The hydrogenation of carbobenzoxy phenylalanine was investigated in order to better understand the influence of mass transfer effects in four-phase fixed-bed reactor systems. In this reaction, the carbobenzoxy phenylalanine is dissolved in an organic solvent and is reacted with a gas in the presence of a hydrophilic catalyst (Pd/Al2O3). An aqueous phase is also required to dissolve the reaction product, leading to a four-phase gas-liquid-liquid-solid system. Results indicate that higher liquid flow rates lead to faster rates of reaction due to improved contact efficiency between the organic phase and catalyst. Similar performance was observed through experiment and modeling in two fixed-bed reactor configurations (trickle-bed reactor and gas-liquid cocurrent upflow reactor) at higher liquid flow rates.