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(Perfluoro)sulfonic acids having an imidazolium tag as homogeneous and reusable ionophilic Brönsted acid catalysts for carboxylic acid esterification

Paper ID Volume ID Publish Year Pages File Format Full-Text
42280 45918 2009 5 PDF Available
Title
(Perfluoro)sulfonic acids having an imidazolium tag as homogeneous and reusable ionophilic Brönsted acid catalysts for carboxylic acid esterification
Abstract

The concept of adding a peripheral imidazolium tag to obtain ionophilic sulfonic acids has been applied to the synthesis of four Brönsted acids having perfluoroalkyl and propyl linkers. The resulting sulfonic acids were tested as homogeneous and reusable Brönsted acid for the esterification of octanoic acid by n-propanol. It was found that while perfluoroalkyl sulfonic acids exhibit low catalytic activity due to miscibility problems, propylsulfonic acids were highly active and reusable. It was concluded that no strong Brönsted sites are necessary to promote this carboxylic esterification and that the fluorous properties of the perfluroalkyl chain (>30% fluorine in the imidazolium cation) play an adverse role on the catalytic activity under the conditions used.

Graphical abstractFour ionophilic Brönsted sulfonic acids having hydrocarbon or perfluorinated (see the structure) have been synthesised and their catalytic activity tested for the esterification of octanoic acid with n-propanol. It was found that imidazolium having a propylsulfonic acid is a highly active and reusable catalyst, while the perfluoro analogs exhibit considerably less activity.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Ioniphilic Brönsted acids; Perfluoroalkylsulfonic acids; Imidazolium Brönsted acids; Ionic liquids as catalysts; Esterification catalysts
First Page Preview
(Perfluoro)sulfonic acids having an imidazolium tag as homogeneous and reusable ionophilic Brönsted acid catalysts for carboxylic acid esterification
Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 369, Issues 1–2, 15 November 2009, Pages 133–137
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis