Method for synthesizing m-trifluoromethyl acetophenone

A technology of trifluoromethyl acetophenone and trifluoromethyl aniline, which is applied in the field of synthesis of m-trifluoromethyl acetophenone, can solve the problems of high raw material prices, high risk, and difficulty in industrialization, and achieve impurity content Low, consistent quality and performance, methodologically safe and controllable results

Active Publication Date: 2013-07-10
ZHEJIANG WEIHUA NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first three methods have difficult sources of raw materials, high risk, and are not easy to industrialize; the last method is easier to industrialize, but the raw materials used are expensive and not competitive

Method used

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  • Method for synthesizing m-trifluoromethyl acetophenone

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Embodiment 1

[0028] A kind of synthetic method of m-trifluoromethyl acetophenone, take m-trifluoromethyl aniline as starting raw material, concrete steps comprise:

[0029] (1), diazotization reaction

[0030] 46 g m-trifluoromethylaniline was slowly added to a four-neck flask containing 280 g sulfuric acid solution (mass concentration 20%), then cooled to 0 °C and started to drop 30% NaNO 2 Aqueous solution 72 g, control temperature 0~5 ℃, heat preservation and stirring for 1 hour after dripping, obtain pale yellow diazonium salt clear liquid, heat preservation for later use.

[0031] (2), coupling reaction

[0032] Add 4.2 g of cuprous chloride, 10.2 g of acetic acid, 50.5 g of 50% acetaldehyde oxime aqueous solution and 100 mL of toluene into the four-neck flask, stir and cool. After cooling below 5°C, start to add the above-mentioned diazonium salt clear solution dropwise, and at the same time add 30% liquid caustic soda dropwise, control the pH at 4~4.5, and the temperature at 0~5°C...

Embodiment 2

[0037] (1), diazotization reaction

[0038] 46 g m-trifluoromethylaniline was slowly added to a four-neck flask containing 280 g sulfuric acid solution (mass concentration 25%), then cooled to 0 °C and started to drop 30% NaNO 2 Aqueous solution 71 g, control temperature 0~5 ℃, heat preservation and stirring for 1 hour after dripping, obtain light yellow diazonium salt clear liquid, heat preservation for later use.

[0039] (2), coupling reaction

[0040] Add 8.6 g of copper acetate, 5.2 g of acetic acid, 45.5 g of 50% acetaldehyde oxime aqueous solution and 100 mL of toluene into the four-neck flask, stir and cool. After cooling below 5°C, start to add the above-mentioned diazonium salt clear solution dropwise, and at the same time add 30% liquid caustic soda dropwise, control the pH at 4~4.5, and the temperature at 0~5°C. After the addition, the temperature was raised to 15°C and stirred, followed by GC analysis. After the reaction was completed, the mixture was separated ...

Embodiment 3

[0045] A kind of synthetic method of m-trifluoromethyl acetophenone, take m-trifluoromethyl aniline as starting raw material, concrete steps comprise:

[0046] (1), diazotization reaction

[0047] 46 g m-trifluoromethylaniline was slowly added to a four-neck flask containing 280 g sulfuric acid solution (mass concentration 25%), then cooled to 0 °C and started to drop 30% NaNO 2 Aqueous solution 72 g, control temperature 0~5 ℃, heat preservation and stirring for 1 hour after dripping, obtain pale yellow diazonium salt clear liquid, heat preservation for later use.

[0048] (2), coupling reaction

[0049] Add 3.9 g cupric chloride, 8.0 g acetic acid, 48.5 g 50% acetaldehyde oxime aqueous solution and 100 mL toluene into the four-neck flask, stir and cool. After cooling below 5°C, start to add the above-mentioned diazonium salt clear solution dropwise, and at the same time add 30% liquid caustic soda dropwise, control the pH at 4~4.5, and the temperature at 0~5°C. After the add...

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Abstract

The invention discloses a method for synthesizing m-trifluoromethyl acetophenone which is an important intermediate for medicine, pesticide and pigment. According to the method, m-trifluoromethylaniline as the initial raw material is diazotized to prepare a diazonium salt which is coupled with acetaldoxime under the catalysis of a copper salt by controlling the pH value at 4-4.5 and the temperature at 0-5 DEG C, and the coupling compound is extracted by an organic solvent and then hydrolyzed by using hydrochloric acid to obtain the m-trifluoromethyl acetophenone. The total yield of the m-trifluoromethyl acetophenone produced according to the method is more than 70 percent; and the reaction conditions of the method are simple, the yield is high, the pollution is small, and the method is applied to industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for synthesizing m-trifluoromethylacetophenone. Background technique [0002] 3'-(Trifluoromethyl)acetophenone (3'-(Trifluoromethyl)acetophenone) referred to as TFAP, light yellow liquid, mainly used in medicine, pesticides and dyes and other fields. It is a key intermediate for the synthesis of trifloxystrobin (Trifloxystrobin, trade name Flint) and an important raw material for the synthesis of medicines and dyes. Its key downstream product trifloxystrobin is a new type of high-efficiency, safe and broad-spectrum fungicide, which has special effects on powdery mildew and leaf spot, and has great effects on rust, downy mildew, blight, apple scab, etc. Good activity, low toxicity to mammals, bees, birds, fish, insects, etc., and fast environmental metabolism, so it is safe to the environment, has no teratogenic, carcinogenic, or mutagenic effects, and has no adverse ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/80C07C45/42
Inventor 李俊奇周洪钟陈静华张泉泉王国荣常绚超葛天权
Owner ZHEJIANG WEIHUA NEW MATERIAL CO LTD
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