2-Amino-4-nitroamine-6-formylnitroamine-1,3,5-triazine nitrogen oxide and its preparation method

A formyl nitramide and nitrogen oxide technology, applied in organic chemistry methods, organic chemistry, etc., can solve the problems of low triazine ring tension and difficulty

Active Publication Date: 2020-04-28
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The triazine ring has low ring tension and good stability, and has three modifiable sites, which can react with nucleophiles to introduce azido groups, nitro groups, nitroamine groups, azo bonds, hydrazine bonds and others. Five-membered heterocyclic ring structure, but it is very difficult to introduce nitrogen oxide groups on 1,3,5-triazine

Method used

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  • 2-Amino-4-nitroamine-6-formylnitroamine-1,3,5-triazine nitrogen oxide and its preparation method
  • 2-Amino-4-nitroamine-6-formylnitroamine-1,3,5-triazine nitrogen oxide and its preparation method
  • 2-Amino-4-nitroamine-6-formylnitroamine-1,3,5-triazine nitrogen oxide and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Under magnetic stirring at 25°C, dissolve 0.83g (5mmol) of 1,3,5-triazino1,2,4-triazole in 10mL (0.135mol) of trifluoroacetic acid, and slowly drop 5mL (0.166mol) of 50% hydrogen peroxide, the feeding temperature should not exceed 40°C. After dropping, reacted at 25°C for 5h, poured into ice water to quench, filtered out the solid, washed with water, and dried to obtain 0.39g of intermediate 1,3,5-triazine nitrogen oxide derivative, with a yield of 42%. At -5°C, dissolve 0.19 g (1 mmol) of the above intermediate in 2 mL of 100% HNO 3 (48mmol), returned to 2°C to continue the reaction for 2h, then poured into ice water to quench, stirred for 0.5h, filtered out the precipitate, washed the filter cake with water, and dried in vacuo to obtain white powder 2-amino-4-nitroamine-6- Formyl nitramide-1,3,5-triazine nitrogen oxide 53 mg, yield 19%.

Embodiment 2

[0027] Under magnetic stirring at 25°C, dissolve 0.83g (5mmol) of 1,3,5-triazino1,2,4-triazole in 20mL (0.269mol) of trifluoroacetic acid, and slowly drop 5mL (0.166mol) of 50% hydrogen peroxide, the feeding temperature should not exceed 40°C. After dropping, react at 25° C. for 5 h, pour into ice water to quench, filter out the solid, wash with water, and dry to obtain 0.28 g of the intermediate 1,3,5-triazine nitrogen oxide derivative, with a yield of 30%. At -5°C, dissolve 0.19 g (1 mmol) of the above intermediate in 2 mL of 100% HNO 3 (48mmol), returned to 2°C to continue the reaction for 2h, then poured into ice water to quench, stirred for 0.5h, filtered out the precipitate, washed the filter cake with water, and dried in vacuo to obtain white powder 2-amino-4-nitroamine-6- Formyl nitramide-1,3,5-triazine nitrogen oxide 53 mg, yield 19%.

Embodiment 3

[0029] Under magnetic stirring at 25°C, dissolve 0.83g (5mmol) of 1,3,5-triazino1,2,4-triazole in 15mL (0.202mol) of trifluoroacetic acid, and slowly drop 8mL (0.266mol) 50% hydrogen peroxide, the feeding temperature should not exceed 40°C. After dropping, reacted at 25°C for 5h, poured into ice water to quench, filtered out the solid, washed with water, and dried to obtain 0.49g of the intermediate 1,3,5-triazine nitrogen oxide derivative, with a yield of 52%. At -5°C, dissolve 0.57 g (3 mmol) of the above intermediate in 8 mL of 100% HNO 3 (0.144mol), return to 2°C and continue to react for 2h, then pour into ice water to quench, stir for 0.5h, filter out the precipitate, wash the filter cake with water, and vacuum dry to obtain white powder 2-amino-4-nitroamine-6 - 0.16 g of formyl nitramide-1,3,5-triazine nitrogen oxide, yield 19%.

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Abstract

The invention discloses 2-amino-4-nitramine-6-formyl nitramine-1,3,5-triazine oxynitride and thea preparation method thereof. The preparation method comprises the following steps: (1) at 25 DEG C, adding 1,3,5-triazine and 1,2,4-triazole into trifluoroacetic acid, and then adding 50% hydrogen peroxide for full reaction at this temperature, and then pouring into ice water to quench, filtering to obtain an intermediate; (2) under low temperature condition, adding the intermediate into 100% HNO3, and then performing full reaction at this temperature, after that pouring into ice water to quench, precipitating solids after stirring for a period of time, filtering and washing, and obtaining a target product.The preparation method provided by the invention facilitates obtaining monocyclic triazine high energetic materials that is 2-amino-4-nitramine-6-formyl nitramine-1,3,5-triazine oxynitride.

Description

technical field [0001] The invention relates to the technical field of energetic materials, in particular to 2-amino-4-nitroamine-6-formylnitroamine-1,3,5-triazine nitrogen oxide and a preparation method thereof. Background technique [0002] Among the six-membered aromatic heterocyclic skeletons, the nitrogen content of 1,3,5-triazine is as high as 51%, second only to 1,2,4,5-tetrazine (68%), triazine-based The compound has the advantages of high density, high positive enthalpy of formation and good thermal stability, and is often used in the construction of chemical raw materials (melamine), gas generating agents, solid propellants, pyrotechnic agents, and primary explosives (azidotriazine), etc. The triazine ring has low ring tension and good stability, and has three modifiable sites, which can react with nucleophiles to introduce azido groups, nitro groups, nitroamine groups, azo bonds, hydrazine bonds and others. It has a five-membered heterocyclic structure, but it is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/66
CPCC07B2200/13C07D251/66
Inventor 马卿王述存卢欢唱廖龙渝范桂娟张祯琦
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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