Jump to main content
Jump to site search

Issue 5, 2014
Previous Article Next Article

p-Sulfonic acid calix[n]arenes: the most active and water tolerant organocatalysts in esterification reactions

Author affiliations

Abstract

This work reports the novel results obtained from an in situ kinetic study, which was conducted via1H NMR, of the palmitic acid esterification reaction with deuterated methanol in the presence of organocatalysts: p-sulfonic acid calix[6]arene, p-hydroxybenzenesulfonic acid and p-toluenesulfonic acid. The kinetic order of reaction relative to the catalyst concentration and the main thermodynamic properties, such as the activation energy (ΔE), entropy variation (ΔS), enthalpy variation (ΔH) and Gibbs free energy variation (ΔG), were obtained. The results indicated that p-sulfonic acid calix[6]arene was the most active organocatalyst in esterification reactions, regardless of temperature or catalyst concentration employed. Additionally, by performing the reactions in the presence of increasing amounts of water, it was found that p-sulfonic acid calix[n]arenes are more tolerant to water than the other catalysts investigated. This result, when combined with the kinetic and thermodynamic measurements, may explain their highest catalytic activity.

Graphical abstract: p-Sulfonic acid calix[n]arenes: the most active and water tolerant organocatalysts in esterification reactions

Back to tab navigation

Supplementary files

Article information


Submitted
20 Dec 2013
Accepted
12 Feb 2014
First published
13 Feb 2014

Catal. Sci. Technol., 2014,4, 1369-1375
Article type
Paper
Author version available

p-Sulfonic acid calix[n]arenes: the most active and water tolerant organocatalysts in esterification reactions

R. Natalino, E. V. V. Varejão, M. J. da Silva, A. L. Cardoso and S. A. Fernandes, Catal. Sci. Technol., 2014, 4, 1369
DOI: 10.1039/C3CY01081C

Social activity

Search articles by author

Spotlight

Advertisements