CN116925004A - N10 chain-containing gas generating agent and synthesis method thereof - Google Patents
N10 chain-containing gas generating agent and synthesis method thereof Download PDFInfo
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- CN116925004A CN116925004A CN202310839706.6A CN202310839706A CN116925004A CN 116925004 A CN116925004 A CN 116925004A CN 202310839706 A CN202310839706 A CN 202310839706A CN 116925004 A CN116925004 A CN 116925004A
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- 238000001308 synthesis method Methods 0.000 title abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 13
- 239000012286 potassium permanganate Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 5
- 238000005576 amination reaction Methods 0.000 claims abstract description 3
- 238000005691 oxidative coupling reaction Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 9
- 229940125782 compound 2 Drugs 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000004449 solid propellant Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000007789 gas Substances 0.000 abstract description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 238000005979 thermal decomposition reaction Methods 0.000 abstract description 4
- 238000005474 detonation Methods 0.000 abstract description 3
- 238000012512 characterization method Methods 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000002076 thermal analysis method Methods 0.000 description 2
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 1
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 1
- -1 5H- [1,5' -bitetrazole ] -2' -amine Chemical compound 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ANGRFWYTDAONDD-UHFFFAOYSA-N [Na].N1N=NN=N1 Chemical compound [Na].N1N=NN=N1 ANGRFWYTDAONDD-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000011151 fibre-reinforced plastic Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06D—MEANS FOR GENERATING SMOKE OR MIST; GAS-ATTACK COMPOSITIONS; GENERATION OF GAS FOR BLASTING OR PROPULSION (CHEMICAL PART)
- C06D5/00—Generation of pressure gas, e.g. for blasting cartridges, starting cartridges, rockets
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a gas generating agent containing N10 chain and a synthesis method thereof, the molecular formula of the gas generating agent is C 4 H 2 N 18 . The method comprises the following steps: dissolving 1,5' -bitetrazole potassium salt obtained by reacting 1,5' -bitetrazole with potassium hydroxide solution in a solvent, and carrying out amination reaction with THA solution to synthesize 5 hydrogen- [1,5' -bitetrazole]-2' -amine; 5H- [1,5' -bitetrazole]And (3) carrying out oxidative coupling reaction on the 2' -amine in the presence of excessive potassium permanganate and concentrated hydrochloric acid to prepare a target product. The thermal decomposition characterization of the compound is carried out by adopting a differential scanning calorimeter, so that the thermal stability of the structure is good, and a large amount of nitrogen is rapidly decomposed and discharged when the compound is heated to 118 ℃, and the compound can be used as an environment-friendly gas generating agent. The compound has high nitrogen content, high positive formation enthalpy and good detonation performance, and the synthesis method is simple, high in yield and low in cost.
Description
Technical Field
The invention relates to a gas generating agent containing N10 chain and a synthesis method thereof, belonging to the technical field of energetic materials.
Background
The gas generating agent is also called as gas generating agent, and refers to various substances capable of generating gas after combustion, and belongs to the category of solid propellant. Because the process of the generating agent of the sodium azide-based gas generating agent is mature, the generating agent is mainly used in the safety airbag at present, but the generating agent has extremely toxic influence on use. The studies of non-azide gas generants have been actively conducted, and gas generants including inflammable agents such as azoles, oxazines, guanidines, and azo compounds have been actively conducted. However, these combustibles may have a risk of loss of combustion in extreme cases such as dangerous or ageing. Thus, development of a green gas generating agent is imperative.
Accordingly, there is a need to provide a method for preparing a green gas generating agent containing an N10 chain to solve the above-mentioned problems.
Disclosure of Invention
The invention aims to provide a gas generating agent containing N10 chains and a synthesis method thereof.
The technical solution for realizing the purpose of the invention is as follows:
a gas generating agent has a chemical formula of C 4 H 2 N 18 The structural formula is as follows:
the crystal structure of the energetic compound has the following characteristics:
and (3) crystal system: monoclinic system;
dot group: p2 1 /c；
Unit cell parameters:α＝γ＝90°，β＝118.069(4)°；
unit cell volume:
Z＝4；
density: 1.746g cm -3 (296K)。
The invention provides a preparation method of a gas generating agent, which comprises the following steps:
(1) Dissolving 1,5 '-bitetrazole potassium salt obtained by reacting 1,5' -bitetrazole with potassium hydroxide solution in a solvent, and carrying out amination reaction with O- (p-toluenesulfonyl) acetoxyethyl ester (THA) solution to synthesize a compound 2;
(2) The step of preparing a target product by carrying out oxidative coupling reaction on the compound 2 in the presence of excessive potassium permanganate and concentrated hydrochloric acid;
preferably, in step (1), the molar ratio of 1,5' -bitetrazole to potassium hydroxide is 1:1.
Preferably, in step (1), the molar ratio of 1,5' -bitetrazole to THA is 1:1-3.5.
Preferably, in step (1), the solvent is acetonitrile and the solvent of the THA solution is dichloromethane.
Preferably, in the step (1), the reaction temperature is room temperature and the reaction time is 8-72h.
Preferably, in the step (2), the compound 2 is added into concentrated hydrochloric acid in batches, a potassium permanganate solution is dropwise added at the temperature of-5-0 ℃ or a potassium permanganate solid is added in batches, the mixture is stirred for 0.5h at the temperature after the addition, the reaction system is gradually warmed to room temperature, and then the mixture is stirred for more than 0.5h at the room temperature.
The use of the above-described N10 chain containing compounds as gas generating agents in solid propellants.
Compared with the prior art, the invention has the beneficial effects that:
(1) The preparation method of the N10 chain-containing compound serving as the green gas generating agent is simple and efficient, has a continuous N10 chain structure, rapidly decomposes and emits a large amount of nitrogen when heated to 118 ℃, and is a green and environment-friendly gas generating agent with excellent comprehensive performance.
(2) The green gas generating agent is an organic molecule, does not contain heavy metal and perchlorate ions, does not generate environmental pollutants in the use process, and has the characteristics of green and environment-friendliness.
(3) The green gas generating agent has the advantages of easily available raw materials, simple synthesis, stable yield, mild reaction conditions and easy engineering amplification.
Drawings
FIG. 1 is a diagram showing the crystal structure of 2',2' -azo-bis (5H- [1,5' -bitetrazole ]).
FIG. 2 is a unit cell stacking diagram of 2',2' -azo-bis (5H- [1,5' -bitetrazole ]).
FIG. 3 is a nuclear magnetic resonance spectrum of 2',2' -azo-bis (5H- [1,5' -bitetrazole ]) of the present invention (solvent is deuterated dimethyl sulfoxide).
FIG. 4 is an infrared spectrum of 2',2' -azo-bis (5H- [1,5' -bitetrazole ]).
FIG. 5 is a thermal analysis of 2',2' -azo-bis (5H- [1,5' -bitetrazole ]).
Detailed Description
The following examples will provide those skilled in the art with a more complete understanding of the invention, but are not intended to limit the invention in any way.
The green gas generating agent provided by the invention is a white powdery solid. Crystal density 1.746g cm -3 (296K) A. The invention relates to a method for producing a fibre-reinforced plastic composite The green gas generating agent provided by the invention has chain energy-containing fragments consisting of N element in the molecule, and can be decomposed into nitrogen under certain conditions, and the thermal decomposition temperature is higher than 110 ℃. There is no risk of causing combustion compared to the combustible gas generating agent. In addition, the green gas generating agent provided by the invention has lower toxicity compared with the high-toxicity azide. In a word, the green gas generating agent based on the N10 chain has the advantages of high detonation velocity, high heat generation, high gas generation amount and low toxicity, and is an ideal choice of the gas generating agent.
