CN108689959B - Compounds and energetic ionic salts thereof - Google Patents
Compounds and energetic ionic salts thereof Download PDFInfo
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- CN108689959B CN108689959B CN201710230524.3A CN201710230524A CN108689959B CN 108689959 B CN108689959 B CN 108689959B CN 201710230524 A CN201710230524 A CN 201710230524A CN 108689959 B CN108689959 B CN 108689959B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
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- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
Abstract
The invention relates to 3, 3' -azobis [1,2, 4-oxadiazole-5-ketone-3-base- ] -1,2, 5-oxadiazole and energetic ionic salts thereof, belonging to the field of synthesis. Coupling 4- [ 5-amino-1, 2, 4-oxadiazol-3-yl- ] -3-amino-1, 2, 5-oxadiazole with potassium permanganate aqueous solution to obtain 3,3 '-azobis [ 5-amino-1, 2, 4-oxadiazol-3-yl- ] -1,2, 5-oxadiazole, carrying out oxidation reaction on the compound 2 with a mixed solution of acetic anhydride and 100wt% nitric acid (mass ratio is 2:1) to obtain 3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl- ] -1,2, 5-oxadiazole, neutralizing the product with an alkaline compound to obtain corresponding energetic ionic salt, the synthesis method has the advantages of safe and reasonable process, short reaction time, high yield, low production cost and no three wastes basically.
Description
Technical Field
The invention relates to synthesis of 3, 3' -azobis [1,2, 4-oxadiazole-5-ketone-3-base- ] -1,2, 5-oxadiazole and a preparation method of energetic ionic salt thereof, belonging to the technical field of synthesis of energetic materials.
Background
High energy density materials are compounds that are used as high energy components of explosives, propellants and explosives. Such materials are used in all strategic and tactical weaponry systems, and in all arms and gear. The improved performance of High Energy Density Materials (HEDM) can have a significant impact on the performance of the weapon system, thereby significantly increasing the effectiveness of the weapon system. For example, if the range of the submarine-launched strategic missile is increased by 10%, the area of the sea area hidden by the submarine is increased by millions of squares, and the survival capacity of strategic weapons is greatly improved. The improvement of the explosive destruction power is the constant requirement of the weapon on the explosive, and the continuous improvement of the energy of the single-substance explosive is the main way of improving the explosive energy power.
High Energy Density Materials (HEDM) have received great attention, with nitrogen-rich energetic ionic salts being one of the hot spots in the field of high energy density material research in recent years. Compared with molecular analogues, the energetic material based on the ionic salt has the advantages of low steam pressure (small toxic steam generated in the processing process), high density, good thermal stability and the like. The use of anions and cations with high nitrogen content allows energetic ionic salts with higher product roast and density because they contain a large number of energetic N-N and C-N bonds. In addition, nitrogen-rich compounds decompose to produce primarily nitrogen gas, making them candidates for environmentally friendly energetic material applications.
Furazan plays an important role in biochemistry, such as NO donors under physiological conditions, anti-cancer agents, and also plays an important role in energetic materials. Furazan rings are considered to be a very useful substructure for the design of new high density energetic materials. Due to the high generation baking of the furazan ring, the introduction of the furazan ring can improve the detonation performance. However, the absence of acidic hydrogens in furazan rings renders them incapable of acting directly as bronsted acids, i.e. of reacting with lewis bases, and therefore they cannot be used directly as anions of energetic ionic salts. This problem can be solved if an electron-withdrawing oxygen atom is introduced into the furazan ring. In addition, the introduction of oxygen atoms improves the oxygen balance of furazan rings, and molecules can form a conjugated structure through multi-nitrogen connection, so that the stability of the furazan rings is improved, the sensitivity is reduced, and the thermal stability is improved. The invention designs and synthesizes nitrogen-rich 3, 3' -azobis [1,2, 4-oxadiazole-5-ketone-3-group- ] -1,2, 5-oxadiazole and energetic ionic salts thereof, and the energetic ionic salts have excellent thermal stability and lower impact sensitivity and can be used in the field of energetic materials.
Disclosure of Invention
The invention aims to provide 3, 3' -azobis [1,2, 4-oxadiazole-5-ketone-3-yl- ] -1,2, 5-oxadiazole and a preparation method of energetic ionic salt thereof, wherein the compounds have good thermal stability (the decomposition temperature is mostly above 200 ℃) and excellent detonation performance, and the decomposition temperature of part of energetic salt exceeds HMX.
The purpose of the invention is realized by the following technical scheme.
