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Application of bis(fluorosulfonyl)imide as catalyst

The technology of bisfluorosulfonimide and catalyst is applied in the application field of bisfluorosulfonimide as a catalyst, which can solve the problems of narrow application field of bisfluorosulfonimide, and achieves strong substrate adaptability and atom economy. High performance and mild reaction conditions

Active Publication Date: 2021-07-16
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is to overcome the narrow defect of the existing bisfluorosulfonimide application field, and provide a kind of application of bisfluorosulfonimide as a catalyst. In the present invention, bisfluorosulfonimide As a catalyst, amines can efficiently catalyze Friedel-Crafts reaction, esterification reaction, lactone ring-opening polymerization reaction, silicon ether polymerization reaction, reductive etherification of carbonyl compounds, alkynyl hydrolysis and other reactions, with mild reaction conditions and high atom economy

Method used

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  • Application of bis(fluorosulfonyl)imide as catalyst
  • Application of bis(fluorosulfonyl)imide as catalyst
  • Application of bis(fluorosulfonyl)imide as catalyst

Examples

Experimental program
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Effect test

preparation Embodiment 1

[0269]

[0270] Add 10 g of potassium bisfluorosulfonimide (45.6 mmol) and 10 g of 98% concentrated sulfuric acid (100 mmol) into the autoclave, feed 60 g of sulfur dioxide at -70°C, slowly rise to room temperature, react for half an hour, and a white solid appears Generate, then slowly release sulfur dioxide gas, add 50ml of dichloromethane, filter, the solid is washed with 50ml of dichloromethane, the filtrate is spin-dried, and distilled under reduced pressure to collect 85 ° C / 20mm Hg fractions to obtain 7.7 g of difluorosulfonimide ( 42.5 mmol), colorless liquid, yield 93%.

[0271] 19 F NMR (dichloromethane as solvent, fluorotrichloromethane as internal standard): +57.3.

preparation Embodiment 2

[0273]

[0274] Add 10g of sodium bisfluorosulfonimide (49.26mmol) and 10g of 98% concentrated sulfuric acid (100mmol) into the autoclave, feed 60g of sulfur dioxide at -70°C, slowly rise to room temperature, react for half an hour, and there is a white solid Generate, then slowly release sulfur dioxide gas, add 50ml of dichloromethane, filter, wash the solid with 50ml of dichloromethane, spin the filtrate, distill under reduced pressure, collect 85 ° C / 20mm Hg fractions, and obtain 8.1 g of difluorosulfonimide ( 44.75 mmol), colorless liquid, yield 91%.

[0275] 19 F NMR (dichloromethane as solvent, fluorotrichloromethane as internal standard): +57.3.

Embodiment 1

[0277]

[0278] In a 25ml three-necked flask, add 1.9998g (17.54mmol, 1eq) of caprolactone, 5ml of dichloromethane, 175ul concentration of phenylpropanol dichloromethane solution (1%eq) of 1mol / L, add 35ul under nitrogen protection conditions The dichloromethane solution (0.1% eq) of bisfluorosulfonylimide acid with a concentration of 0.5mol / L was reacted overnight at room temperature. Lactone solid 1.86g (yield 93%) was detected by GPC, Mn PS =25267, PDI=1.03.

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Abstract

The invention discloses an application of bis(fluorosulfonyl)imide as a catalyst. According to the method disclosed by the invention, the bis(fluorosulfonyl)imide is used as the catalyst, so that various reactions such as a Friedel-Crafts reaction, an esterification reaction, a lactone ring-opening polymerization reaction, a silyl ether polymerization reaction, carbonyl compound reduction etherification and alkynyl hydrolysis can be efficiently catalyzed, the reaction conditions are mild, and the atom economy is high.

Description

technical field [0001] The invention relates to the application of a bisfluorosulfonimide as a catalyst. Background technique [0002] Bisfluorosulfonimide (HN(SO 2 F) 2 ) is a nitrogen-containing strong acid, which is currently mainly used in the field of lithium batteries, such as lithium bisfluorosulfonyl imide, and imidazole ionic liquids. Compared with traditional lithium hexafluorophosphate, lithium bisfluorosulfonyl imide has higher thermal stability and hydrolytic stability as lithium battery electrolyte. p-bisfluorosulfonimide (HN(SO 2 F) 2 ) structure analysis, under the strong electron-withdrawing effect of the fluorosulfonyl group, the negative charge on the N atom will disperse to the entire O-S-N skeleton through resonance to produce a high degree of delocalization, thereby greatly enhancing the (FSO 2 ) 2 N - The second is that the fluorosulfonyl group has a large steric hindrance and a strong electron-withdrawing effect, which greatly reduces the coord...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08G63/87C08G77/08C07D249/18C07D257/04C07C41/01C07C41/30C07C45/54C07C45/69C07C67/08C07C221/00C07C269/06C07F7/02B01J27/24C07C271/18C07C43/205C07C225/22C07C49/84C07C225/16C07C49/825C07C69/78C07C43/164C07C43/174
CPCC08G63/08C08G63/823C08G77/08C07D257/04C07C269/06C07C41/30C07C221/00C07C45/69C07C45/54C07C67/08C07C41/01C07D249/18B01J27/24C07F7/10C08G63/87C07C271/18C07C43/2055C07C225/22C07C49/84C07C225/16C07C49/825C07C69/78C07C43/164C07C43/1742
Inventor 董佳家江营
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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