Chemical Reactions Used in Derivatization

Moldoveanu, Serban C.; David, Víctor

doi:10.1016/s0301-4770(02)80019-7

Cited by 1 publication

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“…Acylation reduces polarity and enhances the separation of chiral compounds in the chromatographic column, as well as conferring better volatility. Typically, only derivatization with acetyl groups or with fluorinated acyl groups up to heptafluorobutyryl improves volatility [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

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

Oromí-Farrús

Torres

Canela

2012

Journal of Analytical Methods in Chemistry

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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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Section: Introductionmentioning

confidence: 99%