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Upstream product

• 423-60-9 perfluorooctanesulphonyl chloride 
• 109-89-7 diethylamine 
• 307-35-7 perfluorooctyl sulfofluorure 

Relevant academic research and scientific papers

N,N-dialkyl perfluoroalkanesulfonamides: Synthesis, characterization and properties

Twenty derivatives of N,N-dialkyl perfluoroalkanesulfonamides, n-C mF2m + 1SO2NRR′ (m = 1, 2, 4, 6, 8; R, R′ = CH3, CH2CH3 or CH2CH 2OCH3), have been prepared and characterized. Their fundamental physicochemical properties, including melting point, density, viscosity and dielectric constant, are determined. The influences of structural variations in both the perfluoroalkyl and alkyl chains on the above properties are extensively studied. Among these N,N-dialkyl perfluoroalkanesulfonamides, 14 compounds are liquid at room temperature, and some of them exhibit low melting points, even lower than -40 °C. The empirical solvent polarity scales for these liquid perfluoroalkanesulfonamides, such as 'energy of transition' E T(30) values and Kamlet-Taft solvent parameters (π*, α, β), are also determined by solvatochromic measurements, and show good linear temperature dependence. The ET(30) values are in the range of 45.36-55.19 kcal mol-1 at 25 °C, comparable to those of short chain alcohols. The π* parameters for the compounds containing alkyl chain are in the range of 0.550-0.651 at 25 °C, being a little higher than those of short chain alcohols. All these prepared compounds show strong hydrogen-bond donating ability (α values ranging from 0.865 to 1.204 at 25 °C), comparable to that of short chain alcohols. Meanwhile, those containing alkoxyalkyl chain display strong hydrogen-bond accepting ability (β values ranging from 0.71 to 0.82 at 25 °C), comparable to that of short chain alcohols.

Synthesis and surface activities of organic solvent-soluble fluorinated surfactants

A variety of fluorinated surfactants soluble in organic solvent were prepared, including C8F17SO2NHCnH2n+1 (n = 2, 4, 6, 8, 10), C8F17SO2NHR (R = C6H11, C6H5), C8F17SO2N(CnH2n+1 )2 (n = 1, 2, 3, 4) and C8F17SO2NH(CH2)nN HO2SC8F17 (n = 6, 10). Their surface activities in various organic solvents were determined by surface tension measurement. The results showed that these fluorinated surfactants can reduce the surface tension of both polar and non-polar organic solvents. In general, organic solvents with strong polarity or long alkyl chain are beneficial to increase the surface activity of these polar fluorinated surfactants. By comparing fluorinated surfactants with the same fluorocarbon segment and connecting group, C8F17SO2N(CnH2n+1 )2 (n = 1, 2, 3, 4) showed lower surface activity in organic solvents than C8F17SO2NHCnH2n+1 (n = 2, 4, 6, 8) with an equal carbon number of the solvophilic group. Through surface tension vs. concentration curves given for N-octyl perfluorooctanesulfonamide in various organic solvents, a break point like the critical micelle concentration of ordinary surfactants in aqueous solutions was observed, and the effect of the different types of organic solvents on adsorption and aggregation behavior was also studied.

Synthesis and structure of environmentally relevant perfluorinated sulfonamides

Alkylated perfluorooctanesulfonamides are compounds of environmental concern. To make these compounds available for environmental and toxicological studies, a series of N-alkylated perfluorooctanesulfonamides and structurally related compounds were synthesized by reaction of the corresponding perfluoroalkanesulfonyl fluoride with a suitable primary or secondary amine. Perfluoroalkanesulfonamidoethanols were obtained from the N-alkyl perfluoroalkanesulfonamides either by direct alkylation with bromoethanol or alkylation with acetic acid 2-bromo-ethyl ester followed by hydrolysis of the acetate. N-Alkyl perfluorooctanesulfonamidoacetates were synthesized in an analogous way by alkylation of N-alkyl perfluoroalkanesulfonamides with a bromo acetic acid ester, followed by basic ester hydrolysis. Alternatively, N-alkyl perfluoroalkanesulfonamides can be alkylated with an appropriate alcohol using the Mitsunobu reaction. Perfluorooctanesulfonamide was synthesized from the perfluorooctanesulfonyl fluoride via the azide by reduction with Zn/HCl. All perfluorooctanesulfonamides contained linear as well as branched C8F17 isomers, typically in a 10:1 to 30:1 ratio. The crystal structures of N-ethyl and N,N-diethyl perfluorooctanesulfonamide show that the S-N bond has considerable double bond character. This double bond character results in a significant rotational barrier around the S-N bond (ΔG≠ = 62-71 kJ mol-1) and a preferred solid state and solution conformation in which the N-alkyl groups are oriented opposite to the perfluorooctyl group to minimize steric crowding around the S-N bond.