CN114573518B - 4-cyano-5-nitro-1, 2, 3-triazole metal salt, preparation method and application thereof - Google Patents

4-cyano-5-nitro-1, 2, 3-triazole metal salt, preparation method and application thereof Download PDF

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CN114573518B
CN114573518B CN202210249602.5A CN202210249602A CN114573518B CN 114573518 B CN114573518 B CN 114573518B CN 202210249602 A CN202210249602 A CN 202210249602A CN 114573518 B CN114573518 B CN 114573518B
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dinitropyrazole
diamino
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sodium
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CN114573518A (en
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杨军
黄海丰
李光磊
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Shanghai Institute of Organic Chemistry of CAS
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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
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B41/00—Compositions containing a nitrated metallo-organic compound

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Abstract

The invention discloses a 4-cyano-5-nitro-1, 2, 3-triazole metal salt, a preparation method and application thereof. The invention discloses a 4-cyano-5-nitro-1, 2, 3-triazole metal salt shown in a formula I. The invention discloses a preparation method of 4-cyano-5-nitro-1, 2, 3-triazole metal salt, which comprises the following steps: dissolving 1, 4-diamino-3, 5-dinitropyrazole (DADNP) shown in a formula II in a solvent, adding an acidified or non-acidified reagent A for reaction, and adding a pH regulator to regulate the pH value to be more than 7 after the reaction is finished. The compounds of the present invention are in the field of energetic materials and are useful in energetic materials.

Description

4-cyano-5-nitro-1, 2, 3-triazole metal salt, preparation method and application thereof
Technical Field
The invention belongs to the field of energetic materials, and particularly relates to a 4-cyano-5-nitro-1, 2, 3-triazole metal salt, a preparation method and application thereof.
Background
The high-nitrogen energetic compound has the characteristics of high nitrogen content, clean decomposition products and the like, so that great attention is paid to the design and synthesis of energetic materials. Wherein, the 1,2, 3-triazole ring contains three adjacent nitrogen atoms, so that the compound has higher formation enthalpy, and two carbon atoms can be connected with an energy-containing group for energy-containing derivatization, therefore, the 1,2, 3-triazole ring is very suitable for being used as a heterocyclic skeleton of a high-nitrogen energy-containing compound, and the introduction of nitro groups on the 1,2, 3-triazole can improve the oxygen balance of the compound and improve the energy level of the compound.
The currently used heat-resistant explosive (with the thermal decomposition temperature higher than 300 ℃) has the impact sensitivity of 2,2', 4', 6' -Hexanitrostilbene (HNS) of only 5J, which proves that the safety is poor, the safety of weapon equipment is not guaranteed, and the application of the heat-resistant explosive is limited to a certain extent.
Disclosure of Invention
The invention aims to solve the technical problem that the existing high-nitrogen energetic compound has poor safety, and provides a 4-cyano-5-nitro-1, 2, 3-triazole metal salt, a preparation method and application thereof. The metal salts can be used as insensitive high nitrogen energy containing compounds.
The invention provides a 4-cyano-5-nitro-1, 2, 3-triazole metal salt, which has a structure shown in a formula I:
wherein n is 1 or 2;
m is an alkali metal or alkaline earth metal; preferably lithium, sodium, potassium, cesium, magnesium, calcium, strontium or barium; more preferably lithium, sodium, potassium or barium; sodium is further preferred.
The invention provides a preparation method of 4-cyano-5-nitro-1, 2, 3-triazole or metal salt thereof, which comprises the following steps: in a solvent, carrying out the reaction of 1, 4-diamino-3, 5-dinitropyrazole (DADNP) shown in a formula II and a reagent A to obtain 4-cyano-5-nitro-1, 2, 3-triazole, or adding a pH regulator to adjust the pH value to be more than 7 after the reaction is finished to obtain 4-cyano-5-nitro-1, 2, 3-triazole metal salt,
wherein n is 1 or 2.
In one embodiment, the solvent is a solvent commonly used in such reactions in the art: preferably one or more of water, methanol, ethanol and acetonitrile; more preferably acetonitrile or a mixed solvent of acetonitrile and water.
In one embodiment, M is an alkali metal or alkaline earth metal; preferably lithium, sodium, potassium, cesium, magnesium, calcium, strontium or barium; more preferably lithium, sodium, potassium or barium; sodium is further preferred.
