Issue 20, 2023

Polystyrene-supported imidazolium acidic ionic liquids: highly efficient catalysts for the synthesis of bisphenols

Abstract

A series of reusable polystyrene-supported imidazolium acidic ionic liquid catalysts were synthesized to replace industrial sulfuric acid for the synthesis of bisphenol compounds. These ionic liquids were covalently bonded to the support, reaching a high loading of 1.62–1.80 mmol g−1, respectively. As expected, they achieved a catalytic effect comparable to that of sulfuric acid in the condensation reaction of 9-fluorenone with phenol. Under the optimum reaction parameters, a high yield and high selectivity of 99.9% and 99.7% were achieved for 9,9-bis(4-hydroxyphenyl)fluorene (BHPF). Moreover, this catalyst was also employed for synthesizing other bisphenol compounds and 99.0% conversion of the substrate was achieved. Based on the experimental results and density functional theory (DFT) calculations, a possible reaction mechanism was proposed, which indicated that 9-fluorenone and phenol were simultaneously activated through the synergistic catalysis of anions and cations in a polystyrene-supported ionic liquid catalyst. The recycling experiment results suggested that [PS-PsIm][CF3SO3] maintained a high catalytic activity in five reaction runs, making this a promising catalyst for the synthesis of bisphenol compounds.

Graphical abstract: Polystyrene-supported imidazolium acidic ionic liquids: highly efficient catalysts for the synthesis of bisphenols

Supplementary files

Article information

Article type
Paper
Submitted
29 Mar 2023
Accepted
25 Apr 2023
First published
25 Apr 2023

New J. Chem., 2023,47, 9894-9904

Polystyrene-supported imidazolium acidic ionic liquids: highly efficient catalysts for the synthesis of bisphenols

D. Su, F. Xu, H. Wang, J. Xie, S. Wang, M. Jiang, M. Feng, Z. Zhang, Z. Song and N. Liu, New J. Chem., 2023, 47, 9894 DOI: 10.1039/D3NJ01453C

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