The 3, 3' -azobis [1,2, 4-oxadiazole-5-ketone-3-group- ] -1,2, 5-oxadiazole has the following structure:
3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl- ] -1,2, 5-oxadiazole energetic ionic salt, which has the general formula:
in the formula (a), n is 1-2, [ Cation [ ]]n+Is one of ammonium cation, monovalent hydrazine cation, guanidine cation, aminoguanidine cation, triaminoguanidine cation, 3, 5-diamino 1,2, 4-triazole cation, 5-aminotetrazole cation, 3-amino-1, 2, 4-triazole cation, 1-amino-1, 2, 3-triazole cation, 3-methyl-1-amino-1, 2, 3-triazole cation or 1, 5-diaminotetrazole cation.
The synthetic route of 3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl- ] -1,2, 5-oxadiazole is as follows:
the specific preparation process comprises the following steps:
step 1) adding a compound 1 into a mixed solution of acetonitrile and concentrated hydrochloric acid at room temperature, slowly adding a saturated potassium permanganate aqueous solution with the same molar weight as the compound 1, continuing to react for 15-60 minutes after the addition is finished, decoloring, filtering and washing with water to obtain a compound 2;
and 2) at the temperature of 20-10 ℃, taking a mixed solution of acetic anhydride and 100wt% nitric acid in a mass ratio of 2:1 as an oxidant, carrying out oxidation reaction on the compound 2 to obtain a compound 3, heating to room temperature, violently stirring until a solid is separated out, stopping the reaction, pouring the obtained suspension into ice water, filtering, and washing with water to obtain a target compound 4.
The synthetic route of the 3, 3' -azobis [1,2, 4-oxadiazole-5-ketone-3-radical ] -1,2, 5-oxadiazole energetic ionic salt is as follows:
the method comprises the following specific steps:
dispersing the compound 4 in a solvent, adding a solution of an alkaline compound with double molar weight of the compound 4 into the solvent, stirring and reacting for 0.5-6 hours at room temperature, filtering when solid is precipitated to obtain a target product, and concentrating a reaction solution when no solid is precipitated to obtain the target product.
The solvent for the reaction can be water, methanol, ethanol, isopropanol, butanol, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran and 1, 4-dioxane, and the mass ratio of the compound 4 to the solvent is 1: 0.5-50.
The basic compound for the above reaction is one of ammonia, hydrazine hydrate, guanidine, aminoguanidine, triaminoguanidine, 3, 5-diamino-1, 2, 4-triazole, 5-aminotetrazole, 3-amino-1, 2, 4-triazole, 1-amino-1, 2, 3-triazole, 3-methyl-1-amino-1, 2, 3-triazole and 1, 5-diaminotetrazole.
Compared with the prior art, the invention has the advantages that:
1) seven energetic ionic salts are obtained, and the density is higher and is between 1.70 and 1.89g/cm through testing3。
2) The energetic ion salt has the detonation velocity of 8013-8914m/s and the detonation pressure of 24.5-32.0GPa, and is a high-energy density explosive.
3) According to the impact sensitivity test, the impact sensitivity of the energetic ionic salt is more than 40J, and the energetic ionic salt belongs to insensitive explosives.
4) The energetic ionic salt has the decomposition temperature of more than 200 ℃ and very good thermal stability through DSC test.
5) The salt has the advantages of simple synthesis method, mild conditions, high yield, and environment-friendly effect by taking deionized water as a reaction solvent.
6) Due to the introduction of anions Xn-The average band has higher nitrogen content, so that the compound is compared with 3, 3' -azobi [1,2, 4-oxadiazole-5-ketone-3-yl-]The nitrogen content of the-1, 2, 5-oxadiazole is improved to a certain extent.
Detailed Description
The present invention is further illustrated by the following examples, but the scope of the invention is not limited thereto.
Example 1
Preparation of 3, 3' -azobis [ 5-amino-1, 2, 4-oxadiazol-3-yl- ] -1,2, 5-oxadiazole, the structure of which is as follows:
compound 1(4g, 23.8mmol) was added to a mixture of acetonitrile (80ml) and concentrated hydrochloric acid (50ml) at room temperature. After mixing uniformly, slowly adding saturated potassium permanganate (3.76g, 23.8mmol) aqueous solution, after the addition is finished, continuing stirring for 15min, adding water (30ml) for dilution, and slowly adding 5% hydrogen peroxide until the solution becomes colorless. Filtration and washing with water gave compound 2(3.5g, 10.5mol) in 87.5% yield.