In one embodiment, the reagent a is one or more of acidified sodium hypochlorite, acidified sodium dichloroisocyanurate, trichloroisocyanuric acid, and t-butyl hypochlorite; preferably acidified sodium dichloroisocyanurate or t-butyl hypochlorite; more preferably acidified sodium dichloroisocyanurate.
In one embodiment, the acidification is by adding the acidifying agent to a solution of non-acidifying agent A and water.
In one embodiment, the acidification temperature is room temperature.
In one embodiment, the molar ratio of the acidifying reagent to the non-acidifying reagent A is from 2:1 to 8:1.
In one embodiment, the molar volume ratio of the non-acidified reagent A to water is 0.2mol/L to 0.5mol/L; for example 0.256-0.387mol/L.
In one scheme, the preparation method comprises the following steps: and adding the mixture of the reagent A and the solvent into the mixture of the 1, 4-diamino-3, 5-dinitropyrazole and the solvent to perform the reaction, and adding a pH regulator to adjust the pH value to be more than 7 after the reaction is finished.
In one embodiment, the starting materials in the preparation method are 1, 4-diamino-3, 5-dinitropyrazole, reagent A and the solvent, or 1, 4-diamino-3, 5-dinitropyrazole, reagent A and the solvent and the pH regulator.
In one embodiment, the reaction is carried out at a temperature of from-5 to 5 ℃; preferably at a temperature of 5 ℃.
In one embodiment, the reaction is carried out at atmospheric pressure.
In one embodiment, the reaction is carried out in the presence of air;
in one embodiment, the acidified acidifying reagent is one or more of acetic acid, hydrochloric acid, and trifluoroacetic acid.
In one embodiment, the pH adjuster is an alkali or alkaline earth metal carbonate, bicarbonate or hydroxide; preferably sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium hydroxide, calcium hydroxide, strontium carbonate or barium hydroxide; sodium carbonate or sodium bicarbonate is more preferred.
In one embodiment, the molar ratio of 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to reagent A is from 1:1 to 1:1.5.
In one embodiment, the molar volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the solvent is 1:8.5-1:10.5 mol/L.
In one scheme, the steps are as follows: adding said aqueous solution of reagent A to a mixture of said 1, 4-diamino-3, 5-dinitropyrazole and said organic solvent at a temperature of from-5 ℃ to effect said reaction; the addition may be dropwise addition.
In one embodiment, the starting materials are the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) of formula III, the reagent A, and the solvent.
In a certain scheme, the temperature is-5 ℃, acidified sodium dichloroisocyanurate is added into a mixture of 1, 4-diamino-3, 5-dinitropyrazole and acetonitrile in a dropwise manner, the reaction is carried out, and a pH regulator is added to regulate the pH value to be more than 7 after the reaction is finished; wherein the pH regulator is sodium carbonate; m is sodium; the molar ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the reagent A is 1:1.5; the molar volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the solvent is 1:10.5mol/L.
In a certain scheme, the temperature is 0 ℃, acidified sodium dichloroisocyanurate is dripped into a mixture of 1, 4-diamino-3, 5-dinitropyrazole and acetonitrile, the reaction is carried out, and a pH regulator is added to regulate the pH value to be more than 7 after the reaction is finished; wherein the pH regulator is sodium carbonate; m is sodium; the molar ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the reagent A is 1:1, and the molar volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the solvent is 1:10.5mol/L.
In a certain scheme, the temperature is 5 ℃, acidified sodium dichloroisocyanurate is dripped into a mixture of 1, 4-diamino-3, 5-dinitropyrazole and acetonitrile, the reaction is carried out, and a pH regulator is added to regulate the pH value to be more than 7 after the reaction is finished; wherein the pH regulator is sodium bicarbonate; m is sodium; the molar ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the reagent A is 1:1, and the molar volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the solvent is 1:10.5mol/L.
In a certain scheme, the temperature is 0 ℃, tert-butyl hypochlorite is dropwise added into a mixture of 1, 4-diamino-3, 5-dinitropyrazole and acetonitrile, the reaction is carried out, and a pH regulator is added to regulate the pH value to be more than 7 after the reaction is finished; wherein the pH regulator is sodium carbonate; m is sodium; the molar ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the reagent A is 1:1; the molar volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole (DADNP) to the solvent is 1:8.5mol/L.
In one embodiment, the preparation method further comprises concentrating the reaction solution and separating the concentrated reaction solution by column chromatography.
