Acylation of chiral alcohols: a simple procedure for chiral GC analysis

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Fecha de publicación
2012
Autor/a
Oromí Farrús, Mireia
Torres i Grifo, Mercè
Canela i Garayoa, Ramon
Cita recomendada
Oromí Farrús, Mireia; Torres i Grifo, Mercè; Canela i Garayoa, Ramon; . (2012) . Acylation of chiral alcohols: a simple procedure for chiral GC analysis. Journal of Analytical Methods in Chemistry, 2012, vol. 2012, ID 452949, p. 1-10. https://doi.org/10.1155/2012/452949.
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Resumen
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.
URI
http://hdl.handle.net/10459.1/46366
DOI
https://doi.org/10.1155/2012/452949
Es parte de
Journal of Analytical Methods in Chemistry, 2012, vol. 2012, ID 452949, p. 1-10
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