Phase-transfer catalytic reaction of 4,4′-bis(chloromethyl)-1,1′-biphenyl and 1-butanol in a two-phase medium

The phase-transfer catalyzed etherification of 4,4'-bis(chloromethyl)-1,1'-biphenyl was investigated in an alkaline aqueous solution/organic solvent two-phase medium. During or after completion of the reaction, the monosubstituted product (4,4'-(butoxymethyl chloromethyl)-1,1'-biphenyl) and disubstituted product (4,4'-bis(butoxymethyl)-1,1'-biphenyl) were both produced. The reaction was enhanced by adding a small quantity of quaternary ammonium salt. A generalized model, which included the aqueous- and organic-phase reactions, the mass transfer of regenerated catalyst and active catalyst, and the phase equilibria of the regenerated catalyst and the active catalyst between two phases, was built up to describe the system performance. The purpose of this work is to examine effects of agitation, amount of organic solvent, quaternary ammonium salts, amount of tetrabutylammonium bromide, amount of potassium hydroxide, amount of water, organic solvents, and temperature on the conversion of the reactant. The kinetics are well described by a pseudo-first-order rate law. A rational explanation of the results was made. Products of high purity were also obtained using pressurized column chromatography.