Enantiomeric separation of chiral sulfoxides by supercritical fluid chromatography

The application of supercritical fluid chromatography (SFC) to the enantiomeric separation of several chiral sulfoxides belonging to the family of the substituted benzimidazoles, including omeprazole, lansoprazole, pantoprazole, rabeprazole, oxfendazole and ricobendazole, is presented in this work. The column employed was Chiralpak AD and the effect of different chromatographic conditions was studied. The results obtained showed that all the compounds can be enantiomerically resolved using SFC, with resolutions higher than 2 and analysis times that in most cases were lower than 10 min. Alcohol type modifiers provided the best results, with ricobendazole, oxfendazole, and omeprazole showing the highest retentions and resolutions. Study of the temperature effect revealed that, in general, the isoelution temperature was above the temperatures assayed, except in the cases of omeprazole, lansoprazole, and oxfendazole with ethanol as modifier and pantoprazole with acetonitrile. Enthalpy-entropy compensation could also be demonstrated for the retention of the first and second eluted enantiomers as well as for the selectivity, with compensation temperatures of 25 degrees C, 45 degrees C, and 83 degrees C, respectively. Reversal of elution on change of the organic modifier was only observed for omeprazole using 2-propanol.