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Sulfonate type and sulfonate inner salt type fluorocarbon surfactant as well as preparation and applications thereof

A technology of fluorocarbon surface and sulfonic acid inner salt, which is applied in the direction of sulfonate preparation, sulfonic acid preparation, transportation and packaging, etc. It can solve the problems of complex synthesis, many steps, and great difficulty, and achieve simple preparation process and low cost , easily degradable effect

Inactive Publication Date: 2013-08-14
DONGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of fluorocarbon surfactants is more complicated than that of general hydrocarbon surfactants, with many steps and great difficulty

Method used

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  • Sulfonate type and sulfonate inner salt type fluorocarbon surfactant as well as preparation and applications thereof
  • Sulfonate type and sulfonate inner salt type fluorocarbon surfactant as well as preparation and applications thereof
  • Sulfonate type and sulfonate inner salt type fluorocarbon surfactant as well as preparation and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of Fluorinated Intermediate Compound 2

[0028] N 2 Protected, 250mL three-necked flask, add p-nitroaniline (6.62g, 48mmol) and chloroform (100mL) at room temperature, after fully dissolved, add Et 3 N (5.05g, 50mmol) was used as an acid-binding agent. Perfluoropolyetheryl fluoride 1 (19.92g, 40mmol) was slowly added dropwise at 0°C. Extract with chloroform (80mL×2), combine the extract with the organic phase, wash once with sodium bicarbonate (5%), then wash with water until neutral, dry the organic phase with anhydrous sodium sulfate, spin to dry the solvent, and perform column chromatography (silica gel, dichloromethane:methanol=20:1) separation and purification to obtain yellow oily solid product 2 (21.19g, yield 86%). m.p.31~31.9℃.IR(KBr,cm -1 )υ max 3325,3132,1720,1567,1511,1106,1033,989,538. 1 H NMR (400MHz, CDCl 3 ): δ8.33(d, J=9.2Hz, 3H, Note: Due to the strong electron-withdrawing property of the nitro group, the chemical shifts of the two hydr...

Embodiment 2

[0030] Synthesis of Fluorinated Intermediate Compound 3

[0031] In a 250mL three-neck flask, dissolve compound 2 (12.32g, 20mmol) in a mixture of 95% ethanol (64mL) and distilled water (24mL) at room temperature, and add reduced iron powder every 15min for a total of 3 times (4.48g, 80mmol), while slowly adding hydrochloric acid (4mL, 6mol / L) dropwise. Then heated to 90°C to continue the reaction for 25h, filtered while hot, and washed the filter residue with hot ethanol solution. After cooling, the filtrate was spin-dried to ethanol, and separated and purified by column chromatography (silica gel, petroleum ether: ethyl acetate = 6:1) to obtain product 3 as a light red solid (10.67 g, yield 91%). m.p.29.0~30.2℃.IR(KBr,cm -1 )υ max 3443,3350,3222,1716,1622,1547,1239,1038,522. 1 H NMR (400MHz, CDCl 3 ):δ7.88(s,1H),7.33(d,J=8.4Hz,2H),6.70(d,J=8.4Hz,2H),7.88(s,2H). 19 F NMR (376MHz, CDCl 3 ): δ-80.03, -81.30, -81.42, -82.13, -82.25, -129.79, -131.59, -145.31.

Embodiment 3

[0033] Synthesis of Fluorinated Intermediate Compound 3

[0034] N 2 Protected, 250mL three-neck flask, dissolved p-phenylenediamine (3.24g, 30mmol) in dry chloroform (120mL) at room temperature, after fully dissolved, added Et 3 N (3.03g, 30mmol) was used as an acid-binding agent, acid fluoride compound 1 (9.96g, 20mmol) was slowly added dropwise at 0°C, and after the dropwise addition was completed, it was raised to room temperature for 3 hours, and water was added to quench the reaction, and the reaction was washed with chloroform ( 100mL×2) extraction, the extract was combined with the organic phase, washed once with sodium bicarbonate (5%), then washed once with water, the organic phase was dried with anhydrous sodium sulfate, spin-dried the solvent, column chromatography (silica gel, petroleum ether: Ethyl acetate=6:1) was separated and purified to obtain product 3 as a light red solid (5.03 g, yield 43%). m.p.29~30.2℃.IR(KBr,cm -1 )υ max 3443,3350,3222,1716,1622,154...

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Abstract

The invention relates to a sulfonate type and sulfonate inner salt type fluorocarbon surfactant as well as a preparation method and applications thereof. The structure formula of the fluorocarbon surfactant is shown in the specification. The preparation method comprises the steps of: with hexafluoropropylene oxide polymer as a raw material, performing amidation on the raw material and 4-nitroaniline to obtain a product, carrying out nitroreduction on the product, and performing an open-loop alkylation reaction on the product subjected to nitroreduction and 1,3-propanesultone to obtain the sulfonate type and sulfonate inner salt type fluorocarbon surfactant. The sulfonate type and sulfonate inner salt type fluorocarbon surfactant is applied in the fields of textiles, chemical industry, papermaking, oil fields, leather and firefighting. The synthesized sulfonate type and sulfonate inner salt type fluorocarbon surfactant is more easily degraded by replacing the traditional perfluoroalkyl chain with a perfluoropolyether chain, belongs to novel environment-friendly fluorocarbon surfactants, and can be widely applied in multiple fields; and the sulfonate type and sulfonate inner salt type fluorocarbon surfactant is simple in preparation technique, and low in cost and has good application prospects.

Description

technical field [0001] The invention belongs to the field of fluorocarbon surfactants and their preparation and application, in particular to a sulfonate type and sulfonic acid inner salt type fluorocarbon surfactants and a preparation method and application thereof. Background technique [0002] Fluorocarbon surfactants are the most important species of special surfactants, and are by far the most active type, and can reduce the surface tension of water or organic solvents to a very low value when used in a small amount. Its unique properties are often summarized as "three highs" and "two phobias", that is, high surface activity, high thermal stability and high chemical stability; its fluorine-containing hydrocarbon group is both water-repellent and oil-repellent. The synthesis of fluorocarbon surfactants is more complicated than that of general hydrocarbon surfactants, with many steps and great difficulty. The synthesis of fluorocarbon surfactants is generally divided int...

Claims

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Application Information

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IPC IPC(8): B01F17/22C07C309/14C07C303/02C07C303/32B01F17/42C09K23/42C09K23/22
Inventor 卿凤翎周杰华黄焰根
Owner DONGHUA UNIV
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