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Preparation method of ethyl 2-chloro-4,4,4-trifluoroacetoacetate

A technology of ethyl trifluoroacetoacetate and sulfurized fatty acid ester, which is applied in the field of pesticide chemistry, can solve the problems of low yield, difficulty in obtaining high-purity target products, and shortened reaction time, so as to achieve short reaction process and reduce polychlorination. Effects of by-products, yield and purity improvement

Inactive Publication Date: 2019-04-05
QINGDAO HANSEN BIOLOGIC SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chlorination reagents include chlorine gas or sulfuryl chloride, etc. During the chlorination reaction process using chlorine gas, if the reaction conditions are not properly controlled, it is easy to generate dichlorinated or trichlorinated chlorinated by-products, and it is difficult to obtain high-purity target products
[0004] "Research on the Synthetic Technology of Fungicide Thiofuramide" (Cui Kai et al. "Applied Chemical Industry" August 2013, Volume 42, No. 8, P1454-1456) discloses a synthetic technology of the fungicide Thiofuramide, its 2-chloro The synthesis of -4,4,4-ethyl trifluoroacetoacetate uses sulfuryl chloride as the chlorination reagent, reacts under vigorous stirring at 30°C, shortens the reaction time to 8h, and adopts atmospheric distillation during post-treatment to obtain a purity greater than 98% intermediate, but only 84.2% yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) The 500mL dry reactor is connected to the HCl absorption device, and 184g (146.2mL) ethyl trifluoroacetoacetate and 0.5g sulfurized fatty acid ester YD-3015 are added to the reactor, stirred, and 202.5g (121.3 mL) Sulfonyl chloride, control the temperature at 20°C, after the addition is completed, continue to stir and keep warm, start timing from the addition, and after the reaction has proceeded for 6 hours, take samples for gas chromatography analysis, the conversion rate reaches 99.2%, and the substitution reaction is complete.

[0026] (2) After the substitution reaction is completed, keep the liquid temperature below 35°C and 0.095 MPa, and remove the excess sulfonyl chloride and dissolved HCl by distillation to obtain 197.86 g of ethyl 2-chloro-4,4,4-trifluoroacetoacetate. It was 98.3%, and the yield was 93.7% (based on ethyl trifluoroacetoacetate).

Embodiment 2

[0028] (1) The 500mL dry reactor is connected to the HCl absorption device, and 184g (146.2mL) of ethyl trifluoroacetoacetate and 0.5g of sulfurized olefin HIPER-3040 are added to the reactor, stirred, and 202.5g (121.3mL) are slowly added dropwise. Control the temperature of sulfonyl chloride at 20°C. After the dripping is completed, continue to stir and keep warm. Start timing from the dripping. After the reaction proceeds for 6 hours, take samples for gas chromatography analysis. The conversion rate reaches 99.3%, and the substitution reaction is completed.

[0029] (2) After the substitution reaction is completed, keep the liquid temperature below 35°C and 0.095MPa, and remove the excess sulfonyl chloride and dissolved HCl by distillation to obtain 197.42g of ethyl 2-chloro-4,4,4-trifluoroacetoacetate. It was 98.1%, and the yield was 93.3% (based on ethyl trifluoroacetoacetate).

Embodiment 3

[0031] (1) The 500mL dry reactor was connected to the HCl absorption device, and 184g (146.2mL) ethyl trifluoroacetoacetate and 0.5g triphenyl thiophosphate T309 were added to the reactor, stirred, and 202.5g (121.3 mL) Sulfonyl chloride, control the temperature at 20°C, after the addition is completed, continue to stir and keep warm, start timing from the addition, and after the reaction has proceeded for 6 hours, take samples for gas chromatography analysis, the conversion rate reaches 99.2%, and the substitution reaction is complete.

[0032] (2) After the substitution reaction is completed, keep the liquid temperature below 35°C and 0.095MPa, and remove the excess sulfonyl chloride and dissolved HCl by distillation to obtain 197.25g of ethyl 2-chloro-4,4,4-trifluoroacetoacetate. It was 98.0%, and the yield was 93.1% (based on ethyl trifluoroacetoacetate).

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Abstract

The invention belongs to the technical field of pesticide chemistry and particularly relates to a preparation method of ethyl 2-chloro-4,4,4-trifluoroacetoacetate. Ethyl trifluoroacetoacetate is usedas a raw material subjected to substitution reaction with sulfonyl chloride before distilling under maintained temperature and reduced pressure is performed to obtain ethyl 2-chloro-4,4,4-trifluoroacetoacetate. A sulfur-bearing lubricant additive is used as a catalyst; reaction temperature is lowered; reaction time is shortened; the quantity of polychlorinated products is reduced; the conversion rate of ethyl trifluoroacetoacetate is > / =99%, product yield is above 93%, and the purity is above 98%.

Description

Technical field [0001] The invention belongs to the technical field of pesticide chemistry, and specifically relates to a preparation method of bactericide intermediate 2-chloro-4,4,4-trifluoroacetic acid ethyl ester. Background technique [0002] Thifluzamide, also known as fluopyram, belongs to the thiazole amide class of fungicides, with strong systemic conductivity and long lasting effect. Ethyl 2-chloro-4,4,4-trifluoroacetoacetate is a key intermediate in the synthesis of thiafluzamide technical, and its quality directly affects the quality of thiafluzamide technical. [0003] At present, the reaction route for preparing ethyl 2-chloro-4,4,4-trifluoroacetoacetate is mainly the substitution reaction of ethyl trifluoroacetoacetate and a chlorinating reagent. Chlorinating reagents include chlorine gas or sulfuryl chloride, etc. In the process of chlorination using chlorine gas, if the reaction conditions are not properly controlled, it is easy to produce dichloro or trichloro ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/72C07C67/307C07C67/54
CPCC07C67/307C07C67/54C07C69/72
Inventor 褚博宇姜红林陈会存丁君
Owner QINGDAO HANSEN BIOLOGIC SCI
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