Fluorinated sulfamido amphoteric surfactants

Per- and polyfluorinated substances (PFASs): Environmental challenges

“…Several sulfonates (e.g. C 3 F 7 OCF 2 CF 2 CH 2 CH 2 SO 3 H, C 6 F 13 CH 2 CF 2 CH 2 CH 2 SO 3 H), sulfamido betaine and sulfamido amine oxide surfactants derived from C 3 F 7 OCF 2 CF 2 CH 2 CH 2 SO 2 Cl and C 4 F 9 (CH 2 CF 2 ) (1 or 2) CH 2 CH 2 SO 2 Cl have been synthesized [411,412], as well as oligo(vinylidene fluoride) telomers C n F 2n+1 (CH 2 CF 2 ) x CH 2 COOH (n = 2, 4; x = 2) [413]. Various surfactants that combine an F-isopropyl terminal group with pending CF 3 groups located on alternate carbons along the hydrophobic backbone had surface tensions comparable to that of PFOA [414].…”

Fluorinated pyridinium and ammonium cationic surfactants

“…The fluoroalkyl ethylene iodide synthesis is shown in Scheme 1 [23,24]. In the case of fluoroalkyl chains interrupted with methylene groups, the thermal or redox-initiated insertion of vinylidene fluoride (VDF) into fluoroalkyl iodide bonds has been studied extensively by Ameduri and others [25][26][27][28][29].…”

“…In the case of fluoroalkyl chains interrupted with methylene groups, the thermal or redox-initiated insertion of vinylidene fluoride (VDF) into fluoroalkyl iodide bonds has been studied extensively by Ameduri and others [25][26][27][28][29]. Here a metalmeditated vinylidene fluoride Insertion of fluoroiodide, followed by radicalmediated ethylene insertion is employed [24]. Access to the fluorinated ethers was accomplished by reaction of perfluorovinyl ether with I2 and IF5 to give the fluorinated ether iodides [24], subsequent thermal telomerization with tetrafluoroethylene to extend the chain length, and then insertion of one equivalent of ethylene.…”

“…Here a metalmeditated vinylidene fluoride Insertion of fluoroiodide, followed by radicalmediated ethylene insertion is employed [24]. Access to the fluorinated ethers was accomplished by reaction of perfluorovinyl ether with I2 and IF5 to give the fluorinated ether iodides [24], subsequent thermal telomerization with tetrafluoroethylene to extend the chain length, and then insertion of one equivalent of ethylene. The example of a double ethylene insertion in the case of C6F13(CH2CH2)2I was achieved by reaction of C6F13I and ethylene in the presence of radical initiator [30].…”

Perfluoroalkylation of alkenes and alkynes in water

“…1 New types of fluorochemicals have been reported as useful for surface modification of various materials (clothes, leathers, domestic house-wares, papers, etc). 2 Perfluoroalkyl compounds have been also described as greener surfactants, for a wide variety of industrial applications, [3][4][5] and PFAS have been recently described as antifouling materials [6][7][8] and epoxy resins. 9 Though the role of these fluorine derivatives in various fields is generally recognized, a problem is the lack of selective and convenient fluoroalkylation methods tolerant to various functionalities, so active research is being devoted to the search of effective methodologies for the introduction of perfluoroalkyl moieties.…”