CN113968851A - 3- (3-nitro-1, 2, 4-triazole-5-yl) -azasdeone compound, preparation method and application - Google Patents
3- (3-nitro-1, 2, 4-triazole-5-yl) -azasdeone compound, preparation method and application Download PDFInfo
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- -1 3-nitro-1, 2, 4-triazole-5-yl Chemical group 0.000 title claims abstract description 58
- 150000001875 compounds Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000243 solution Substances 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 15
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 14
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 12
- CEYAABCXMIRIGC-UHFFFAOYSA-N 3-nitro-1h-1,2,4-triazol-5-amine Chemical compound NC1=NC([N+]([O-])=O)=NN1 CEYAABCXMIRIGC-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 9
- DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- 235000011056 potassium acetate Nutrition 0.000 claims description 7
- 239000004317 sodium nitrate Substances 0.000 claims description 7
- 235000010344 sodium nitrate Nutrition 0.000 claims description 7
- 239000012065 filter cake Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 229910002651 NO3 Inorganic materials 0.000 claims description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000002360 explosive Substances 0.000 abstract description 2
- 238000005474 detonation Methods 0.000 description 10
- 239000012954 diazonium Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical group C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B49/00—Use of single substances as explosives
Abstract
The invention discloses a 3- (3-nitro-1, 2, 4-triazole-5-yl) -aza-sdeone compound, the structural formula of which is shown in (I), and the compound is mainly used in the field of explosives.
Description
Technical Field
The invention relates to the technical field of energetic materials, and particularly relates to a 3- (3-nitro-1, 2, 4-triazole-5-yl) -aza-sdeone compound and a preparation method and application thereof.
Background
The azasdeone structure is a novel nitrogen-oxygen five-membered heterocycle, and has the structural characteristics that: having a higher oxygen content relative to the tetrazole ring and a higher nitrogen content relative to the furazan ring, can be considered by itself as a "mixture" of one molecule of azide with one molecule of carbon dioxide. Therefore, complete and sufficient oxidation can be achieved without external oxygen, and the structure unit is very ideal for constructing a novel high-energy density compound.
Dalinger et al, Azasydnone-novel "green" building block for designing high-energy compounds, 2018, J.Mater.chem.A.2018, 6, 18669-18676, disclose a synthetic method of 3- (4-nitrophenyl-1-yl) azasdeone, and partial performance data thereof, the structure of the compound is shown as (II):
the density of the compound is reported to be 1.65g/cm3The detonation velocity was 6440m/s and the detonation pressure was 17.4GPa, but the compound had a lower density and lower energy.
Disclosure of Invention
Aiming at the defects or shortcomings of the prior art, the invention provides a 3- (3-nitro-1, 2, 4-triazole-5-yl) -azasdeone compound.
To this end, the compounds provided by the present invention have the structural formula shown in (I):
the invention also provides a preparation method of the compound. Therefore, the preparation method provided by the invention comprises the following steps:
(1) synthesis of 3-nitro-1, 2, 4-triazole diazonium salt
Dripping a sodium nitrite aqueous solution into a hydrochloric acid solution of 3-nitro-5-amino-1, 2, 4-triazole for reaction to prepare a 3-nitro-1, 2, 4-triazole diazonium salt solution, wherein the reaction temperature of the step is-10-5 ℃, and the reaction time is 0.5-2 h;
(2) synthesis of 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone
Dripping the 3-nitro-1, 2, 4-triazole diazonium salt solution obtained in the step (1) into a mixed solution of sodium hydroxide, bromonitromethane, potassium acetate, water and ethanol for reaction, collecting reactants to obtain 3-nitro-1, 2, 4-triazole formaldehyde hydrazone, wherein the reaction temperature in the step is-10-5 ℃, and the reaction time is 1-4 hours;
(3) synthesis of 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone
In the presence of nitrate, 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone reacts in acetonitrile, reactants are collected to obtain 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone, the reaction temperature in the step is normal temperature, and the reaction time is 24-48 h.
Further, the molar ratio of the 3-nitro-5-amino-1, 2, 4-triazole, hydrochloric acid and sodium nitrite in the step (1) is 1: 1-2.5.
Further, in the step (2), the molar ratio of the 3-nitro-5-amino-1, 2, 4-triazole to the sodium hydroxide, the bromonitromethane and the potassium acetate is 1: 1-2: 2-4.
Further, the molar ratio of the 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone to the sodium nitrate in the step (3) is 1: 2-4.
Further, the step (2) of collecting the reactant comprises the steps of filtering the reaction solution, washing a filter cake with water, and drying to obtain the 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone.
Further, the step (3) of collecting the reactant comprises the steps of filtering the reaction solution, evaporating to dryness, and recrystallizing the solid with methanol to obtain the 3- (3-nitro-1, 2, 4-triazole-5-yl) -azasdenone.
Further, the nitrate in the step (3) is selected from sodium nitrate.
