Catalytic synthesis of N-alkylacrylamide from acrylonitrile and alcohol with solid acids

Catalytic synthesis of N-alkylacrylamides, which are useful monomers for fu nctional polymers, from acrylonitrile and alcohols, such as 1-adamantanol, tert-butyl alcohol, and isopropyl alcohol has been studied using various so lid acids including heteropoly compounds and zeolites. For the reaction wit h 1-adamantanol or tert-butyl alcohol, a heteropoly compound, Cs2.5H0.5PW12 O40, exhibited a high catalytic performance and water-tolerance. On the oth er hand, for the synthesis of N-isopropylacrylamide from isopropyl alcohol, a high-silica zeolite, H-ZSM-5 with Si/Al ratio of 37, showed an exception ally high activity, while it was less active in the reaction with tert-buty l alcohol or 1-adamantanol. This marked effect of reactant alcohol observed for H-ZSM-5 is probably due to shape selectivity. The prominent performanc e for N-isopropylacrylamide synthesis is attributable to a steric effect of the constrained pores; two reactants might be arranged adequately to form an intermediate in the pores. (C) 2000 Elsevier Science B.V. All rights res erved.