In one embodiment, the eluent of the column chromatography is petroleum ether, ethyl acetate=10:1 to 5:1 to 1:1 to 1:2, ethyl acetate in sequence.
The invention also provides application of the 4-cyano-5-nitro-1, 2, 3-triazole metal salt in the field of high-energy materials.
On the basis of conforming to the common knowledge in the field, the above preferred conditions can be arbitrarily combined to obtain the preferred examples of the invention.
The reagents and materials used in the present invention are commercially available.
The invention has the positive progress effects that: the novel high-nitrogen energetic compound is provided, the impact sensitivity is greater than 40J, the friction sensitivity is greater than 360N, the thermal decomposition temperature is higher than 300 ℃, and the novel high-nitrogen energetic compound can be used in the field of high-energy materials.
Detailed Description
The invention is further illustrated by means of the following examples, which are not intended to limit the scope of the invention. The experimental methods, in which specific conditions are not noted in the following examples, were selected according to conventional methods and conditions, or according to the commercial specifications.
The 1, 4-diamino-3, 5-dinitropyrazole was prepared using literature methods: J.am.chem.Soc.2015,137,4778-4786.
Example 1
Sodium dichloroisocyanurate (SDIC, 255mg,1.16mmol,1.5 eq) was dissolved in water (3 mL) at room temperature. To this was added dropwise acetic acid (6.19 mmol,8.0 eq) under stirring, followed by stirring for 0.5 h. 1, 4-diamino-3, 5-dinitropyrazole (DADNP, 145mg,0.77 mmol) was dissolved in 8mL of acetonitrile, cooled to-5℃and stirred with an aqueous solution of SDIC/acetic acid dropwise over 0.5 h. And adding sodium carbonate into the reaction solution until the pH value is more than 7 after the consumption of the DADNP is finished, and concentrating to obtain a crude product. Column chromatography was performed using silica gel eluting with pure petroleum ether, petroleum ether: ethyl acetate=10:1, then 5:1 and 1:1, 1:2 and pure ethyl acetate to give 94mg of a yellowish white powdery solid in 57% yield. 13 CNMR(100MHz,DMSO-d 6 ,ppm)δ:155.73,114.81,113.83；IR(cm -1 ):3432,2927,2856,2465,2262,1545,1504,1400,1354,1315,1170,1158,1065,993,834,766,676,647。
Example 2
Sodium dichloroisocyanurate (SDIC, 170mg,0.77mmol,1.0 eq) was dissolved in water (3 mL) at room temperature. To this was added dropwise acetic acid (6.19 mmol,8.0 eq) under stirring, followed by stirring for 0.5 h. 1, 4-diamino-3, 5-dinitropyrazole (DADNP, 145mg,0.77 mmol) was dissolved in 8mL of acetonitrile, cooled to 0℃and stirred with an aqueous solution of SDIC/acetic acid dropwise. And adding sodium carbonate into the reaction solution until the pH value is more than 7 after the consumption of the DADNP is finished, and concentrating to obtain a crude product. Column chromatography was performed using silica gel eluting with pure petroleum ether, petroleum ether: ethyl acetate=10:1, then 5:1 and 1:1, 1:2 and pure ethyl acetate to give 86mg of a yellowish white powdery solid in 52% yield.
Example 3
Sodium dichloroisocyanurate (SDIC, 170mg,0.77mmol,1.0 eq) was dissolved in water (3 mL) at room temperature. To this was added dropwise acetic acid (6.19 mmol,8.0 eq) under stirring, followed by stirring for 0.5 h. 1, 4-diamino-3, 5-dinitropyrazole (DADNP, 145mg,0.77 mmol) was dissolved in 8mL of acetonitrile, cooled to 5℃and stirred with an aqueous solution of SDIC/acetic acid dropwise. And after the DADNP is consumed, adding sodium bicarbonate into the reaction solution until the pH value is more than 7, and concentrating to obtain a crude product. Column chromatography was performed using silica gel eluting with pure petroleum ether, petroleum ether: ethyl acetate=10:1, then 5:1 and 1:1, 1:2 and pure ethyl acetate to give 89mg of a yellowish white powdery solid in 54% yield.
