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Preparation method for trifluoroacetylacetone

A technology of trifluoroacetylacetone and trifluoroacetate, applied in the field of preparation of trifluoroacetylacetone, can solve the problems of complicated post-processing, unfavorable industrialization amplification, low yield and the like, and achieves mild process conditions and low production cost , the effect of high raw material yield

Inactive Publication Date: 2017-10-27
浙江化工院科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Trifluoroacetylacetone is an important organic intermediate, which can be used to synthesize pesticides and pharmaceutical intermediates, such as: (1) synthetic trifluoromethyl pyrazole, which can selectively inhibit cyclooxygenase and treat diabetes; 2) Synthesis of 5-aryl-8-aminoquinoline compounds, which retain their antimalarial activity and anti-macrophage activity relative to the two drugs, Tafenoquine and Primaquine The cytotoxic effect has a stable metabolism in the microsomes of humans and mice, but the toxic side effects and disease prevention effects disappear
Although the best favorable conditions for catalysts, raw material ratios, reaction temperatures, etc. have been studied, the highest yield of this method is only 33%, which cannot be further improved.
[0008] In the above preparation method, the catalysts NaH and Na used are not easy to store, and NaH presents a solid phase in the solution, which is unfavorable for the formation of a homogeneous reaction system, and sodium-ethanol and NaH all produce hydrogen in the reaction, which is prone to explosion hazards and is not suitable It is beneficial to industrial scale-up, and the post-processing is complicated and the yield is low

Method used

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  • Preparation method for trifluoroacetylacetone
  • Preparation method for trifluoroacetylacetone
  • Preparation method for trifluoroacetylacetone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 1000 mL three-necked flask, add 500 mL of methanol, add 162 g (3 moles) of sodium methylate, 128 g (1 mole) of methyl trifluoroacetate and 174 g (3 moles) of acetone while stirring, and heat the reaction to 40 ° C. After 4 hours of reaction, the Under a vacuum of 0.01Mpa, heat to 40°C to distill methanol, add 294g (3mol) of sulfuric acid to the reaction solution for acidification, and distill trifluoroacetylacetone under reduced pressure under a vacuum of 0.09MPa, collect the fractions at 31 to 33°C to obtain 70.5 g of colorless liquid, GC content of trifluoroacetylacetone 99.2%, yield 45.4%.

Embodiment 2

[0027] In a 1000 mL three-necked flask, add 500 mL of ethanol, add 204 g (3 moles) of sodium ethylate, 142 g (1 mole) of ethyl trifluoroacetate and 174 g (3 moles) of acetone under stirring, and heat the reaction to 50 ° C. After 4 hours of reaction, the Under a vacuum of 0.01Mpa, heat to 50°C to distill ethanol, add 294g (3mol) sulfuric acid to the reaction solution for acidification, and distill trifluoroacetylacetone under reduced pressure under a vacuum of 0.09MPa, collect the cuts at 31 to 33°C to obtain 63.6 g of colorless liquid, GC content of trifluoroacetylacetone 99.1%, yield 40.1%.

Embodiment 3

[0029] In a 1000 mL three-neck flask, add 500 mL of toluene, add 136 g (2 moles) of sodium ethylate, 156 g (1 mole) of 4-methoxyphenyl trifluoroacetate and 116 g (2 moles) of acetone under stirring, and heat the reaction to 60 ° C , after reacting for 1 hour, under the vacuum of 0.01Mpa, be heated to 70 DEG C and distill out toluene, add 138g (3mol) formic acid acidification in the reaction liquid, under the vacuum of 0.09MPa, distill out trifluoroacetylacetone under reduced pressure, collect 31 From the fraction at ~33°C, 75.6 g of colorless liquid was obtained, the GC content of trifluoroacetylacetone was 99.2%, and the yield was 50.3%.

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Abstract

The invention discloses a preparation method for trifluoroacetylacetone by a two-stage method. Firstly, a trifluoroacetate is reacted with acetone to obtain a enol sodium salt under the effect of sodium methylate and / or sodium ethylate; and secondly, the enol sodium salt is subjected to acidification, and then reduced pressure distillation is carried out, so that the trifluoroacetylacetone is obtained. The preparation method disclosed in the invention has the characteristics that the product yield is high, the method is safe and friendly to environment, the process is simple and the like.

Description

technical field [0001] The invention relates to a preparation method of trifluoroacetylacetone. Background technique [0002] Trifluoroacetylacetone is an important organic intermediate, which can be used to synthesize pesticides and pharmaceutical intermediates, such as: (1) synthetic trifluoromethyl pyrazole, which can selectively inhibit cyclooxygenase and treat diabetes; 2) Synthesis of 5-aryl-8-aminoquinoline compounds, which retain their antimalarial activity and anti-macrophage activity relative to the two drugs, Tafenoquine and Primaquine The toxicity of cells has stable metabolism in the microsomes of human and rodents, but the toxic side effects and disease prevention effects disappear. Trifluoroacetylacetone can also be used to prepare luminescent materials. The complex formed by trifluoroacetylacetone and rare earth has good stability and excellent luminescent performance, and is widely used in the field of luminescence. The chelation of trifluoroacetylacetone ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C49/167C07C45/45C07C49/227
CPCC07C45/00C07C45/45C07C49/24C07C49/167C07C49/227
Inventor 陈伟李华徐卫国
Owner 浙江化工院科技有限公司
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