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Methylation synthesis method based on pyraclostrobin intermediate

A technology for pyraclostrobin and intermediates, which is applied in the field of organic compound synthesis, can solve the problems of unsuitability for large-scale industrialization, great harm to the human body and the environment, and high cost, so as to reduce production costs and reduce environmental pressure. , the effect of reducing environmental pressure

Inactive Publication Date: 2018-05-01
SICHUAN FOURSTAR BIOTECH RANDD CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the methylating reagent methyl iodide is a strong carcinogen that is harmful to the human body and the environment. At the same time, it will decompose under light and is very volatile, which is extremely inconvenient to store. The price is very expensive and the cost remains high. Therefore, it is not suitable for large-scale industrialization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048]This embodiment relates to pyraclostrobin intermediate The methylation synthesis method performed.

[0049] The process steps are as follows:

[0050] 1) Add the pyraclostrobin intermediate, phase transfer catalyst, solvent, and alkali solution into the autoclave, and replace the gas in the autoclave with methylene chloride gas.

[0051] The phase transfer catalyst is tetrabutylammonium chloride.

[0052] The solvent is selected from a water-insoluble organic solvent, such as a mixture of dichloroethane selected from halogenated alkanes, chlorobenzene selected from aromatic hydrocarbons, and methyl tert-butyl ether selected from ethers.

[0053] The alkaline solution is 20% sodium hydroxide aqueous solution.

[0054] Control the mass ratio of pyraclostrobin intermediate to the selected phase transfer catalyst and solvent at 1:0.01:20; control the equivalent ratio with alkali and methylene chloride gas at 1:2:1.

[0055] 2) The temperature is controlled at 10°C, and ...

Embodiment 2

[0058] This embodiment relates to pyraclostrobin intermediate The methylation synthesis method performed.

[0059] The process steps are as follows:

[0060] 1) Add the pyraclostrobin intermediate, phase transfer catalyst, solvent, and alkali solution into the autoclave, and replace the gas in the autoclave with methylene chloride gas.

[0061] The phase transfer catalyst is selected from benzyltriethylammonium bromide and PEG800.

[0062] The solvent is an organic solvent miscible with water, such as methanol, ethanol, etc. selected from esters.

[0063] The alkaline solution is an aqueous solution composed of lithium hydroxide, lithium carbonate and sodium hydroxide with a concentration of 5%.

[0064] Control the mass ratio of pyraclostrobin intermediate to the selected phase transfer catalyst and solvent at 1:0.2:1; control the equivalent ratio with alkali and methylene chloride gas at 1:3:5.

[0065] 2) The temperature is controlled at 95°C, and the pressure of the m...

Embodiment 3

[0068] This embodiment relates to pyraclostrobin intermediate The methylation synthesis method performed.

[0069] The process steps are as follows:

[0070] 1) Add the pyraclostrobin intermediate, phase transfer catalyst, solvent, and alkali solution into the autoclave, and replace the gas in the autoclave with methylene chloride gas.

[0071] The phase transfer catalyst is selected from benzyl triethyl ammonium chloride.

[0072] The solvent is selected from water-insoluble organic solvents, such as chlorobenzene or dichlorobenzene selected from (halogenated) aromatic hydrocarbons.

[0073] The alkaline solution is 40% sodium hydroxide aqueous solution.

[0074] The mass ratio of the pyraclostrobin intermediate to the phase transfer catalyst and solvent selected above is controlled at 1:0.02:5; the equivalent ratio to the alkali and methylene chloride gas is controlled at 1:1.4:2.

[0075] 2) The temperature is controlled at 80°C, and the pressure of the monochlorometha...

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PUM

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Abstract

The invention discloses a methylation synthesis method based on a pyraclostrobin intermediate. According to the methylation synthesis method, a pyraclostrobin intermediate, a phase transfer catalyst,a solvent, an alkali solution and methyl chloride gas are subjected to a reaction, wherein the reaction temperature and the pressure are controlled; and after the reaction is completed, cooling is performed to obtain the methylated product of the pyraclostrobin intermediate. According to the present invention, the synthesis method is the methylation method for the pyraclostrobin N-hydroxyl intermediate, and dimethyl sulfate, dimethyl carbonate, iodomethane and the like are replaced with methyl chloride so as to be used as the methylation reagent in the pyraclostrobin production process, such that the production cost and the amount of the three-waste are effectively reduced, the methylation yield is more than or equal to 95.0%, and the HPLC external standard content is more than or equal to98.0%.

Description

technical field [0001] The present invention is based on the methylation synthesis method of pyraclostrobin intermediate, specifically relates to pyraclostrobin N The invention relates to a methylation synthesis reaction of a hydroxyl intermediate, which belongs to the field of synthesis of organic compounds. Background technique [0002] In the synthetic route of the new broad-spectrum fungicide pyraclostrobin, it is necessary to perform methylation reaction on the N-hydroxyl intermediate, for example: [0003] Synthetic route 1 of pyraclostrobin: [0004] [0005] In, (6) → (1) carried out N -Hydroxyl intermediate methylation synthesis reaction; [0006] Synthetic route 2 of pyraclostrobin: [0007] In, (8) → (9) carried out N -Methylation synthesis reaction of hydroxyl intermediates. [0008] Dimethyl sulfate is commonly used as a methylating reagent in the methods reported so far. BASF Company just reported dimethyl sulfate as the method of methylation reagen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/22C07C269/06C07C271/28C07C291/00
CPCC07C269/06C07C291/00C07D231/22C07C271/28
Inventor 王文刘虎陈熙马青伟李舟王蕾张华
Owner SICHUAN FOURSTAR BIOTECH RANDD CORP