Gas Chromatographic Enantiomer Separation of Polychlorinated Biphenyls (PCBs): Methods,Metabolisms, Enantiomeric Composition in Environmental Samples and their Interpretation

The year 2016 not only marks the 50^th anniversary of the first successful discovery of gas chromatographic (GC) enantiomer separations in 1966 by Gil-Av, but also the less appraised 50^th anniversary of the discovery of polychlorinated biphenyls (PCBs) in the environment. This article reports on GC enantiomer separations of axially stable, chiral PCBs (PCB atropisomers) with modified cyclodextrins. Nineteen atropisomeric PCBs exist, but most data exists for four PCB atropisomers (PCB 95, PCB 132, PCB 149, and PCB 136), which can be resolved without significant coelutions on three columns coated with modified cyclodextrins. Nonracemic compositions of PCB atropisomers and their hydroxylated metabolites have been documented in various studies. However, the measured enantiomer fractions are currently difficult to interpret und understand. The most plausible reasons for these difficulties are discussed and interpreted with the help of selected examples from the literature.