Modeling of Toluene Acetylation with Acetic Anhydride on H-USY Zeolite

The liquid-phase acetylation of toluene with acetic anhydride was carried out in a continuous-flow reactor over H-USY zeolites with different Si/Al ratios at 180 °C, at different contact times and feed compositions. H-USY is an active catalyst for this reaction because the main reaction products at all times on stream are the desired methylacetophenone (MAP) and its reaction byproduct acetic acid. Within the different MAP isomers, the selectivity toward 4-MAP equals 85%. Although the initial acetic anhydride conversion is 100%, the zeolite is subject to deactivation. Small amounts of side products such as methylbenzoic acid and isopropenyltoluene were also identified and their formation explained. The data and insights obtained during these experiments were used to obtain models describing the formation of MAP and the other components present in the reactor effluent. The most plausible model, obtained via model discrimination, was validated at different reaction conditions and takes into account adsorption of the chemical compounds, the catalytic reactions, and deactivation of the catalyst. It also includes hydrolysis of acetic anhydride and the formation of side products originating from MAP. According to this model, catalyst deactivation starts from MAP and acetic anhydride, whereby acetic acid is liberated. Fitting of the model to the experimental data shows that the kinetic constant for the formation of 4-MAP is comparable to that of the deactivation reaction.