Decomposition temperature>250℃.1H NMR(500MHz,d6-DMSO):δ8.37ppm.13C NMR(500MHz,d6-DMSO):δ173.66,163.11,158.33,142.52ppm.
Example 2
Preparation of 4- (5-amino-1, 2, 4-oxadiazol-3-yl-) -4 '- (4H-5-O-1,2, 4-oxadiazol-3-yl) -3, 3' -azobis 1,2, 5-oxadiazole having the following structure:
and (2) carrying out oxidation reaction on the compound 2 by using a mixed solution of acetic anhydride and 100wt% of nitric acid (in a mass ratio of 2:1) at the temperature of-20-10 ℃ to obtain a compound 3.
1H NMR(500MHz,d6-DMSO):δ8.42ppm(s,2H).IR(KBr):υ3450 3280 1770 1670 1610 1560 1490 1340 1240 1170 1030 973 895 811 764 615 526cm-1；Elemental analysis:C 28.83,H 0.92,N 46.26％。
The decomposition temperature of the compound 3 is 270 ℃ through differential scanning calorimetry test; the density was found to be 1.80g/cm-3(ii) a The enthalpy of formation is 942.6kJ/mol calculated by an isochain equation; calculated by software of Explo5, the detonation velocity is 8419m/s, and the detonation pressure is 29.6 GPa; the impact sensitivity of the sensor is 26J and the friction sensitivity is 240N.
Example 3
Preparation of 3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl- ] -1,2, 5-oxadiazole, the structure of which is as follows:
2(3.32g, 10mmol) was slowly added to a mixture of acetic anhydride (10ml) and 100% nitric acid (5ml) at 0 ℃. After the reaction is carried out for 30min at the temperature of 0 ℃, the reaction temperature is raised to room temperature, the mixture is stirred vigorously until solid is separated out, and the reaction is stopped. The suspension was poured into ice water, and a large amount of insoluble substances were precipitated. Filtration and washing with water gave 4(1.8g, 5.4mmol) in 53.9% yield.
1H NMR(500MHz,d6-DMSO):No peak.13C NMR(500MHz,d6-DMSO):δ162.18,159.52,148.26,139.89ppm.IR(KBr):υ2990 2820 2700 1800 1760 1620 1540 1430 1310 1250 1140 1020 991 943 906 873 795 749 698 618 526cm-1。
The decomposition temperature of the compound 4 is 322 ℃ through differential scanning calorimetry test; the density was found to be 1.89g/cm-3(ii) a The enthalpy of formation is 529.7kJ/mol calculated by an isochain equation; calculated by software of Explo5, the detonation velocity is 8507m/s, and the detonation pressure is 30.7 GPa; the impact sensitivity of the sensor is 16J and the friction sensitivity is 160N.
Example 4
The preparation of 3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl- ] -1,2, 5-oxadiazole bisammonium salt has the following structure:
the method comprises the following specific steps: at room temperature, 4(3.34g, 10mmol) is dissolved in a mixed solution of methanol (10ml) and acetonitrile (10ml), ammonia water with twice equivalent is added for reaction for 2 hours, solid is separated out, and the product is filtered and washed by acetonitrile to obtain the target product with the yield of 82.7%.
1H NMR(500MHz,d6-DMSO):δ7.11ppm(s,8H).13C NMR(500MHz,d6-DMSO):δ173.53 162.54 157.89 144.32ppm.IR(KBr):υ3175 2826 1843 1670 1588 1504 1472 1425 1218 1177 1039 990 946 871 792 776 613 546cm-1。
3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl-]The decomposition temperature of the-1, 2, 5-oxadiazole bisamide salt is 318 ℃; the density was found to be 1.71g/cm-3(ii) a The enthalpy of formation is 1119.9kJ/mol calculated by an isochain equation; calculated by software of Explo5, the detonation velocity is 8464m/s, and the detonation pressure is 29.4 GPa; the impact sensitivity is measured to be>40J, friction sensitivity of>360N。
Example 5
The preparation of 3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl- ] -1,2, 5-oxadiazol biguanide salts has the following structure:
the method comprises the following specific steps: at room temperature, 4(3.34g, 10mmol) was dissolved in a mixture of methanol (10ml) and acetonitrile (10ml), and a solution of guanidine in water was added in an amount twice the equivalent, and the reaction was carried out for 2 hours, whereupon a solid precipitated, filtered, and washed with acetonitrile to obtain the desired product in 83.2% yield.
