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.