Synthesis and analytical follow-up of the mineralization of a new fluorosurfactant prototype.
Fluorinated surfactants have become essential in numerous technical applications due to their unparalleled effectiveness and efficiency. The environmental persistence of the non-biodegradable perfluorinated alkyl moiety has become a matter of concern. Therefore, it was searched for new molecules with chemically stable fluorinated end groups which can be microbially transformed into labile fluorinated substances. One prototype substance, 10-(trifluoromethoxy)decane-1-sulfonate, has shown biomineralization. Monitoring the formation of metabolites over time elucidated the mechanism of biotransformation. Analysis was performed utilizing liquid chromatography-single quadrupole mass spectrometry (LC-MS) and quadrupole-time of flight tandem mass spectrometry (QqTOF-MS). It was possible to distinguish between two major degradation pathways of the fluorinated alkylsulfonate derivative: (i) a desulfonation and subsequent oxidation and degradation of the alkyl chain being predominant and (ii) an insertion of oxygen with a subsequent cleavage and degradation of the molecule. The utilized trifluoromethoxy-endgroup resulted in instable trifluoromethanol after degradation of the alkyl chain, which led to a high degree of mineralization of the molecule.
Peschka
M
M
University of Applied Sciences Fresenius, Limburger Str. 2, 65510 Idstein, Germany.
Fichtner
N
N
Merck KGaA, Frankfurter Str. 250, 64293 Darmstadt, Germany.
Hierse
W
W
Merck KGaA, Frankfurter Str. 250, 64293 Darmstadt, Germany.
Kirsch
P
P
Merck KGaA, Frankfurter Str. 250, 64293 Darmstadt, Germany.
Montenegro
E
E
Merck KGaA, Frankfurter Str. 250, 64293 Darmstadt, Germany.
Seidel
M
M
Merck KGaA, Frankfurter Str. 250, 64293 Darmstadt, Germany.
Wilken
R D
RD
Rhine-Main Water Research gGmbH, Justus-von-Liebig-Str. 10, 64584 Biebesheim am Rhein, Germany.
Knepper
T P
TP
University of Applied Sciences Fresenius, Limburger Str. 2, 65510 Idstein, Germany. Electronic address: knepper@fh-fresenius.de.
D001673:Biodegradation, Environmental; D019149:Bioreactors; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D004783:Environmental Microbiology; D005461:Fluorine / Q000737:chemistry*; D013058:Mass Spectrometry; D008903:Minerals / Q000737:chemistry*; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis / Q000737:chemistry; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism
D008903:Minerals; D009930:Organic Chemicals; D013501:Surface-Active Agents; D005461:Fluorine