CN-122010921-A - [1,2,5] Oxadiazole-bis [1,2,4] triazole explosive and preparation method thereof

CN122010921ACN 122010921 ACN122010921 ACN 122010921ACN-122010921-A

Abstract

The invention discloses a [1,2,5] oxadiazole-1, 2,4] triazole explosive, which is N 3 ,N 4 bis (5-nitro-1H-1, 2, 4-triazole-3-yl) -1,2, 5-oxadiazole-3, 4-diamine. The invention also discloses a preparation method of the [1,2,5] oxadiazole-1, 2,4] triazole explosive. The invention discloses a [1,2,5] oxadiazole-1, 2,4] triazole explosive with high-energy low-sense flexible imino characteristic, which is structurally characterized in that a five-membered azole ring (1, 2,5] oxadiazole and [1,2,4] triazole) is taken as a basic skeleton, flexible imino is taken as a bridging center, and amino and nitro are taken as substituents. The invention provides a synthesis method of the compound. The compound disclosed by the invention has the characteristics of high energy and low sensitivity, excellent detonation performance, simple synthesis method and the like, and has application potential in the aspect of the linked explosive.

Inventors

LIU TIANLIN
LIAO SICHENG
Chen Shiluo
ZHOU ZHIYU

Assignees

中国工程物理研究院化工材料研究所

Dates

Publication Date: 20260512
Application Date: 20260108

Claims (3)

1. The [1,2,5] oxadiazole-1, 2,4] triazole explosive is characterized in that the [1,2,5] oxadiazole-1, 2,4] triazole explosive is N 3 ,N 4 bis (5-nitro-1H-1, 2, 4-triazole-3-yl) -1,2, 5-oxadiazole-3, 4-diamine with the following structural formula: 。
2. A process for preparing an explosive of [1,2,5] oxadiazole-1, 2,4] triazole type as claimed in claim 1, characterized in that, The reaction formula is as follows: 。
3. the method for preparing [1,2,5] oxadiazole-1, 2,4] triazole explosive according to claim 2, which is characterized in that: Step one, synthesis of Compound 1 3, 4-Diamino [1,2,5] oxadiazole and N-cyano dithioimine dimethyl carbonate are taken as raw materials, after the raw materials are completely consumed by a dot board monitoring method, the raw materials are quenched by a small amount of crushed ice, filtered, washed and dried to obtain N, N ' ' - (1, 2, 5-oxadiazole-3, 4-diyl) (Z, Z) -bis (N ' -cyano amino thioimine) dimethyl ester, namely a compound 1; Step two, synthesis of Compound 2 After the compound 1 is completely dissolved in a solvent, cyclizing under the action of hydrazine hydrate to obtain N 3 ,N 3' - (1, 2, 5-oxadiazole-3, 4-diyl) bis (1H-1, 2, 4-triazole-3, 5-diamine), namely a compound 2; step three, synthesis of Compound 3 The compound 2 is oxidized into nitro under HNO 3 / NaNO 2 , quenched, extracted and combined with organic phase, dried with anhydrous sodium sulfate, and the solvent is removed by rotary evaporation to obtain N 3 ,N 4 bis (5-nitro-1H-1, 2, 4-triazole-3-yl) -1,2, 5-oxadiazole-3, 4-diamine, namely the compound 3.

