Friedel-Crafts alkylation of mesitylene with tert-butyl alcohol over novel solid acid catalyst UDCaT-5

Abstract

Alkylation of mesitylene with tert-butyl alcohol in the presence of novel mesoporous superacidic catalysts, namely, UDCaT-4, UDCaT-5 and UDCaT-6 was investigated. The catalysts are modified versions of zirconia showing high catalytic activity, stability and reusability in the presence of water as compared to conventional sulfated zirconia. The catalytic activity is in the order: UDCaT-5 (most active) > UDCaT-6 > UDCaT-4 > sulfated zirconia (S-ZrO2) (least active). The synergistic effect of the very high sulfur content present (9% w/w S) and the preservation of the tetragonal phase in UDCaT-5, in comparison with sulfated zirconia (4% w/w S), were responsible for higher catalytic activity. A catalyst ensuring the production of 2-tert-butyl-mesitylene (2-TBMT) with 98% selectivity and 94% conversion of tert-butanol (TBA) was developed under optimum reaction conditions. The formation of products is correlated with the acidity of the catalyst. The reactions were conducted in liquid phase at relatively low reaction temperatures (120150 °C). A systematic investigation of the effects of various operating parameters was accomplished and a mathematical model is developed to describe the reaction pathway and validated with experimental results. The reaction was carried out without using any solvent in order to make the process cleaner and greener. An overall second order kinetic equation was used to fit the experimental data, under the assumption that both mesitylene and tert-butanol are weakly adsorbed. An independent dehydration study of tert-butanol (TBA) was also done.