Polymer-supported pyridinium catalysts for synthesis of cyclic carbonate by reaction of carbon dioxide and oxirane

Abstract

Polymer-supported pyridinium salts, prepared by quaternarization of crosslinked poly(4-vinylpyridine) with alkyl halides, effectively catalyze the reaction of carbon dioxide (1 atm) and glycidyl phenyl ether (GPE) to afford the corresponding five-membered cyclic carbonate (4-phenoxymethyl-1,3-dioxolan-2-one). Poly(4-vinylpyridine) quarternarized with alkyl bromides show high catalytic activities, and the reaction of carbon dioxide (1 atm) and GPE at 100 °C affords 4-phenoxymethyl-1,3-dioxolan-2-one quantitatively in 6 h. The rate constant in the reaction of GPE and carbon dioxide in N-methyl pyrrolidinone using poly(4-vinylpyridine) quarternarized with n-butyl bromide (kobs = 102 min−1) is almost comparable with those for homogeneous catalysts with good activities (e.g., LiI), and the rate of the reaction obeys the first-order kinetics. A used catalyst may be recovered by centrifugation, and the recycled catalyst also promotes the reaction of GPE and carbon dioxide. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 5673–5678, 2007