The invention relates to a preparation method of a gas generating agent containing N10 chains, which comprises the following reaction equation:
the starting material 1,5' -bitetrazole (compound 1) is prepared by taking commercially available 5-aminotetrazole as a substrate and carrying out one-step cyclization reaction according to literature (Chemistry-A European Journal,2013, 19:8948-8957). The green gas generating agent 2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]) is prepared from 5 hydrogen- [1,5' -bitetrazole ] -2' -amine through one-step reaction.
The preparation method of the N10 chain-containing green gas generating agent comprises the following specific steps:
dispersing 1,5 '-bitetrazole in water at room temperature, adding 1 equivalent of potassium hydroxide, and performing rotary evaporation to obtain 1,5' -bitetrazole potassium salt. Dissolving in acetonitrile, pouring a freshly prepared dichloromethane solution of O- (p-toluenesulfonyl) acetoxy ethyl ester into the solution, and reacting for 8-72h. After the reaction is finished, filtering, and carrying out silica gel column chromatography on the obtained filtrate to obtain 5 hydrogen- [1,5 '-bitetrazole ] -2' -amine.
Slowly adding 5 hydrogen- [1,5' -bitetrazole ] -2' -amine into excessive concentrated hydrochloric acid at the temperature of-5-0 ℃, dropwise adding excessive potassium permanganate solution or adding excessive potassium permanganate solid in batches, stirring for 0.5h at the temperature after the addition is finished, gradually heating the reaction system to room temperature, stirring for reacting for more than 0.5h at the temperature, quenching the reaction by hydrogen peroxide water solution, filtering the precipitate, washing with ice water, and drying to obtain the target product, namely the 2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]).
Example 1:
1,5 '-bitetrazole (7.3 mmol,1.00 g) was dispersed in 20mL of water, 0.41g (7.3 mmol) of an aqueous potassium hydroxide solution was slowly added to the solution, and after the completion of the dropwise addition, the mixture was stirred at room temperature for 0.5 hours, and after the completion of the reaction, the reaction solution was subjected to rotary evaporation to obtain 1,5' -bitetrazole potassium salt. The potassium 1,5' -bitetrazole salt was dissolved in 20mL of acetonitrile, and a freshly prepared dichloromethane solution of O- (p-toluenesulfonyl) acetoxyethyl ester was poured into the above solution and reacted for 8-72 hours. After the reaction was completed, the filtrate was filtered and subjected to silica gel column chromatography to give 5 hydrogen- [1,5 '-bistetrazole ] -2' -amine in a yield of 0.71g and a yield of 64%.
Example 2:
5H- [1,5' -bitetrazole ] -2' -amine (0.65 mmol,0.1 g) was added to 37% concentrated hydrochloric acid (5 mL) in portions at 0℃and potassium permanganate (0.5 g,3.16 mmol) was slowly added in portions, stirred at this temperature for 0.5h after the addition was completed, the reaction system was slowly warmed to room temperature, then stirred at this temperature for 2h, after the reaction was completed, aqueous hydrogen peroxide solution was added dropwise to the reaction solution for quenching, the precipitate was filtered, washed with ice water and dried to give 0.07g of pure 2',2' -azo-bis (5H- [1,5' -bitetrazole ]) in 71% yield.
Example 3:
assuming that 2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]) is decomposed by heating in a closed vacuum environment, the decomposition equation is as follows:
2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]) decomposition occurs with the formation of C solids with a small amount of hydrogen accompanying the formation of C. Calculated in terms of unit mole, 1 mole of 2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]) can produce 10 moles of gas; when converted to unit mass, 1g of 2',2' -azo-bis (5 hydrogen- [1,5' -bistetrazole ]) can produce 0.74 liter of gas.
