Soluble polymer-bound phase-transfer catalysts

New soluble polymer-bound phase-transfer catalysts (PTCs) were synthesized using commercially available oxidized polyethylene as the substrate polymer. These new polymeric compounds are bifunctional catalysts containing ether and quaternary ammonium groups attached to a polyethylene skeleton. They were prepared by direct amidation of oxidized polyethylene with diamino Jeffamines - diamino derivatives of poly(alkene) glycols - followed by a quaternization reaction. Their catalytic activity was studied in the nucleophilic substitution reaction of bromine atoms in 1,6-dibromohexane by cyanide and iodide anions. The activity of the PTCs was dependent on the nature of the starting reagents (oxidized polyethylene and polyglycol diamine), the procedure by which catalysts were synthesized, and the conditions of the substitution reaction. The temperature-dependent solubility of the PTC facilitates their use as homogeneous catalysts, since they can be separated out by filtration at the end of the reaction. The new catalysts can then easily be separated from the products and recovered without loss of activity.