Preparation method of sulfate surfactant containing fluoride anion and use thereof

[0021] Example 1: N-methyl-N-hydroxyethyl-4-perfluoro-(1,3-dimethyl-2-isopropyl)-1-butenoxybenzenesulfonamide

[0022] In a 100 mL four-necked flask with a reflux condenser, add 4-perfluoro-(1,3-dimethyl-2-isopropyl)-1-butenoxybenzenesulfonyl chloride (3.11 g, 0.005 mol) dissolved in 20 mL of acetonitrile and stirred to dissolve. Add 2-methylaminoethanol (0.75 g, 0.01 mol) dropwise at room temperature for about 0.5 h. After the addition was completed, the reaction was stirred at room temperature for 3.0 h. After the reaction was completed, the solvent was removed under reduced pressure, washed with 3×10 mL of water, the obtained white turbid viscous liquid was dried, and white solid powder was obtained after recrystallization, about 3.01 g, with a yield of 92%. IR(cm ?1 ): υ(O-H) 3497.1,υ(C-H)2963.2,υ(C=C) 1592.0,1491.4, υ(S=O) 1012.1,υ(C-F)1287.2,1185.0,1127.1,980.1; 1 H-NMR ((CD 3 ) 2 SO)δ: 7.92(d,2H,ArH),7.37 (d,2H,ArH),3.51(t,2H,CH 2 ),3.03(t,2H,CH 2 ),2.74(s,3H, CH 3 ); ESI-MS: 661.02.

[0023] Example 2: Preparation of [N-methyl-(4-perfluoro-(1,3-dimethyl-2-isopropyl)-1-butenoxy)benzenesulfonamido]ethyl sodium sulfate

[0024] In a 100 mL four-necked flask, add N-methyl-N-hydroxyethyl-4-perfluoro-(1,3-dimethyl-2-isopropyl)-1-butenyloxybenzenesulfonate Amide (3.30 g, 0.005mol) was dissolved in 40 mL carbon tetrachloride, stirred and heated to reflux, slowly added chlorosulfonic acid (1.16 g, 0.01mol) dropwise for about 30 min, and the reaction was continued for 6 h. After the reaction, let stand and cool to room temperature, after decolorization, remove the solvent under reduced pressure, add to 10% NaOH solution, stir and neutralize to obtain a white viscous liquid, add 50mL saturated brine, precipitate a white solid, filter and dry Obtained [N-methyl-(4-perfluoro-(1,3-dimethyl-2-isopropyl)-1-butenoxy)benzenesulfonamido]ethyl sodium sulfate with a yield of 80% . IR(cm -1 ): υ(N-H)3446.3,υ(C=C)1626.6,1590.9,1491.5,υ(C-O)1241.8;υ(S=O)1014.2,υ(C-F)1240.8,979.50,742.06; 1 H-NMR(DMSO-d6)δ: 7.93(d,2H,ArH), 7.38(d,2H, ArH), 3.83(t,2H,CH 2 ),3.19(t,2H,CH 2 ),2.73(s,3H,CH 3 ); ESI-MS: 726.96.

[0025] Example 3 Surface tension test (Wilhelmy method)

[0026] The hanging piece method, also known as the Wilhelmy method, uses a cover glass, mica sheet, filter paper, platinum foil, and a vertical plate inserted into the test liquid, so that the bottom edge of the test liquid is in contact with the liquid surface, and the surface tension is determined when the hanging piece is separated from the liquid. The maximum pulling force F. This method is intuitive and reliable, and does not require a correction factor, which is different from other separation methods. It can also measure liquid-liquid interfacial tension. By attaching figure 1 , It can be concluded that the critical micelle concentration is 4.8×10 -4 mol/L, the surface tension of its aqueous solution (γ CMC ) Is 19.5mN/m (the surface tension of pure water is 71.0 mN/m).