Perfluorooctanesulfonate

Many superacid-catalyzed reactions were found to be carried out advantageously not only using liquid superacids but also over solid superacids, including Nafion-H or certain zeolites. We extensively studied the catalytic activity of Nafion-H and related solid acid catalysts (including supported perfluorooctanesulfonic acid and its higher ho-... 

ECF is successfully used on a commercial scale to produce certain perfluoroacyl fluorides, perfluoroalkylsulfonyl fluorides, perfluoroalkyl ethers, and perfluoroalkylamines. The perfluoroacyl fluorides and perfluoroalkylsulfonyl fluorides can be hydrolyzed to form the corresponding acid and acid derivatives. Examples include perfluorooctanoyl fluoride [335-66-0] perfluorooctanoic acid [335-67-1] perfluorooctanesulfonyl fluoride [307-35-7] perfluorooctanesulfonic acid [763-23-1] and tris(perfluoro- -butyl)amine [311-89-7]. 

Tertiary, benzyl, and aHyhc nitro compounds can also be used as Friedel-Crafts alkylating agents eg, reaction of (CH2)3CN02 (2-nitro-2-methyl propane [594-70-7]) with anisole in the presence of SnCl gives 4-/-butylanisole [5396-38-3] (7). SoHd acids, such as perfluorodecanesulfonic acid [335-77-3], and perfluorooctanesulfonic acid [1763-23-1] have been used as catalysts for regio-selective alkylations (8). 

The electrofluorinated organics of principal industrial importance are perfluorooctanoic acid [335-67-1/, CE2(CE2)gCOOH, and perfluorooctanesulfonic acid [1763-23-1/, CE2(CE2)yS02H. Typical conditions for preparation of the latter compound involve batch electrolysis of a 10 wt... 

Scandium(lll) perfluorooctanesulfonate [Sc(OPf)3 a novel catalyst for the hetero-Diels-Alder reaction of aldehydes with non-activated dienes [108]... 

PFCs have been manufactured since 1940s. Because of their properties, these compounds are employed in a wide variety of industrial and consumer products. Perfluorooctanoic acid (PFOA) and perfluorooctanesulfonate (PFOS) have been two of the most used and studied PFCs, but due to their resistance to degradation, widespread in the environment, bioaccumulation and toxicological properties, these two compounds are limited in use and production practically worldwide. However,... 

Oliaei F, Kriens D, Kessler K (2006) Investigation of perfluorochemical (pfc) contamination in minessota - phase one. Tech, rep., Report to Senate Environment Commitee Olsen GW, Church TR, Miller JP, Burris JM, Hansen KJ, Lundberg JK, Armitage JB, Herron RB (2003) Perfluorooctanesulfonate and other fluorochemicals in the serum of American Red Cross adult blood donators. EnvironHealth Perspect 111 1892-1901 Olsen GW, Burris JM, Ehresman DJ, Froehlich JW, Seacat JW, Butenhoff JL, Zobel LR... 

Half-life of serum elimination of perfluorooctanesulfonate, perfluorohexanesulfonate, and perfluorooctonate in retired fluorochemical production workers. Environ Health Perspect 155 1298-1305... 

Loos R, Wollgast J, Huber T, Hanke G (2007) Polar herbicides, pharmaceutical products, perfluorooctanesulfonate (PFOS), perfluorooctanoate (PFOA), and nonylphenol and its carboxylates and ethoxylates in surface and tap waters around Lake Maggiore in Northern Italy. Anal Bioanal Chem 387 1469-1478... 

The POP protocol elaborated on occasion of the Stockholm Convention in 2001 contained 12 compounds, known as the dirty dozen aldrin, chlordane, DDT, dieldrin, endrin, heptachlor, HCB, mirex, PCBs, pol veil I orod i be nzo-/ -d i ox ins. polychlorodibenzofurans and toxaphene. After several years of implementation other compounds, were also included HCHs, PAHs, certain brominated flame retardants, perfluorooctanesulfonic acid (PFOS) and pentachlorobenzene (http // www.chem.unep.ch/pops/). This protocol is aimed to control, reduce and/or eliminate discharges, emissions and spills of POPs into the environment. 

Butenhoff, J.L., G.W. Olsen, and A. Pfahles-Hutchens. In press. The applicability of biomonitoring data for perfluorooctanesulfonate (PFOS) to the environmental public health continuum. Environ. Health Perspect. [online]. Available http //ehp.niehs.nih.gov/docs/ 2006/9060/abstract.html [accessed Aug. 21, 2006]. 

Midasch O, Drexler H, Hart N, Beckmann MW, Angerer J. Transplacental exposure of neonates to perfluorooctanesulfonate and perfluorooctanoate a pilot study. International Archives of Occupational and Environmental Health 2007, 80, 643-648. 

In addition to the electrolytic preparation of fluorine, the electrochemical fluorination of carboxylic acid and sulfonic acid derivatives have also become important industrially. The Simons process (Ni anodes, HF as solvent) has been realized industrially by 3 M 69). The most important products are perfluorooctanecarboxylic and perfluorooctanesulfonic acids, which are used as surfactants and for surface treatments. 

A general method for fluorous Suzuki reaction of perfluorooctanesulfonates has been developed using [Pd(dppf)Cl2 ] (dppf = l,l/-bis(diphenyl-... 

Perfluoroalkylsulfonic acids have the general structure F(CF2) S03H, where typically = 4, 6, 8 or 10 (Table 3.1). The most common PFSA is perfluorooctanesulfonic acid (PFOS, = 8). Given the small pAa values of these compounds, approximately—12 [1], PFSAs dissociate completely in the environment ... 

Berthiaume, J., Wallace, K. B. Perfluorooctanoate, perfluorooctanesulfonate, and A-ethyl perfluorooctanesulfonamido ethanol peroxisome proliferation and mitochondrial biogenesis. Toxicol Lett., 129 23-32 (2002). 

Olsen, G. W., Burris, J. M., Ehresman, D. J., Eroehlich, J. W., Seacat, A. M., Butenhoff, J. L., et al. Half-life of semm elimination of perfluorooctanesulfonate, perfluorohexanesulfonate, and perfluorooctanoate in retired fluorochemical production workers. Environ. Health Perspect., 115 1298-1305 (2007). 

Moody, C. A., Herbert, G. N., Strauss, S. H., Field, J. A. Occurrence and persistence of perfluorooctanesulfonate and other perfiuorinated surfactants in groundwater at a fire-... 

Tseng, C.-L., Liu, L.-L., Chen, C.-M., Ding, W.-H. Analysis of perfluorooctanesulfonate and related fluorochemicals in water and hiological tissue samples hy hquid chromatography-ion trap mass spectrometry. J. Chromatogr. A, 1105 119-126 (2006). 

Kannan, K., Corsohni, S., Falandysz, J., Oehme, G., Eocardi, S., Giesy, J. P. Perfluorooctanesulfonate and related fluorinated hydrocarbons in marine mammals, fishes and birds from coasts of the Baltic and Mediterranean Seas. Environ. Sci. TechnoL, 36 3210-3216 (2002). 

The exceptional stability of fluorinated compounds, however, can have deleterious environmental impacts. Recently, for example, it has become apparent that fluorinated compounds such as perfluorooctanesulfonate are widespread in nature and in living systems. ... 

SYNS PERFLUOROOCTANESULFONIC ACID PFOS SAFETY PROFILE A poison by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of SOx and F. ... 

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