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Preparation method of sulfate surfactant containing fluoride anion and use thereof

A surfactant and sulfate-based technology, applied in the preparation of sulfonamides, chemical instruments and methods, organic chemistry, etc., can solve problems such as no literature reports

Inactive Publication Date: 2013-04-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no bibliographical report of this sulfate-type fluorinated anionic surfactant

Method used

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  • Preparation method of sulfate surfactant containing fluoride anion and use thereof
  • Preparation method of sulfate surfactant containing fluoride anion and use thereof
  • Preparation method of sulfate surfactant containing fluoride anion and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

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

[0022] In a 100 mL four-necked flask with a reflux condenser, 4-perfluoro-(1,3-dimethyl-2-isopropyl)-1-butenyloxybenzenesulfonyl chloride (3.11 g, 0.005 mol) was dissolved in 20 mL of acetonitrile and stirred to dissolve. 2-Methylaminoethanol (0.75 g, 0.01 mol) was added dropwise at room temperature for about 0.5 h. After the dropwise 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, and the resulting white turbid viscous liquid was dried and recrystallized to obtain a white solid powder, 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 ),...

example 2

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

[0024] In a 100 mL four-neck 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 of carbon tetrachloride, stirred and heated to reflux, and chlorosulfonic acid (1.16 g, 0.01mol) was slowly added dropwise for about 30 min, and the reaction was continued for 6 h. After the reaction, let stand to cool to room temperature, remove the solvent under reduced pressure after decolorization, add to 10% NaOH solution, stir, and neutralize to obtain a white viscous liquid, add 50mL saturated saline, precipitate a white solid, filter, and dry Obtain [N-methyl-(4-perfluoro-(1,3-dimethyl-2-isopropyl)-1-butenyloxy) benzenesulfonamido] sodium ethyl sulfate, yield 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)1240.8,979.5...

example 3

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

[0026] The hanging piece method, also known as the Wilhelmy method, uses cover glass, mica piece, filter paper, platinum foil, and a vertical plate is inserted into the test liquid, so that the bottom edge is in contact with the liquid surface, and the surface tension required when the hanging piece is separated from the liquid is measured. The maximum pulling force F. This method is intuitive and reliable, does not require a correction factor, which is different from other detachment methods, and can also measure liquid-liquid interfacial tension. by attaching figure 1 , it can be concluded that its 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).

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Abstract

The invention discloses synthesis of sulfate surfactant [N-methyl-(4-perfluor-(1,3-dimethyl-2-isopropyl)-1-butylene ether) benzene sulfonamido] sodium ethylsulfate containing fluoride anion and use thereof, and discloses a preparation method thereof. The surface properties such as surface tension, interfacial tension, contact angle, water repellency, oil repellency, oil displacement efficiency, wettability, foamability and emulsibility are researched so as to find out the low surface tension and interfacial tension, and excellent water repellency, oil repellency, wettability, foamability and emulsibility; and the sulfate surfactant has certain oil displacement efficiency after a hydrocarbon surfactant is compounded.

Description

technical field [0001] The invention relates to a sulfate type fluorine-containing anionic surfactant [N-methyl-(4-perfluoro-(1,3-dimethyl-2-isopropyl)-1-butenyloxy)benzene Preparation and use of sodium sulfonamido]ethylsulfate. Background technique [0002] Fluorinated surfactants have the characteristics of "three highs and two phobias". With the increasing demand in the international and domestic markets, fluorinated surfactants have excellent performance, high technical content, and large added value, which has attracted researchers at home and abroad. of great interest. Its fluorine-containing hydrocarbon group has water repellency and oil repellency [Chemical New Materials, 2004, 32(8): 46], and is widely used in industrial and agricultural fields such as petroleum, coal, mining and metallurgy, machinery, textiles, and medicine [Daily Chemicals Products, 2011, 41(4):40-43]. [0003] As one of the important varieties, anionic surfactants mainly include carboxylate ty...

Claims

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Application Information

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IPC IPC(8): B01F17/26B01F17/42B01F17/04C07C303/40C07C311/29C09K23/26C09K23/04C09K23/42
Inventor 武宏科史鸿鑫沈海民
Owner ZHEJIANG UNIV OF TECH
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