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Method for preparing difluoroacetic acid esters

A technology of difluoroacetate and difluoroacetyl fluoride, which is applied in the preparation of alkyl esters and cycloalkyl esters, and in the field of difluoroacetate preparation, which can solve problems such as pollution and achieve easy-to-achieve effects

Inactive Publication Date: 2012-05-23
RHODIA OPERATIONS SAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Another disadvantage of this method is the generation of heavily polluted waste due to the presence of amines

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] In Teflon with air inlet and Rushton turbine type agitation system The resulting autoclave was charged with ethanol (50 g, 1.09 mol) and sodium carbonate (116.2 g, 1.1 mol).

[0081] The autoclave was closed and the temperature of the mixture was lowered to 5°C.

[0082] A gas stream of difluoroacetyl fluoride (mass flow rate 190 g / h) was then introduced into the mixture for 30 minutes, keeping the temperature below 15°C.

[0083] The amount of difluoroacetyl fluoride added was 95 g (0.97 mol).

[0084] Stirred at 15°C for 1 hour, then purged the top of the reactor with nitrogen for 30 minutes to return the temperature to room temperature (20°C). The autoclave was then vented.

[0085] The reaction mixture was then filtered and the salts were rinsed with 100 mL of dichloromethane.

[0086] The filtrates were combined and distilled under atmospheric pressure.

[0087] The collected fractions boiled between 96 and 99°C.

[0088] 92 g of ethyl difluoroacetate are ob...

Embodiment 2

[0091] The autoclave described in Example 1 was charged with methanol (80 g, 2.5 mol) and sodium carbonate (270.3 g, 2.55 mol).

[0092] The autoclave was closed and the temperature of the mixture was lowered to 5°C.

[0093] A gas stream of difluoroacetyl fluoride (mass flow rate 190 g / h) was then added to the mixture for 94 minutes, keeping the temperature below 15°C.

[0094] The amount of difluoroacetyl fluoride added was 256 g (2.5 mol).

[0095] Stirred at 15°C for 1 hour, then purged the top of the reactor with nitrogen for 30 minutes to return the temperature to room temperature (20°C). The autoclave was then vented.

[0096] The reaction mixture was then filtered, rinsing the salts with 250 mL of dichloromethane.

[0097] The filtrates were combined and distilled under atmospheric pressure.

[0098] The collected fractions boiled between 85 and 86°C.

[0099] 189 g of methyl difluoroacetate are obtained.

[0100] The yield was 69 wt.%.

Embodiment 3

[0102] The autoclave described in Example 1 was charged with ethanol (50 g, 1.09 mol), xylene (800 mL) and sodium carbonate (477 g, 4.5 mol).

[0103] The autoclave was closed and the temperature of the mixture was lowered to 5°C.

[0104] A mixture of difluoroacetyl fluoride and anhydrous hydrofluoric acid (molar ratio of HF / difluoroacetyl fluoride = 1 / 3.2) was then added to the mixture to keep the temperature below 10°C.

[0105] The amount of difluoroacetyl fluoride added was 105 g (1.07 mol), and the amount of HF added was 68.6 g (3.4 mol).

[0106] Stirred at 15°C for 1 hour, then purged the top of the reactor with nitrogen for 30 minutes to return the temperature to room temperature (20°C). The autoclave was then vented.

[0107] The reaction mixture was distilled under atmospheric pressure.

[0108] The collected fractions boiled between 96 and 98°C.

[0109] 87.8 g of ethyl difluoroacetate are obtained.

[0110] The yield was 65 wt.%.

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PUM

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Abstract

The present invention relates to a method for preparing difluoroacetic acid esters. The method of the invention for preparing difluoroacetic acid esters is characterized in that it includes reacting difluoroacetyl fluorine with an aliphatic or cycloaliphatic alcohol in the presence of a heterogeneous mineral base.

Description

technical field [0001] The present invention relates to a process for the preparation of difluoroacetates. [0002] This invention relates to the preparation of alkyl and cycloalkyl esters of difluoroacetic acid. [0003] The present invention relates more particularly to the preparation of methyl difluoroacetate or ethyl difluoroacetate. Background technique [0004] Difluoroacetate is a known product described in the literature. [0005] One way to obtain is to make an alcohol R 1 OH and the general formula is H-CF 2 -Difluoroacetyl fluoride reaction of COF. We refer in particular to the preparation process described in EP-A 0 694 523. [0006] The alcoholysis reaction is carried out continuously without catalyst. However, when the reaction is carried out in a batch manner, the presence of a reaction catalyst is required in order to adapt the reaction time to industrial applications. [0007] The process described in EP-A 0 694 523 proposes the use of tertiary amine...

Claims

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Application Information

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IPC IPC(8): C07C67/14C07C69/63
CPCC07C67/14C07C69/63C07C67/62C07B61/00
Inventor O·比西纳
Owner RHODIA OPERATIONS SAS
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