CN114605345A - Oxadiazole ring-bridged dinitromethyl energetic salt and preparation method thereof - Google Patents
Oxadiazole ring-bridged dinitromethyl energetic salt and preparation method thereof Download PDFInfo
- Publication number
- CN114605345A CN114605345A CN202210401189.XA CN202210401189A CN114605345A CN 114605345 A CN114605345 A CN 114605345A CN 202210401189 A CN202210401189 A CN 202210401189A CN 114605345 A CN114605345 A CN 114605345A
- Authority
- CN
- China
- Prior art keywords
- compound
- energetic
- formula
- dinitromethyl
- bridged
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- 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
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention discloses a series of oxadiazole-containing ring bridged dinitromethyl energetic salts, which improve the density and the formation enthalpy by introducing nitro groups, and further improve the detonation performance of energetic materials; the introduction of the amino group can effectively construct a hydrogen bond system among molecules, so that the arrangement of molecular crystals is more regular, the sensitivity of the energetic material is reduced, and the method has positive significance for the research and development of insensitive explosives. According to the invention, the nitro compound is obtained by an amino oxidation method, and then different energetic compounds with nitro and amino are obtained by different ammoniation methods, so that the simultaneous development of the two energetic compounds is realized.
Description
Technical Field
The invention relates to the technical field of energetic materials, in particular to an oxadiazole ring-containing bridged dinitromethyl energetic salt and a preparation method thereof.
Background
With the continuous expansion of the types of energetic materials and the continuous improvement of the requirements of weapons and equipment on the performance of the energetic materials, the high-energy density materials have the characteristics of high energy, high density, high thermal stability, insensitivity to external stimulation and the like, so that the high-energy density materials become hot explosive materials, and high-energy low-sense energetic compounds serving as the core of the high-energy density materials become hot spots for the research of the energetic materials in recent years.
In the research of high-energy energetic materials, the sensitivity of the energetic materials is further reduced while the detonation performance of the energetic materials is improved, and the improvement of the stability of the energetic materials is always the direction of efforts of researchers.
Disclosure of Invention
An object of the present invention is to solve at least the above problems and/or disadvantages and to provide at least the advantages described hereinafter.
The invention also aims to provide an oxadiazole-containing ring bridged dinitromethyl energetic salt which has great help to improve the density and the enthalpy of formation by introducing a nitro group, improves the high detonation characteristic of an energetic compound, and improves the stability of the energetic compound by introducing an amino group; the introduction of the coordinated oxygen effectively raises the density of the energetic compound.
Still another object of the present invention is to provide a method for preparing oxadiazole ring-bridged dinitromethyl energetic salt, which realizes synthesis of novel oxadiazole ring-bridged dinitromethyl energetic salt through multi-step reaction from known available raw materials, and provides a new idea for synthesizing novel high-energy-density energetic compounds in energetic materials.
To achieve these objects and other advantages in accordance with the present invention, there is provided an oxadiazole ring-bridged dinitromethyl energetic salt, wherein the energetic salt has the following structure of formula (I):
wherein R is an oxadiazole ring or a furoxan ring containing a substituent;
are nitrogen-containing cations.
Preferably, wherein R is
It is preferred that, among others,
is composed of
The object of the present invention can be further achieved by a process for the preparation of a bridged dinitromethyl energetic salt containing an oxadiazole ring, comprising the steps of:
step one, synthesis of compound of formula (III)
Obtaining a compound of a formula (II) under the action of a compound of the formula (II), concentrated sulfuric acid and fuming nitric acid;
step two, synthesis of compound of formula (I)
Reacting the compound of formula (III) obtained in the first step with a basic compound to obtain a compound of formula (I);
preferably, in the first step, the volume ratio of the concentrated sulfuric acid to the fuming nitric acid is 2: 1.
Preferably, the first step specifically comprises: and (3) dropwise adding concentrated sulfuric acid into the compound of the formula (II), stirring for 30min until the concentrated sulfuric acid is completely dissolved, dropwise adding fuming nitric acid, keeping the temperature below 0 ℃, reacting for 3h at a low temperature, pouring the reaction solution into 20mL of ice water after the reaction is finished, filtering, collecting the precipitate, washing and drying the precipitate with ice water to obtain the compound of the formula (III).
Preferably, in the second step, the alkaline compound is ammonia gas, ammonia water, an aqueous hydroxylamine solution or hydrazine hydrate.
Preferably, in the first step, the concentrated sulfuric acid is 98% sulfuric acid by mass fraction.
The invention at least comprises the following beneficial effects:
1. according to the invention, an oxadiazole ring containing nitryl, amino and coordinated oxygen is introduced into an energetic skeleton to obtain an oxadiazole ring-containing bridged dinitromethyl energetic salt, so that the density and the formation enthalpy are improved, and the detonation performance of an energetic material is facilitated; by effectively constructing a hydrogen bond system, the arrangement of molecular crystals is more regular, so that the sensitivity of the energetic material is reduced, and the method has positive significance for the research and development of insensitive explosives;
2. according to the preparation method, synthesis of the oxadiazole-containing ring bridged dinitromethyl energetic salt is realized by starting from known available raw materials through multiple steps of HOF oxidation and nitration, and a new thought is provided for synthesizing a novel high-energy-density energetic compound in the energetic material.