Example 4
Sodium dichloroisocyanurate (SDIC, 170mg,0.77mmol,1.0 eq) was dissolved in water (3 mL) at room temperature. To this was added dropwise 0.18mL of acetic acid (3.10 mmol,4.0 eq) with stirring, and the mixture was stirred for 0.5h for further use. 1, 4-diamino-3, 5-dinitropyrazole (DADNP, 145mg,0.77 mmol) was dissolved in 8mL of acetonitrile, cooled to 5℃and stirred with an aqueous solution of SDIC/acetic acid dropwise. And after the DADNP is consumed, adding sodium bicarbonate into the reaction solution until the pH value is more than 7, and concentrating to obtain a crude product. Column chromatography was performed using silica gel eluting with pure petroleum ether, petroleum ether: ethyl acetate=10:1, then 5:1 and 1:1, 1:2 and pure ethyl acetate to give 89mg of a yellowish white powdery solid in 54% yield.
Example 5
Sodium dichloroisocyanurate (SDIC, 170mg,0.77mmol,1.0 eq) was dissolved in water (3 mL) at room temperature. To this was added dropwise 0.04mL of acetic acid (0.77 mmol,2.0 eq) with stirring, and the mixture was stirred for 0.5h for further use. 1, 4-diamino-3, 5-dinitropyrazole (DADNP, 145mg,0.77 mmol) was dissolved in 8mL of acetonitrile, cooled to 5℃and stirred with an aqueous solution of SDIC/acetic acid dropwise. And after the DADNP is consumed, adding sodium bicarbonate into the reaction solution until the pH value is more than 7, and concentrating to obtain a crude product. Column chromatography was performed using silica gel eluting with pure petroleum ether, petroleum ether: ethyl acetate=10:1, then 5:1 and 1:1, 1:2 and pure ethyl acetate to give 89mg of a yellowish white powdery solid in 54% yield.
Example 6
After 1, 4-diamino-3, 5-dinitropyrazole (DADNP, 353mg,1.88 mmol) was dissolved in 16mL of acetonitrile, the temperature was lowered to 0℃and 0.21mL of t-butyl hypochlorite (t-BuClO, 1.86mmol,1.0 eq) was added dropwise with stirring, and the liquid color was changed from Huang Biangong to 15min (0 ℃). And adding sodium carbonate into the reaction solution until the pH value is more than 7 after the consumption of the DADNP is finished, and concentrating to obtain a crude product. Column chromatography using silica gel followed by pure petroleum ether, petroleum ether: ethyl acetate=10:1 to 5:1 and 1:1, 1:2 and pureEthyl acetate eluted to give a pure product, 44mg of a yellow-white powdery solid, yield 11%. 13 CNMR(100MHz,DMSO-d 6 ,ppm)δ:155.73,114.81,113.83；IR(cm -1 ):3432,2927,2856,2465,2262,1545,1504,1400,1354,1315,1170,1158,1065,993,834,766,676,647。
Example 7
The impact sensitivity (5 kg drop weight), the friction sensitivity and the thermal decomposition temperature (temperature rise rate of 5 Kmin) of the 4-cyano-5-nitro-1, 2, 3-triazole sodium salt and the barium salt were measured -1 ) The comparison of the properties of the materials with conventional explosives is shown in Table 1:
table 1: naCNT and Ba (CNT) 2 Compared with the material performance of common explosive
Compounds of formula (I) Thermal decomposition temperature (. Degree. C.) Impact sensitivity (J) Friction sensitivity (N)
NaCNT 327 >40 >360
Ba(CNT) 2 310 >40 >360
HNS 320 5 >360
RDX 210 7.5 120
The impact sensitivity of the 4-cyano-5-nitro-1, 2, 3-triazole sodium salt and the barium salt is more than 40J, the friction sensitivity is more than 360N, the heat-resistant explosive belongs to insensitive energetic ion salts, the thermal decomposition temperature is 327 ℃ and 310 ℃, and the thermal decomposition temperature is higher than 300 ℃.

Claims (7)

1. A process for the preparation of 4-cyano-5-nitro-1, 2, 3-triazole or a metal salt thereof comprising the steps of: in a solvent, carrying out the reaction of 1, 4-diamino-3, 5-dinitropyrazole shown in a formula II and a reagent A to obtain 4-cyano-5-nitro-1, 2, 3-triazole, or adding a pH regulator to adjust the pH value to be more than 7 after the reaction is finished to obtain 4-cyano-5-nitro-1, 2, 3-triazole metal salt,
wherein n is 1 or 2; the pH regulator is carbonate, bicarbonate or hydroxide of alkali metal or alkaline earth metal; m is the corresponding alkali metal or alkaline earth metal; the reagent A is acidified sodium dichloroisocyanurate or tert-butyl hypochlorite;
the acidifying reagent is acetic acid;
the reaction is carried out at the temperature of-5 to 5 ℃;
the reaction is carried out at normal pressure;
the reaction is carried out in the presence of air;
the molar ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the reagent A is 1:1-1:1.5;
the mol volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the solvent is 1:8.5-1:10.5 mol/L;
the solvent is acetonitrile or a mixed solvent of acetonitrile and water.
