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Ampholytic fluorine-containing surfactant as well as preparation method and application thereof

A solvent and oxidant technology, applied in chemical instruments and methods, fire protection equipment, organic chemistry, etc., can solve the problems of difficult degradation of fluorocarbon surfactants, difficulty in synthesis of fluorocarbon surfactants, and difficulty in promotion.

Active Publication Date: 2019-06-07
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the difficult degradation of PFOS / PFOA class fluorocarbon surfactant in the prior art, therefore need to develop brand-new alternative degradable fluorocarbon surfactant; And existing water film-forming foam fire extinguishing agent Because the fluorocarbon surfactant is difficult to synthesize, expensive and difficult to popularize, it provides an amphoteric fluorosurfactant and its preparation method and application

Method used

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  • Ampholytic fluorine-containing surfactant as well as preparation method and application thereof
  • Ampholytic fluorine-containing surfactant as well as preparation method and application thereof
  • Ampholytic fluorine-containing surfactant as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0093] The synthesis of embodiment 1 fluorine-containing intermediate compound 1

[0094] 6.00g (39.5mmol, 1.5equiv) cesium fluoride, 6.00g (26.3mmol, 1.0equiv) methyl p-bromomethylbenzoate, 15.78g (52.6mmol, 2.0equiv) perfluoro-2-methyl-2 -Pentene, 0.08g (0.26mmol, 0.01equiv) tetrabutylammonium bromide and 40.0mL of anhydrous acetonitrile were sequentially added to a 100mL sealed tube, sealed and stirred at 50°C for 2 days. The mixed system was poured into ether, and the organic phase was first washed twice with deionized water, then washed with saturated brine, and finally dried with anhydrous sodium sulfate, filtered, and the solvent removed. The mixture was separated by EA:PE=1:48 eluent column chromatography to obtain 11.69 g of fluorine-containing intermediate compound 1 with a yield of 95%.

[0095] 1 H NMR (CDCl 3 ,300MHz)δ:3.58(s,2H),3.91(s,3H),7.37(d,J=8.4Hz,2H),7.98(d,J=8.4Hz,2H). 19 F NMR (CDCl 3 ,282MHz)δ:-62.65~-62.85(m,6F),-80.57(t,J=13.7Hz,3F),-106.20~-106...

Embodiment 2

[0096] Synthesis of embodiment 2 fluorine-containing intermediate compound 2

[0097] 2.34g (5.0mmol, 1.0equiv) of fluorine-containing intermediate compound 1 was dissolved in 50.0mL of tetrahydrofuran, and 12.0mL (6.0mmol, 1.2equiv) of 0.5mol / L aqueous sodium hydroxide solution was added dropwise in an ice-water bath. After dropping, the mixed system was moved to room temperature for 12 h. Add deionized water to the system, wash with ether, and adjust the water phase to pH=3 with 1 mol / L HCl solution in an ice-water bath. After the aqueous solution was extracted three times with ether, the ether phases were combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed to obtain 2.25 g of fluorine-containing intermediate compound 2 with a yield of 99%.

[0098] 1 H NMR (DMSO-d6, 300MHz) δ: 3.82(s, 2H), 7.45(d, J=7.8Hz, 2H), 7.92(d, J=7.8Hz, 2H). 19 F NMR (DMSO-d6, 282MHz) δ: -61.95~-62.20(m, 6F), -80.04(t, J=13.1Hz, 3F), -106.00~-106.30(m, 2F), -122.9...

Embodiment 3

[0099] Embodiment 3: the synthesis of fluorine-containing intermediate compound 3a

[0100] Add 5.00g (11.0mmol, 1.0equiv) compound 2, 0.14g (1.1mmol, 0.1equiv) DMAP and 3.15g (16.5mmol, 1.5equiv) 1-ethyl-(3-di Methylaminopropyl) carbodiimide hydrochloride (EDCI), after pumping and exchanging gas three times, add 50.0 mL of anhydrous dichloromethane under ice-water bath, and stir for 10 min. Add 1.8mL (16.5mmol, 1.5equiv) N,N-dimethylethylenediamine dropwise to the system, and after the drop is complete, the system is moved to room temperature for reaction. The reaction process was monitored by TLC, and the reaction was completed after 5 h. The system was washed successively with deionized water and saturated brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed. Finally, the mixture was separated by column chromatography to obtain 5.13 g of fluorine-containing intermediate compound 3a, with a yield of 89%.

[0101] 1 H NM...

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Abstract

The invention discloses an ampholytic fluorine-containing surfactant as well as a preparation method and application thereof. The structure of the ampholytic fluorine-containing surfactant disclosed by the invention is shown as a formula 4, wherein n is selected from any one integer in a range of 1 to 4, R1 is -CH2- or -CH(OH)- and R2 and R3 are independently selected from -CH3- or -CH2CH3. The ampholytic fluorine-containing surfactant disclosed by the invention is easy to degrade, is easily dissolved in water and has high surface activity and good compounding performance; a synthesis method of the ampholytic fluorine-containing surfactant provided by the invention is simple and the total yield is high; the cost problem of an aqueous film-forming foam fire extinguishing agent can be extremely reduced; and the ampholytic fluorine-containing surfactant has relatively high actual value and a wide market prospect. The formula 4 is shown in the description.

Description

technical field [0001] The invention relates to the field of surfactants, in particular to an amphoteric fluorocarbon surfactant and a preparation method and application thereof. Background technique [0002] Fluorocarbon surfactants are surfactants in which all or part of the hydrogen atoms in the hydrocarbon hydrophobic chain are replaced by fluorine atoms, so they have extremely high surface activity. Fluorocarbon surfactants have the unique properties of "three highs and two phobias" (high surface activity, high thermal stability and high chemical stability; hydrophobic and oil-repellent). Its high surface activity and hydrophobic and oleophobic properties can effectively reduce the surface tension of water and organic solvents, and its high thermal stability and high chemical stability make it suitable for applications under the conditions of high temperature, strong acid, strong alkali and the presence of oxides , these properties are beyond the reach of hydrocarbon s...

Claims

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Application Information

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IPC IPC(8): C07C291/04C07C233/78B01F17/22B01F17/00A62D1/02C09K23/00C09K23/22
Inventor 姜标林超邢萍
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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