Mechanistic studies in biodegradation of the new synthesized fluorosurfactant 9-[4-(trifluoromethyl)phenoxy]nonane-1-sulfonate.
As a new potentially mineralizable fluorinated surfactant, 9-[4-(trifluoromethyl)phenoxy]nonane-1-sulfonate was synthesized and exposed to a standardized Zahn-Wellens test (OECD 302B). After the release of fluoride indicating the mineralization of the trifluoromethyl group, 9-[4-(trifluoromethyl)phenoxy]nonane-1-sulfonate was subjected to a further biodegradation test carried out in a fixed bed bioreactor (FBBR). Evolution of biodegradation routes and pursuit was done by quadrupole linear ion trap mass spectrometer (QqLIT-MS) and quadrupole time-of-flight tandem mass spectrometer (QqTOF-MS). Biotransformation was initiated via hydroxylation in the alkyl chain at different positions. Hydroxy-9-[4-(trifluoromethyl)phenoxy]nonane-1-sulfonate was further oxidized with subsequent scission of the molecule forming mainly p-(trifluoromethyl)phenolate, which was mineralized releasing inorganic fluoride. These results demonstrate, that the new synthesized fluorosurfactant 9-[4-(trifluoromethyl)phenoxy]nonane-1-sulfonate is completely biotransformed. However, some intermediates, depending on the position of hydroxylation, impede further mineralization.
Peschka
Manuela
M
University of Applied Sciences Fresenius, Limburger Strasse 2, 65510 Idstein, Germany.
Frömel
Tobias
T
Fichtner
Norbert
N
Hierse
Wolfgang
W
Kleineidam
Melanie
M
Montenegro
Elvira
E
Knepper
Thomas P
TP
D001673:Biodegradation, Environmental; D019149:Bioreactors; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D013451:Sulfonic Acids / Q000138:chemical synthesis / Q000378:metabolism*; D013501:Surface-Active Agents / Q000378:metabolism*; D053719:Tandem Mass Spectrometry
C529655:9-(4-(trifluoromethyl)phenoxy)nonane-1-sulfonate; D013451:Sulfonic Acids; D013501:Surface-Active Agents