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Method for synthesizing dichloroglyoxime

A technology of dichloroglyoxime and glyoxime, applied in oxime preparation, organic chemistry, etc., can solve the problems of short reaction time, low yield, large heat release, etc., and achieve mild and controllable conditions, stable and reliable yield , The effect of stable yield

Inactive Publication Date: 2015-01-14
HUBEI INST OF AEROSPACE CHEMOTECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] (3) US Patent US5476967 in 1995 studied the method reported in US4539405, and believed that this method had shortcomings. It was found that the synthesis method must be carried out below -20°C, and the reaction time must be short enough. After the reaction time is prolonged, the product The rate is much lower, maybe only 10%
[0011] As can be seen from the above several methods for preparing dichloroglyoxime, the disadvantages of these methods are: method one productive rate is relatively low
Method 2 has a very large heat release, and the heating rate is not easy to control. It is only suitable for the preparation of dichloroglyoxime samples in small batches. Scaling up with this process (even at the 100-gram scale) may lead to a rapid rise in internal temperature and increase the risk of the test. And the yield decreases rapidly, and even the product cannot be obtained
Method 3 is only applicable to the preparation of ethylene glycol solution of dichloroglyoxime

Method used

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  • Method for synthesizing dichloroglyoxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 500ml of methanol solvent and 10g of glyoxime into a 1000ml beaker, dissolve and set aside. Add 500ml of methanol solvent into a 3000ml three-neck flask. After the methanol solution was cooled to -40°C, chlorine gas was introduced into the solution. After 30 minutes, the acetoxime solution was added dropwise to the three-neck flask, and the dropping rate was controlled. After 0.5 hours, the stirring was started. After the dropwise addition, react for 1 hour and slowly return to room temperature. The solvent was removed and washed with chloroform to obtain 16.41 g of the product with a yield of 92%.

Embodiment 2

[0028] Add 500ml of ethanol solvent and 100g of glyoxime into a 1000ml beaker, dissolve and set aside. Add 1000ml of ethanol solvent in a 3000ml three-necked flask. After the ethanol solution was cooled to -10°C, chlorine gas was introduced into the solution. After 1 hour, the glyoxime solution was added dropwise to the three-neck flask, and the dropping speed was controlled. After 5 hours, the stirring was started. After the dropwise addition was completed, the reaction was carried out for 20 hours and then slowly returned to room temperature. The solvent was removed and washed with chloroform to obtain 169.48 g of the product with a yield of 95%.

Embodiment 3

[0030] Add 600ml of isopropanol solvent and 50g of glyoxime into a 1000ml beaker, dissolve and set aside. Add 500ml of isopropanol solvent into a 3000ml three-necked flask. After the isopropanol solution was cooled to 20°C, chlorine gas was introduced into the solution. After 30 minutes, the glyoxime solution was added dropwise to the three-neck flask, and the dropping rate was controlled. After 10 hours, the stirring was started. After the dropwise addition was completed, the reaction was carried out for 48 hours and then slowly returned to room temperature. The solvent was removed and washed with chloroform to obtain 85.632 g of the product with a yield of 96%.

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Abstract

The invention relates to a method for synthesizing dichloroglyoxime. In the method, glyoxime and chlorine are taken as raw materials to have chlorination reaction under the temperature condition of -40 DEG C to 20 DEG C by taking alcohol as a solvent. The method comprises the following steps of: firstly introducing chlorine to an alcohol reaction solvent, and dissolving glyoxime into an alcohol solution; then dropwise adding the glyoxime solution into a reaction system. Compared with the prior art, the method disclosed by the invention has the advantages of moderate and controllable reaction condition, stable yield, low cost and easiness in operation, can be used for producing solid dichloroglyoxime products in a large quantity and is a high-efficiency and reliable synthetic method.

Description

technical field [0001] The invention relates to a new method for the preparation of an industrial bactericide and a synthetic intermediate of an energetic compound - dichloroglyoxime (DCG) Background technique [0002] Dichloroglyoxime, English name Dichloroglyoxim, referred to as DCG. Molecular formula C 2 h 2 Cl 2 N 2 o 2 , molecular weight 156.95. The appearance of DCG is white crystal, the melting point is 204°C, and it is easily soluble in polar organic solvents. α-haloxime-based compounds have antibacterial activity, and most of the fungicides commonly used in the market are such substances, but the actual bactericidal and inhibitory effects are not very strong. However, the dichloroglyoxime formed by the combination of two active groups has a very strong bactericidal ability. Recent studies have found that DCG is used in papermaking white water sizing agent, and its bactericidal ability is about 10 times stronger than that of bactericide DBNPA (2,2-dibromo-3-c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/32C07C249/12
Inventor 何金选叶丹阳卢艳华雷晴郭滢媛曹一林
Owner HUBEI INST OF AEROSPACE CHEMOTECHNOLOGY