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3-oxa perfluoro-nonyl fluorocarbon surfactant, its synthesizing method and usages

A synthetic method and oxa technology, applied in chemical instruments and methods, sulfonate preparation, sulfonamide preparation, etc., can solve the problem of less application

Inactive Publication Date: 2005-11-30
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Industrially, perfluoroalkyl ether sulfonate surfactants are only used in the suppression of chromic acid mist, and have very good effects (see Acta Chemica Sinica, 1977, 35, 209), and are less used in other aspects

Method used

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  • 3-oxa perfluoro-nonyl fluorocarbon surfactant, its synthesizing method and usages
  • 3-oxa perfluoro-nonyl fluorocarbon surfactant, its synthesizing method and usages
  • 3-oxa perfluoro-nonyl fluorocarbon surfactant, its synthesizing method and usages

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The synthesis of embodiment 1 compound 1 and 2

[0038]

[0039]

[0040] 1M=Na, 2M=K

[0041] For the synthesis of 3-oxaperfluorononylsulfonyl fluoride, add 0.06mol antimony trifluoride and 5mL antimony pentachloride to a three-necked flask equipped with a condenser tube and a dropping funnel, and heat the oil bath to 30- 75°C, inject about 5mL of chlorine gas within 2 hours, raise the temperature to 115°C, add 0.048mol of 9-iodo-3-oxaperfluorononylsulfonyl fluoride dropwise within 1 hour under magnetic stirring, and continue the reaction for 4 hours , the product 3-oxaperfluorononylsulfonyl fluoride was distilled off with a yield of 83.6%.

[0042] 0.01 mol of 3-oxaperfluorononylsulfonyl fluoride was added to 0.021 mol of sodium hydroxide solution, stirred by magnetic force, and heated under reflux in an oil bath for 1 hour to obtain compound 1 with a yield of 98%. The same method can synthesize compound 2 yield 100%.

[0043] Compound 1C 8 f 17 S0 ...

Embodiment 2

[0053] The synthesis of embodiment 2 compound 3

[0054]

[0055] 0.01mol sulfonyl fluoride was added dropwise to 30mL chlorobenzene solution of 0.012mol triethylamine and 0.012mol triethoxymethyl silicon, stirred at room temperature for 8 hours, a white precipitate was precipitated, filtered and recrystallized with chlorobenzene to obtain 3, Yield 92%.

[0056] Compound 3C 16 h 20 f 17 NO 4 S

[0057] White solid, melting point: 178.4°C

[0058] IR(KBr): υ=1266, 1204, 1123cm -1 .

[0059] 19 F NMR, δ F : -4.77 (3F,t,CF 3 ), -5.58 (2F, m, OCF 2 ), -6.63 (2F, m, OCF 2 ), -41.90 (2F, s, CF 2 SO 3 ), -45.80 (2F, m, CF 2 ), -46.54 (2F, m, CF 2 ), -49.16 (2F, s, CF 2 ), -49.77~-49.88 (2F, m, CF 3 CF 2 ).

[0060] 1 H NMR, δ H : 3.47 (8H, q, CH 2 ), 1.37 (12H, t, CH 3 ).

[0061] Elemental analysis: Calculated (%): C 29.77, H 3.1, N 2.17, F 50.08. Found values ​​(%): C 29.61, H 3.3, N 2.08, F 51.23.

Embodiment 3

[0062] The synthesis of embodiment 3 compound 4 and 5

[0063]

[0064]

[0065]

[0066] Add 0.01mol sulfonyl fluoride and 0.02mol N,N-dimethylpropylenediamine to a mixture of 0.01mol potassium hydroxide and 20mL ethyl acetate, magnetically stir, reflux for 2 hours, filter while hot, and cool the filtrate Precipitated solid, recrystallized from ethanol to give CF 3 (CF 2 ) 5 OCF 2 CF 2 SO 2 NHCH 2 CH 2 CH 2 N(CH 3 ) 2 , yield 72.4%.

[0067] Add 3.5mmol methyl iodide dropwise to 0.5mmol CF in ice bath 3 (CF 2 ) 5 OCF 2 CF 2 SO 2 NHCH 2 CH 2 CH 2 N(CH 3 ) 2 and 20 mL of ethyl acetate, stirred magnetically at room temperature for 48 hours, evaporated the solvent, washed the column with diethyl ether and separated to obtain compound 4 with a yield of 66.6%.

[0068] Compound 4C 14 h 16 f 17 IN 2 o 3 S

[0069] Pale yellow solid, melting point: 105.1°C

[0070] IR(KBr): υ=3508, 3159, 3008, 1203, 1144cm -1 .

[007...

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Abstract

A compound containing 3-oxyheteroperfluoro nonylsulfuryl has the molecular formula: C6F13OC2F4SOnR, where R=NR4' or N(R2)(CH2)mNR*4X, n=2 or 3, and m=1-12. It can be used as a good surfactant. Its aqueous solution has better surface activity to reduce its surface tension to 16-20 mN / m.

Description

technical field [0001] This patent relates to a 3-oxaperfluorononyl compound, its synthesis method and application. Using ω-iodo-3-oxaperfluorononanesulfonyl fluoride as raw material to generate 3-oxaperfluorononanesulfonyl fluoride through fluorination, and use it to further synthesize 3-oxaperfluorononane Sulfonyl cationic and anionic surfactants. Background technique [0002] Among the fluorine-containing materials, there are not only solid materials such as the famous polytetrafluoroethylene (Teflon) plastic and fluororubber, but also freon gas and inert liquids that have become environmental problems. These gas and liquid materials also have important application value. The advantages of the physical properties of these fluorine-containing materials are excellent heat resistance and chemical resistance, etc. [0003] Ordinary surfactants or hydrocarbon surfactants have been studied and applied extensively for many years, and the ones synthesized in this paper are mai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/24C09K23/26
Inventor 刘金涛魏启华黄维垣
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI