Fluorotelomer alcohols production

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. 

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). 

Abstract In the past years, elucidation of transformation products of per- and polyfluorinated chemicals (PFC) has been a task frequently approached by analytical chemists. PCT, such as perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) are persistent and thus, the analytical quest to detect transformation products has failed so far. Their prominence as contaminants is mainly due to their extreme persistence, which is linked to their perfluoroalkyl chain length. Molecules that are less heavily fluorinated can show very complex metabolic behavior, as is the case for fluorotelomer alcohols. These compounds are degraded via different but simultaneous pathways, which produce different stable metabolites. Biotransformation processes of PFC may occur when these compounds enter the environment, and thus known and unknown PFC may be generated in these compartments. Therefore, it is essential to determine metabolic pathways of such compounds in order to entirely understand their fate in the environment. This chapter summarizes methodological approaches and instmmental setups which have been implemented in biotransformation studies of PFC and focuses on mass spectrometric methods and the separation techniques coupled to the mass spectrometer (MS). Valuable MS approaches that have not been frequently used in studies on PFC are presented as well. Since compounds carrying C-F bonds exhibit unique properties, these will be initially presented to address the meaning of these properties both for analytical tasks and for the setup of biotransformation experiments. 

Loveless SE, Hoban D, Sykes G et al (2008) Evaluation of the immune system in rats and mice administered linear ammonium perfluorooctanoate. Toxicol Sci 105(l) 86-96 Lundin JI, Alexander BH, Olsen GW et al (2009) Ammonium perfluorooctanoate production and occupational mortality. Epidemiology 20(6) 921-928 Maras M, Vanparys C, Muylle F et al (2006) Estrogen-like properties of fluorotelomer alcohols as revealed by MCF-7 breast cancer cell proliferation. Environ Health Perspect 114(1) 100-105 Melzer D, Rice N, Depledge MH et al (2010) Association between serum perfluorooctanoic acid (PFOA) and thyroid disease in the US National Health and Nutrition Examination Survey. Environ Health Perspect 118(5) 686-692... 

Hurley, M.D., J.C. Ball, T.J. Wallington, M.P.S. Andersen, D.A. Ellis, J.W. Martin, and S.A. Mabmy (2004b), Atmospheric chemistry of 4 2 fluorotelomer alcohol (C4F9CH2CH2OH) products and mechanism of Cl atom initiated oxidation, J. Phys. Chem. A, 108, 5635-5642. 

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