CeO2-Catalyzed Synthesis of 2-Imidazolidinone from Ethylenediamine Carbamate.

Abstract

CeO2 acted as an effective and reusable heterogeneous catalyst for the direct synthesis of 2-imidazolidinone from ethylenediamine carbamate (EDA-CA) without further addition of CO2 in the reaction system. 2-Propanol was the best solvent among the solvents tested from the viewpoint of selectivity to 2-imidazolidinone, and the use of an adequate amount of 2-propanol provided high conversion and selectivity for the reaction. This positive effect of 2-propanol on the catalytic reaction can be explained by the solubility of EDA-CA in 2-propanol under the reaction conditions and no formation of solvent-derived byproducts. This catalytic system using the combination of the CeO2 catalyst and the 2-propanol solvent provided 2-imidazolidinone in up to 83% yield on the EDA-CA basis at 413 K under Ar. The reaction conducted under Ar showed a higher reaction rate than that with pressured CO2, which clearly demonstrated the advantage of the catalytic system operated at low CO2 pressure or even without CO2.