Imine alkali metal salt and ion liquid as well as application thereof as non-water electrolyte

A technology of ionic liquids and electrolytes, applied in the preparation of sulfonamides, organic chemistry, etc., can solve the problems of long synthetic routes, low overall yields, and high cost of preparation methods

Inactive Publication Date: 2014-03-12
HUAZHONG UNIV OF SCI & TECH +1
View PDF1 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the shortcoming of this preparation method is: (1) with trifluoromethanesulfonyl isothiocyanate (CF 3 SO 2 N=S=O) is the raw material, and the yield of synthesizing the raw material is low; (2) Ruppert reagent (trimethyltrifluoromethylsilane, CF 3 SiMe 3 ), the price is more expensive, not suitable for large-scale preparation; (3) from the raw material trifluoromethylsulfonyl isothiocyanate (CF 3 SO 2 N=S=O) to the final product, the synthetic route is long and the overall yield is low
[0010] 2) Trifluoromethyl (S-trifluoromethylsulfonylimido)sulfonyl chloride (CF 3 (CF 3 SO 2 N)SOCl, formula (II)) through fluorination reaction to obtain trifluoromethyl (S-trifluoromethylsulfonylimide) sulfonyl fluoride (CF 3 (CF 3 SO 2 N)SOF), further and lithium nitride (Li 3 N) reaction to synthesize lithium bis(trifluoromethyl(S-trifluoromethylsulfonylimide)sulfonyl)imide ([(CF 3 (CF 3 SO 2 N)SO) 2 N]Li formula (Ⅴ)), but this synthetic route is only suitable for preparing symmetrical target products (US6340716B1)
[0020] So far, the relevant "S-fluoroalkylsulfonylimide (R F SO 2 There are few reports on the synthesis of fluoroalkylsulfonylimides and their derivatives with N=S)” group, and the existing preparation methods have disadvantages such as high cost and low yield, especially the ionic liquid of the anion and its derivatives. The application of lithium salts as electrolyte materials in the field of electronic devices (such as lithium-ion batteries, carbon-based supercapacitors) has not been reported yet
Especially (fluoroalkyl(S-fluoroalkylsulfonimido)sulfonyl)(fluorosulfonyl)imide and (fluoroalkyl(S-fluoroalkylsulfonimido)sulfonyl)(bis The preparation and application of fluorophosphoryl imine compounds and their derivatives have not been reported yet.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Imine alkali metal salt and ion liquid as well as application thereof as non-water electrolyte
  • Imine alkali metal salt and ion liquid as well as application thereof as non-water electrolyte
  • Imine alkali metal salt and ion liquid as well as application thereof as non-water electrolyte

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-9

[0115] Embodiment 1-9 relates to the preparation of imide alkali metal salt containing "S-fluoroalkylsulfonylimide group"

Embodiment 1

[0116] Embodiment 1: (trifluoromethylsulfonyl) (trifluoromethylsulfinyl) potassium imide ([(CF 3 SO 2 )(SOCF 3 )N]K) The preparation synthesis reaction route is as follows:

[0117]

[0118] Add sodium trifluoromethanesulfinate (CF 3 SO 2 Na) (65.5g, 0.42mol), 100mL chlorobenzene. Stir mechanically, heat to 30°C, slowly add SOCl dropwise 2 (59.5 g, 0.5 mol), stirring was continued for 2 hours after the dropwise addition was completed. Atmospheric distillation, collecting fractions at 30°C. 55 g of trifluoromethanesulfonyl chloride (pale brown liquid) were obtained, yield 87%.

[0119] Add trifluoromethanesulfonamide (CF 3 SO 2 NH 2 ) (29.8g, 0.2mol), acetonitrile (80mL), pyridine (31.6g, 0.4mol) as acid-binding agent, stirred to dissolve, and added dropwise trifluoromethylsulfinyl chloride (CF 3 SOCl) (35g, 0.23mol), remove the ice bath after the dropwise addition, continue to stir at room temperature for 24h, and remove the solvent and unreacted CF by rotary eva...

Embodiment 2

[0120] Example 2: Trifluoromethyl (S-trifluoromethylsulfonylimido) sulfonamide (CF 3 (CF 3 SO 2 N)SONH 2 ) preparation

[0121]

[0122] Potassium (trifluoromethylsulfonyl)(trifluoromethylsulfinyl)imide ([(CF 3 SO 2 )(SOCF 3 )N]K) (66.7g, 0.22mol) was dissolved in 200mL distilled water, and was added successively under mechanical stirring 2 OSO 3 H) (38.2g, 0.34mol) and sodium acetate (CH 3 CO 2 Na) (27.9g, 0.34mol), after stirring for 8 hours, extracted with ether (50mLx3), and combined the organic phases. After adding anhydrous magnesium sulfate to dry, filter, collect the filtrate, and remove ether by rotary evaporation to obtain a white flaky solid. Yield 34.8g, yield 60%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
particle sizeaaaaaaaaaa
melting pointaaaaaaaaaa
thermal decomposition temperatureaaaaaaaaaa
Login to view more

Abstract

The invention discloses an application of imine alkali metal salt and an ion liquid as non-water electrolyte, and provides an ion liquid consisting of perfluoroalkyl sulfimide alkali metal salt with 'S-perfluoroalkyl sulfimide', perfluoroalkyl sulfimide anion with 'S-perfluoroalkyl sulfimide', as well as sulfonium salt, ammonium salt, microcosmic salt cation. According to the application, an intermediate fluoro-alkyl(S-perfluoroalkyl imino) sulfamide of perfluoroalkyl sulfimide is prepared by reacting (perfluoroalkyl sulfonyl)(perfluoroalkyl sulfinyl) imino with sulfur valence state of +4 and hydroxylamine oxygen sulfonic acid, the routes that fluoro-alkyl(S-perfluoroalkyl imino) sulfamide is prepared from (perfluoroalkyl sulfonyl)(perfluoroalkyl sulfinyl) imino through three steps of chlorination, fluorination and amination are effectively shortened, the operation is simple and convenient, the yield and the purity are high, the alkali metal salt has relatively good thermal stability and hydrolysis resistance, has high conductivity and oxidation potential in the conventional carbonic ester solution, and is good in compatibility with widely applied electrode materials, and the ion liquid can be applied to lithium ion batteries and carbon-based super capacitors.

Description

technical field [0001] The invention belongs to the field of organic fluorine chemistry, new materials and advanced power supply technology, and specifically relates to an alkali metal salt of a fluoroalkylsulfonimide containing an "S-fluoroalkylsulfonimide group", an ionic liquid and its preparation Method, and the application of the alkali metal salt and ionic liquid as electrolyte materials in secondary lithium (ion) batteries and carbon-based supercapacitors. Background technique [0002] Fluorine-containing sulfonylimides and their alkali metal salts, especially lithium salts, are important fluorine-containing ion compounds. They are used in high-performance nonaqueous Electrolyte materials, new high-efficiency catalysts and other fields have important industrial application value. [0003] At present, the research on fluorine-containing sulfonimides is mostly concentrated on monofluorine-containing sulfonimides (Coord.Chem.Revs., 1997, 158, 413.), that is, the anion s...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/48C07C303/36
Inventor 韩鸿波周志彬聂进程小荣巩守则
Owner HUAZHONG UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products