Methanolysis of amides under high-temperature and high-pressure conditions with a continuous tubular reactor

Abstract

The methanolysis of amides, which is widely employed in the synthetic organic chemistry, hardly occurs under mild conditions. To safely and controllably intensify the methanolysis reaction with high-temperature and high-pressure environment, a continuous tubular reaction technology is developed, whose space–time yield is over twice of that of the conventional batch reaction. The methanolysis of acetanilide is selected as the representative reaction, and the influences of temperature, pressure, reactant and catalyst concentration, and residence time on the reaction performances are systematically investigated. Taking the advantages of precise temperature and reaction time control by the tubular reactor, the kinetics of acetanilide methanolysis are determined and compared to the kinetics of acetanilide hydrolysis reaction. The tubular reaction method is also employed to test a variety of other amides to show the effects of substituents, steric hindrance, and alkalinity on the reaction rate of methanolysis.