Utilizing a Simulated Moving Bed (SMB), the conditions for separating bupivacaine enantiomers, a racemic local anesthetic, were determined by triangle theory and simulations using the gPROMS software and the Aspen Chromatography package. The 5MB model in this study assumed an axial dispersion flow for the liquid phase and the intraparticle mass transfer was described in terms of a simple Linear Driving Force (LDF) approximation. The parameters (a and b) of the Langmuir Adsorption Isotherm (LAI) were determined using a dynamic method. In the optimal condition the calculated concentrations were confirmed by the experimental results. Values projected by the gPROMS software more closely matched experimental values than those projected by the Aspen Chromatography package.