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Anionic fluorocarbon surfactant and preparation method thereof

An anionic, fluorocarbon surface technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve the problems of application limitations, low surface activity of branched chain products, etc.

Active Publication Date: 2014-06-25
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The production process of this type of branched fluorocarbon surfactant is simple and the cost is relatively cheap, but because the surface activity of the branched chain product is not high, its application is greatly restricted

Method used

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  • Anionic fluorocarbon surfactant and preparation method thereof
  • Anionic fluorocarbon surfactant and preparation method thereof
  • Anionic fluorocarbon surfactant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of fluorine-containing intermediate compound 1

[0035]

[0036]5g of p-bromobenzyl bromide, 12g of perfluoro-2-methyl-2-pentene, 2.32g of potassium fluoride and 30mL of DMF were successively added into a 50mL sealed tube, and reacted at 100°C for 24 hours. The system was cooled down to room temperature, and the mixed system was poured into diethyl ether. The organic phase was 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 purified through a silica gel column with petroleum ether as the eluent to obtain 5.86 g of compound 1.

[0037] 1 H NMR (CDCl 3 ,300MHz): δ(ppm)3.50(s,CH 2 ,2H),7.12-7.22(d,J=8.4Hz,Ar-H,2H),7.40-7.50(d,J=8.4Hz,Ar-H,2H); 19 F NMR (CDCl 3 ,282MHz,):δ(ppm)-62.63~-62.85(m,6F),-80.40~-80.60(t,3F),-106.20~-106.60(m,2F),-123.30~-123.60(m, 2F).

Embodiment 2

[0038] Embodiment 2: the synthesis of fluorine-containing intermediate compound 2

[0039]

[0040] Add 0.046g tetrakis(triphenylphosphine) palladium to 50mL sealed tube, after three times of gas exchange, add 1.952g compound 1, 0.54mL HPO(OMe) under the protection of argon 2 , 0.83mL Et 3 N and 20mL of toluene, after the addition, the system was sealed and reacted at 100°C for 12 hours. The system was lowered to room temperature, ether was added, filtered, the filtrate was decompressed to remove the solvent, the mixture was purified by silica gel column, the polarity of the eluent was increased from PE:EA=1:1 to 1:4, and finally 1.55 g of colorless liquid was obtained 2.

[0041] 1 H NMR (CDCl 3 ,300MHz): δ(ppm)3.54(s,CH 2 ,2H),3.73(d,J=11.1Hz,6H),7.38(dd,J=7.8,3.4Hz,Ar-H,2H),7.72(dd,J=13.1,8.2Hz,Ar-H,2H ); 19 F NMR (CDCl 3 ,282MHz,):δ(ppm)-62.70~-62.90(m,6F),-80.50~-80.70(t,3F),-106.30~-106.60(m,2F),-123.40~-123.60(m, 2F); 31 P NMR (CDCl 3 ,121MHz):δ(ppm)22.27(...

Embodiment 3

[0042] Embodiment 3: the synthesis of fluorine-containing intermediate compound 3

[0043]

[0044] 5g of compound 2, 30mL of water and 20mL of concentrated hydrochloric acid were refluxed for two days. The product became a massive solid, which was filtered, washed with water, and then washed with chloroform, and the solvent was removed under reduced pressure to obtain 4.5 g of white solid 3.

[0045] 1 H NMR (DMSO-d 6 ,300MHz): δ(ppm)3.69(s,CH 2 ,2H),7.31~7.40(m,Ar-H,2H),7.58~7.70(m,Ar-H,2H); 19 F NMR (DMSO-d 6 ,282MHz,):δ(ppm)-62.60~-62.83(m,6F),-80.95~-81.15(t,3F),-106.50~-106.90(m,2F),-123.50~-123.80(m, 2F); 31 P NMR (DMSO-d 6 ,121MHz): δ(ppm)13.70(s); 13 C NMR (DMSO-d 6 ,100MHz): δ(ppm)31.56,110~130,130.41,131.46,132.86,133.76,134.67; IR(cm -1 ):3400~3600,1455.2;LRMS(EI):490,171.;HRMS(EI):m / z calcd for C 6 f 13 CH 2 C 6 h 4 PO(OH) 2 :490.0005,found490.0003.

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Abstract

The invention relates to an anionic fluorocarbon surfactant and a preparation method thereof. The structural formula of the anionic fluorocarbon surfactant is as follows: CF3CF2CF2C(CF3)2CH2C6H4PO(OM)2, wherein M is equal to Li, Na, K or NH4. The preparation method comprises the following steps: (1) reacting hexafluoropropylene dimer and p-Bromobenzyl bromide to generate a fluorine-containing intermediate compound 1; (2) coupling the fluorine-containing intermediate compound 1 with dimethyl phosphite to obtain a fluorine-containing intermediate compound 2; (3) hydrolyzing the fluorine-containing intermediate compound 2 to generate a fluorine-containing organic acid 3; and (4) neutralizing the fluorine-containing organic acid 3 with alkali to obtain a product. The method has the advantages of being, simple, low in cost and good in repeatability, and raw materials can be easily obtained. The surface tension performance of the product is good.

Description

technical field [0001] The invention belongs to the preparation technology of fluorocarbon surfactants, in particular to an environment-friendly high surface tension active anionic fluorocarbon surfactant containing branched fluorocarbon chains and the preparation technology thereof. Background technique [0002] Fluorocarbon surfactants are the most important varieties of special surfactants. In many fields with special requirements, there are many irreplaceable important uses of hydrocarbon surfactants. [0003] The unique properties of fluorocarbon surfactants are often summarized as "three highs" and "two phobias", that is, high surface activity, high heat resistance stability and high chemical stability; its fluorine-containing hydrocarbon group is both water-repellent and oil-repellent. [0004] Fluorocarbon surfactants have high heat resistance and high chemical stability. They can resist the effects of strong oxidants, strong acids and strong alkalis, and can still m...

Claims

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Application Information

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IPC IPC(8): B01F17/14C07F9/38C09K23/14
Inventor 姜标沙敏潘仁明
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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