Kinetics of N-Substituted Amide Hydrolysis in Hot Compressed Water Using ZrO2 Catalyst

Hydrolysis reactions of N-substituted amides in hot compressed water with ZrO2 were investigated. ZrO2 was used as a typical solid base catalyst. Through the kinetic analysis of several N-substituted amides with the Taft equation, the inductive, steric, and hydrogen bonding effects of N-substituent on the hydrolysis reaction rate were evaluated quantitatively. The N-substitution strongly affected the hydrolysis reaction rate with ZrO2. The inductive and steric effects of N-substituent on the reaction rate with ZrO2 were suggested to be almost the same as that with homogeneous base catalyst (NaOH). On the other hand, the reaction rate with ZrO2 was less suppressed by hydrogen bonding between the amide groups H atom and water or the other amide compared to that with NaOH.