Description

[1,2,5] Oxadiazole-bis [1,2,4] triazole explosive and preparation method thereof Technical Field The invention relates to a ring-linked explosive and a preparation method thereof, in particular to a [1,2,5] oxadiazole [1,2,4] triazole explosive and a preparation method thereof, belonging to the technical field of energetic material preparation. Background The linked explosive can be connected with a plurality of ring structures through the connecting unit, so that the formation enthalpy and density can be effectively improved, a plurality of derivative sites are expanded, and the substrate structure of the energetic material is enriched. In general, the methods of carbon-carbon direct connection, azo bridging, carbon-nitrogen bridging, alkyl bridging and the like are mainly adopted, and the research on the ring-linked explosive taking imino bridging as a flexible center is relatively less. The existence of imino group is favorable for forming intramolecular and intermolecular hydrogen bonds, so that weak interaction force between molecules is enhanced, close packing is formed to improve the density of the compound, delta-pi super conjugation can be formed by lone pair electrons on nitrogen and connected heterocycle, and further the stability of the compound is improved, and the contradiction between energy and sensitivity can be effectively relieved. Therefore, the imino bridging strategy is one of the effective methods for obtaining high energy low inductance energetic compounds. In the single ring structure selection of the interlinked explosive, the balance of the safety and the energy level of the single ring is fully considered, and the [1,2,5] oxadiazole and the [1,2,4] triazole are finally selected. Wherein, the [1,2,5] oxadiazole has two nitrogen atoms and one oxygen atom, the nitrogen content is up to 40 percent, and unpaired electrons on the atoms can form a conjugated structure similar to a benzene ring through pi bond interaction, and the conjugation has positive effects on improving the thermal stability and the safety of the compound. In addition, the skeleton energetic compound has higher density and oxygen balance due to the existence of oxygen atoms on the [1,2,5] oxadiazole ring. Compared with other single-ring structures, the [1,2,4] triazole has more stable and modifiable sites compared with tetrazoles, can introduce more energy-containing groups, and has better energy performance than pyrazole with more carbon content due to higher nitrogen content. Therefore, the [1,2,4] triazole skeleton can well balance energy and sensitivity, and is one of preferable skeletons for constructing novel low-sensitivity high-energy explosive molecules. In conclusion, the coupling ring structure of the [1,2,5] oxadiazole and the [1,2,4] triazole is constructed through flexible imino central bridging, so that the balance of energy and safety can be met, and a novel bridging explosive with excellent comprehensive performance is developed. Disclosure of Invention The present invention provides a brand new [1,2,5] oxadiazole [1,2,4] triazole explosive. The invention is realized in particular as follows: an [1,2,5] oxadiazole-bis [1,2,4] triazole explosive is N 3,N4 bis (5-nitro-1H-1, 2, 4-triazole-3-yl) -1,2, 5-oxadiazole-3, 4-diamine with the following structural formula: 。 The invention also discloses a preparation method of the [1,2,5] oxadiazole-1, 2,4] triazole explosive, which comprises the following steps: Step one, synthesis of Compound 1 3, 4-Diamino [1,2,5] oxadiazole and N-cyano dithioimine dimethyl carbonate are taken as raw materials, after the raw materials are completely consumed by a point plate monitoring method, the raw materials are quenched by a small amount of crushed ice, filtered, washed and dried to obtain N, N ' ' - (1, 2, 5-oxadiazole-3, 4-diyl) (Z, Z) -bis (N ' -cyano amino thioimine) dimethyl ester, namely the compound 1. Step two, synthesis of Compound 2 After the compound 1 is completely dissolved in a solvent, cyclizing is carried out under the action of hydrazine hydrate, and N 3,N3' - (1, 2, 5-oxadiazole-3, 4-diyl) bis (1H-1, 2, 4-triazole-3, 5-diamine) is obtained, namely the compound 2. Step three, synthesis of Compound 3 The compound 2 is oxidized into nitro under HNO 3 / NaNO2, quenched, extracted and combined with organic phase, dried with anhydrous sodium sulfate, and the solvent is removed by rotary evaporation to obtain target molecule- -N 3,N4 bis (5-nitro-1H-1, 2, 4-triazol-3-yl) -1,2, 5-oxadiazole-3, 4-diamine, namely the compound 3. The invention discloses a preparation method of [1,2,5] oxadiazole-1, 2,4] triazole explosive, which has the following reaction formula: 。 The invention discloses a [1,2,5] oxadiazole-1, 2,4] triazole explosive (compound 3) with high-energy low-sense flexible imino characteristic, which is structurally characterized in that a five-membered azole ring ([ 1,2,5] oxadiazole and [1,2,4] triazole) is taken as a basic skeleton, flexible imino