2. The method of claim 1, wherein M is lithium, sodium, potassium, cesium, magnesium, calcium, strontium, or barium.
3. The method of preparation of claim 2, wherein the method of preparation satisfies one or more of the following conditions:
a) The reaction is carried out at a temperature of 5 ℃;
b) M is lithium, sodium, potassium or barium;
c) The pH regulator is sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium hydroxide, calcium hydroxide, strontium carbonate or barium hydroxide;
d) The acidification is to add the acidifying reagent to a solution of non-acidified reagent a and water.
4. A method of preparation as claimed in claim 3, wherein the method of preparation satisfies one or more of the following conditions:
e) The reagent A is acidified sodium dichloroisocyanurate;
f) M is sodium;
g) The pH regulator is sodium carbonate or sodium bicarbonate;
h) The acidification temperature is room temperature;
i) In the acidification, the mol ratio of the acidifying reagent to the non-acidifying reagent A is 2:1-8:1;
j) In the acidification, the mol volume ratio of the non-acidified reagent A to water is 0.2mol/L-0.5mol/L;
k) The preparation method comprises the following steps: adding the mixture of the reagent A and the solvent into the mixture of the 1, 4-diamino-3, 5-dinitropyrazole and the solvent to perform the reaction, and adding a pH regulator to adjust the pH value to be more than 7 after the reaction is finished;
l) the raw materials in the preparation method are 1, 4-diamino-3, 5-dinitropyrazole, reagent A and the solvent, or 1, 4-diamino-3, 5-dinitropyrazole, reagent A and the solvent and the pH regulator.
5. The preparation method according to claim 1, which is any one of the following schemes:
scheme 1, at the temperature of-5 ℃, adding acidified sodium dichloroisocyanurate into a mixture of 1, 4-diamino-3, 5-dinitropyrazole and acetonitrile in a dropwise manner, performing the reaction, and adding a pH regulator to adjust the pH value to be more than 7 after the reaction is finished; wherein the pH regulator is sodium carbonate; m is sodium; the molar ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the reagent A is 1:1.5; the mol volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the solvent is 1:10.5mol/L;
scheme 2, dropwise adding acidified sodium dichloroisocyanurate into a mixture of 1, 4-diamino-3, 5-dinitropyrazole and acetonitrile at the temperature of 0 ℃, carrying out the shown reaction, and adding a pH regulator to adjust the pH value to be more than 7 after the reaction is finished; wherein the pH regulator is sodium carbonate; m is sodium; the mol ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the reagent A is 1:1, and the mol volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the solvent is 1:10.5mol/L;
scheme 3, at 5 ℃, adding acidified sodium dichloroisocyanurate into a mixture of 1, 4-diamino-3, 5-dinitropyrazole and acetonitrile in a dropwise manner, performing the reaction, and adding a pH regulator to adjust the pH value to be more than 7 after the reaction is finished; wherein the pH regulator is sodium bicarbonate; m is sodium; the mol ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the reagent A is 1:1, and the mol volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the solvent is 1:10.5mol/L;
scheme 4, dropwise adding tert-butyl hypochlorite into a mixture of 1, 4-diamino-3, 5-dinitropyrazole and acetonitrile at the temperature of 0 ℃, carrying out the reaction, and adding a pH regulator to adjust the pH value to be more than 7 after the reaction is finished; wherein the pH regulator is sodium carbonate; m is sodium; the molar ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the reagent A is 1:1; the molar volume ratio of the 1, 4-diamino-3, 5-dinitropyrazole to the solvent is 1:8.5mol/L.
6. The method according to any one of claims 1 to 5, wherein the method further comprises concentrating the reaction solution and separating and purifying the concentrated reaction solution by column chromatography.
7. The method according to claim 6, wherein the eluent of the column chromatography is petroleum ether, ethyl acetate=10:1 to 5:1 to 1:1 to 1:2, ethyl acetate in this order.
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