Perfluorooctane sulfonamide

Keywords Perfluorinated acid Precursors Perfluorooctane sulfonamides ... 

N-Ethyl perfluorooctane sulfonamide (NEtFOSA) 4151-50-2 C8Fi7S02NH(C2H5) ... 

R.G. Schenellmann, R.O. Manning, Perfluorooctane sulfonamide a structurally novel uncoupler of oxidative phosphorylation, Biochim. Biophys. Acta 1016 (3)... 

Tomy, G. T., Tittlemier, S. A., Palace, V. R, Budakowski, W. R., Braekevelt, E., Brinkworth, L., et al. Biotransformation of 7/-ethyl perfluorooctane sulfonamide by rainbow trout Onchor-hynchus mykiss) liver microsomes. Environ. Set TechnoL, 38 758-762 (2004). 

Some insecticides are known to affect the process of oxidative phosphorylation (Figure 7.27). Sulfluramid is first N-deethylated by cytochrome P450 monooxygenases to become perfluorooctane sulfonamide in vivo (Figure 7.28). This oxidative metabolite acts... 

Higgins and Luthy [23] examined the organic carbon normalized distribution coefficients (Koc) of eight long chain PFC (four PFCA, two PFSA and two perfluorooctane sulfonamide acetic acids) with batch experiments (initial PFC concentrations 0.5-100 pg/L) (results see Table 1). They displayed the dependency of sorption and chain length, showing that the log Kqc values increase by between 0.3 and 0.6 log units with each additional CF2 moiety. When comparing the results... 

Tomy et al. [20] detected a relatively high mean concentration (92.8 ng/g wwt) of AT-ethyl perfluorooctane sulfonamide in Arctic cod, ranging between 9.6 and 144.6 ng/g wwt. Since transformation of IV-EtPFOSA to PFOS and PFOSA by rainbow trout microsomes has been reported [89], IV-EtPFOSA is an important compound to measure in biota and in human samples. 

PFOS and related perfluorinated compounds have been found in many organisms around the world. Generally, they are found in the highest amounts in the tissues of predators at the top of the food chain, which have fish as the major food component. In addition to PFOS, perfluorooctane sulfonamide (PFOSA) is usually present, one of the precursors of PFOS. In fish there are often higher PFOSA concentrations than PFOS concentrations, whereas in mammals the opposite is true. This may indicate that mammals have metabolic apparatus that can metabolise PFOSA to PFOS. 

The ECF process has been used by the 3M Company since around 1947 [4]. Primarily, ECF was used to produce PFOA and a line of perfluorooctane sulfonyl fluoride (PFOSF)-based products including PFOS andperfluorooctyl sulfonamides. However, in 2000, the 3M Company announced that it would be phasing out its line of perfluorooctyl products from 2001 to 2003 [10]. These products have since been replaced by analogous butyl-based substances [11], including the perfluorobutyl sulfonamides produced using the ECF process. 

Fluorous tags can also be introduced as acid-labile protecting groups in the synthesis of carboxamides and sulfonamides. In this context, parallel generation of an 18-member library of biaryl carboxamides has been reported perfluorooctane-tagged iodopropane (C8Fi7(CH2)3l) was used to prepare the corresponding fluorous substrates (Scheme 16.63) [96]. After removal of the fluorous tag purification... 

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