Chiral microemulsion electrokinetic chromatography: Effect of cosurfactant identity on enantioselectivity, methylene selectivity, resolution, and other chromatographic figures of merit

The effect of cosurfactant identity on microemulsion size, elution range, retention factor, enantioselectivity, methylene selectivity, efficiency, and resolution in chiral microemulsion formulations was examined. The chiral surfactant dodecoxycarbonylvaline was used in conjunction with the cosurfact...

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Bibliographic Details
Published in:Electrophoresis 2006-11, Vol.27 (21), p.4321-4333
Main Authors: Kahle, Kimberly A., Foley, Joe P.
Format: Article
Language:English
Subjects:
Acetates - chemistry
Capillary Electrochromatography - methods
Chiral separation
Cosurfactant
Dodecoxycarbonylvaline
Emulsions
Ephedrine - analogs & derivatives
Ephedrine - isolation & purification
Fatty Alcohols - chemistry
Microemulsion EKC
Particle Size
Sensitivity and Specificity
Stereoisomerism
Surface-Active Agents - chemistry
Valine - analogs & derivatives
Valine - chemistry
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Summary:The effect of cosurfactant identity on microemulsion size, elution range, retention factor, enantioselectivity, methylene selectivity, efficiency, and resolution in chiral microemulsion formulations was examined. The chiral surfactant dodecoxycarbonylvaline was used in conjunction with the cosurfactants 1‐butanol, 1‐pentanol, 2‐pentanol, 1‐hexanol, 2‐hexanol, cyclopentanol, and cyclohexanol. The millimolar concentration of cosurfactant was held constant regardless of identity. Ethyl acetate was incorporated as the microemulsion oil core and the buffer utilized was 50 mM phosphate at a pH of 7.0. In general, secondary alcohols improved enantioselectivities and primary alcohols had the opposite effect, with the exception of the 1‐butanol. The trends observed varied slightly depending on analyte. Of the six chiral analytes tested, cyclopentanol provided the best enantioselectivity for three, 1‐butanol for two compounds, and 2‐pentanol for one analyte. The lowest enantioselectivities were achieved with 1‐pentanol or 1‐hexanol for all compounds. Methylene selectivity was found to decrease with reductions in alcohol chain length. Among equal carbon number alcohols, methylene selectivity was lower for secondary alcohols. Efficiency and resolution values varied with different cosurfactants and depended on analyte identity.
ISSN:0173-0835
1522-2683
DOI:10.1002/elps.200600261