoreductases has been carried out in an aqueous organic solvent at room temperature under air. The monomers used in this study were 4hydroxybenzoic acid, 3,5-dimethoxy-4-hydroxybenzoic acid (syringic acid) and 3,5-dimethyl-4-hydroxybenzoic acid. The latter two monomers were subjected to oxidative polymerization using horseradish peroxidase (HRP), which involved elimination of carbon dioxide and hydrogen from the monomer to produce poly(1,4-oxyphenylene). Oxidoreductases, soybean and Coprinus cinerius peroxidases, Pycnoporus coccineus and Myceliophthore laccases, were active for the polymerization and the enzyme type and its origin greatly a †ected the polymerization behaviour. The e †ects of solvent composition have been systematically investigated with respect to polymer yield and molecular weight. In the case of HRP-catalysed polymerization of syringic acid, the highest molecular weight (1É5 ] 104) was achieved in acetone/phosphate bu †er (pH 7) (40 : 60 vol%). NMR, IR and matrix-assisted laser desorption/ionizationÈtime of Ñight mass spectroscopic analyses of the polymer showed that the present polymer consisted made exclusively of 1,4-oxyphenylene unit and that the terminal structure was a carboxylic acid group at one end and a phenolic hydroxyl group at the other.

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