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Alkali metal salt of (sulfonyl fluoride)( multi-fluorine alkoxy sulfonyl) imine and ionic liquids

A technology of polyfluoroalkoxysulfonyl and polyfluoroalkyl, which is used in the synthesis of imine alkali metal salts and ionic liquids, and can solve problems such as strong corrosion, inapplicability to large-scale preparation, and harsh reaction conditions

Active Publication Date: 2014-11-19
武汉市瑞华新能源科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Thanks to SO 2 f 2 The use of gas makes the reaction conditions of the method harsh, the operation is complicated, and the productive rate of the product is not high (WO1997 / 023448)
4) from trifluoromethanesulfonamide potassium salt (CF 3 SO 2 NHK) and fluorosulfonic anhydride (FSO 2 ) 2 O) Reaction preparation, but fluorosulfonic anhydride is highly toxic, therefore, not suitable for mass production (JP2005200359)
5) Through fluorosulfonic acid (FSO 3 H) to sulfur trioxide (SO 3 ) into trifluoromethanesulfonamide (CF 3 SO 2 NH 2 ), but the productive rate of this method is not high, while raw material FSO 3 H and SO 3 etc. are highly corrosive (WO2011148961)
[0006] But so far, the preparation of asymmetric (fluorosulfonyl) (polyfluoroalkoxysulfonyl) imide alkali metal salts and their ionic liquids has not been reported.

Method used

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  • Alkali metal salt of (sulfonyl fluoride)( multi-fluorine alkoxy sulfonyl) imine and ionic liquids

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Embodiment 1

[0034] Embodiment 1: Potassium (fluorosulfonyl) (2,2,2-trifluoroethoxysulfonyl)imide (K[(FSO 2 )(CF 3 CH 2 OSO 2 )N], K[TFE-FSI]) synthesis

[0035] Mix 100g (1.0mol) trifluoroethanol (CF 3 CH 2 OH), 120g (1.2mol) triethylamine mixed system, slowly drop 92.4g (0.8mol) chlorosulfonamide (ClSO 2 NH 2 ) and 50mL of ethyl acetate, reflux for 20h, acidify with concentrated hydrochloric acid, extract with ether, and evaporate organic matter with a low boiling point under reduced pressure to obtain a colorless solid that is 2,2,2-trifluoroethoxysulfonamide ( CF 3 CH 2 OSO 2 NH 2 ) 143g, yield 80%.

[0036] 89.5g (0.5mol) CF 3 CH 2 OSO 2 NH 2 Add 100mL of acetonitrile to dissolve it, slowly add 67.5g (0.5mol) of sulfuryl chloride dropwise in an ice-salt bath, and react in the dark at 25°C for 20h, add 48g (0.3mol) of pyridine-hydrogen fluoride ((C 5 h 5 N)-(HF) 4 ), reacted at 60°C for 20h. Stop the reaction, add base K in ice bath 2 CO 3 Neutralize to pH 7-8, col...

Embodiment 2-11

[0037] Examples 2-11: According to the reaction conditions and operation sequence of Example 1, the preparation conditions and results of other alkali metal salts are shown in Table 1.

[0038]Table 1. Partial synthesis conditions and yields based on (fluorosulfonyl) (2,2,2-trifluoroethoxysulfonyl) imide anion alkali metal salts (SO in the table 2 Cl 2 The dosage is 0.5mol)

[0039]

[0040]

[0041] Note: [TFE-FSI] - =[(FSO 2 )(CF 3 CH 2 OSO 2 )N] - ;

Embodiment 12

[0043] Embodiment 12: Ionic liquid [IM(CH 3 )(CH 2 CH 3 )][TFE-FSI]([TFE-FSI] - =[(FSO 2 )(CF 3 CH 2 OSO 2 )N] - )

[0044] By K[TFE-FSI] and Im(CH 3 )(CH 2 CH 3 ) Br prepared at room temperature. The specific operation is as follows: 6.3g (21mmol) K[TFE-FSI] and 3.80g (20mmol) IM (CH 3 )(CH 2 CH 3 )Br were dissolved in appropriate amount of deionized water respectively, then mixed at room temperature, and after 30 minutes of magnetic stirring reaction, the stratification was allowed to stand, and the lower layer liquid was separated with a separatory funnel. The lower layer liquid was the crude ionic liquid, and the crude product was dissolved in Dichloromethane was washed three times with deionized water, and the dichloromethane solvent was removed under reduced pressure, and dried under reduced pressure at 90° C. for 12 hours to obtain 6.30 g of a colorless transparent liquid with a yield of 85%. 1 H NMR (400MHz; CDCl 3 ;TMS): 1.57(t, J=7.2Hz, 3H), 4.04(s, 3...

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Abstract

The invention provides a method for preparing an alkali metal salt of (sulfonyl fluoride)( multi-fluorine alkoxy sulfonyl) imine, and preparing corresponding ionic liquids through a replacement reaction of the alkali metal salt and an ammonium salt, a phosphor salt, a sulfonium salt and the like. The invention provides an electrolyte material of a secondary lithium battery or carbon-based super capacitor based on an ionic liquid of an asymmetric (sulfonyl fluoride)( multi-fluorine alkoxy sulfonyl) imine negative ion. The electrolyte material has good compatibility with electrode materials of LiCoO2, LiFePO4, Li, graphite, Li4Ti5O12 and active carbon and the like.

Description

technical field [0001] The invention belongs to the field of organic fluorine chemistry and new energy materials, in particular to a synthesis method of (fluorosulfonyl)(polyfluoroalkoxysulfonyl)imide alkali metal salt and ionic liquid, and the prepared ionic liquid and alkali metal Application of salt as electrolyte material in lithium secondary batteries and supercapacitors. Background technique: [0002] Fluorine-containing sulfonylimides and their alkali metal salts, especially lithium salts, are important fluorine-containing organic ion compounds. They have important application value in the fields of high-performance non-aqueous electrolyte materials for energy conversion devices such as secondary lithium (ion) batteries, supercapacitors, and aluminum electrolytic capacitors, as well as new high-efficiency catalysts. Therefore, people have been devoting themselves to research on the synthesis and application of novel fluorine-containing sulfonimides and their derivati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C307/02C07C303/34H01M10/056
CPCY02E60/10
Inventor 周志彬刘成勇聂进
Owner 武汉市瑞华新能源科技有限公司
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