Highly efficient synthesis of cyclic ureas from CO2 and diamines by a pure CeO2 catalyst using a 2-propanol solvent

Masazumi Tamura, Kensuke Noro, Masayoshi Honda, Yoshinao Nakagawa, Keiichi Tomishige

Research output: Contribution to journalArticlepeer-review

77 Citations (Scopus)

Abstract

Pure cerium oxide (CeO2) acts as an effective and reusable heterogeneous catalyst for direct synthesis of cyclic ureas from CO2 and diamines even at a low CO2 pressure of 0.3 MPa. 2-Propanol is the most preferable solvent to provide good selectivity. The system composed of a CeO2 catalyst and a 2-propanol solvent is applied to various diamines to provide the corresponding cyclic ureas in high yields (78-98%), including six-membered-ring ureas that are difficult to be synthesized from CO 2. Based on the kinetic studies on the effect of CO2 pressure and amine concentration and FTIR studies on adsorption of ethylenediamine and CO2 onto CeO2, the following mechanism for the synthesis of cyclic urea is proposed: (1) formation of carbamic acid and carbamate species on CeO2, (2) decomposition of carbamic acid to a free amino group and CO2, (3) nucleophilic attack of the amino group on the carbamate on CeO2 to produce the cyclic urea and (4) desorption of the product and regeneration of CeO2.

Original languageEnglish
Pages (from-to)1567-1577
Number of pages11
JournalGreen Chemistry
Volume15
Issue number6
DOIs
Publication statusPublished - 2013 Jun

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution

Fingerprint

Dive into the research topics of 'Highly efficient synthesis of cyclic ureas from CO<sub>2</sub> and diamines by a pure CeO<sub>2</sub> catalyst using a 2-propanol solvent'. Together they form a unique fingerprint.

Cite this