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Hydrothermal synthesis method of 3,5-diamino-1,2,4-triazole

A technology of hydrothermal synthesis and diamino, which is applied in the direction of organic chemistry, can solve the problem of low yield, achieve the effect of high product purity, strong practicability, and simplified steps

Active Publication Date: 2016-09-28
NINGXIA SIKEDA BIOTECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to overcome the problem of low yield under high pressure conditions of the synthetic method of 3,5-disubstituted 1,2,4-triazole derivatives reported by Wei Qing et al. (Wei Qing, et al.Synthetic Communications, 2013) , the present invention has carried out systematic analysis and a large number of experiments on its synthesis mechanism and limiting factors, and proposes: using copper hydroxide instead of copper sulfate, while providing copper ions, promotes the decomposition of ammonium salts, thereby increasing the formation rate of biguanide copper complexes and reactivity

Method used

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Embodiment 1

[0050] (1) Add copper hydroxide (98%) 2.5Kg, ammonium chloride (99%) 3.0Kg and cyanamide (50%) 4.2Kg successively in 10L autoclave. The mass ratio of the feed materials is only 1:2.2:2. Under the sealed stirring state, the reactor is pressurized and the temperature is slowly raised to 110 degrees Celsius. After 3 hours of reaction, the reaction temperature is slowly lowered to room temperature, and a deep red solid is obtained after filtration.

[0051] (2) Transfer the red solid to a 50L glass reactor, and add 1.4kg of sodium sulfide into 25L of aqueous solution. Heat to reflux for 30 minutes to produce a red precipitate, heat the mixed solution through the filter cartridge to the extraction kettle, add 15L dichloromethane to the extraction kettle, extract the organic phase, evaporate the dichloromethane to obtain a white solid, and dry it in a hot air oven 2.2 kg of white 3,5-diamino 1,2,4-triazole was obtained (88% yield based on cyanamide).

Embodiment 2

[0053] (1) Add copper hydroxide (98%) 2.5Kg, ammonium acetate (99%) 4.3Kg and cyanamide (31%) 6.8Kg successively in 10L autoclave. The mass ratio of the feed materials is only 1:2.2:2. Under the sealed stirring state, the reactor is pressurized and the temperature is slowly raised to 110 degrees Celsius. After 3 hours of reaction, the reaction temperature is slowly lowered to room temperature, and a deep red solid is obtained after filtration.

[0054] (2) Transfer the red solid to a 50L glass reactor, and add 1.4kg of sodium sulfide into 25L of aqueous solution. Heat to reflux for 30 minutes to produce a red precipitate, heat the mixed solution through the filter cartridge to the extraction kettle, add 15L dichloromethane to the extraction kettle, extract the organic phase, evaporate the dichloromethane to obtain a white solid, and dry it in a hot air oven 2.2 kg of white 3,5-diamino 1,2,4-triazole was obtained (88% yield based on cyanamide).

Embodiment 3

[0056] (1) Add copper hydroxide (98%) 2.5Kg, ammonium dihydrogen phosphate (99%) 6.4Kg and cyanamide (31%) 6.8Kg successively in 10L autoclave. The mass ratio of the feed materials is only 1:2.2:2. Under the sealed stirring state, the reactor is pressurized and the temperature is slowly raised to 110 degrees Celsius. After 3 hours of reaction, the reaction temperature is slowly lowered to room temperature, and a deep red solid is obtained after filtration.

[0057] (2) Transfer the red solid to a 50L glass reactor, and add 1.4kg of sodium sulfide into 25L of aqueous solution. Heat to reflux for 30 minutes to produce a red precipitate, heat the mixed solution through the filter cartridge to the extraction kettle, add 15L dichloromethane to the extraction kettle, extract the organic phase, evaporate the dichloromethane to obtain a white solid, and dry it in a hot air oven 1.75 kg of white 3,5-diamino 1,2,4-triazole was obtained (70% yield based on cyanamide).

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Abstract

The invention provides a hydrothermal synthesis method of 3,5-diamino-1,2,4-triazole. The method comprises the following steps: cyan substituted derivatives, ammonium salt, copper hydroxide and water are used as raw materials, hydrothermal synthesis is carried out in a condition with high pressure, and 3,5-diamino-1,2,4-triazole is obtained. Cyanamide, ammonium salt, and copper hydroxide are used as raw materials, a high pressure reaction apparatus is used, ammonia which is decomposed from the ammonium salt in the effects of copper hydroxide and two molecules of cyanamide are condensed, in order to generate a copper biguanide complex. Copper(I) sulfide is eliminated from the copper biguanide complex in a condition with existence of sulfide, and 3,5-diamino-triazole is obtained by a cyclocondensation reaction. A high pressure reaction vessel is used for increasing the concentration of ammonia in a water system, which is good for generation of the condensation reaction, and at the same time, time and temperature required for condensation of cyanamide are effectively reduced. Existence of excess ammonium salt is used, in order to stabilize the pH value of the whole reaction system, and generation of the side reaction of polymerization of cyanamide is avoided. The method has the advantages of simple process, low raw material cost, and high purity of the final product.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a hydrothermal synthesis method of 3,5-diamino-1,2,4-triazole. Background technique [0002] 3,5-Diamino 1,2,4-triazole, English abbreviation (DAT), is an important fine chemical intermediate. It is a synthetic intermediate of many pharmaceutical chemicals based on 1,2,4-triazole, and is widely used in medicine, dyes, pesticides, disinfection and daily chemical products. Metal complexes based on 1,5-diaminotriazole exhibit rich optical, electrical and magnetic properties due to their structural diversity, and are a class of functional materials with broad application prospects. At the same time, DAT is also an important raw material for explosive intermediates. [0003] U.S. Patent 2648671 disclosed a kind of 3,5-diaminotriazole synthetic technique in 1953 (see figure 1 ): using water as a solvent, directly mixing dicyandiamide and hydrazine hydrochloride at 40 degrees Celsius...

Claims

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Application Information

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IPC IPC(8): C07D249/14
CPCC07D249/14
Inventor 陈红余田永富孙风程王科李平
Owner NINGXIA SIKEDA BIOTECH CO LTD