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Synthesis method of 2-cyano-2-oximido acetamide sodium salt and cymoxanil

An oxime-acetamide sodium salt and a synthesis method technology, applied in the field of pesticide synthesis, can solve the problems of large amount of three wastes, high cost of raw materials, low reaction yield, etc., to reduce the pressure of environmental protection treatment, easy to recycle, high product yield rate effect

Pending Publication Date: 2022-08-05
利民化学有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, when using traditional oximation and methylation reactions to synthesize cymoxanil, there are generally disadvantages such as low reaction yield, large amount of three wastes, difficult environmental protection treatment, and high cost of raw materials, and green and clean production cannot be realized.

Method used

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  • Synthesis method of 2-cyano-2-oximido acetamide sodium salt and cymoxanil
  • Synthesis method of 2-cyano-2-oximido acetamide sodium salt and cymoxanil
  • Synthesis method of 2-cyano-2-oximido acetamide sodium salt and cymoxanil

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preparation example Construction

[0033] The method for synthesizing the trioxuron comprises the following steps: carrying out a methylation reaction with the 2-cyano-2-oximoacetamide sodium salt reaction solution obtained by the oximation reaction, a methylating reagent and an alkali solution, and after the reaction is completed, Cooling and crystallization.

[0034] For reference, the alkaline solution includes aqueous sodium hydroxide solution, aqueous potassium hydroxide solution, aqueous sodium carbonate solution or aqueous triethylamine solution. In a preferred embodiment, the alkaline solution is an aqueous sodium hydroxide solution.

Embodiment 1

[0060] Add 86.2 g of cyanoacetoethyl urea (content 90%, 0.5 mol), 300 g of methanol, 27 g (0.5 mol) of sodium methoxide, and 0.087 g of DPhEG to a four-necked flask, stir to cool down to 0 °C, and slowly add isopropyl nitrite dropwise. 44.6 g (0.5 mol) of the ester was dripped, and the reaction was incubated for 8 h to obtain a light yellow turbid solution of 2-cyano-2-oximinoacetamide sodium salt.

[0061] The reaction solution in the previous step was heated to 30°C, and 45 g (0.5 mol) of dimethyl carbonate was added dropwise. The pH value was adjusted with liquid caustic soda in the range of 8 to 8.5 during the dropwise addition. Cool to -5°C for crystallization, filter, rinse the filter cake twice with water, and recover the solvent methanol by distillation of the mother liquor. The filter cake was dried to obtain 95.0 g of a white cyanamide product with a content of 99.1% and a yield of 95.0%.

Embodiment 2

[0063] In a four-necked flask, add 86.2 g of cyanoacetoethyl urea (content 90%, 0.5 mol), 300 g of ethanol, 37.4 g (0.55 mol) of sodium ethoxide, and 0.43 g of DPhEG, stir and cool down to 10 °C, and slowly add tertiary nitrite dropwise. 56.7 g (0.55 mol) of butyl ester was dripped, and the reaction was incubated for 6 h to obtain a light yellow turbid solution of 2-cyano-2-oximinoacetamide sodium salt.

[0064] The reaction solution in the previous step was heated to 40°C, dimethyl carbonate 49.5g (0.55mol) was added dropwise, the pH value was adjusted with liquid caustic soda in the range of 8 to 8.5 during the dropwise addition, the dropping was completed, the reaction was incubated for 3h, and the reaction was completed in HPLC. . Cool to 0°C for crystallization, filter, rinse the filter cake twice with water, and recover the solvent ethanol by distillation of the mother liquor. The filter cake was dried to obtain 95.4 g of a white cyanamide product with a content of 99.2...

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Abstract

The invention discloses a synthesis method of 2-cyano-2-oximido acetamide sodium salt and cymoxanil, and belongs to the technical field of pesticide synthesis. The synthesis of the 2-cyano-2-oximido acetamide sodium salt comprises the following steps: in the presence of a catalyst and organic alkali, carrying out oximation reaction on cyanoacetyl ethyl urea and nitrite ester in an alcohol solvent; the catalyst is diphenylethylenediamine guanidine salt. According to the present invention, the diphenylethylenediamine guanidine salt is added to the alcohol solvent as the catalyst to carry out the oximation reaction, the 2-cyano-2-oximido acetamide sodium salt can be obtained without dilute acid acidification and alkalization, the alcohol solvent is easy to recycle, the wastewater amount is less, the environmental protection treatment pressure is substantially reduced, and the method has characteristics of environmental protection and safety, and is suitable for industrial production. 2-cyano-2-oximido acetamide sodium salt reaction liquid obtained after the oximation reaction, a methylation reagent and a sodium hydroxide aqueous solution are subjected to a methylation reaction, after the reaction is completed, cooling crystallization is conducted, and the high product yield can be obtained.

Description

technical field [0001] The invention relates to the technical field of pesticide synthesis, in particular to a method for synthesizing 2-cyano-2-oximinoacetamide sodium salt and trioxuron. Background technique [0002] Thiamuron, CAS No. 57966-95-7, the chemical name is 1-(2-cyano-2-methoxyimino)-3-ethylurea, and the structural formula is as follows: It is an efficient, low-toxicity fungicide, effective against downy mildew fungi (such as Phytophthora, Downy mildew, Uniaxial Fructus), and has low toxicity to humans and animals. It is mixed with other protective fungicides and widely used in cruciferous vegetables such as cucumbers, grapes, tomatoes, lychees, giant vegetables, and tobacco. [0003] However, when the traditional oximation and methylation reactions are currently used to synthesize cyanamide, there are generally shortcomings such as low reaction yield, large amount of three wastes, difficult environmental protection treatment, and high raw material cost, and g...

Claims

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Application Information

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IPC IPC(8): C07C273/18C07C275/50
CPCC07C273/1863C07C273/189C07C275/50
Inventor 李新生孙敬权李林虎徐宁许宜伟马衍峰许辉孙丽梅
Owner 利民化学有限责任公司
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