Example 4:
hydration of sodium pentazole and NaN as common gas generating agent 3 The results of thermal decomposition theoretical analysis of several compounds, guanidine nitrate, and nitroguanidine, were carried out in a closed vacuum environment as set forth in example 3 and are shown in Table 1. As can be seen from Table 1, the 2',2' -azo-bis (5H- [1,5' -bistetrazole) of the present invention]) Is a green environment-friendly gas generating agent with excellent comprehensive performance.
Table 1
The single crystals of 2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]) obtained in example 2 were obtained by dissolving it in a mixed solvent of acetone and water (2 mL of acetone+1 mL of water) and slowly volatilizing it at room temperature, and then subjected to X-ray single crystal diffraction test, the crystal structure of which is shown in FIG. 1 and FIG. 2, and the unit cell parameters of which are shown in the following Table:
table 2 attached
The 2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]) obtained in example 2 was characterized and the analysis result thereof was as follows:
as shown in the nuclear magnetic carbon spectrum of figure 3, 13 C NMR(DMSO-d 6 ):δ156.49,144.62ppm。
as shown in fig. 4, IR (ATR):3116,1583,1469,1265,1173,1084,992,960,747,650,600cm -1 。
as shown in the thermal analysis chart of FIG. 5, the thermal decomposition temperature of 2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]) was 117.8 ℃.
Elemental analysis C 4 H 2 N 18 (302.07): found (calculated) C15.13 (15.90), N82.96 (83.43). The molecule does not contain heavy metal and chlorine element, and the environment pollution can not be caused after the use.
The 2',2' -azo-bis (5 hydrogen- [1,5' -bitetrazole ]) obtained in example 2 was tested with an impact sensitivity of 1J and a friction sensitivity of 5N.
For the 2',2' -azo-bis (5H- [1,5' -bistetrazole) obtained in example 2]) Calculated to have extremely high formation enthalpy of 5.13kJ g -1 At the same time, has excellent detonation performance, the explosion pressure calculated by EXPLO5 is 26.82GPa, and the explosion speed is 8594 m.s -1 。
Claims (9)
1. A gas generating agent containing N10 chain is characterized in that the chemical formula is C 4 H 2 N 18 The structural formula is as follows:
2. the N10 chain-containing gas generant of claim 1 having a crystal structure characterized by:
and (3) crystal system: monoclinic system;
dot group: p2 1 /c；
Unit cell parameters:α＝γ＝90°，β＝118.069(4)°；
unit cell volume:
Z＝4；
density: 1.746g cm -3 (296K)。
3. A method for producing a gas generating agent containing an N10 chain, comprising:
(1) Dissolving 1,5 '-bitetrazole potassium salt obtained by reacting 1,5' -bitetrazole with potassium hydroxide solution in a solvent, and performing amination reaction with THA solution to synthesize a compound 2;
(2) The step of preparing a target product by carrying out oxidative coupling reaction on the compound 2 in the presence of excessive potassium permanganate and concentrated hydrochloric acid;
4. a process according to claim 3, wherein in step (1) the molar ratio of 1,5' -bitetrazole to potassium hydroxide is 1:1.
5. A method according to claim 3, wherein in step (1) the molar ratio of 1,5' -bitetrazole to THA is from 1:1 to 3.5.
6. A process according to claim 3, wherein in step (1) the solvent is acetonitrile and the solvent of the THA solution is dichloromethane.
7. A method according to claim 3, wherein in step (1), the reaction temperature is room temperature and the reaction time is 8 to 72 hours.
8. A process according to claim 3, wherein in step (2) compound 2 is added in portions to concentrated hydrochloric acid. Dropwise adding potassium permanganate solution at-5-0 ℃ or adding potassium permanganate solid in batches, stirring at the temperature for 0.5h after the addition, gradually heating the reaction system to room temperature, and stirring at the room temperature for more than 0.5h for reaction.
9. Use of a compound containing an N10 chain as claimed in claim 1 or 2 as a gas generating agent in a solid propellant.
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