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Bis[(fluoroalkyl)sulfonyl]imides, fluoroalkyl sulphonyl iminium salt thereof, preparation and use

A technology of fluoroalkylsulfonylimide salt and fluoroalkylsulfonylimide, which is applied in the preparation of sulfonamides and organic chemistry, and can solve problems such as harsh process conditions and difficult raw material sources

Inactive Publication Date: 2009-08-12
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

Unfortunately, the preparation methods reported in the literature either have difficult source of raw materials or harsh process conditions.

Method used

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  • Bis[(fluoroalkyl)sulfonyl]imides, fluoroalkyl sulphonyl iminium salt thereof, preparation and use
  • Bis[(fluoroalkyl)sulfonyl]imides, fluoroalkyl sulphonyl iminium salt thereof, preparation and use
  • Bis[(fluoroalkyl)sulfonyl]imides, fluoroalkyl sulphonyl iminium salt thereof, preparation and use

Examples

Experimental program
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Effect test

example 1

[0039] Example 1: Cl(CF 2 ) 2 SO 2 Cl and Cl(CF 2 ) 2 SO 2 Preparation of F

[0040] Dissolve 1-chloro-2-iodo-tetrafluoroethane (256.1g, 0.707mol) in acetonitrile (40m), add sodium bicarbonate (219.0g, 90%, 1.13mol), sodium bicarbonate (104.9g, 1.25mol ) and water (40ml), reacted at room temperature for 22h. The solvent in the reaction solution was distilled off under reduced pressure, and the resulting residue was extracted three times with ethyl acetate (3x50ml), the ethyl acetate layers were combined, and washed with anhydrous Na 2 SO 4 Let dry overnight. The ethyl acetate layer was evaporated to dryness under reduced pressure, and the resulting solid was sucked dry to obtain Cl(CF 2 ) 2 SO 2 Na (188.5 g, 84%).

[0041] Sodium chlorotetrafluoroethylsulfinate (148g, 0.667mol) was dissolved in water (150mL). Under cooling in an ice-water bath, chlorine gas was introduced. After the reaction system changed from light yellow to yellowish brown, the reaction was stop...

example 2

[0045] Example 2: Cl(CF 2 ) 2 SO 2 NH 2 preparation of

[0046] In a dry ice-acetone bath, liquid ammonia (40ml) was mixed with Cl(CF 2 ) 2 SO 2 F (27.54g, 0.12mol) was reacted for 2h. Then return to room temperature naturally and acidify with sulfuric acid. Diethyl ether was added for extraction (80ml). The resulting ether layer was washed three times with water (3 x 20ml). The ether layer was pumped dry under reduced pressure to obtain Cl(CF 2 ) 2 SO 2 NH 2 (23.90 g, 88%).

[0047] Cl(CF 2 ) 2 SO 2 NH 2 : 1 H NMR (CD 3 COCD 3 ): δ 8.05(s, 2H). 19 F NMR (CD 3 COCD 3 ): δ-112.3(s, 2F), -66.1(s, 2F).ESIMS(m / e): 214.0[M] - (100), 216.0[M+2] - (32). Elemental analysis (Anal. Calcd for) C 2 h 2 CIF 4 NO 2 S: C, 11.14; H, 0.94; N, 6.50. Found: C, 11.15; H, 0.93; N, 6.54.

example 3

[0048] Example 3: I(CF 2 ) 2 O(CF 2 ) 2 SO 2 NH 2 preparation of

[0049] In a dry ice-acetone bath, mix liquid ammonia (100ml) with I(CF 2 ) 2 O(CF 2 ) 2 SO 2 F (77.17g, 0.18mol) was reacted for 2h. Stop the reaction, then return to room temperature naturally, and acidify with sulfuric acid. The system is divided into two layers, and the lower layer is separated. The lower layer was washed three times with water (3×20ml), and dried under reduced pressure to obtain I(CF 2 ) 2 O(CF 2 ) 2 SO 2 NH 2 (70.20g, 92%)

[0050] I(CF 2 ) 2 O(CF 2 ) 2 SO 2 NH 2 : 1 H NMR (CDCl 3 ): δ 5.36(s, 2H). 19 F NMR (CDCl 3 ): δ-115.8(s, 2F), -84.8(m, 2F), -81.0(t, J=12.4Hz, 2F), -64.3(t, J=12.4Hz, 2F).ESIMS(m / e ): 421.9[M] - (100).Elemental analysis (Anal.Calcd for)C 4 h 2 f 8 INO 3 S: C, 11.36; H, 0.48; N, 3.31. Found: C, 11.48; H, 0.78; N, 3.51.

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Abstract

The invention relates to a new fluoroalkyl sulfonyl imide and fluoroalkyl sulfonyl imides thereof, a preparation method and usage. The fluoroalkyl sulfonyl imide and fluoroalkyl sulfonyl imides are prepared by taking fluoroalkyl sulfonyl chloride or fluoroalkyl vikane and can be high-efficiently used in ion exchange reaction.

Description

technical field [0001] The invention relates to a novel fluoroalkylsulfonylimide or fluoroalkylsulfonylimide salt, a preparation method and use. Background technique [0002] Perfluoroalkylsulfonylimide salts are a class of salts with important application value developed in the process of superacid research. They can be used not only as surfactants and lithium battery materials (J.Power Sources, 1997,68,307; J.Power Sources, 2000,90,27), but also as Lewis acid catalysts (Synlett.1995,975; Tetrahedron Lett.1995, 36, 49, 8977) and ion exchangers (J.Am.Chem.Soc., 2000, 122, 7264; J.Fluorine Chem.2000, 102, 135), for catalytic reactions and preparation of high-density of ionic liquids. The current representative perfluoroalkylsulfonimide salt is trifluoromethanesulfonimide salt. We know that trifluoromethanesulfonyl imide salt is a lithium battery electrolyte material and ion exchange reagent with excellent performance. Unfortunately, the preparation methods reported in the...

Claims

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Application Information

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IPC IPC(8): C07C311/48C07C303/38C07D233/58
Inventor 肖吉昌张成潘严冲强震卫
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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