Enzymatic oxidative polymerization of bisphenol-a to a new class of soluble polyphenol

Abstract

SUMMARY Enzymatic oxidative polymerization of bisphenol-A was carried out in an aqueous organic solvent using horseradish and soybean peroxidases (HRP and SBP, respectively) as catalysts. The SBP-catalyzed polymerization in an equivolume mixture of methanol and phosphate buffer (pH 7.0) affords a new class of polyphenol quantitatively, which is readily soluble in polar organic solvents such as acetone, methanol, N,Ndimethylformamide, and dimethyl sulfoxide, but insoluble in chloroform, diethyl ether, and water. NMR and IR analyses show that the polymer is mainly composed of a mixture of phenylene and oxyphenylene units. The effects of the type of enzyme and the solvent composition were systematically investigated in respect to the yield and molecular weight of the polymer. The thermal treatment of the polymer produces an insoluble product and the curing temperature and the molecular weight of the starting polymer affect the thermal properties of the product. Crosslinking reaction of the present polyphenol with an epoxide resin affords insoluble polymeric material showing high thermal stability.

A multidisciplinary investigation of the technical and environmental performances of TAML/peroxide elimination of Bisphenol A compounds from water

“…Oligomers such as those reported are commonly produced in enzyme-catalysed polymerizations of phenols [347][348][349] including 1a. [350][351][352][353][354] The initial step is often proposed to be a one-electron oxidation of the AH 2 or AH − forms of 1a to produce phenolate radicals which can then couple to give higher molecular weight products. [350][351][352][353][354] Our study mirrors the enzymatic results.…”

“…[350][351][352][353][354] The initial step is often proposed to be a one-electron oxidation of the AH 2 or AH − forms of 1a to produce phenolate radicals which can then couple to give higher molecular weight products. [350][351][352][353][354] Our study mirrors the enzymatic results. There is little doubt that the oxidation starts with 1-electron oxidation of either AH 2 or AH − forms of 1a.…”

Hydrophobic Polymers from Food Waste: Resources and Synthesis

“…Research in the polymerization of phenol derivatives has also used HRP [231][232][233][234][235] and lacasse [236][237][238] as catalytic enzymes. Of interest for this review is the polymerization of caffeic acid, which is found in the phenolic compounds of potato waste.…”

Thermal behavior and phase morphology of miscible hydrogen‐bonded blends of poly(ϵ‐caprolactone) and enzymatically polymerized polyphenol

“…PDHDPE has the same characteristic hydroxyl groups as its monomer DHDPE, which has the ability to form intermolecular hydrogen bonds with PCL. The polymer has better thermostability than the monomer in the process, since enzymatically polymerized polyphenol can be thermally cured at appropriate temperature under vacuum 13. It is reasonable to expect that the addition of PDHDPE would greatly improve the Young's modulus of PCL, if a miscible blend system was achieved.…”