OXIDATIVE POLYMERIZATION OF 2,6-DISUBSTITUTED PHENOLS CATALYZED BY IRON-SALEN COMPLEX
- 22 June 1999
- journal article
- Published by Taylor & Francis in Journal of Macromolecular Science, Part A
- Vol. 36 (5) , 719-730
- https://doi.org/10.1081/ma-100101559
Abstract
Oxidative polymerization of 2,6-disubstituted phenols has been performed by using iron(III)-salen complex and hydrogen peroxide as catalyst and oxidizing agent, respectively. The oxidative reaction of 2,6-dimethylphenol produced the polymer along with a byproduct dimer of 3,5,3',5'-tetramethyl-4,4'-dipheno-quinone. The addition of pyridine suppressed the formation of the dimer to mainly give the polymer with molecular weight of more than 1×104 in high yields. From NMR analysis, the polymer was found to consist of exclusively 1,4-oxyphenylene unit. Effects of the solvent composition, added amount and type of amine, and catalyst amount have been systematically investigated. 2-Allyl-6-methylphenol and 2,6-diphenylphenol produced the corresponding polymer under the similar polymerizaconditions, whereas the formation of C-C coupling dimer was observed in using 2,6-diisopropylphenol and 2,6-dimethoxyphenol as monomer.Keywords
This publication has 25 references indexed in Scilit:
- A versatile and efficient synthesis of alkoxyamine LFR initiators via manganese based asymmetric epoxidation catalystsJournal of Polymer Science Part A: Polymer Chemistry, 1998
- Chemoselective Polymerization of a Phenol Derivative Having a Methacryl Group by Peroxidase CatalystMacromolecules, 1998
- Modified Poly(2,6-dimethyl-1,4-phenylene ether)s Prepared by RedistributionMacromolecules, 1997
- Polymeric catalysts for chemo- and enantioselective epoxidation of olefins: New crosslinked chiral transition metal complexing polymersJournal of Polymer Science Part A: Polymer Chemistry, 1997
- Enzymatic Synthesis and Thermal Properties of a New Class of PolyphenolBulletin of the Chemical Society of Japan, 1996
- Synthesis of a New Family of Phenol Resin by Enzymatic Oxidative PolymerizationChemistry Letters, 1994
- Catalytic Asymmetric Epoxidation with (Salen)manganese(III) Complex Bearing Binaphthyl Groups of Axial ChiralitySynlett, 1993
- Polyaniline: A historical surveySynthetic Metals, 1990
- PolyethersPublished by American Chemical Society (ACS) ,1975
- Polymerization by oxidative coupling. II. Oxidation of 2,6‐disubstituted phenolsJournal of Polymer Science, 1962