(54e) Kinetic Examination and Scale up of a Pt/V Catalyzed Nitro Reduction

In this presentation, we will discuss our kinetic and mechanistic observations of an industrially relevant metal catalyzed nitro reduction. The starting material for the reaction is a potential genotoxin; hence, there is a driver to understand the reaction mechanism and be able to forecast the starting material concentration profile. ReactIR monitoring was coupled with HPLC analysis to follow the starting material and product concentrations as a function of time. Experimental observations suggested the contribution of two reaction pathways, with one reaction pathway being strongly favored at normal reaction conditions. A reaction model was generated to forecast the starting material concentration profile as a function of temperature, catalyst concentration and starting material concentration. In addition, the purity of the starting material was determined to impact the reaction rate and was accounted for in the reaction rate model. The reaction model was used to optimize the reaction conditions and as a diagnostic tool to determine the extent of catalyst poisoning observed in a different vessel. Data will be presented from multiple scales (from 400 mL to 650 L).