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Effect of polymer characteristics on Beckmann rearrangement of polymer supported ketoximes
Author(s) -
Baby Shiney,
Devaky K S
Publication year - 2002
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.1067
Subject(s) - beckmann rearrangement , polymer chemistry , copolymer , polymer , chemistry , styrene , polystyrene , oxime , pyridine , organic chemistry
Abstract Beckmann rearrangement has been carried out in polymeric oximes synthesised from rigid styrene–divinylbenzene copolymer and flexible styrene–hexanediol diacrylate (HDODA) copolymer. Oxime functions were incorporated into these polymers through a series of polymer‐analogous reactions. First the polymers were subjected to Friedel‐Crafts acylation reactions with low molecular weight acid chlorides to give a set of polymeric ketones. These polymeric ketones were converted to oximes by treating with hydroxylamine hydrochloride in the presence of pyridine. The oximes were subjected to rearrangement under acidic conditions into substituted amides. The polymeric amides obtained were characterised by IR spectroscopy and chemical degradative analysis. The rearrangement in the macromolecular matrices were found to follow the same mechanistic path as in the low molecular weight analogues. The rate of rearrangement was found to be faster in the HDODA crosslinked polystyrene system. © 2002 Society of Chemical Industry