Formation of a Third Liquid Phase and Its Reuse for Dibenzyl Ether Synthesis in a Tetraalkylammonium Salt Phase Transfer Catalytic System

This paper describes the formation of a third liquid phase in a phase transfer catalytic system in the presence of benzyl alcohol and potassium hydroxide, where dodecane and tetraalkylammonium bromide serve as organic solvent and catalyst, respectively. In this kind of system, a symmetrical ether (dibenzyl ether) was synthesized from benzyl chloride and benzyl alcohol at 323 K. In particular, the investigation demonstrates that the observed reaction rate constant depends on the length of the alkyl group of the catalyst. Tetrabutylammonium bromide exhibits the highest catalytic activity among the catalysts explored. With respect to the reuse of the third liquid phase, the results confirm that there is no decrease in phase transfer catalytic activity in three consecutive runs.