Journal article
Structural isomers of polyfluorinated di- and tri-alkylated phosphate ester surfactants present in industrial blends and in microwave popcorn bags
Introduction In this study, we provide strategies for detecting and quantifying the structural isomers of polyfluorinated di- and tri-alkyl surfactants (PFAS) by mass spectrometry (MS). We specifically investigate polyfluorinated dialkylated phosphate ester surfactants (x:2/y:2 diPAPS, (F(CF2) x CH2CH2O-P(O)(O)−-OCH2CH2(CF2) y F)) and their thioether analogues (x:2/y:2 S-diPAPS, F(CF2) x CH2CH2SCH2-C[CH2O)2P(O)(O)−]-CH2SCH2CH2(CF2) y F), which are used for industrial applications, such as oil- and water-repellent coatings on paper and board.
DiPAPS have been found in human blood and are metabolised to the persistent perfluoroalkyl carboxylic acids (PFCA) in rats. Materials and methods A microwave popcorn bag extract was analysed by ultrahigh-pressure liquid chromatography coupled to a negative electrospray ionisation-quadrupole time-of-flight MS.
Results and discussion The extract contained S-diPAPS, diPAPS and trialkylated (triPAPS) impurities. TriPAPS were also present in industrial and synthetic diPAPS standards, and were verified with an 8:2/8:2/8:2 triPAPS standard. The eight elemental compositions (m/z’s) of diPAPS in the extract represent 19 precursor ion structures, and the six S-diPAPS m/z’s represent at least 13 structures.
The diPAPS had [M-H]− precursor ions of m/z 789, 889,…1,489 and the S-diPAPS of m/z 921, 1,021,…1,421, corresponding to fluorinated chains from C6–18. Each m/z appeared as one to three chromatographic peaks of structural isomers, where, e.g. m/z 1,189 was present as 10:2/10:2, 8:2/12:2 and 6:2/14:2 diPAPS.
The isomers formed different products ions, thus only half of the m/z 1,189 diPAPS concentration was measured with one precursor ion > product ion transition. Conclusion In general, knowledge about structural isomers of poly-alkylated PFAS is needed for the estimation of types and amounts of perfluorinated degradation products, such as PFCA from diPAPS.
Language: | English |
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Publisher: | Springer-Verlag |
Year: | 2011 |
Pages: | 1422-1432 |
ISSN: | 16147499 and 09441344 |
Types: | Journal article |
DOI: | 10.1007/s11356-011-0488-2 |
ORCIDs: | Trier, Xenia , 0000-0002-3614-7851 and 0000-0003-1414-1886 |
Fluorinated Food contact material Identification points Isomers LC-MS Mass spectrometry Migration Paper and board Quantification S-diPAPS Surfactants diPAPS triPAPS
Alkylation Atmospheric Protection/Air Quality Control/Air Pollution Environment Environment, general Environmental Monitoring Esters Food Contamination Food Packaging Halogenation Industrial Pollution Prevention Phosphates Surface-Active Agents Waste Water Technology / Water Pollution Control / Water Management / Aquatic Pollution