Open AccessCeO2-Catalyzed Synthesis of 2-Imidazolidinone from Ethylenediamine Carbamate
Author(s) -
Jie Peng,
Masazumi Tamura,
Mizuho Yabushita,
Ryotaro Fujii,
Yoshinao Nakagawa,
Keiichi Tomishige
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.1c04516
Subject(s) - ethylenediamine , chemistry , catalysis , selectivity , yield (engineering) , solvent , carbamate , solubility , propanol , organic chemistry , inorganic chemistry , materials science , ethanol , metallurgy
CeO 2 acted as an effective and reusable heterogeneous catalyst for the direct synthesis of 2-imidazolidinone from ethylenediamine carbamate (EDA-CA) without further addition of CO 2 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 CeO 2 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 CO 2 , which clearly demonstrated the advantage of the catalytic system operated at low CO 2 pressure or even without CO 2 .