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

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Fecha de publicación
2012Cita 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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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.
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Journal of Analytical Methods in Chemistry, 2012, vol. 2012, ID 452949, p. 1-10Proyectos de investigación europeos
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