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Structural identification of isomers present in technical perfluorooctane sulfonate by tandem mass spectrometry
Author(s) -
Langlois Ingrid,
Oehme Michael
Publication year - 2006
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2383
Subject(s) - chemistry , geminal , mass spectrometry , tandem mass spectrometry , perfluorooctane , sulfonate , structural isomer , tandem , chromatography , quadrupole ion trap , ion trap , medicinal chemistry , organic chemistry , composite material , sodium , materials science
The structures of isomeric by‐products of technical perfluorooctane sulfonate (PFOS, C 8 F 17 SO 3 − ) were characterized by high‐performance liquid chromatography coupled to mass spectrometry. Ion trap (IT) as well as triple quadrupole (TQ) tandem mass spectrometry (MS/MS) identified ten PFOS isomers with best results being achieved by ion trap MS/MS. In addition to the linear isomer, the main by‐products were isomers with geminal diperfluoromethyl groups and perfluoromethyl‐substituted compounds. Purified fractions of the perfluoromethyl isomers allowed the elucidation of structures and the assignment of the retention times of perfluoroisopropyl‐, 5‐perfluoromethyl‐, 4‐perfluoromethyl‐, 3‐perfluoromethyl‐ and 1‐perfluoromethyl‐PFOS. The concentration of 2‐perfluoromethyl‐PFOS was too low in technical PFOS for a proper identification. Retention times of the geminal substituted diperfluoromethyl isomers could not be properly assigned due to co‐elutions. The number and position of the CF 3 groups can be derived from the MS/MS spectra, which allow an unequivocal identification of the isomers. TQ‐MS/MS also allowed us to identify most of the isomers. Copyright © 2006 John Wiley & Sons, Ltd.