In the present study, the kinetics for synthesizing dibenzyl phthalate via solid-liquid phase-transfer catalysis under anhydrous conditions was investigated. The esterification of benzyl bromide and solid reactant dipotassium phthalate was carried out in a stirred batch reactor. The behavior of the active intermediate in solid-liquid phases was explored to understand its catalytic characteristics. The effects of agitation speeds, concentration of reactants, phase-transfer catalysts, organic solvents, amounts of catalysts used, and reaction temperatures were all investigated. A kinetic model describing the reactions in a solid-liquid system was also proposed. From the experimental results, the reaction rate increases with increasing agitation speed, polarity of organic solvent, and temperature even without adding water and can be described by the pseudo-second-order kinetics. The reaction rate was extremely slow without using catalysts even at a higher temperature. The apparent rate constants as well as the activation energies for various phase-transfer catalysts were obtained. The present study provides an insight on the catalytic behaviors of solid-liquid phase-transfer catalysis.