Perfluoroalkyl sulfonates

Arylsulfmic acids are perfluoroalkylated under the conditions, but the yield IS low [77 (equation 70) The isolated product is an aryl perfluoroalkyl sulfone. The possible formation of a perfluoroalkyl aryl sulfinate intermediate, arising from an 0-alkylation reachon, has not been discussed. 

Figure 10. Slurry electrochemical voltage spectroscopy experiments with tetragonal [Si(Pc)0]n and various perfluoroalkyl-sulfonates (as the tetrabutylammonium salts in acetonitrile).

US Environmental Protection Agency. Perfluoroalkyl sulfonates, significant new use rule flnal rule and supplemental proposed rule. Fed. Regist., 61 11007-11013 (2002). 

Also under development is use of the alternative feedstock, toluene, for PTA and/or DMT production. Carbonylation of toluene to produce p-tolualdehyde was shown to proceed in 90-95% yield when catalyzed by HF BF3 [31], or by higher perfluoroalkyl sulfonic acids [32], or in greater than 99% yield when catalyzed by trifloromethanesulfonic acid [33]. The p-tolualdehyde, which is regularly an intermediate in both the Witten DMT and Amoco TPA processes (see Schemes 2 and 3, respectively), can then be readily oxidized with minimal changes to the oxidation process. 

The development of new polymeric materials for polymer electrolyte fuel cell is one of the most active research areas, aiming at the new energy sources for electric cars and other devices. The mainstream of the material research for fuel cell is perfluoroalkyl sulfonic acid membranes such as Nafion, Acipex, and Flemion. The most well-known one is Nafion of Du Pont, which is derived from copolymers of tetrafluoro-ethylene and perfluorovinyl ether terminated by a sulfonic acid group.Protons, when dissociated from the sulfonic acid groups in aqueous environment, become mobile and the membrane becomes a proton conducting electrolyte membrane. 

C11-14-branched alkyl acetate CIS-rich. See Oxo-dodecyl acetate C9-C10 alkanes, perfluoro-, sulfonic acid, ammonium salts. See Ammonium C9-10 perfluoroalkyl sulfonate... 

Ammonium C9-10 perfluoroalkyl sulfonate Synonyms C9-C10 alkanes, perfluoro-, sulfonic... 

Ammonium C12-15 pareth sulfate Ammonium C9-10 perfluoroalkyl sulfonate Ammonium cumenesulfonate Ammonium dimethicone copolyol sulfate Ammonium dodecylbenzene sulfonate... 

Poly(phenylene ether) s with pendant perfluoroalkyl sulfonic acids with an ion exchange capacity of 1.17-1.83 equivalents/g have been synthesized by an aromatic nucleophilic substitution reaction of a perfluo-romonomer, such as decafluorobiphenyl or hexafluo-robenzene with 2,5-bis(4 -iodophenyl)hydroquinone, followed by a Ullman coupling reaction with potassium 1,1,2,2-tetrafluoro-2-(l, 1,2,2-tetrafluoro-2-iodoethoxy)ethanesulfonate [100]. 

Nakabayashi K, Higashihara T, Ueda M. Polymer electrolyte membranes based on poly-(phenylene ether)s with pendant perfluoroalkyl sulfonic acids. Macromolecules 2011 44(6) 1603-9. 

S. A. Ullrich, G. L. Gard, R. L. Nafshun, M. M. Lemer, J. Fluor. Chem. 1996, 79, 33-38. Lithium salts of bis (perfluoroalkyl) sulfonic adds synthesis, characterization and conductivity studies. 

Polyfluorinated compounds comprise hundreds of chemicals characterized by hydrophobic linear alkyl chains partially or fully fluorinated (as the perfluorinated compounds [PFCs]) and containing different functional groups. Polyfluorinated compounds include perfluoroalkyl sulfonamides (PFASAs), fluorotelomer alcohols (FTOHs), polyfluorinated alkyl phosphates (PFAPs), fluorotelomer unsaturated carboxylic acids (FTUCAs), perfluoroalkyl acids (PFAAs), and their salts. The most common PFAAs are perfluoroalkyl carboxylic acids (PFCAs) and perfluoroalkyl sulfonic acids (PFASs). In particular, PFASs contain one or more fluorinated alkyl chains bonded to a polar head, which at neutral pH can be charged (anionic, cationic, and amphiphilic surfactants) or noncharged (nonionic surfactants). 

Qiu, Y, He, J., and Shi, H. 2010. Perfluorocarboxylic acids (PFCAs) and perfluoroalkyl sulfonates (PFASs) in surface and tap water around Lake Taihu in China. Front. Environ. 

Abstract Fluorinated surfactants have been conunercially available since the 1950s. The first available were perfluoroalkyl sulfonic acids. The unique properties e.g., surface tension lowering in aqueous systems, high chemical and thermal stability of these acids and their derivatives when used at low concentrations resulted in their widespread use in industrial processes and consumer uses. The most common commercially produced peifluorinated surfactants are the perfluoroalkyl acids. 

PFSA Perfluoroalkyl sulfonic acid PHxSF perfluorohexane sulfonyl fluoride POSF Perfluorooctane sulfonyl fluoride... 

The world of fluorinated surfactants is full of many useful and unique products tailored for specific end users who take advantage of their exceptional performance properties. Recently, major global manufacturers have made commitments to work toward eliminating the manufacture of long-chain perfluoroalkyl carboxylates and perfluoroalkyl sulfonates and substances that may break down to them in the environment [108-110]. As a result, commercial production has shifted to short chain alternatives [24] and new fluorinated moieties such as the per- and poly fluorinated ethers. Clearly, there remains a need for fluorinated surfactants in many industries to obtain the beneficial performance properties of these substances that cannot be achieved with other types of surfactants. 

Rayne S, Forest K (2009) Perfluoroalkyl sulfonic and carboxylic acids A critical review of physicochemical properties, levels and patterns in waters and wastewaters, and treatment methods. J Environ Sci Health A Tox Hazard Subst Environ Eng 44 1145-1199... 

Loganathan BG, Sajwan KS, Sinclair E, Kiunar KS, Kannan K (2007) Perfluoroalkyl sulfonates and perfluraocarboxylates in two wastewater treatment facilities in Kentucky and Georgia. Water Res 41(20) 4611-4620... 

Scheme 2.50 Structures of poly(phenylene ether)s with pendant perfluoroalkyl sulfonic acid groups. Taken from Ref. [183],...

K. Yoshimura, K. Iwasaki, Aromatic polymer with pendant perfluoroalkyl sulfonic acid for fuel cell applications. Macromolecules 42 (23) (2009)9302-9306. 

FC-99 is a 25% active solution of amine perfluoroalkyl sulfonates in water. 

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