Macroporous Monolithic Poly(4-vinylbenzyl chloride) Columns for Organic Synthesis Facilitation by In Situ Polymerization of High Internal Phase Emulsions

摘要

PolyHIPE materials are produced by polymerizing the continuous phase of emulsions where the internal phase volume fraction is higher than 74%. Columns of flow-through supports for immobilized scavengers and reagents were prepared by polymerizing the continuous phase of high internal phase emulsions containing 4-vinylbenzyl chloride and divinylbenzene. Emulsions were placed in containers and polymerized in situ. Highly porous (80% pore volume) monolithic columns with chloromethyl functionalities and crosslinked with divinylbenzene (6% or 40%) were obtained and functionalized by a flow-through method, immobilizing tris(2-amino-ethyl)amine, diethanolamine, and 4-bromopherylboronic acid. Columns with immobilized tris(2-aminoethyl)amine were applied for the effective removal of acid chlorides from the solution pumped through the column. Flow properties (back pressure versus flow rate) were characterized for dichloromethane, N,N-dimethylformamide and acetonitrile. High effectiveness of columns were demonstrated by an over 90% of acid chloride removal from the solution after a single pass-flow of the solution through the column. The morphology of the column material was characterized by scanning electron microscopy and showed no damage of the material after the flow-through utilization. Good permeative properties of the interconnected porous structure make polyHIPE columns good candidates for supports for reagents and catalysts.