The 3- (3-nitro-1, 2, 4-triazole-5-yl) -azasdeone compound has high density of 1.86g/cm3The density of the prior art 3- (4-nitrophenyl-1-yl) azasdeone is 1.65g/cm3(ii) a The 3- (3-nitro-1, 2, 4-triazole-5-yl) -azasdeone compound has higher energy, the detonation velocity is 8560m/s, the detonation pressure is 33.1GPa, the detonation velocity of the 3- (4-nitrobenzene-1-yl) azasdeone in the prior art is 6440m/s, and the detonation pressure is 17.4 GPa.
Detailed Description
Unless otherwise specified, the terms or methods herein are understood or implemented using known methods as would be recognized by one of ordinary skill in the relevant art.
The synthetic route of the 3- (3-nitro-1, 2, 4-triazole-5-yl) -azasdeone compound is as follows:
The following are specific examples provided by the inventors to further illustrate the invention, all reagents and reactants in the following examples being commercially available products.
Example 1:
(1) synthesis of 3-nitro-1, 2, 4-triazole diazonium salt
0.82g (6.4mmol) of 3-nitro-5-amino-1, 2, 4-triazole and 9.5ml of 19% hydrochloric acid are mixed and then cooled to 0 ℃; dissolving 0.59g of sodium nitrite in 2ml of water, slowly dripping the hydrochloric acid solution into the water, keeping the temperature at minus 5-0 ℃, and reacting for 60min to obtain a 3-nitro-1, 2, 4-triazole diazonium salt solution;
(2) synthesis of 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone
Mixing 0.30g of sodium hydroxide, 1.06g of bromonitromethane, 1.52g of potassium acetate, 1ml of water and 2ml of ethanol, cooling to 0 ℃, and reacting for 30 min; slowly dripping the diazonium salt solution obtained in the step (1), controlling the temperature to be-5-0 ℃, reacting for 3 hours, filtering the reaction solution, washing a filter cake with water, and airing to obtain an orange solid substance; and (3) structural identification:
nuclear magnetic spectrum:1H NMR(600MHz,CDCl3)δ3.52(br,NH)；13CNMR(DMS0,l50MHz):162.11,159.23,130.96.
infrared spectrum: IR (KBr) 3530, 1620, 1552, 1521, 1392, 1311, 1638,1056,838cm-1.
Elemental analysis: molecular formula C3H2BrN7O4
Theoretical value: c12.87, H0.72, N35.02
Measured value: c12.75, H0.75, N35.10
Mass spectrum: MS (ESI) M/z 279[ M-H ]]-Is indeed 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone;
(3) synthesis of 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone
Dissolving and mixing 40ml of acetonitrile and 0.22g of 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone, adding 0.24g of sodium nitrate, reacting at room temperature for 24 hours, filtering after the reaction is finished, evaporating reaction liquid to dryness, and recrystallizing a solid with methanol to obtain a light yellow solid substance; structural characterization:
infrared spectrum: IR (KBr) 3450,1803,1649,1571,1265,1010,840,746cm-1；
Nuclear magnetic spectrum:1H NMR(DMSO-d6):δ6.40(s,NH).13C NMR(DMSO-d6,ppm):δ165.1,163.9,151.6；
elemental analysis: molecular formula C3HN7O4
Theoretical value: c18.10, H0.51, N49.25
Measured value: c18.15, H0.49, N49.28
Mass spectrum: MS (ESI) M/z 198[ M-H ]]-
The above structural identification data confirms that the material obtained in this step is 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdenone.
Example 2:
(1) synthesis of 3-nitro-1, 2, 4-triazole diazonium salt
Mixing 0.82g (6.4mmol) of 3-nitro-5-amino-1, 2, 4-triazole and 10.5ml of 19% hydrochloric acid, cooling to 0 ℃, dissolving 0.65g of sodium nitrite in 2ml of water, slowly dropping the hydrochloric acid solution, keeping the temperature at minus 5-0 ℃, and reacting for 90min to obtain a 3-nitro-1, 2, 4-triazole diazonium salt solution;
(2) synthesis of 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone
Mixing 0.25g of sodium hydroxide, 0.88g of bromonitromethane, 1.27g of potassium acetate, 1ml of water and 2ml of ethanol, cooling to 0 ℃ and reacting for 20 min; slowly dropping the diazonium salt solution obtained in the step (1), controlling the temperature to be-5-0 ℃, reacting for 2 hours, filtering the reaction solution, washing a filter cake with water, and airing to obtain orange-yellow solid 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone.
(3) Synthesis of 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone
Dissolving and mixing 40ml of acetonitrile and 0.22g of 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone, adding 0.30g of sodium nitrate, reacting at room temperature for 24 hours, filtering, evaporating the reaction solution to dryness, and recrystallizing the solid with methanol to obtain light yellow solid 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdenone.
