Issue 3, 2024

A study on the reaction pathway and mechanism of urea alcoholysis by the disassociation and conjugation of groups

Abstract

The chemical conversion of alcohols to carbonates, which are high value-added products, is considered a green transformation route; however, the underlying reaction mechanism remains unclear and needs further study. Considering the synthesis of ethylene carbonate (EC) from urea and ethylene glycol (EG) as a model reaction using tetrabutylphosphonium bromide ([P4444][Br]) and zinc bromide (ZnBr2) as the binary catalyst, the yield and selectivity of EC could reach 83.07% and 95.38%, respectively. Subsequently, the qualitative and quantitative analyses of major components in the reaction were performed via GC-MS, 1H NMR, 13C NMR, and kinetics studies. Additionally, three catalysis processes catalyzed by [P4444][Br], ZnBr2, and [P4444][Br]/ZnBr2 catalysts were detected by in situ FT-IR spectra. Meanwhile, the possible reaction pathway and mechanism of the formation of EC from urea and EG was systematically studied according to the variation tendencies of a range of functional groups. The introduction of a catalyst as a judging criterion for determining the rates of group disassociation and conjugation on substrates and products provided a new reference basis for the evaluation of catalytic reaction processes and the performance of catalysts.

Graphical abstract: A study on the reaction pathway and mechanism of urea alcoholysis by the disassociation and conjugation of groups

Supplementary files

Article information

Article type
Paper
Submitted
24 Oct 2023
Accepted
16 Nov 2023
First published
20 Nov 2023

React. Chem. Eng., 2024,9, 604-618

A study on the reaction pathway and mechanism of urea alcoholysis by the disassociation and conjugation of groups

J. Wang, J. Huang, S. Chen, J. Zhang, L. Dong and X. Zhang, React. Chem. Eng., 2024, 9, 604 DOI: 10.1039/D3RE00558E

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