Separation of chiral biodegradation intermediates of linear alkylbenzenesulfonates by capillary electrophoresis

High-performance capillary electrophoresis (HPCE) with alpha-cyclodextrin as the chiral selector was applied to separate the enantiomers of p-sulfophenyl-2-butyrate (SP2B) and p-sulfophenyl-3-butyrate (SP3B), which occur as biodegradation intermediates of linear alkylbenzenesulfonates (LAS), the widely used anionic surfactants. With this analytical method, we studied the transformation of both SP3B enantiomers in a laboratory batch incubation with activated sewage sludge of a municipal wastewater treatment plant, (S)-(+)-SP3B and (R)-(-)-SP3B could be detected in mechanically treated sewage effluent. After enrichment on graphitized carbon black (Carbopack B), the extracts were analyzed by HPLC with UV diode array and fluorescence detection as well as by HPCE with UV diode array detection. Quantification of SP3B in a 24-h composite sample of primary sewage effluent yielded 34 mu g/L (limit of detection, 0.1 mu g/L) of the racemic mixture determined by HPLC and 18 mu g/L of each enantiomer measured by HPCE (limit of detection, 1 mu g/L).