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Preparation method for surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide

A technology of dimethylaminopropyl and sulfonamides, which is applied in the preparation of sulfonamides, chemical instruments and methods, fire prevention equipment, etc., can solve the problems that the products are not purified and affect the performance of the products, and avoid many by-products , reduce volatilization, reduce the effect of self-polymerization reaction

Active Publication Date: 2015-11-04
应城市武化研化工新材料有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And the final product is not purified, the residual polymerization inhibitor phenothiazine may affect the performance of the product

Method used

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  • Preparation method for surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide
  • Preparation method for surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide
  • Preparation method for surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Synthesis of N-3-dimethylaminopropyl-perfluorohexylsulfonamide

[0032] Add 84g of dimethylaminopropylamine and 600g of toluene into a 1000ml flask, start stirring, add 164g of perfluorohexylsulfonyl fluoride dropwise at room temperature, and the addition is completed within 30 minutes. The reaction was stirred at 30-40°C for 6h. Suction filtration, washing with water 3 times, and drying to obtain a white powder solid with a yield of 99.3% and a melting point of 128-130°C.

[0033] Anhydrous ethanol was recrystallized to obtain a white solid with a yield of 86.3% and a melting point of 129-131°C.

[0034] 1HNMR(600M,CDCl3):δ1.765(t,2H,-CH2-),δ2.3(s,6H,-CH3),δ2.616(t,2H,-CH2-),δ3.490(t ,2H,-CH2-).

[0035] IR(KBr): ν520.20cm-1 has -CF2- flexural vibration absorption peak, 1147.07cm-1 has -CF2- asymmetric stretching vibration peak, and 1193.71cm-1 has S=O strong absorption peak of stretching vibration , 1363.27cm-1 has a strong characteristic absorption peak of SN as...

Embodiment 2

[0036] Example 2 Synthesis of N-3-Dimethylaminopropyl-perfluorohexylsulfonamide

[0037] In a 500ml flask, 21g of dimethylaminopropylamine, 21g of triethylamine and 150g of toluene were added, stirring was started, 82g of perfluorohexylsulfonyl fluoride was added dropwise at room temperature, and the addition was completed in 30 minutes. The reaction was stirred at 30-40°C for 4h. Suction filtration, washing with water 3 times, and drying to obtain a white powder solid with a yield of 97.3% and a melting point of 116-119°C. .

[0038] Recrystallization from methanol gave a white solid with a yield of 76.5% and a melting point of 128-131°C.

Embodiment 3

[0039] Example 3 Synthesis of N-carboxyethyl, N-3-dimethylaminopropyl-perfluorohexylsulfonamide

[0040] 100g of N-3-dimethylaminopropyl-perfluorohexylsulfonamide and 160g of toluene were added to a 1000ml flask, the temperature was raised to 100°C, and 16g of acrylic acid was added dropwise. The reaction was stirred at 100-110°C for 12h. The solvent was evaporated to obtain a pale yellow solid with a yield of 99.8% and a melting point of 143-147°C.

[0041] Anhydrous ethanol was recrystallized to obtain a white solid product with a yield of 80.0% and a melting point of 160-163°C.

[0042] 1HNMR(600M, MeOD): δ2.063(d,2H,-CH2-),δ2.555(d,2H,-CH2-),δ2.847(s,6H,-CH3),δ3.055(d ,2H,-CH2-),δ3.499(d,2H,-CH2-),δ3.651(d,2H,-CH2-).

[0043] 19FNMR(565M, MeOD): δ-82.37(CF3-), δ-112.92(-CF2-SO2-), δ-121.38(-CF2-C-SO2-), δ-122.76(-CF2-CC-SO2- ), δ-123.76(-CF2-CCC-SO2-), δ-127.32(-CF2-CCCC-SO2-).

[0044] IR(KBr): ν557.90cm-1 has -CF2- flexural vibration absorption peak, 1148.69cm-1 has -CF2- asym...

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Abstract

The invention discloses a preparation method for a surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide, wherein the surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide is prepared by carrying out a two-step reaction on perfluoro hexyl sulfonyl fluoride and dimethylamino propylamine. According to the method, the reaction is carried out at a relatively low temperature, thereby avoiding byproduct increase caused by a high temperature reaction; a solvent is added into a second step of the reaction, thereby reducing polymerization reaction of acrylic acid. The fluorine-containing amphoteric surfactant product prepared by the invention is high in purity, and the surface tension (has extremely low surface tension) of an aqueous solution under extremely low addition concentration can be reduced; moreover, the product does not have poisonous and harmful effects on human body and the environment, and is expected to replace perfluorooctylsulfonyl (PFOS) surfactants.

Description

Technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluorohexylsulfonamide. Background technique [0002] Fluorinated surfactants are by far the best surface active, with special excellent properties, such as low surface tension, low concentration, high surface activity, high thermal stability, high chemical stability and excellent water and oil repellency Therefore, fluorosurfactants have application value that cannot be replaced by ordinary surfactants in many fields. They are widely used in petroleum, chemical, fire protection, textile, leather, paper, paint, pesticide, machinery, electroplating and other industries. At present, the most commonly used fluorinated surfactants are mainly perfluorooctyl sulfonyl compounds (PFOS) and perfluorooctanoic acid and its salts (PFOA). However, recent studies have shown that this perfluorooctyl-based long-chain f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/09C07C303/36C07C303/38B01F17/26B01F17/28A62D1/02C09K23/26C09K23/28
Inventor 张小余王会丽徐玲玲雷红成关海兰李桂徐巨林
Owner 应城市武化研化工新材料有限责任公司
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