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Synthesis methods of alkali metal salt containing sulfonyl chloride or phosphorus imide and alkali metal salt containing fluorine sulfonyl or phosphorus imide

A technology of phosphoroimide base and fluorine-containing sulfonyl, which is applied in the field of preparation of fluorine compounds, and can solve the problems of high price of fluorine-containing acid anhydrides, large power consumption, and low atomic economy

Active Publication Date: 2012-08-01
武汉市瑞华新能源科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] 1) The reaction needs to be carried out at low temperature, which consumes a lot of electric energy
[0010] 2) Perfluoroalkyl sulfonyl fluorides with low carbon chains have a low boiling point, making production and storage inconvenient
[0011] 3) The preparation method of acid anhydride is adopted, in which fluorosulfonic anhydride is highly toxic and highly corrosive, and other fluorine-containing anhydrides are expensive
[0023] 3) Synthesis of (chlorosulfonyl) (perfluoroalkylsulfonyl) imide by "one-pot method" of perfluoroalkylsulfonamide, thionyl chloride, and chlorosulfonic acid, and a higher yield is obtained, but the preparation process There are tons of SO 2 and HCl acid gas, the environmental pollution is relatively serious, and the atom economy is not high (Zhou Zhibin et al., CN 1O1747242A; H.-B.Han et al, Chem Lett, 2010, 39, 472; M.Beran et al, Polyhedron, 2010 , 29, 991)

Method used

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  • Synthesis methods of alkali metal salt containing sulfonyl chloride or phosphorus imide and alkali metal salt containing fluorine sulfonyl or phosphorus imide
  • Synthesis methods of alkali metal salt containing sulfonyl chloride or phosphorus imide and alkali metal salt containing fluorine sulfonyl or phosphorus imide
  • Synthesis methods of alkali metal salt containing sulfonyl chloride or phosphorus imide and alkali metal salt containing fluorine sulfonyl or phosphorus imide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Preparation of trifluoromethanesulfonamide:

[0072] The reaction formula is as follows:

[0073]

[0074] Add 156g (1mol) sodium trifluoromethanesulfinate (CF 3 SO 2 Na), 500mL water, 113g hydroxylamine oxysulfonic acid (NH 2 OSO 3 H) (1mol), 82g (1mol) sodium acetate (CH 3 COONa) was used as a buffer, and the reaction temperature was controlled by an ice-salt bath to be -10°C. After 10 hours of reaction, the reaction was stopped. Add an appropriate amount of sulfuric acid to adjust the pH of the system to 2-3. Add 100mL ether to extract, repeat twice. After the organic phases were combined, anhydrous sodium sulfate was added to dry, and ether was removed by rotary evaporation to obtain 104 g of a white solid product with a yield of 70%.

Embodiment 10

[0080] Preparation of (fluorosulfonyl) (trifluoromethylsulfonyl)imide potassium salt:

[0081]

[0082] In a 500mL three-necked flask, add 94g (0.5mol) trifluoromethanesulfonamide potassium salt, 80g (0.5mol) [(CH 3 ) 3 Si] 2 NH, 200mL 1,4-dioxane, heated to 145°C and refluxed for 12h. After completion of the reaction, the remaining [(CH 3 ) 3 Si] 2 NH and 1,4-dioxane to give the off-white solid product [CF 3 SO 2 ]NK[(CH 3 ) 3 Si] 2 . Then add 200mL 1,4-dioxane, dropwise add SO at room temperature 2 Cl 2 (0.5mol), after the dropwise addition, heat up to 80°C and reflux for 8h, distill off the by-product trimethylchlorosilane, add anhydrous 58g (1mol) KF, reflux at 80°C for 8h, suction filter, concentrate the filtrate, add etc. volume of CH 2 Cl 2 Perform recrystallization. After filtration, washing and drying, 77 g (0.35 mol) of a colorless crystalline solid of potassium salt of (fluorosulfonyl)(trifluoromethylsulfonyl)imide was obtained, with a yield of 78...

Embodiment 11

[0084] Preparation of (fluorophosphoryl) (trifluoromethylsulfonyl)imide potassium salt:

[0085]

[0086] To the 500mL flask, add 94g (0.5mol) CF 3 SO 2 NKSi(CH 3 ) 3 , 200mL nitromethane, phosphorus oxychloride was added dropwise at room temperature, after the dropwise addition was completed, reflux at 80°C for 10 hours. After completion of the reaction, the by-product trimethylchlorosilane was steamed, and the reaction system was transferred to a 500mL PFA bottle, and (C 2 h 5 ) 3 N(HF) 4 , Stirring for 4h at 40°C to stop the reaction. Use dry nitrogen flow at 50°C to remove excess residual hydrogen chloride and other volatile components, add saturated potassium carbonate solid under stirring at -30°C until there is no CO in the solution 2 Gas generation, add diethyl carbonate for extraction three times, 100mL each time, collect the diethyl carbonate phase, add 25g potassium carbonate to dry, filter, collect the filtrate, evaporate the solvent under reduced pressu...

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Abstract

The invention discloses a synthesis method of an alkali metal salt containing sulfonyl chloride or phosphorus imide: the alkali metal salt is prepared by subjecting compound (V-2) and sulfuryl chloride or phosphorus oxychloride to nucleophilic substitution under the presentation of acid binding agents; the invention further discloses a synthesis method of an alkali metal salt containing fluorine sulfonyl or phosphorus imide, the alkali metal salt is prepared by reacting (sulfonyl chloride) (perfluorinated alkyl) imide salt (V-1) or (dichloro phosphoryl) (perfluorinated alkyl sulfonyl) imide salt (V-2) with fluorinated reagents. The synthesis methods have the advantages that the experiment condition is mild, and the used materials are convenient to store and prepare; the preparation rate is high, the purification is simple, the preparation cost is low, and the methods are suitable for mass industrial preparation. The preparation rate and the purity of the resultants are high, and the resultants can be used as lithium salt electrolyte materials for lithium batteries, or for preparing catalytic agents, and for synthesizing high-performance ionic liquids.

Description

technical field [0001] The invention belongs to the preparation method of fluorine compound, be specifically related to bis(chlorosulfonyl)imide (HN(SO 2 Cl) 2 ), (perfluoroalkylsulfonyl chloridesulfonyl)imide (HN(SO 2 Cl)(SO 2 R f ), R f =C m f 2m+1 , m=0-8), (perfluoroalkylsulfonyl dichlorophosphoryl)imide (HN(POCl 2 )(SO 2 R f ), R f =C m f 2m+1 , m is an integer, m=0-8) and the corresponding fluorinated products of the above-mentioned chlorosulfonyl / phosphorimide containing fluorosulfonyl / phosphorimide; and fluorine-containing / chlorosulfonyl / phosphorimide base Process for the preparation of metal salts. Background technique [0002] Perfluoroalkyl sulfonamides are the basic raw materials for the synthesis of fluorine-containing sulfonyl (phosphoryl) imides. In addition, various fluorine-containing imide salts derived from fluorine-containing sulfonyl (phosphoryl) imides are used in many fields. to an extremely important role. In particular, lithium salts o...

Claims

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Application Information

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IPC IPC(8): C07C311/48C07C303/36C07C303/40C07F9/26
Inventor 周志彬韩鸿波付世涛陈瀚林
Owner 武汉市瑞华新能源科技有限公司
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