Issue 30, 2021

Covalent anchoring of N-hydroxyphthalimide on silica via robust imide bonds as a reusable catalyst for the selective aerobic oxidation of ethylbenzene to acetophenone

Abstract

Currently, the aerobic oxidation of ethylbenzene to acetophenone has been found to be efficient and environmentally friendly, but homogeneous N-hydroxyphthalimide (NHPI), being active in the catalytic transformation suffers from separation and recovery. Here, NHPI was covalently anchored on commercial SiO2 using symmetric aromatic dianhydrides and (3-aminopropyl) triethoxysilane as precursors and a linking molecule, respectively, and the grafting bonds formed were convincing based on their IR absorption, chemical state(s) of N atoms, and the decomposition temperatures. Also, the catalyst synthesized using pyromellitic dianhydride (PMDA) as the precursor presented a grafting density of 0.70 mmolN–OH gsilica−1. The immobilized NHPI catalyzed the selective aerobic oxidation of ethylbenzene to acetophenone, and an ethylbenzene conversion of 63.8% and a selectivity to acetophenone of 79.0% were observed under optimal reaction conditions. An excellent catalytic reusability of the grafted NHPI catalyst was observed in repeated evaluations and this could be attributed to the confirmed stability of the structure and composition arising from the robust imide bonds anchoring. The anchoring method and the resulting NHPI catalysts could open access to converting organics with benzylic C–H bond(s) into their oxygenated value-added products, suggesting a promising application prospect.

Graphical abstract: Covalent anchoring of N-hydroxyphthalimide on silica via robust imide bonds as a reusable catalyst for the selective aerobic oxidation of ethylbenzene to acetophenone

Supplementary files

Article information

Article type
Paper
Submitted
15 Mar 2021
Accepted
27 Jun 2021
First published
28 Jun 2021

New J. Chem., 2021,45, 13441-13450

Covalent anchoring of N-hydroxyphthalimide on silica via robust imide bonds as a reusable catalyst for the selective aerobic oxidation of ethylbenzene to acetophenone

G. Shi, Y. Feng, S. Xu, Q. Lu, Y. Liang, E. Yuan and L. Ji, New J. Chem., 2021, 45, 13441 DOI: 10.1039/D1NJ01268A

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