Example 3:
(1) synthesis of 3-nitro-1, 2, 4-triazole diazonium salt
Mixing 0.82g (6.4mmol) of 3-nitro-5-amino-1, 2, 4-triazole and 9.5ml of 19% hydrochloric acid, cooling to 0 ℃, then dissolving 0.59g of sodium nitrite in 2ml of water, slowly dropping the hydrochloric acid solution, keeping the temperature at 0-5 ℃, and reacting for 60min to obtain a 3-nitro-1, 2, 4-triazole diazonium salt solution;
(2) synthesis of 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone
Mixing 0.35g of sodium hydroxide, 0.88g of bromonitromethane, 1.78g of potassium acetate, 2ml of water and 3ml of ethanol, cooling to 0 ℃, reacting for 20min, slowly dropping the diazonium salt solution obtained in the step (1), controlling the temperature to be 0-5 ℃, reacting for 2h, filtering the reaction solution, washing a filter cake with water, and drying to obtain orange-yellow solid 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone;
(3) synthesis of 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone
40ml acetonitrile and 0.22g 3-nitro-1, 2, 4-triazole formaldehyde hydrazone mixture, adding 0.45g sodium nitrate, room temperature reaction for 36h, filtering, evaporating the reaction solution, solid with methanol recrystallization, get pale yellow solid 3- (3-nitro-1, 2, 4-triazole-5-yl) -aza-sdeone.
Performance testing of 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone prepared in example 1 above. The density of the compound is measured by an ULTRAPYC 1200 type true densitometer, and the detonation pressure is calculated by EXPLO5 v6.01 software.
(1) Physical and chemical properties: appearance: a light yellow solid; density: 1.86g/cm3。
(2) Detonation performance
Explosion speed: the density was 1.86g/cm3And the calculated detonation velocity is 8560m/s
Explosion pressure: the density was 1.86g/cm3Meter for measuringCalculated detonation pressure is 33.1GPa
The 3- (3-nitro-1, 2, 4-triazole-5-yl) -azasdeone has the characteristics of higher density, higher energy and the like, and can be used as an energetic material component in the field of mixed explosives.
Claims (9)
1. A 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone compound having the structural formula (I):
2. a process for the preparation of a compound according to claim 1, which process comprises:
(1) synthesis of 3-nitro-1, 2, 4-triazole diazonium salt
Dripping a sodium nitrite aqueous solution into a hydrochloric acid solution of 3-nitro-5-amino-1, 2, 4-triazole for reaction to prepare a 3-nitro-1, 2, 4-triazole diazonium salt solution, wherein the reaction temperature of the step is-10-5 ℃, and the reaction time is 0.5-2 h;
(2) synthesis of 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone
Dripping the 3-nitro-1, 2, 4-triazole diazonium salt solution obtained in the step (1) into a mixed solution of sodium hydroxide, bromonitromethane, potassium acetate, water and ethanol for reaction, collecting reactants to obtain 3-nitro-1, 2, 4-triazole formaldehyde hydrazone, wherein the reaction temperature in the step is-10-5 ℃, and the reaction time is 1-4 hours;
(3) synthesis of 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone
In the presence of nitrate, 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone reacts in acetonitrile, reactants are collected to obtain 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdeone, the reaction temperature in the step is normal temperature, and the reaction time is 24-48 h.
3. The method for preparing a compound according to claim 2, wherein the molar ratio of the 3-nitro-5-amino-1, 2, 4-triazole, the hydrochloric acid, and the sodium nitrite in step (1) is 1:1 to 2.5.
4. The method for preparing the compound according to claim 2, wherein the molar ratio of the 3-nitro-5-amino-1, 2, 4-triazole to the sodium hydroxide, the bromonitromethane and the potassium acetate in the step (2) is 1:1 to 2:2 to 4.
5. The method for preparing the compound according to claim 2, wherein the molar ratio of the 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone to the sodium nitrate in the step (3) is 1:2 to 4.
6. The method for preparing the compound according to claim 2, wherein the step (2) of collecting the reactant comprises filtering the reaction solution, washing a filter cake with water, and drying the filter cake to obtain the 3-nitro-1, 2, 4-triazolecarboxaldehyde hydrazone.
7. The method of claim 2, wherein the step of collecting the reactants in step (3) comprises filtering the reaction mixture, evaporating the reaction mixture to dryness, and recrystallizing the solid from methanol to obtain 3- (3-nitro-1, 2, 4-triazol-5-yl) -azasdenone.
8. The method of claim 2, wherein the nitrate in step (3) is selected from sodium nitrate.
9. Use of the compound of claim 1 as an energetic material.
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| CN109020906A (en) * | 2018-06-14 | 2018-12-18 | 西南科技大学 | A kind of energy-containing compound and its synthetic method and application |
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| CN109020906A (en) * | 2018-06-14 | 2018-12-18 | 西南科技大学 | A kind of energy-containing compound and its synthetic method and application |
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| MATTHEW L. GETTINGS ET AL.: "Heterocyclic Nitrilimines and Their Use in the Synthesis of Complex High-Nitrogen Materials", 《INORG. CHEM.》 * |
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| CN115403537A (en) * | 2022-09-02 | 2022-11-29 | 武汉工程大学 | 2,3,5-trisubstituted-2,3-dihydro-oxatriazole derivative and preparation method thereof |
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