The potential of reactive distillation for xylenes manufacture via the toluene disproportionation reaction is considered in detail. The conventional process is carried out in the vapour phase over a fixed bed catalyst at elevated temperature and pressure. Process design and flowsheeting were carried out for both the conventional and reactive distillation processes using the Aspen Plus simulation package, specifically using the facility for evaluation of simultaneous reaction and physical equilibrium within a distillation column calculation block. Using the flowsheeting based process and equipment designs, a detailed comparative cost assessment and economic analysis of the two processes was performed. The economic evaluation is equivocal, and the reactive distillation process does not appear to offer significant benefits. While the reactive distillation approach does allow significant flowsheet simplification, the design compromises required to enable simultaneous reaction and distillation, particularly relating to design pressure, negate the inherent process benefits. Further, changes in reaction selectivity between the two reaction environments influenced not only the process product slate but also forced process design features to suppress an unwanted (heavy) by-product.