Synthesis method of 3,5,6-trichloropyridyl-2-sodium alkoxide

A technology of triclopyridine and synthetic method, which is applied in the field of synthesis of 3,5,6-trichloropyridin-2-alcohol sodium, can solve the problem of low yield of triclopyridine sodium, difficult recovery of by-products, and unsuitability for industry Large-scale production and other issues, to achieve the effect of inhibiting side reactions

Inactive Publication Date: 2014-12-03
ANHUI COSTAR BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The acrylic acid method first needs to prepare acryloyl chloride. There are many synthesis steps and a long route. The reaction process also needs to add expensive catalysts such as organophosphorus and organotin, which is not suitable for large-scale industrial production.
The phenyl trichloroacetate method requires a large amount of valuable solvent sulfolane, and the by-products are not easy to recover, the yield is low, and it is not easy to produce on a large scale
But adopt the trichloroacetyl chloride method to synthesize the yield of triclopyridin sodium at present is relatively low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In a 3000L enamel glass reactor, add 364Kg trichloroacetyl chloride, 169.6kg acrylonitrile, 1351.6kg ethyl benzoate, 7.28Kg cuprous chloride, 10.92Kg tetrabutylammonium chloride and 15.4Kg bipyridyl, react The temperature was controlled at 125°C, and the reaction was carried out for 30 hours. After the addition reaction is over, the catalyst is filtered off, and 3 / 4 of the filtrate is removed at -0.8~0.9MP. Then the remaining liquid was put into a ring-closing kettle, fed with anhydrous HCl gas, and reacted at 75° C. for 6 h. After the cyclization is completed, put the cyclization solution into the aromatization reaction kettle, add 180kg of NaOH solution with a concentration of 15% to the reaction kettle, and carry out the aromatization reaction under the conditions of 40°C and PH=11, and then Filtration to obtain sodium triclopyridinate, the yield was 80%.

Embodiment 2

[0023] In a 3000L enamel glass reactor, add 364Kg trichloroacetyl chloride, 169.6kg acrylonitrile, 1351.6kg ethyl benzoate, 7.28Kg cuprous chloride, 10.92Kg tetrabutylammonium chloride and 19.3Kg triphenylphosphine , the reaction temperature was controlled at 125° C., and the reaction was carried out for 30 h. After the addition reaction is over, the catalyst is filtered off, and 3 / 4 of the filtrate is removed at -0.8~0.9MP. Then the remaining liquid was put into a ring-closing kettle, fed with anhydrous HCl gas, and reacted at 75° C. for 6 h. After the cyclization is completed, put the cyclization liquid into the aromatization reaction kettle, add 180kg of NaOH solution with a concentration of 15% into the reaction kettle, and carry out the aromatization reaction under the conditions of 40°C and PH=11, and then Filtrate to obtain sodium triclopyridinate with a yield of 85%.

Embodiment 3

[0025] In a 3000L enamel glass reactor, add 364Kg trichloroacetyl chloride, 169.6kg acrylonitrile, 1351.6kg ethyl benzoate, 7.28Kg cuprous chloride, 10.92Kg tetrabutylammonium chloride and 23.2Kg triphenylphosphine , the reaction temperature was controlled at 125°C,

[0026] Reaction 30h. After the addition reaction is over, the catalyst is filtered off, and 3 / 4 of the filtrate is removed at -0.8~0.9MP. Then the remaining liquid

[0027] Put it in a ring-closing kettle, feed anhydrous HCl gas, and react at 75°C for 6h. After the cyclization is completed, put the cyclization liquid into the aromatization reaction kettle, add 180kg of NaOH solution with a concentration of 15% into the reaction kettle, and carry out the aromatization reaction under the conditions of 40°C and PH=11, and then Filtrate to obtain sodium triclopyridinate, the yield is 82%.

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PUM

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Abstract

The invention provides a synthesis method of 3,5,6-trichloropyridyl-2-sodium alkoxide, which comprises the following steps: by using trichloro-acetic chloride and acrylonitrile as raw materials and cuprous chloride and tetrabutyl ammonium chloride as catalysts, adding a cocatalyst, carrying out addition, cyclization and aromatization reaction to prepare the 3,5,6-trichloropyridyl-2-sodium alkoxide. The method maximally controls the generation of the side reaction, and the yield of the 3,5,6-trichloropyridyl-2-sodium alkoxide can reach higher than 80%. Meanwhile, the method has the advantages of accessible raw materials, low price and mild technological conditions, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to the field of organic compound synthesis, in particular to a synthesis method of 3,5,6-trichloropyridin-2-alcohol sodium. Background technique [0002] Sodium triclopyridinate (that is, sodium 3,5,6-trichloropyridin-2-ol) has the molecular formula CSNC1 3 ONa, the relative molecular weight is 220.5. The pure product is a light yellow solid. It is an important chemical raw material and a chelating flotation agent with excellent performance. It is also an important intermediate for the synthesis of various pesticides, especially for the production of broad-spectrum organophosphorus insecticide and acaricide chlorpyrifos. . [0003] The synthetic method of triclopyridinate sodium is divided according to the starting material adopted, and mainly contains two major routes of pyridine or pyridine derivative method and ring-closing synthesis method. The pyridine method includes pyridine liquid-phase chlorination method and pyridine ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64
CPCC07D213/64
Inventor 方红新刘敏周浩
Owner ANHUI COSTAR BIOCHEM CO LTD
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