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Aerobic Soil Biodegradation of 8:2 Fluorotelomer Stearate Monoester

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Department of Agronomy, Purdue University, West Lafayette, Indiana 47907-2054, United States
*Phone: (765) 494-8612; fax: (765) 496-2926; e-mail: [email protected]
Cite this: Environ. Sci. Technol. 2012, 46, 7, 3831–3836
Publication Date (Web):February 28, 2012
Copyright © 2012 American Chemical Society

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A laboratory investigation on the biotransformation of 8:2 fluorotelomer stearate monoester (8:2 FTS) in aerobic soils was conducted by monitoring the loss of 8:2 FTS, production of 8:2 fluorotelomer alcohol (8:2 FTOH) and stearic acid, which would be released by cleavage of the ester linkage, and subsequent degradation products from FTOH for 80 d. Soil microcosms were extracted with ethyl acetate followed by two heated 90/10 v/v acetonitrile/200 mM NaOH extractions. 8:2 FTS was degraded with an observed half-life (t1/2) of 10.3 d. The rate of 8:2 FTS biotransformation substantially decreased after 20 d with 22% of 8:2 FTS still remaining on day 80. No biotransformation of 8:2 FTS occurred in autoclaved soil controls, which remained sterile with 102 ± 6% recovery, through day 20. 8:2 FTOH was generated with cleavage of the ester linkage of 8:2 FTS followed by a rapid decline (t1/2 ∼ 2 d) due to subsequent biodegradation. All the expected 8:2 FTOH degradation products were detected including 8:2 fluorotelomer unsaturated and saturated carboxylic acids, 7:2s FTOH, 7:3 acid, and three perfluoroalkyl carboxylic acids with the most prominent being perfluorooctanoic acid (PFOA). PFOA consistently increased over time reaching 1.7 ± 0.07 mol % by day 80. Although cleavage of the ester linkage was evidenced by 8:2 FTOH production, an associated trend in stearic acid concentrations was not clear because of complex fatty acid metabolism dynamics in soil. Further analysis of mass spectrometry fragmentation patterns and chromatography supported the conclusion that hydrolysis of the ester linkage is predominantly the first step in the degradation of 8:2 FTS with the ultimate formation of terminal products such as PFOA.

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Details of the analytical methods, list of analytes, information on chemicals used, details on experimental methods and extraction efficiencies, matrix recovery, recoveries of degradation products over time, degradation products in Raub-33, degradation products in autoclaved controls of Raub-42P, and stearic acid and palmitic acid levels over time. This material is available free of charge via the Internet at

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