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Fluorosurfactants in Firefighting Foams
Published in David M. Kempisty, Yun Xing, LeeAnn Racz, Perfluoroalkyl Substances in the Environment, 2018
Stephen H. Korzeniowski, Robert C. Buck, David M. Kempisty, Martial Pabon
The two primary commercial production processes employed to synthesize the perfluoroalkyl moiety that is used to make fluorosurfactants are electrochemical fluorination (ECF) and the fluorotelomer process (Figure 1.2) (Taylor 1999; Kissa 2001; Pabon and Corpart 2002; Buck et al. 2011, 2012). Among the first commercially available fluorosurfactants were perfluoroalkyl sulfonates (PFSAs) (e.g., perfluorooctane sulfonate [PFOS], C8F17SO3–) and perfluoroalkyl carboxylic acids (PFCAs) (e.g., perfluorooctanoic acid [PFOA], C7F15COOH), manufactured using the ECF process (Taylor 1999; Kissa 2001; Pabon and Corpart 2002; Buck et al. 2012). Subsequently, fluorosurfactants derived from the fluorotelomer process were introduced some time later (10–15 years after ECF products). A wide array of fluorosurfactants containing typical surfactant terminal functionalities (e.g., anionic, cationic, amphoteric, and nonionic) have been made and used (Taylor 1999; Pabon and Corpart 2002; Buck et al. 2012).
Repellent Finishes
Published in Menachem Lewin, Stephen B. Sello, Handbook of Fiber Science and Technology: Chemical Processing of Fibers and Fabrics, 2018
The patent literature on fluorocarbon repellents is voluminous. However, most patents disclose variations of nonfluorinated structural features of the repellent molecule. Structural variations of the fluorinated segment are limited by the small number of practical chemical routes to fluorinated intermediates. The most important commercial processes for producing fluorinated intermediates are based on either electrochemical fluorination or telomerization of tetrafluoroethylene.
Per- and Polyfluoroalkyl Substances
Published in Caitlin H. Bell, Margaret Gentile, Erica Kalve, Ian Ross, John Horst, Suthan Suthersan, Emerging Contaminants Handbook, 2019
Ian Ross, Erica Kalve, Jeff McDonough, Jake Hurst, Jonathan A L Miles, Tessa Pancras
Electrochemical fluorination (ECF) has been used to manufacture a variety of polyfluoroalkane sulfonamide (FASA) based substances. This process attached additional functional groups and alkyl chains to a perfluoroalkyl sulfonamide moiety to create hundreds of differing polyfluorinated compounds (Wang et al. 2017). A selection of the FASA-based compounds characterized to date include the following (with some molecular structures presented in Figure 3.9): FASAs, such as perfluorooctane sulfonamide (FOSA) and methyl/ethyl derivatives, such as N-methyl perfluorooctane sulfonamide (N-MeFOSA) and N-ethyl perfluorooctane perfluorooctane sulfonamide (N-EtFOSA).Perfluoroalkane sulfonamidoethanols (FASEs), such as perfluorooctane sulfonamidoethanol (FOSE) and their methyl and ethyl derivatives, such as N-methyl perfluorooctane sulfonamidoethanol (N-MeFOSE) and N-ethyl perfluororooctane sulfonamidoethanol (N-EtFOSE).Perfluoroalkane sulfonamidoacetates, such as perfluorooctane sulfonamidoacetate (FOSAA) and their methyl and ethyl derivatives, such as N-methyl perfluorooctane sulfonamidoacetate (N-MeFOSAA) and N-ethyl perfluororooctane sulfonamidoacetate (N-EtFOSAA).EtFOSE-based phosphate esters such as sulfonamidoethanol-based phosphate esters (SAmPAP) including mono, di and triesters, such as 2-(N-ethylperfluorooctane-1-sulfonamideo)ethyl phosphate (SAmPAP) and bis-[2-(N-ethylperfluorooctane-1-sulfonamido)ethyl] phosphate (diSAmPAP).Perfluoroalkyl sulfonamide amines such as N,N-dimethyl-3-{[(trideca-perfluorohexyl)sulfonyl]amino}propan-1-aminium (PFHxSaAm), N,N-dimethyl-3-{[(trideca-perfluorooctyl)sulfonyl]amino}propan-1-aminium (PFOSaAm), 3-(N-(2-carboxyethyl)-trideca-perfluorohexylsulfonamido)-N,N-dimethylpropan-1-aminium (PFHxSaAmA) and 3-(N-(2-carboxyethyl)-trideca-perfluorohoctylsulfonamido)-N,N-dimethylpropan-1-aminium (PFOSaAmA).
Surface activity, salt and pH tolerance, and wettability of novel nonionic fluorinated surfactants with a short fluorocarbon chain
Published in Journal of Dispersion Science and Technology, 2020
Rong Zhou, Yong Jin, Yichao Shen, Shuangquan Lai, Yutang Zhou, Peng Zhao
To address this issue, some strategies have been proposed, including shortening perfluorocarbon chain length, introducing branches, and inserting hetero atoms into the fluorocarbon chain, to develop alternatives of the long fluorocarbon chain surfactants.[13] At present, a lot of researches have focused on the development of the novel fluorinated surfactants with short fluorocarbon chains, because the raw materials with short fluorocarbon chains are more easily accessed by the electrochemical fluorination method and these compounds with short fluorocarbon chains have less toxicity and lower bioaccumulation.[10,14] For example, Yang et al.[15] provided a synthetic route for the preparation of pyridine-based cationic fluorinated surfactants with a perfluorohexyl group. Zhang et al.[2] synthesized a kind of novel succinic acid sulfonate fluorinated surfactants with two short fluorocarbon chains. However, most of these novel fluorinated surfactants were ionic surfactants whose hydrophilic groups included pyridinium, quaternary ammonium, sulfonate, and so forth.