Preparing method for ethyl 4,4,4-trifluoroacetoacetate

A technology of ethyl trifluoroacetoacetate and ethyl trifluoroacetate is applied in the field of preparation of ethyl 4,4,4-trifluoroacetoacetate, and can solve the problem that the end point of the dealcoholization process is difficult to control, the feeding process is difficult to control, and the solvent is difficult to control. Recycling energy consumption increases and other problems, to achieve the effect of novel process, convenient and easy-to-obtain raw materials, and shortened operation cycle

Inactive Publication Date: 2017-04-19
SINOCHEM LANTIAN +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this production process: solid sodium alkali releases heat violently during the feeding process, the feeding process is difficult to control, and it is easy to cause dust pollution; using metal sodium and ethanol to prepare sodium ethoxide will generate a large amount of hydrogen, which has potential safety hazards in industrial production; Boiling dealcoholization, high energy consumption, difficult to control the end point of the dealcoholization process, resulting in unstable process; dealcoholization uses a large amount of cyclohexane, resulting in increased energy consumption and reaction time for solvent recovery

Method used

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  • Preparing method for ethyl 4,4,4-trifluoroacetoacetate
  • Preparing method for ethyl 4,4,4-trifluoroacetoacetate
  • Preparing method for ethyl 4,4,4-trifluoroacetoacetate

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Embodiment 1

[0032] At 25°C, 200 mL of absolute ethanol was added to the reactor, followed by 510 g (1.5 mol) of 20% sodium ethoxide ethanol solution, and then 105.6 g (1.2 mol) of ethyl acetate. Cool the reaction liquid to 5-10°C, then start to dropwise add 142g (1.0mol) ethyl trifluoroacetate, and control the temperature at 10-20°C. After the addition, the temperature was raised to 60°C to react for 2 hours, and then the reaction solution was cooled to 10-15°C. Add 166.6 g (1.7 mol) of concentrated sulfuric acid dropwise to the reaction solution, control the temperature at 20-30° C., and react at 30° C. for 2.5 hours after dropping, to obtain a turbid solution containing sodium sulfate precipitate.

[0033] The sodium sulfate precipitate is removed by filtration, and the filter cake is washed with ethyl acetate, and the filtrate obtained is subjected to rectification under reduced pressure to obtain 157.0g ethyl trifluoroacetoacetate, and the yield is 85.3% (in terms of ethyl trifluoroac...

Embodiment 2

[0035] At 25°C, 100 mL of cyclohexane was added to the reactor, followed by 374 g (0.55 mol) of 10% sodium ethoxide ethanol solution, and then 57.2 g (0.65 mol) of ethyl acetate. Cool the reaction solution to 5-10°C, then start to drop 71g (0.5mol) ethyl trifluoroacetate, and control the temperature at 15-20°C. After the addition, the temperature was raised to 50°C to react for 3 hours, and then the reaction solution was cooled to 10-15°C. Add 59.2g (0.6mol) 37% concentrated hydrochloric acid dropwise to the reaction solution, control the temperature at 20-30°C, and react at 40°C for 1.5 hours after the dropwise completion to obtain a turbid solution containing sodium chloride precipitate.

[0036] The sodium chloride precipitate was removed by filtration, the filter cake was washed with ethyl acetate, and the obtained filtrate was subjected to rectification under reduced pressure to obtain 75.6 g of ethyl trifluoroacetoacetate, with a yield of 82.2% (in terms of ethyl trifluo...

Embodiment 3

[0038] At 25°C, 100 mL of tetrahydrofuran was added to the reactor, followed by 385.3 g (0.85 mol) of 15% sodium ethoxide ethanol solution, and then 70.4 g (0.8 mol) of ethyl acetate. Cool the reaction liquid to 5-10°C, then start to drop 99.4g (0.7mol) ethyl trifluoroacetate, and control the temperature at 10-20°C. After the addition, the temperature was raised to 40°C to react for 4 hours, and then the reaction solution was cooled to 10-15°C. Add 54 g (0.9 mol) of acetic acid dropwise to the reaction solution, control the temperature at 20-30° C., and react at 35° C. for 2.0 hours after the drop is completed, to obtain a turbid solution containing sodium acetate precipitate.

[0039]The sodium acetate precipitate is removed by filtration, and the filter cake is washed with ethyl acetate, and the filtrate obtained is subjected to rectification under reduced pressure to obtain 107.4g ethyl trifluoroacetoacetate, and the yield is 83.4% (in terms of ethyl trifluoroacetate), The...

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Abstract

The invention discloses a preparing method for ethyl 4,4,4-trifluoroacetoacetate. Ethyl trifluoroacetate and ethyl acetate are subjected to a Claisen ester condensation reaction under the existence of an organic solvent with an ethanol solution of sodium ethoxide serving as a catalyst, and the ethyl 4,4,4-trifluoroacetoacetate is synthesized. The method has the beneficial effects that conditions are mild, operation is simple, the conversion rate of raw materials and selectivity of products are high, products are easy to separate, energy consumption is low, and the preparing method is suitable for industrial production. The prepared ethyl 4,4,4-trifluoroacetoacetate is an important pesticide and medicine intermediate and can be used for preparing pesticides such as thifluzamide, fluacrypyrim and thiazopyr and can also be used for preparing medicines such as befloxatone.

Description

technical field [0001] The invention relates to a preparation method of ethyl 4,4,4-trifluoroacetoacetate. Background technique [0002] 4,4,4-Ethyl trifluoroacetoacetate (hereinafter referred to as ethyl trifluoroacetoacetate), the English name is ethyl 4,4,4-trifluoroacetoacetate, and the CAS number is 372-31-6. Molecular formula is C 6 h 7 f 3 o 3 , the molecular weight is 184.11, the density is 1.259, the melting point is -39°C, the boiling point is 129.5°C (760mmHg), the refractive index is 1.375-1.378, the flash point is 28°C, and the solubility in water is 10g / L (20°C). Ethyl trifluoroacetoacetate has two configurations, enol and ketone, which can be converted freely under normal circumstances. The specific structure is as follows: [0003] [0004] Ethyl trifluoroacetoacetate is an important pesticide and pharmaceutical intermediate, which can be used to prepare pesticides such as flufenam, pyrimidin, and thiazopyr, and can also be used to prepare medicines s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C69/716
CPCC07C67/343C07C69/716
Inventor 蒋强徐卫国李华戴佳亮杨汪松
Owner SINOCHEM LANTIAN
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