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Solid acid catalysis of tandem isomerization-lactonization of olefinic acids

Paper ID Volume ID Publish Year Pages File Format Full-Text
43902 45994 2007 7 PDF Available
Title
Solid acid catalysis of tandem isomerization-lactonization of olefinic acids
Abstract

The conversion of unsaturated acids to γ-lactones is catalyzed by the solid sulfonic acid catalysts Amberlyst-15 and Nafion SAC-13 in refluxing chlorobenzene. For 3- and 4-enoic acids, in which double bond migration is not required for γ-lactone formation, yields are 95–100%. For 5-, 6-, 9-, and 10-enoic acids, the lactone yield decreases from 95% to 25% as the distance between the olefin and carboxylic acid groups increases. Amberlyst-15 is the preferred catalyst in these reactions because of its lower cost and reusability.

Graphical abstractThe 5-, 6-, 9-, and 10-enoic acids (a) undergo tandem olefin migration followed by cyclization to give γ-lactone (b) products in 25-95% yields in the presence of Amberlyst-15 in refluxing chlorobenzene. In all of these reactions, the δ-lactone (c) forms initially and then rearranges to the final γ-lactone (b) product.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Lactonization; Tandem catalysis; Unsaturated carboxylic acids; Amberlyst-15; Nafion®
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Solid acid catalysis of tandem isomerization-lactonization of olefinic acids
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 333, Issue 2, 15 December 2007, Pages 238–244
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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