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Fluorocarbon surfactant and preparation method thereof

A technology of fluorocarbon surfactants and active agents, which is applied in the field of fluorocarbon surfactants and their preparation, and can solve the problems of application limitations and low surface activity of branched chain products.

Active Publication Date: 2016-01-20
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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  • Fluorocarbon surfactant and preparation method thereof
  • Fluorocarbon surfactant and preparation method thereof
  • Fluorocarbon surfactant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Embodiment 1: the synthesis of fluorine-containing intermediate organic acid compound 3

[0071]

[0072] 2.14g of p-bromomethylbenzoic acid, 0.61g of DMAP and 4.12g of DCC were sequentially added into a 100mL jacketed reaction tube. After three times of ventilation, 50mL of anhydrous dichloromethane was added in an ice-water bath, and stirred for a while. Excess methanol was added to the system, and the system was moved to room temperature for reaction after the drop was completed, and the reaction was monitored by TLC. After 5 hours the reaction was complete. System filtration, filtrate successively with KHSO 4 solution, deionized water and saturated brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed. Finally, the mixture was passed through a silica gel column with an eluent of EA:PE=1:20 to obtain 1.942g of compound 1.

[0073] 1 HNMR (CDCl 3 ,300MHz): δ(ppm)3.92(s,CH 3 ,3H),4.50(s,CH 2 ,2H),7.44-7.48(d,...

Embodiment 2

[0079]Example 2: Synthesis of anionic fluorocarbon surfactants containing branched fluorocarbon chains

[0080]

[0081] 3.6 g of compound 3 was dissolved in 20 mL of tetrahydrofuran, and lithium hydroxide aqueous solution was slowly added dropwise until the system pH=7-8. After dropping, the mixed system was spin-dried to obtain a viscous solid. The solid was washed and filtered with acetone, the filter cake was dissolved with methanol, and the solvent was removed to obtain 3.1 g of white powdery anionic fluorocarbon surfactant.

[0082] 1 HNMR (CD 3 OD,300MHz):δ(ppm)3.71(s,CH 2 ,2H),7.30-7.37(d,J=8.4Hz,Ar-H,2H),7.86-7.93(d,J=8.4Hz,Ar-H,2H); 19 FNMR (CD 3 OD,282MHz,):δ(ppm)-63.68~-63.90(m,6F),-81.98~-82.14(t,3F),-106.90~-107.20(m,2F),-124.05~-124.40(m ,2F). 13 CNMR (CD 3 OD,100MHz,):δ(ppm)33.32,110~127,130.12,132.18,134.28,139.15,174.80;LRMS(EI):454,437.Anal.CalcdforC 14 h 6 f 13 LiO 2 :Li,1.51.Found:Li,1.48.

Embodiment 3

[0083] Example 3: Synthesis of quaternary ammonium salt cationic fluorocarbon surfactants containing branched fluorocarbon chains

[0084]

[0085] Add 5 g of compound 3, 0.675 g of DMAP and 4.2 g of EDCI in sequence in a 100 mL jacketed reaction tube,

[0086] After pumping and exchanging air three times, add 50 mL of dichloromethane under an ice-water bath, and stir for a while. Add excess N,N-dimethylethylenediamine to the system, and after the drop is complete, the system is moved to room temperature for reaction. The reaction was monitored by TLC, and the reaction was completed after 5 hours.

[0087] 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 passed through a silica gel column with dichloromethane:methanol:triethylamine=20:1:a small amount of eluent to obtain 5.126g of compound 7.

[0088] 1 HNMR (DMSO-d 6 ,...

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Abstract

The invention relates to a fluorocarbon surfactant containing CF3CF2CF2C(CF3)2 groups and a preparation method thereof. The method takes perfluoro-2-methyl-2-pentene as the initial raw material, and firstly nucleophilically substituted with benzyl bromide to prepare a fluorine-containing intermediate carboxylic acid. Anionic fluorocarbon surfactant is obtained by neutralizing carboxylic acid and alkaline solution; carboxylic acid and amine are condensed to form fluorine-containing intermediate amide. The corresponding quaternary ammonium salt-type cationic fluorocarbon surfactants, betaine-type amphoteric fluorocarbon surfactants and gemini-type fluorocarbon surfactants are prepared by reacting amides with alkyl halides, sodium chloroacetate or biphenyl dichlorobenzyl, respectively. The method has the following advantages: readily available raw materials, simple process, low price, good repeatability and good surface tension properties of the product.

Description

technical field [0001] The invention belongs to a fluorocarbon surfactant and a preparation method thereof, in particular to a preparation technology of an environment-friendly high surface tension active fluorocarbon surfactant containing branched fluorocarbon chains. 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 maintain good su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01F17/00B01F17/22B01F17/18C07C63/70C07C51/41C07C233/78C07C231/12C09K23/00C09K23/18C09K23/22
Inventor 姜标沙敏潘仁明
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI