CN117186025A - Energetic complex based on 1,2, 4-oxadiazolone and preparation method and application thereof - Google Patents
Energetic complex based on 1,2, 4-oxadiazolone and preparation method and application thereof Download PDFInfo
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- BXTWRMNZAGYXQQ-UHFFFAOYSA-N 1,2,4-oxadiazol-3-one Chemical compound O=C1N=CON1 BXTWRMNZAGYXQQ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 239000003446 ligand Substances 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 239000013078 crystal Substances 0.000 claims description 16
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- XMJJPCJUQLGGND-UHFFFAOYSA-N n-hydroxy-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NO)C=C1 XMJJPCJUQLGGND-UHFFFAOYSA-N 0.000 claims description 7
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- -1 1,2, 4-oxadiazolone compound Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 31
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 abstract description 8
- 239000001301 oxygen Substances 0.000 abstract description 8
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 6
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 238000005576 amination reaction Methods 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 239000002360 explosive Substances 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000013110 organic ligand Substances 0.000 description 3
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005474 detonation Methods 0.000 description 2
- 239000000203 mixture Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical group [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000003853 pentazoles Chemical class 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses an energetic complex based on 1,2, 4-oxadiazolone, which introduces more amino groups into a ligand through a nitrogen amination reaction, improves the nitrogen content level of molecules, increases the electronegativity of the molecules and is beneficial to forming a complex with inorganic metal salts. The invention also discloses a preparation method of the energetic complex based on the 1,2, 4-oxadiazolone, wherein water is used for replacing an organic solvent in the preparation, and the preparation method is environment-friendly and pollution-free. The energetic complex based on 1,2, 4-oxadiazolone has high nitrogen content, high oxygen content and good thermal stability, improves the oxygen content of the energetic material, improves the mechanical stability of the energetic material, and further comprehensively improves the application potential of the energetic complex.
Description
Technical Field
The invention relates to the technical field of energetic materials, in particular to an energetic complex based on 1,2, 4-oxadiazolone, and a preparation method and application thereof.
Background
Energetic materials are a class of compounds or mixtures that contain explosive groups or contain oxidizing agents, undergo severe redox reactions under certain external stimuli, and release large amounts of energy and gas in a short period of time. Energetic complexes are an important branch of today's energetic materials, exhibiting great potential for use in high explosive, propellant and pyrotechnic formulations. Compared with the traditional energetic molecules, the energetic complex formed by taking the nitrogen-rich organic molecules as neutral ligands and inorganic metal salts has attracted extensive attention of researchers due to the unique crystal structure, simple preparation method, high energy performance and the like.
Nitrogen-rich heterocyclic molecules such as 1,3, 4-triazoles, tetrazoles, pentazoles and the like have higher nitrogen content and positive enthalpy of formation besides the ability to form coordination bonds, and are often used as organic ligands. However, the variety of organic ligands is still slow to develop, greatly limiting the diverse derivatization of energetic complexes. Development of more organic ligands to prepare energetic complexes with excellent properties is one of the key points of research on energetic materials nowadays.
Disclosure of Invention
It is an object of the present invention to address at least the above problems and/or disadvantages and to provide at least the advantages described below.
It is still another object of the present invention to provide an energetic complex based on 1,2, 4-oxadiazolone, which introduces more amino groups into the ligand through a nitrogen amination reaction, thus increasing the nitrogen content level of the molecule, and at the same time increasing the electronegativity of the molecule, facilitating the formation of the complex with inorganic metal salts, high nitrogen content, high oxygen content, good thermal stability, improving the mechanical stability of the energetic material, and thus comprehensively increasing the application potential of the energetic complex.
Still another object of the present invention is to provide a method for preparing an energetic complex based on 1,2, 4-oxadiazolone, which uses water instead of an organic solvent, is environmentally friendly, has no pollution, and has simple synthesis steps.
To achieve these objects and other advantages and in accordance with the purpose of the invention, there is provided a baseEnergetic complexes of 1,2, 4-oxadiazolone with the general structural formula M + 1 L (2～4) A - 1 Is ligand L and metal ion M + 、A - A complex formed;
wherein M is + Is Ag + Ligand L is 1,2, 4-oxadiazolone compound, A - Is NO 3 - Or ClO 4 - The ligand L has a structure of the following formula (I):
wherein R is 1 、R 2 Is a nitrogen-containing group.
Preferably, wherein R 1 、R 2 All are amino groups.
Preferably, the energetic complex has the following structural formula:
the object of the invention is further achieved by a process for the preparation of an energetic complex based on 1,2, 4-oxadiazolone comprising the steps of:
step one, synthesizing a ligand L: 3-amino-1, 2, 4-oxadiazolone is used as a raw material, and ligand L is prepared under the action of 1, 8-diazabicyclo [5.4.0] undec-7-ene and p-toluenesulfonyl hydroxylamine;
step two, synthesizing an energetic complex: dispersing ligand L in water, heating until all solids disappear, adding aqueous solution of silver salt, dropwise adding corresponding acid until the solids disappear, stirring, cooling to room temperature, standing, filtering, washing with water, and vacuum drying to obtain energetic complex.
Preferably, the first step specifically includes: dissolving 3-amino-1, 2, 4-oxadiazolone and 1, 8-diazabicyclo [5.4.0] undec-7-ene in acetonitrile at room temperature, continuously stirring for 30min, dropwise adding a new methylene dichloride solution of tosyl hydroxylamine, continuously stirring for 3h, stopping the reaction, volatilizing the solvent in air, separating out a crude product, washing with water, filtering, and drying in vacuum to obtain colorless crystals of the ligand L.
Preferably, in the first step, the molar ratio of 3-amino-1, 2, 4-oxadiazolone to 1, 8-diazabicyclo [5.4.0] undec-7-ene to tosyl hydroxylamine is: 1:1:1.2.
Preferably, in the second step, the heating temperature is 60 ℃.
Preferably, in the second step, the molar ratio of the ligand L to the silver salt is 1:1.
The object of the invention is further achieved by the use of energetic complexes based on 1,2, 4-oxadiazolones as energetic oxidants.
The invention at least comprises the following beneficial effects:
1. the energetic complex based on 1,2, 4-oxadiazolone further improves the oxygen balance level of the energetic material, solves the technical problem that most of the energetic compounds are negative oxygen balance, further comprehensively improves the detonation performance of the energetic material, introduces sensitive groups such as nitrate, perchlorate, azide and the like into the nitrogen-rich complex, and can be used as a strategy for preparing novel energetic materials.
2. The energetic complex based on 1,2, 4-oxadiazolone improves the nitrogen content level of molecules, increases electronegativity of the molecules, is favorable for forming the complex with inorganic metal salt, improves the mechanical stability of the energetic complex, has good thermal stability, and shows great development potential as an energetic material.
3. The preparation method of the invention uses water to replace organic solvent, is environment-friendly and pollution-free, and has simple synthesis steps.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a schematic illustration of the ligand 3, 4-diamino-1, 2, 4-oxadiazolone of example 1 of the present invention 1 H NMR chart;
FIG. 2 is a schematic illustration of the ligand 3, 4-diamino-1, 2, 4-oxadiazolone of example 1 of the present invention 13 C NMR chart;
FIG. 3 is a single crystal structure of the ligand 3, 4-diamino-1, 2, 4-oxadiazolone of example 1 of the present invention;
FIG. 4 is a single crystal structure diagram of Compound 1 in example 1 of the present invention;
FIG. 5 is a DSC of Compound 1 of example 1 of the present invention;
FIG. 6 is a single crystal structure of Compound 2 in example 2 of the present invention;
FIG. 7 is a DSC of Compound 2 of example 2 of the present invention.
Detailed Description
The present invention is described in further detail below with reference to the drawings to enable those skilled in the art to practice the invention by referring to the description.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
The experimental methods described in the following embodiments are conventional methods unless otherwise indicated, and the reagents and materials are commercially available.
Example 1 ]
Energetic complex 1 based on 1,2, 4-oxadiazolone has the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
step one, synthesis of ligand 3, 4-diamino-1, 2, 4-oxadiazolone:
3-amino-1, 2, 4-oxadiazolone (10 mmol,1.01 g) and 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) (10 mmol,1.525 g) were dissolved in 80mL of acetonitrile at room temperature, continuously stirred for 30 minutes, then a solution of freshly prepared p-Toluenesulfonyl Hydroxylamine (THA) (12 mmol,2.052 g) in 40mL of dichloromethane was added dropwise, stirring was continued after the dropwise addition was completed, the reaction was stopped after three hours, the solvent was evaporated in air, the crude product was precipitated, washed with 2mL of water, collected by filtration, and dried in vacuo to give 0.31g of colorless crystals of 3, 4-diamino-1, 2, 4-oxadiazolone in 26.7% yield.
Wherein the ligand 3, 4-diamino-1, 2, 4-oxadiazolone 1 The H NMR chart is shown in figure 1, 13 the C NMR chart is shown in FIG. 2, and the single crystal structure chart is shown in FIG. 3.
Step two, synthesizing an energetic complex 1:
3, 4-diamino-1, 2, 4-oxadiazolone (1 mmol,0.11 g) was dispersed in 2mL of water and heated to 60℃until the solid had completely disappeared. Then adding 2mL of aqueous solution of silver nitrate (1 mmol,0.17 g), precipitating a large amount of white solid immediately, dropwise adding 0.5mL of 60% nitric acid until the solid disappears, stirring for 30 minutes, cooling to room temperature, standing for two days, filtering, washing with 1mL of water, and vacuum drying to obtain 0.11g of colorless crystals of the nitric acid bis (3, 4-diamino-1, 2, 4-oxadiazolone silver energetic complex (compound 1) with the yield of 55%.
Wherein, the single crystal structure diagram of the compound 1 is shown in figure 4, and the DSC diagram is shown in figure 5.
Example 2 ]
Energetic complex 2 based on 1,2, 4-oxadiazolone has the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
step one, synthesis of ligand 3, 4-diamino-1, 2, 4-oxadiazolone: the same synthesis procedure as in example 1;
step two, synthesizing an energetic complex 1:
3, 4-diamino-1, 2, 4-oxadiazolone (1 mmol,0.11 g) was dispersed in 2mL of water and heated to 60℃until the solid had completely disappeared. Then adding 2mL of aqueous solution of silver perchlorate (1 mmol,0.21 g), precipitating a large amount of white solid immediately, dropwise adding 0.5mL of 60% nitric acid until the solid disappears, stirring for 30 minutes, cooling to room temperature, standing for two days, filtering, washing with 1mL of water, and vacuum drying to obtain 0.1g of colorless crystals of the perchloric acid bis-3, 4-diamino-1, 2, 4-oxadiazolone-silver energetic complex, wherein the yield is 60%.
Wherein, the single crystal structure diagram of the compound 2 is shown in FIG. 6, and the DSC diagram is shown in FIG. 7.
Example 3 ]
Comparison of the properties of inventive example 1, example 2, conventional detonating explosive Lead Azide (LA), lead Stevenate (LS).
The performance of compound 1, compound 2, LA, LS are compared to table 1 below.
Table 1, comparison of Properties of Compound 1, compound 2, LA, LS
As shown in the table above, the energetic complex of the 3, 4-diamino-1, 2, 4-oxadiazolone synthesized by the invention has good thermal stability and high density, and compared with the traditional initiating explosive LA and LS, the energetic complex has better mechanical stability, and can greatly avoid the safety problems in the use, transportation and storage processes of energetic materials.
According to the invention, more amino groups are introduced into the ligand through the nitrogen amination reaction, so that the nitrogen content level of the molecule is improved, and meanwhile, the electronegativity of the molecule is increased, thereby being beneficial to forming a complex with inorganic metal salt. The preparation method is simple, water is used for replacing organic solvent in the preparation, and the preparation method is environment-friendly and pollution-free. Nitric acid, bis 3, 4-diamino-1, 2, 4-oxadiazolone prepared by the inventionSilver and perchloric acid tetra 3, 4-diamino-1, 2, 4-oxadiazolone silver both exhibit high density (2.321 gcm at 170K respectively) -3 And 2.447g cm -3 ) Oxygen content (27.86% and 28.59%, respectively) and thermal stability were good (178 ℃ C. And 188 ℃ C., respectively)
The diamino 1,2, 4-oxadiazolone has a nitrogen atom and an oxygen atom capable of providing lone pair electrons and has a plurality of coordination points capable of forming coordination bonds. In addition, diamino 1,2, 4-oxadiazolone exhibits high nitrogen and oxygen content, which can further enhance the performance of energetic complexes.
