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3,5,6-trichloropyridin-2-ol sodium synthesis method

A technology of sodium clopyridinate and a synthetic method, which is applied in the field of organic compound synthesis, can solve the problems of short reaction process, low conversion rate, long process, etc., increase product content and yield, reduce product loss, and have mild reaction conditions Effect

Inactive Publication Date: 2014-11-26
ANHUI COSTAR BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method is further divided into "step-by-step method" and "one-pot method".
The "step-by-step method" avoids the mutual interference of materials in the reaction process, and the product selectivity is low. However, the "step-by-step method" that has been disclosed so far generally has complex processes, long processes, difficult operations, large equipment investment, and low yields. question
[0005] Patent CN02157262.3 reports a "one-pot method" method for synthesizing sodium triclopyridinate. Addition, cyclization, aromatization and neutralization are carried out in one pot to form a salt, and conventional organic solvents are used instead of highly toxic nitrobenzene, the reaction process is short, easy to operate, but the content of by-product tetrachloropyridine is high and the yield of sodium pyridyl alcohol is only about 65%; In the reaction process, the materials interfere with each other, the product selectivity is low, and tetrachloropyridine is hardly produced in the process, but HCl gas needs to be introduced into the ring closure process under pressure, which corrodes the equipment and increases the difficulty of operation, which is not conducive to industrial production; patent CN200510045501.2 has reported a kind of processing method to by-product tetrachloropyridine, and tetrachloropyridine is converted into sodium triclopyridine alkoxide under the effect of phase transfer catalyst polyethylene glycol with sodium hydroxide or potassium hydroxide aqueous solution, Wherein polyethylene glycol consumption is bigger, and cost is higher, and conversion rate is low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1, a kind of synthetic method of 3,5,6-trichloropyridin-2-alcohol sodium:

[0027] In a 1000 ml three-necked flask equipped with a thermometer and mechanical stirring, add 200 g of trichloroacetyl chloride, 90 g of acrylonitrile, and 500 g of nitrobenzene, stir well at room temperature, then add 0.8532 g of CuCl2, 1.9624 g of hydroquinone, The temperature was raised to 108°C for reaction, and after about 15 h of reaction, the catalyst was filtered out. The filtrate is distilled under reduced pressure to reclaim unreacted raw materials and part of the solvent, then add 1.7685 g ZnCl 2 , stirred at 80°C for 2 h to obtain a pyridone solution. After the system was cooled to normal temperature, 350 g of water was added, and 30% NaOH aqueous solution was slowly added dropwise until the pH of the system was maintained at 10-13. After stirring for 3 h, an aqueous solution of sodium pyridinate was obtained, and the temperature was controlled at about 25°C during the ...

Embodiment 2

[0028] Embodiment 2, a kind of synthetic method of 3,5,6-trichloropyridin-2-alcohol sodium:

[0029] To a 1000 ml three-neck flask equipped with a thermometer and mechanical stirring, add 200 g of trichloroacetyl chloride, 90 g of acrylonitrile, and 500 g of o-dichlorobenzene, stir well at room temperature, and then add 0.7932 g of FeCl 2 , 1.9624 g hydroquinone, be warming up to 110 ℃ and react, after reacting about 13 h, filter out catalyst. The filtrate was distilled under reduced pressure to recover unreacted raw materials and part of the solvent, then added 1.9564 g HCl, and stirred at 80°C for 2 h to obtain a pyridone solution. After the system was cooled to normal temperature, 350 g of water was added, and 40% NaOH aqueous solution was slowly added dropwise until the pH of the system was maintained at 10-13, and stirred for 3 h to obtain an aqueous solution of sodium pyridinate. During the process, the temperature was controlled at about 25°C. Add 0.2035 g of cetyltrim...

Embodiment 3

[0030] Embodiment 3, a kind of synthetic method of 3,5,6-trichloropyridin-2-alcohol sodium:

[0031] Into a 1000 ml three-necked flask equipped with a thermometer and mechanical stirring, add 200 g of trichloroacetyl chloride, 90 g of acrylonitrile, and 500 g of p-xylene, and stir evenly at room temperature. Then add 0.8532 g CuCl2, 2.0536 g azobisisobutyronitrile, heat up to 120 ° C for reaction, after about 13 h of reaction, filter out the catalyst. The filtrate is distilled under reduced pressure to reclaim unreacted raw materials and part of the solvent, then add 1.7685 g ZnCl 2, stirred at 90°C for 2 h to obtain a pyridone solution. After the system was cooled to normal temperature, 350 g of water was added, and 25% NaOH aqueous solution was slowly added dropwise until the pH of the system was maintained at 10-13, and stirred for 3 h to obtain an aqueous solution of sodium pyridinate, during which the temperature was controlled at about 35°C. Add 0.3026 g of benzyltriet...

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Abstract

The invention discloses a novel method for fractional step method-based preparation of 3,5,6-trichloropyridin-2-ol sodium from trichloro-acetic chloride and acrylonitrile as main raw materials. Trichloro-acetic chloride and acrylonitrile undergo a series of reactions under the action of a solvent and a catalyst to produce 3,5,6-trichloropyridin-2-ol sodium, and tetrachloropyridine as a side product does not need separation and purification and can be directly treated and transformed into 3,5,6-trichloropyridin-2-ol sodium as a target product by an alkali liquid so that a yield is greatly improved. The 3,5,6-trichloropyridin-2-ol sodium synthesis method is simple, has a less waste water discharge capacity, realizes high-efficiency 3,5,6-trichloropyridin-2-ol sodium synthesis by simple and easy processes, produces the high-purity high-yield product and is suitable for large-scale 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 3,5,6-trichloropyridin-2-olate, molecular formula C 5 HONCl 3 Na, the pure product is light yellow solid, is an important chemical raw material and a chelating flotation agent with excellent performance, and it is also an important intermediate for the synthesis of various pesticides, especially for the production of broad-spectrum organophosphorus pesticides Chlorpyrifos. The synthetic yield of clopyridox sodium plays a decisive role in the production cost of chlorpyrifos. [0003] The synthetic route of triclopyridinate sodium can be divided into four categories according to different starting materials: pyridine route, acryloyl chloride route, phenyl trichloroacetate route and trichloroacetyl chloride route. Except for the pyridine route, the other three types belon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64
CPCC07D213/64
Inventor 方红新强金凤陆媛
Owner ANHUI COSTAR BIOCHEM CO LTD
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