Fluorotelomer alcohols

Ellis DA, JW Martin, AO De Silva, SA Mabury, MD Hurley, MPS Andersen, TJ Wallington (2004) Degradation of fluorotelomer alcohols a likely atmospheric source of perfluorinated carboxylic acids. Environ Sci Technol 38 3316-3321. 

These considerations apply also to the fluorotelomer alcohol CF3(CF2)7-CH2CH20H that was degraded in a mixed cnltnre obtained by enrichment with ethanol. Terminal dehydrogenation followed by elimination of flnoride, hydration and further loss of fluoride produced perfluorooctanoate (Dinglasan et al. 2004). 

Wallington TJ, Hurley MD, Xia J, Wuebbles DJ, Sillman S, Ito A, Penner JE, Ellis DA, Martin J, Mabury SA, Nielsen OJ, Andersen MPS (2006) Formation of C7F15COOH (PFOA) and other perfluorocarboxylic acids during the atmospheric oxidation of 8 2 Fluorotelomer Alcohol. Environ Sci Technol 40 924-930... 

Under the agreement, companies will reduce emissions of these compounds from their facilities and consumer products by 95 per cent by 2010, and work towards eliminating the sources of PFOA by no later than 2015. Furthermore, PFOS and PFOA as well as other perfluorocarboxylic acids (PFCAs) are stable degradation products and/or metabolites of neutral PFCs such as fluorotelomer alcohols (PFTOHs), perfluorinated sulphonamides (PFASAs) and perfluorinated sulphonamide ethanols (PFASEs) [22]. Therefore, the largest global manufacturer and supplier of fluorotelomers such as Capstone, DuPont have adapted its entire product line to utilise short-chain chemistry because short-chain molecules cannot break down to PFOA in the environment. 

Fluorotelomer alcohols Bioaccumulation Food web Surface waters Toxicity ... 

Perfluoroalkyl acids (PFAs) are synthetic, perfluorinated, straight- or bran-ched-chain organic acids characterized by a carboxylate or sulfonate moiety [1]. PFAs are manufactured directly but can also be formed through transformation of many precursor molecules containing a perfluoroalkyl moiety [2], These include fluorotelomer alcohols (FTOHs) and perfluoroalkyl-sulfonamides (Table 1, Fig. 1), however, others likely exist. Collectively, this family of chemicals including PFAs and their polyfluorinated precursors will be referred to in this document as perfluoroalkyl substances (PFSs). 

Fig. 2 a Overall metabolic scheme for the perfluoroalkylsulfonamide alcohols based on rat and fish studies. Presumably the conversion of the alcohol to the corresponding acetates (e.g., N-EtFOSAA and FOSAA) proceed via the aldehyde intermediate though this has yet to be identified. Secondary metabolites for the alcohols (e.g., glucoronide and sulfate) and the carboxylic acids have been omitted, b Overall metabolic scheme for fluorotelomer alcohols (FTOH) derived from published work from microbial and rat studies [52-54,85]... 

Fig. 3 Overall scheme for the atmospheric processing of fluorotelomer alcohols (FTOHs) [26]...

The general structure of fluorotelomer alcohols is F(CF2) CH2CH20H, where usually = 4, 6, 8, 10 or 12 (Table 3.1). FTOHs are named based on the ratio of fluorinated carbons to... 

Fluorotelomer sulfonamidoethanol 4 2 fluorotelomer alcohol 4 2 FTOH CH2CH20H F(CF2)4CH2CH20H... 

De Silva, A. O., Stock, N. L., Bonin, J. L., Wong, G. W.-Y, Mabury, S. A. Water solubility and octanol-water partition coefficient of perfluorooctylsulfonamices and fluorotelomer alcohols. J. Chem. Eng. Data, 2008 (to be submitted). 

Cobranchi, D. R, Botelho, M. W. B., Buck, R. C., Kaiser, M. A. Vaporpressure determinations of 8-2 fluorotelomer alcohol and 1-H perfluorooctane by capillary gas chromatography. Relative retention time versus headspace methods. J. Chromatogr. A, 1108 248-251 (2006). 

Muir, D.C. G., Smithwick, M., Brandsma, S., Bujas, T, Small, J.M., Martin, J.W., eta/. Uptake, transformation and elimination of fluorotelomer alcohols and PFOSA by rainbow trout... 

Wang, N., Szostek, B., Buck, R. C., Folsom, P. W., Sulecki, M., Capka, V., et al. Fluorotelomer alcohol hiodegradation - direct evidence that perfluorinated carbon chain breaks down. Environ. Sci. TechnoL, 39 7516-7528 (2005). 

Martin, J. W., Mabury, S. A., O Brien, P. J. Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepatoc)des. Chenr Biol. Interac., 155 165-180 (2005). 

Taniyasu, S., Kannan, K., So, M. K., Gulkowska, A., Sinclair, E., Okazawa, T., et al. Analysis of fluorotelomer alcohols, fluorotelomer acids, and short- and long-chain perfluorinated acids in water and biota. J. Chromatogr. A, 1093 89-97 (2005). 

Szostek, B., Prickett, K. B., Buck, R. C. Determination of fluorotelomer alcohols by liquid chromatography/tandem mass spectrometry in water. Rapid Commun. Mass Spectrom., 20 2837-2844 (2006). 

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