In the process of forming a complex of 3, 4-diamino-1, 2, 4-oxadiazolone and silver nitrate, the nitrogen atom on the 1,2, 4-oxadiazolone participates in the formation of coordination bonds, the coordination number is 2, and the calculated crystal density is 2.321g cm at 170K -3 The thermal decomposition temperature was 178 ℃. In the process of forming the complex of 3, 4-diamino-1, 2, 4-oxadiazolone and silver perchlorate, the nitrogen atom on the 1,2, 4-oxadiazolone, the carbonyl oxygen atom and the nitrogen atom of the nitrogen amino participate in the formation of coordination bonds, the coordination number is 4, the crystal stacking presents a two-dimensional structure, and the calculated crystal density is 2.447g cm at 170K -3 The thermal decomposition temperature was 188 ℃. Therefore, with the change of the kind of the inorganic metal salt involved in coordination, the atoms involved in coordination in the ligand are changed, thereby causing the change of coordination number and further affecting the crystal stacking and thermal stability.
The two energetic complexes of 3, 4-diamino-1, 2, 4-oxadiazolone of the invention show great development potential for applications in the energetic field.
The energetic complex based on 1,2, 4-oxadiazolone and the preparation method thereof enrich the ligand types of the energetic complex; secondly, the successful preparation of the energetic complex of 3, 4-diamino-1, 2, 4-oxadiazolone further improves the mechanical stability of the energetic material, solves the problem that most of the energetic compounds are negative oxygen balance, further comprehensively improves the detonation performance of the energetic material, introduces sensitive groups such as nitrate radical, perchlorate radical and the like into the nitrogen-rich complex, and can be used as a strategy for preparing novel energetic materials.
Although embodiments of the invention have been disclosed above, they are not limited to the use listed in the specification and embodiments. It can be applied to various fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. Therefore, the invention is not to be limited to the specific details and illustrations shown and described herein, without departing from the general concepts defined in the claims and their equivalents.
Claims (9)
1. Energetic complex based on 1,2, 4-oxadiazolone and having the general structural formula M + 1 L (2～4) A - 1 Is ligand L and metal ion M + 、A - A complex formed;
wherein M is + Is Ag + Ligand L is 1,2, 4-oxadiazolone compound, A - Is NO 3 - Or ClO 4 - The ligand L has a structure of the following formula (I):
wherein R is 1 、R 2 Is a nitrogen-containing group.
2. The energetic complex based on 1,2, 4-oxadiazolone of claim 1, wherein R 1 、R 2 All are amino groups.
3. The energetic complex based on 1,2, 4-oxadiazolone of claim 1, wherein the energetic complex has the following structural formula:
4. a process for preparing the energetic complex based on 1,2, 4-oxadiazolone according to any one of claims 1 to 3, comprising the steps of:
step one, synthesizing a ligand L: 3-amino-1, 2, 4-oxadiazolone is used as a raw material, and ligand L is prepared under the action of 1, 8-diazabicyclo [5.4.0] undec-7-ene and p-toluenesulfonyl hydroxylamine;
step two, synthesizing an energetic complex: dispersing ligand L in water, heating until all solids disappear, adding aqueous solution of silver salt, dropwise adding corresponding acid until the solids disappear, stirring, cooling to room temperature, standing, filtering, washing with water, and vacuum drying to obtain energetic complex.
5. The method of claim 4, wherein the first step specifically comprises: dissolving 3-amino-1, 2, 4-oxadiazolone and 1, 8-diazabicyclo [5.4.0] undec-7-ene in acetonitrile at room temperature, continuously stirring for 30min, dropwise adding a new methylene dichloride solution of tosyl hydroxylamine, continuously stirring for 3h, stopping the reaction, volatilizing the solvent in air, separating out a crude product, washing with water, filtering, and drying in vacuum to obtain colorless crystals of the ligand L.
6. The process of claim 4 wherein in step one, the molar ratio of 3-amino-1, 2, 4-oxadiazolone, 1, 8-diazabicyclo [5.4.0] undec-7-ene, tosyl hydroxylamine is: 1:1:1.2.
7. The method according to claim 4, wherein in the second step, the heating temperature is 60 ℃.
8. The method according to claim 4, wherein in the second step, the molar ratio of the ligand L to the silver salt is 1:1.
9. Use of an energetic complex based on 1,2, 4-oxadiazolone according to claim 1 as an energetic material.
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