Branch fluorocarbon chain containing fluorocarbon surfactant and preparation method thereof

A technology of fluorocarbon surface and active agent, which is applied in the preparation of sulfonic acid, sulfonate ester, sulfonamide, etc., and can solve problems such as less research

Active Publication Date: 2015-09-30
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the branched fluorosurfactants synthesized by hexafluoropropylene oligomerization at home and abroad are based on hexafluoropropylene trimer, and there are very few reports on the synthesis of fluorosurfactants with hexafluoropropylene dimer, and the hexafluoropropylene dimer is used to

Method used

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  • Branch fluorocarbon chain containing fluorocarbon surfactant and preparation method thereof
  • Branch fluorocarbon chain containing fluorocarbon surfactant and preparation method thereof
  • Branch fluorocarbon chain containing fluorocarbon surfactant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: the synthesis of fluorine-containing intermediate amide compound 6

[0055]

[0056] 1.84g (10mmol, 1equiv) 4-methylbenzyl bromide, 1.16g (20mmol, 2equiv) potassium fluoride, 20mL DMF and 4.5g (15mmol, 1.5equiv) perfluoro-2-methyl-2 - Pentene. The system was reacted at 80°C for 10h. The system was poured into water, extracted with petroleum ether, the combined PE extracts were washed successively with saturated sodium bicarbonate and saturated brine, then dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was passed through a PE column to obtain 3.3g Colorless liquid compound 1, yield 77.8%.

[0057] 1 H NMR (CDCl 3 ,300MHz): δ(ppm)2.36(s,CH 3 ,3H),3.53(s,CH 2 ,2H),7.15-7.17(d,J=8.1Hz,Ar-H,2H),7.17-7.24(d,J=8.1Hz,Ar-H,2H); 19 F NMR (CDCl 3 ,282MHz,):δ(ppm)-61.05~-61.25(m,6F),-78.85~-78.98(t,3F),-104.60~-104.95(m,2F),-121.65~-121.90(m, 2F); 13 C NMR (100MHz, CDCl 3 ): δ (ppm) 20...

Embodiment 2

[0062] Example 2: Synthesis of quaternary ammonium salt cationic fluorocarbon surfactants containing branched fluorocarbon chains

[0063]

[0064] 0.287g (0.5mmol, 1equiv) of compound 6, 0.156g (1mmol, 2equiv) of iodoethane and 1mL of acetonitrile were reacted at 80°C for 5h in a 5mL sealed tube under the protection of argon. The system was lowered to room temperature, and the solvent was removed by rotary evaporation under reduced pressure, and the crude product was subjected to CH 2 Cl 2 :methanol=9:1 column to obtain 200mg white powder compound.

[0065] 1 H NMR (DMSO-d 6 ,300MHz): δ(ppm)1.15-1.25(t, J=6.6Hz, N(CH 3 ) 2 CH 2 CH 3 ,3H),2.57(s,CH 3 ,3H),3.02(s,N(CH 3 ) 2 ,6H),3.06-3.16(q,N(CH 3 ) 2 CH 2 CH 3 ,2H),3.30~3.36(m,NHCH 2 CH 2 N(CH 3 ) 2 CH 2 CH 3 ,4H),3.85(s,C 6 f 13 CH 2 C 6 h 3 ,2H),7.42-7.48(d,J=8.1Hz,Ar-H,1H),7.48-7.55(d,J=8.1Hz,Ar-H,1H),7.84(s,Ar-H,1H) ,8.08-8.15(t,J=5.7Hz,NH,1H); 19 F NMR (DMSO-d 6 ,282MHz,):δ(ppm)-61.95~-62.14...

Embodiment 3

[0066] Example 3: Synthesis of betaine-type amphoteric fluorocarbon surfactants containing branched fluorocarbon chains

[0067]

[0068] 0.316g (0.55mmol, 1.1equiv) of compound 6, 0.058g (0.5mmol, 1equiv) of sodium chloroacetate and 1mL of acetonitrile were reacted at 80°C for 12h in a 5mL sealed tube under argon protection. The system was filtered, and the solid was first washed with acetonitrile, then washed with acetone, then dissolved in methanol, filtered, and the solvent was removed from the filtrate to obtain 0.178 g of a white solid compound.

[0069] 1 H NMR (CD 3 OD,300MHz)δ:2.60(s,C 6 h 3 CH 3 ,3H),3.20~3.30(m,8H),3.70~3.85(m,6H),7.37(d,J=7.8Hz,Ar-H,1H),7.48(d,J=7.8Hz,Ar-H ,1H),7.92(s,Ar-H,1H); 19 F NMR (CD 3 OD,282MHz)δ:-63.60~-63.85(m,6F),-81.94(t,J=13.7Hz,3F),-106.90~-107.30(m,2F),-124.00~-124.30(m,2F ); 13 C NMR (100MHz, CD 3 OD): δ (ppm) 19.7, 37.9, 52.4, 62.6, 63.5, 65.5, 130.7, 133.4, 133.7, 137.1, 138.5, 138.6, 168.2; LRMS (MALDI): 655.0 (M-Cl)...

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Abstract

The invention relates to a branch fluorocarbon chain containing fluorocarbon surfactant and a preparation method thereof. The preparation method comprises the following steps: with perfluoro-2-methyl-2-pentene as the initial raw material, carrying out nucleophilic substitution with p-methylbenzyl bromine to prepare a fluorine containing intermediate 1, reacting the fluorine containing intermediate 1 with chlorosulfonic acid to obtain a fluorine containing intermediate 2 and a surfactant I, carrying out condensation with the fluorine containing intermediate 2 and amine to prepare a fluorine containing intermediate amide 4, separately reacting the fluorine containing intermediate amide 4 with haloalkane, sodium chloroacetate or 4,4-bis(chloromethyl)-1,1-biphenyl to correspondingly prepare a hyamine type cation fluorocarbon surfactant II, lycine-derived ampholytic fluorocarbon surfactant III and Gemini type fluorocarbon surfactant IV, and carrying out condensation with the fluorine containing intermediate 2 and alcohol to prepare a non-ionic fluorocarbon surfactant V. The preparation method has the following advantages that the raw material is easily available, the process is simple, the cost is low, the repeating performance is good and the product surface tension performance is good.

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] Due to its excellent and unique properties such as high surface activity, high heat resistance stability, high chemical stability, and both water and oil repellency, fluorosurfactants have extremely broad uses. At present, fluorosurfactants have been widely used in many industries such as chemical industry, machinery, textile, papermaking, paint, glass, ceramics, household goods, etc. It can also be used to manufacture fire extinguishing agents with excellent performance. necessary fire-fighting drugs. However, due to the current high price, it has not been used in large quantities in the fields where hydrocarbon surfactants can usually be used. Fluorosurfactants are currently m...

Claims

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Application Information

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IPC IPC(8): B01F17/26B01F17/28B01F17/12B01F17/42C07C311/18C07C303/40C07C309/73C07C303/28C07C309/39C07C303/08C09K23/26C09K23/12C09K23/28C09K23/42
Inventor 姜标沙敏邢萍潘仁明
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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