Fluorine-containing imine cationic surfactant preparation method and application thereof

A fluorine-containing imine type, surfactant technology, applied in the preparation of sulfonic acid amides, the preparation of organic compounds, the preparation of amino compounds, etc., can solve the problem of refractory organic pollutants, high bioaccumulation and human body multi-organ toxicity and other problems, to achieve the effect of high surface activity, high practical value and excellent surface performance

Inactive Publication Date: 2012-02-15
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, perfluorooctane sulfonyl compounds (PFOS) and perfluorooctanoic acid and its salts (PFOA), which are widely used at present, have attracted people's attention for their potential impact on the environment and human health. Various experiments have shown that PFOS and PFOA are Almost no observable degradation will occur under various physical and chemical conditions. It is currently one of the most difficult to degrade organic pollutants in the world. It has high bioaccumulation and multi-organ toxicity in the human body. Its use has been banned in various countries.

Method used

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  • Fluorine-containing imine cationic surfactant preparation method and application thereof
  • Fluorine-containing imine cationic surfactant preparation method and application thereof
  • Fluorine-containing imine cationic surfactant preparation method and application thereof

Examples

Experimental program
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Effect test

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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Abstract

A fluorine-containing imine cationic surfactant preparation method and an application thereof. The preparation method provided by the invention comprises the following steps of: performing an amidation reaction between perfluoroalkyl sulfonyl fluoride and N,N'-dimethyl(ethyl)-1,3-propane diamine to obtain an intermediate 1, refining, performing an amidation reaction between the intermediate and alkyl sulfonic acid fluoride (chlorine) or alkyl acyl fluoride (chlorine) to obtain an intermediate 2, refining, reacting with substances such as iodomethane to obtain the fluorine-containing imine cationic surfactant. The surfactant can be used as an emulsifier, a metal surface conditioning agent, a leveling agent, an extinguishing chemical additive, a foam flotation agent and a crude oil evaporating inhibitor. The invention has the following advantages: the surfactant production cost is low; the preparation method is simple; the requirement on production equipment is low; the production technology is concise; the product is environment friendly; the yield is high and the conversion rate of the fluorine containing monomer reaches 100%; the surface performance is excellent, and the lowest water surface tension of some compounds is below 18mN/m.

Description

Technical field: [0001] The invention relates to a preparation method and application of a fluorine-containing surfactant, in particular to a class of fluorine-containing imine type cationic surfactants and a preparation method and application thereof. Background technique: [0002] Commonly used surfactants, whose hydrophobic groups are hydrocarbon groups, may also contain other elements such as oxygen, sulfur, nitrogen, chlorine, bromine, iodine, etc., such commonly used surfactants are called ordinary surfactants . Surfactants containing elements such as fluorine, phosphorus, silicon and boron in the surfactant molecule other than the above eight elements are called special surfactants. Fluorocarbon surfactants are a class of special surfactants that have attracted much attention and obtained a lot of research results. They have outstanding characteristics such as high surface activity, high thermal stability and high chemical stability. [0003] Fluorocarbon surfactant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/48C07C303/40C07C211/63C07C209/12B01F17/18B01F17/26C09K23/18C09K23/26
Inventor 龙光斗黄澄华王绍磊李中华肖舒付冬梅李训生田德美吴蓉
Owner HUAZHONG NORMAL UNIV
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