1H NMR(500MHz,d6-DMSO):δ6.98ppm(s,12H).13C NMR(500MHz,d6-DMSO):δ173.67 162.49 158.64 157.86 152.50ppm.IR(KBr):υ3360 3166 1649 1504 1370 1338 1216 1174 1041 988 938 868 786 767 701 610cm-1。
3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl-]The decomposition temperature of the 1,2, 5-oxadiazole biguanide salt is 261 ℃; the density was found to be 1.83g/cm-3(ii) a The enthalpy of formation is 1112.8kJ/mol calculated by an isochain equation; calculated by software of Explo5, the detonation velocity is 8853m/s, and the detonation pressure is 31.4 GPa; the impact sensitivity is measured to be>40J, friction sensitivity of>360N。
Example 6
Preparation of 3, 3' -azobis [1,2, 4-oxadiazol-5-on-3-yl- ] -1,2, 5-oxadiazolidis-3, 5-diamino-1, 2, 4-triazolate, the structure of which is as follows:
the method comprises the following specific steps: at room temperature, 4(3.34g, 10mmol) is dissolved in a mixed solution of methanol (10ml) and acetonitrile (10ml), and twice equivalent of 3, 5-diamino-1, 2, 4-triazole aqueous solution is added for reaction for 2h, solid is precipitated, filtered and washed by acetonitrile to obtain the target product with the yield of 88.6%.
1H NMR(500MHz,d6-DMSO):δ7.02ppm(br).13C NMR(500MHz,d6-DMSO):δ171.58 162.48 156.34 143.65ppm.IR(KBr):υ3356 1701 1598 1509 1493 1344 1286 1231 1175 1094 1000 945 870 785 726 661 614 547cm-1。
3, 3' -azobis [1,2, 4-oxadiazol-5-one-3-yl-]The decomposition temperature of the-1, 2, 5-oxabis 3, 5-diamino-1, 2, 4-triazolate is 239 ℃; the density was found to be 1.71g/cm-3(ii) a The enthalpy of formation is 1181.2kJ/mol calculated by an isochain equation; calculated by software of Explo5, the detonation velocity is 8013m/s, and the detonation pressure is 24.5 GPa; the impact sensitivity is measured to be>40J, friction sensitivity of>360N。
Claims (4)
1. An energetic ionic salt of a compound characterized by the general formula:
wherein n is 1-2;
2. a method for synthesizing an energetic ionic salt of a compound, comprising the steps of:
step 1) adding a compound 1 into a mixed solution of acetonitrile and concentrated hydrochloric acid at room temperature, slowly adding a saturated potassium permanganate aqueous solution with the same molar weight as the compound 1, continuing to react for 15-60 minutes after the addition is finished, decoloring, filtering and washing with water to obtain a compound 2;
step 2) -at the temperature of 20-10 ℃, taking a mixed solution of acetic anhydride and 100wt% nitric acid with the mass ratio of 2:1 as an oxidant, carrying out oxidation reaction on the compound 2 to obtain a compound 3, heating to room temperature, violently stirring until a solid is separated out, stopping the reaction, pouring the obtained suspension into ice water, filtering, washing with water to obtain a compound 4,
step 3) dispersing the compound 4 in a solvent, then adding a solution of an alkaline compound with double molar weight of the compound 4 into the solvent, stirring and reacting for 0.5-6 hours at room temperature, filtering to obtain a target product when solid is precipitated, concentrating a reaction solution to obtain the target product when no solid is precipitated,
wherein the alkaline compound is one of ammonia water, guanidine and 3, 5-diamino-1, 2, 4-triazole.
3. The method according to claim 2, wherein the solvent is selected from the group consisting of water, methanol, ethanol, isopropanol, butanol, N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, and 1, 4-dioxane.
4. The synthesis method according to claim 2, wherein the mass ratio of the compound 4 to the solvent is 1: 0.5-50.
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| CN112724100B (en) * | 2019-10-28 | 2022-08-16 | 中国工程物理研究院化工材料研究所 | (5-imino-4, 5-dihydro-1, 3, 4-oxadiazol-2-yl) dinitromethane and preparation method thereof |
| CN112724099B (en) * | 2019-10-28 | 2022-08-19 | 中国工程物理研究院化工材料研究所 | (4-amino-5-imino-4, 5-dihydro-1, 3, 4-oxadiazol-2-yl) dinitromethane |
| CN112661749B (en) * | 2021-01-18 | 2022-04-08 | 北京理工大学 | Oxadiazole-containing cyclic gem-dinitro energetic salt and preparation method thereof |
| CN114605345B (en) * | 2022-04-15 | 2023-09-15 | 北京理工大学 | Oxadiazole ring-containing bridged dinitromethyl energetic salt and preparation method thereof |
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