Phase-Transfer-Catalyzed Etherification of 4,4-Bis(chloromethyl)-1,1-biphenyl with 1-Butanol by Polymer-Supported Catalysis

The synthesis of 4,4ʹ-bis(butanoxymethyl)-1,1ʹ-biphenyl from the reaction of 4,4ʹ-bis(chloromethyl)-1,1ʹ-biphenyl and 1-butanol catalyzed by a polymer with quaternary ammonium groups (triphase catalysis) was carried out in a chlorobenzene/aqueous solution of a KOH two-phase medium. The polymer-supported phase-transfer catalysts were prepared using free-radical polymerization of styrene (St) and 4-vinylbenzyl chloride (4-VBC), followed by quaternized copolymer beads with various tertiary amines. The copolymer particles thus produced are uniform without sieving. This work emphasizes the comparison of the reactivity of the various functional groups attached to the copolymer beads. The effects of the various reaction conditions such as the agitation speed, amount of water, triphase catalyst, potassium hydroxide, organic solvents, temperature, and reusability of the triphase catalyst on the conversion and the reaction rate were investigated. Experimental results show that the triphase catalysts with quaternary ammonium groups facilitate the etherification. A comparison of the reactivity between twophase and triphase catalysis in synthesizing 4,4ʹ-bis(butanoxymethyl)-1,1ʹ-biphenyl was made.