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Synthesis method of difluoroacetate ester

A technology of difluoroacetic acid ester and synthesis method, which is applied to the preparation of carboxylic acid ester, chemical instruments and methods, and the preparation of carboxylic acid amide, and can solve the problems of low yield, difficult removal of difluoroacetic acid moisture, long process route, etc. , to achieve the effects of high yield, less discharge of three wastes and simple process

Active Publication Date: 2013-05-22
JUHUA GRP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The disadvantage of this method is that the yield of N,N-diethyldifluoroacetamide synthesis is low, and the process of generating difluoroacetic acid by acid hydrolysis and re-esterification has a long process route, which produces a large amount of waste acid. moisture is difficult to remove

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In a 2L stirred autoclave, replace the gas in the autoclave with high-purity nitrogen. When the oxygen content in the autoclave is less than 20ppm, add 540g (12mol) of anhydrous dimethylamine. The temperature in the kettle drops to -5°C, feed tetrafluoroethylene until the pressure of the reactor reaches 0.3MPa, and start the reaction, the temperature is controlled at 0°C, when the pressure of the reactor drops to 0.2MPa, feed tetrafluoroethylene to 0.3MPa, And so on and on. When the pressure of the reactor no longer drops, the reaction is terminated, a total of 1160g (11.6mol) of tetrafluoroethylene is introduced, and the reaction liquid is released to obtain 1690g (11.1mol) of N,N-dimethyl-1,1 with a purity of 95%. 2,2-Tetrafluoroethylamine crude product.

[0041] 205g (11.4mol) of water was carefully added to the above crude N,N-dimethyl-1,1,2,2-tetrafluoroethylamine, and the reaction temperature was controlled at -20°C. After the addition was complete, stir for 30 ...

Embodiment 2

[0044] In a 2L stirred autoclave, replace the gas in the autoclave with high-purity nitrogen. When the oxygen content in the autoclave is less than 20ppm, add 876g (12mol) of diethylamine, and heat the jacket to raise the temperature in the autoclave to 40 ℃, feed tetrafluoroethylene until the pressure of the reactor reaches 0.5MPa, start the reaction, control the temperature at 40℃, when the pressure of the reactor drops to 0.4MPa, feed tetrafluoroethylene to 0.5MPa, and continue like this. After feeding 600g (6mol) of tetrafluoroethylene, the reaction was terminated to obtain 1474g of reaction liquid.

[0045] The above reaction solution was carefully added dropwise to 5.4kg (300mol) of ice water, and the reaction temperature was controlled at 10°C. After the addition, stir for 30min, static layering, the aqueous layer was extracted 3 times with 500ml dichloromethane respectively, the organic layer was combined, the organic layer was washed with 500ml saturated sodium bicarb...

Embodiment 3

[0048] In a 2L stirred autoclave, replace the gas in the autoclave with high-purity nitrogen. When the oxygen content in the autoclave is less than 20ppm, add 876g (12mol) of diethylamine, and heat the jacket to raise the temperature in the autoclave to 50 ℃, feed tetrafluoroethylene until the pressure of the reactor reaches 0.6MPa, start the reaction, control the temperature at 50℃, when the pressure of the reactor drops to 0.5MPa, feed tetrafluoroethylene to 0.6MPa, and continue like this. After feeding 500g (5mol) of tetrafluoroethylene, the reaction was terminated to obtain 1372g of reaction liquid.

[0049] The above reaction solution was carefully added dropwise to 1.8kg (100mol) of ice water, and the reaction temperature was controlled at 50°C. After the addition, stir for 30 minutes, static layering, the aqueous layer was extracted 3 times with 300ml ether, the organic layer was combined, the organic layer was washed with saturated sodium bicarbonate, dried over sodium...

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PUM

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Abstract

The invention discloses a synthesis method of difluoroacetate ester, which comprises the following steps: reacting tetrafluoroethylene and organic amine to obtain N,N-dialkyl-1,1,2,2-tetrafluoroethylamine; reacting the N,N-dialkyl-1,1,2,2-tetrafluoroethylamine and water to generate N,N-dialkyl difluoroacetamide; performing hydrolysis reaction on the N,N-dialkyl difluoroacetamide and metal hydroxide to generate difluoroacetate salt; and reacting the difluoroacetate salt and halogenated hydrocarbon in the presence of a catalyst and solvent to generate the difluoroacetate ester. The invention has the advantages of simple process, high yield and low discharge of three wastes; through the hydrolysis of the N,N-dialkyl-1,1,2,2-tetrafluoroethylamine, the N,N-dialkyl difluoroacetamide can be obtained at a high yield, and the yield of the N,N-dialkyl difluoroacetamide is 88% or above; and the maximum yield in the process of preparing the difluoroacetate ester from the N,N-dialkyl difluoroacetamide can be up to 92%.

Description

technical field [0001] The invention relates to a synthesis method of fluoroacetate, in particular to a synthesis method of difluoroacetate. Background technique [0002] Difluoroacetate is an intermediate mainly used in pesticides, pharmaceuticals, and fluorine-containing fine chemicals, and can also be used as a solvent in lithium battery electrolytes. [0003] JP2008280305 discloses a method for preparing a fluorine-containing carboxylic acid ester that does not produce harmful substances. Tetrafluoroethylene and alcohol generate 1,12,2-tetrafluoroethyl alkyl ether under alkali catalysis, and then react in the presence of concentrated sulfuric acid and alkali metal or alkaline earth metal oxide to obtain difluoroacetate. [0004] WO2008078479 discloses a method for producing difluoroacetate from 1,1,2,2-tetrafluoroethyl alkyl ether. 1,12,2-Tetrafluoroethyl methyl ether reacts with potassium hydroxide at 50°C in methanol as a solvent to generate sodium difluoroacetate, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/11C07C69/63C07C231/10C07C233/05
Inventor 叶立峰周强姜永清余燕
Owner JUHUA GRP
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