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Journal of Analytical Methods in Chemistry
Volume 2012 (2012), Article ID 452949, 10 pages
http://dx.doi.org/10.1155/2012/452949
Research Article

Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis

1Chemistry Department, University of Lleida, 25198 Lleida, Spain
2Food Technology Department, University of Lleida, 25198 Lleida, Spain

Received 30 November 2011; Revised 4 February 2012; Accepted 15 February 2012

Academic Editor: Boryana M. Nikolova-Damyanova

Copyright © 2012 Mireia Oromí-Farrús et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The use of iodine as a catalyst and either acetic or trifluoroacetic acid as a derivatizing reagent for determining the enantiomeric composition of acyclic and cyclic aliphatic chiral alcohols was investigated. Optimal conditions were selected according to the molar ratio of alcohol to acid, the reaction time, and the reaction temperature. Afterwards, chiral stability of chiral carbons was studied. Although no isomerization was observed when acetic acid was used, partial isomerization was detected with the trifluoroacetic acid. A series of chiral alcohols of a widely varying structural type were then derivatized with acetic acid using the optimal conditions. The resolution of the enantiomeric esters and the free chiral alcohols was measured using a capillary gas chromatograph equipped with a CP Chirasil-DEX CB column. The best resolutions were obtained with 2-pentyl acetates (α=3.00) and 2-hexyl acetates (α=1.95). This method provides a very simple and efficient experimental workup procedure for analyzing chiral alcohols by chiral-phase GC.