Issue 20, 2019

Epoxide ring-opening reaction promoted by ionic liquid reactivity: interplay of experimental and theoretical studies

Abstract

Ionic liquids (ILs) have been widely introduced recently into the epoxide ring-opening reaction as catalysts or solvent without considering the chemical stability of ILs in propylene oxide (PO). Through a combination of electrospray-ionization quadrupole time-of-flight mass spectrometry (ESI-QTOF-MS) investigations and quantum-chemical calculations, we demonstrate that AC- (acetate) and MC-(methylcarbonate) based ILs exhibit modified activity for ring opening of PO compared with the reaction between ILs and epoxide compounds. The chemically unstable ILs and the solvent effect can also dominate the catalytic performance of the coupling reaction of PO with methanol. Based on these findings, we further design the reaction process for highly efficient synthesis of propylene glycol methyl ether, in which the yield of the main product increased more than 40% under the same ILs catalysts. The results explained how the chemical instability and substrate affected the PO coupling reaction and further controlled it.

Graphical abstract: Epoxide ring-opening reaction promoted by ionic liquid reactivity: interplay of experimental and theoretical studies

Associated articles

Supplementary files

Article information

Article type
Communication
Submitted
17 May 2019
Accepted
20 Aug 2019
First published
21 Aug 2019

Catal. Sci. Technol., 2019,9, 5567-5571

Epoxide ring-opening reaction promoted by ionic liquid reactivity: interplay of experimental and theoretical studies

S. Chen, G. Zeng, Y. Li, B. He, R. Liu and S. Zhang, Catal. Sci. Technol., 2019, 9, 5567 DOI: 10.1039/C9CY00953A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements