Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis
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 rea...
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| Format: | Article |
| Language: | English |
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Wiley
2012-01-01
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| Series: | Journal of Analytical Methods in Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2012/452949 |
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| author | Mireia Oromí-Farrús Mercè Torres Ramon Canela |
| author_facet | Mireia Oromí-Farrús Mercè Torres Ramon Canela |
| author_sort | Mireia Oromí-Farrús |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-3c4e0b97692c444d8e57abf6b576cc6c |
| institution | OA Journals |
| issn | 2090-8865 2090-8873 |
| language | English |
| publishDate | 2012-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Analytical Methods in Chemistry |
| spelling | doaj-art-3c4e0b97692c444d8e57abf6b576cc6c2025-08-20T02:08:18ZengWileyJournal of Analytical Methods in Chemistry2090-88652090-88732012-01-01201210.1155/2012/452949452949Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC AnalysisMireia Oromí-Farrús0Mercè Torres1Ramon Canela2Chemistry Department, University of Lleida, 25198 Lleida, SpainFood Technology Department, University of Lleida, 25198 Lleida, SpainChemistry Department, University of Lleida, 25198 Lleida, SpainThe 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.http://dx.doi.org/10.1155/2012/452949 |
| spellingShingle | Mireia Oromí-Farrús Mercè Torres Ramon Canela Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis Journal of Analytical Methods in Chemistry |
| title | Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis |
| title_full | Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis |
| title_fullStr | Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis |
| title_full_unstemmed | Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis |
| title_short | Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis |
| title_sort | acylation of chiral alcohols a simple procedure for chiral gc analysis |
| url | http://dx.doi.org/10.1155/2012/452949 |
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