Fluorine-containing imine cationic surfactant preparation method and application thereof
A fluorine-containing imine type and surfactant technology, which is applied in the preparation of sulfonamides, organic compounds, amino compounds, etc., can solve refractory organic pollutants, high bioaccumulation and multi-organ toxicity of human body problems such as high surface activity, high practical value and simple preparation method
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Embodiment 1
[0023] Preparation of fluorine-containing imine cationic surfactant.
[0024] Get 1mol perfluorobutylsulfonyl fluoride and 1mol N,N'-dimethyl-1,3-propanediamine for amidation reaction to obtain intermediate (N-[3-(dimethylamino)-propyl ] perfluorobutylsulfonamide), and then carry out amidation reaction with octylsulfonyl chloride to obtain the intermediate (N'-3-(dimethyl)-propyl-(N-perfluorobutylsulfonyl-N- octylsulfonyl)-imine), after recrystallization with dichloromethane, acetonitrile as solvent, reacted with iodomethane to give N′-3-(trimethyl)-propyl-(N-perfluorobutylsulfonyl Acyl-N-octylsulfonyl)-tertiary amine iodide salt; react with hydrogen peroxide to give N'-3-(dimethyl)-propyl-(N-perfluorobutylsulfonyl-N-octylsulfonyl )-amine oxide.
Embodiment 2
[0026] The synthesis of N-[3-(dimethylamino)-propyl] perfluorobutylsulfonamide in embodiment 1
[0027] The synthesis process is as follows: In a three-necked round bottom flask equipped with a magnet, add 100ml of benzene, 1mol of triethylamine and 1mol of N,N'-dimethyl-1,3-propanediamine, and drop 1mol of Perfluorobutylsulfonyl fluoride, then reacted for 8 hours, suction filtered, and recrystallized with dichloromethane to obtain white crystals, the chemical expression of which is:
[0028]
[0029] MS (623.9); F 19 NMR: -85.952, -115.049, -123.705, -128.212; H 1 NMR: 2.322 (6H, -CH 3 ), 3.502 (2H, -CH 2 -), 2.617 (2H, -CH 2 -,), 1.766 (2H, -CH 2 -), 3.488 (-NH).
Embodiment 3
[0031] Synthesis of N'-3-(dimethyl)-propyl-(N-perfluorobutylsulfonyl-N-octylsulfonyl)-imine in Example 1
[0032] The synthesis process is as follows: In a three-neck round bottom flask equipped with a magnet, add 100ml of benzene, 1mol of triethylamine and 1mol of N-[3-(dimethylammonia)-propyl]perfluorobutylsulfonamide, and place in an ice-water bath Next, 1mol octylsulfonyl chloride was added dropwise, then reacted for 6 hours, filtered with suction, and recrystallized with dichloromethane to obtain white crystals, the expression of the product was:
[0033]
[0034] MS(561.2); F 19 NMR: -85.932, -115.041, -123.694, -128.022; H 1 NMR: 3.419 (2H, -CH 2 -), 2.316 (6H, -CH 3 ), 2.608 (2H, -CH 2 -,), 1.721 (2H, -CH 2 -), 3.412 (2H, -CH 2 -), 1.856 (2H, -CH 2 -), 1.294 (10H, -CH 2 -,), 1.022 (3H, -CH 3 ).
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