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Synthesis, characterization and use of polymer-supported phase transfer catalyst in organic reactions

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Abstract

A polymer-supported (PS) phase transfer catalyst, polyethylene-g-quaternary ammonium salt (PE-g-QN+), is prepared through a three-step graft copolymerization of maleic anhydride (MAn) onto polyethylene (PE) by photochemical method using 1% benzophenone (Bz) as photosensitizer. Post grafted acid hydrolysis of polyethylene-g-maleic anhydride (PE-g-MAn) results in the preparation of PE-g-succinic acid which on further treatment with tetrabutylammonium bromide (TBAB) under basic conditions in tetrahydrofuran (THF) gives PE-g-QN+. Optimum conditions pertaining to maximum percentage of grafting have been evaluated as a function of concentration of maleic anhydride, amount of photosensitizer, and time of reaction. Maximum percentage of grafting (25%) was obtained using 3.57 mol of MAn and 0.5 mL of 1% Bz in 120 min. The PE and graft copolymers, PE-g-MAn, and PE-g-QN+ were characterized by FTIR Spectroscopy and thermogravimetric analysis (TGA). The ionic nature of quaternary ammonium salt, PE-g-QN+ has also been confirmed by conductance measurements. PE-g-QN+ reagent have been used successfully for polymerization, amidation, and esterification reactions. The products obtained were characterized by FTIR and H1NMR spectral methods. The reagent was reused for the further reactions and it was observed that the polymeric reagent polymerize, amidate, and esterificate the compounds successfully but with little lower product yield. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011

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