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 structural representation of compound e of example 1 of the present invention;
FIG. 2 is a single crystal structural view of Compound 1 in example 1 of the present invention;
FIG. 3 is a structural representation of Compound 1 of example 1 of the present invention;
FIG. 4 is a structural representation of Compound 2 of example 1 of the present invention;
FIG. 5 is a schematic diagram showing the structural representation of Compound 3 in example 1 of the present invention;
FIG. 6 is a single crystal structural view of Compound 4 in example 2 of the present invention;
FIG. 7 is a structural representation of Compound 4 in example 2 of the present invention;
FIG. 8 is a single crystal structural view of Compound 5 in example 2 of the present invention;
FIG. 9 is a structural representation of Compound 5 in example 2 of the present invention;
FIG. 10 is a structural representation of Compound 6 in example 2 of the present invention;
FIG. 11 is a single crystal structural view of Compound 7 in example 3 of the present invention;
FIG. 12 is a structural representation of Compound 7 in example 3 of the present invention;
FIG. 13 is a structural representation of Compound f of example 4 of the present invention
FIG. 14 is a single crystal structural view of Compound 8 in example 4 of the present invention;
FIG. 15 is a structural representation of Compound 8 of example 4 of the present invention;
FIG. 16 is a schematic representation of the structure of Compound 9 of example 4 of the present invention;
FIG. 17 is a schematic representation of the structure of Compound 10 of example 4 of the present invention;
FIG. 18 is a single crystal structural view of Compound 11 in example 5 of the present invention;
FIG. 19 is a schematic representation of the structure of Compound 11 of example 5 of the present invention;
FIG. 20 is a single crystal structural view of Compound 12 in example 5 of the present invention;
FIG. 21 is a schematic representation of the structure of Compound 12 in example 5 of the present invention;
FIG. 22 is a schematic representation of the structure of Compound 13 in example 5 of the present invention;
FIG. 23 is a single crystal structural view of Compound 14 in example 6 of the present invention;
FIG. 24 is a structural representation of Compound 14 of example 6 of the present invention.
Detailed Description
The present invention is further described in detail below with reference to the attached drawings so that those skilled in the art can implement the invention by referring to the description text.
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.
It is to be noted that the experimental methods described in the following embodiments are all conventional methods unless otherwise specified, and the reagents and materials are commercially available unless otherwise specified.
< example 1>
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
step one, synthesis of compound c
Compound a (112mg, 0.5mmol) was added in one portion to 8mL of freshly prepared solution of HOF in acetonitrile (0.2mmol/mL), reacted well and the solvent was removed to give viscous product b; and (3) cooling the round-bottom flask of the product b to-5 ℃ by using ice water, dropwise adding 98% concentrated sulfuric acid (3mL), stirring for 30min until the solid is completely dissolved, dropwise adding 1.5mL fuming nitric acid, keeping the temperature lower than 0 ℃, reacting at a low temperature for 3h, wherein a large amount of white precipitate appears in the process, pouring the reaction solution into 20mL of ice water after the reaction is finished, filtering and collecting the precipitate, washing and drying the precipitate by using ice water (3mL) to obtain a white solid product 152mg, wherein the yield is 88.1%. The NMR spectrum of compound c is shown in FIG. 1A, and the NMR spectrum is shown in FIG. 1B.
Step two, synthesis of Compound 1
And c (345mg 1mmol) is dissolved in acetonitrile (10mL) at normal temperature, ammonia gas is slowly introduced into the reaction solution, the solution gradually changes from colorless to yellow, a small amount of precipitate appears, the introduction of ammonia gas is stopped after the reaction is completed, the precipitate is filtered, and the solvent is removed from the filtrate in vacuum, so that 280mg of white solid product is obtained, and the yield is 92.1%. The structure of the single crystal of compound 1 is shown in FIG. 2, the DSC chart of compound 1 is shown in FIG. 3A, the NMR spectrum is shown in FIG. 3B, and the NMR spectrum is shown in FIG. 3C.
Step three
(1) Synthesis of Compound 2
Compound 1(304mg 1mmol) was dissolved in water (10mL) and AgNO was added in the dark3(680mg 4mmol) in 5mL of water. Reacting for 2h, filtering and collecting yellow precipitate obtained in the reaction, and drying to obtain 380mg of a product with the yield of 96.7%; the product was suspended in methanol (10mL) and NH was added dropwise3A solution of OHCl (67mg 0.96mmol) in methanol (10mL) appeared as a white precipitate over the course of addition, which was filtered off after 3h and dried in vacuo to yield 280mg of white product in 87.5% yield. The DSC chart of the compound 2 is shown in figure 4A, the NMR spectrum is shown in figure 4B, and the NMR spectrum is shown in figure 4C.
(2) Synthesis of Compound 3
Compound 1(304mg 1mmol) was dissolved in water (10mL) and AgNO was added in the dark3(680mg 4mmol) in 5mL of water. Reacting for 2h, filtering and collecting yellow precipitate obtained in the reaction, and drying to obtain 380mg of a product with the yield of 96.7%; the product was suspended in water (10mL) and NH was added dropwise2NH3A solution of Cl (65mg 0.96mmol) in water (5mL) gave a white precipitate on dropwise addition, which was filtered off after 6h and dried in vacuo to give 287mg of white product in 88.0% yield. The DSC chart of the compound 2 is shown in figure 5A, the NMR spectrum chart is shown in figure 5B, and the NMR spectrum chart is shown in figure 5C.
< example 2>
compound 5, having the formula:
compound 6, having the structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
synthesis of Compound 4:
dissolve c (345mg 1mmol) in 20mL acetonitrile at room temperature, add ammonia (0.74mL, 10mmol) dropwise, react for 48h, remove the solvent in vacuo after completion of the reaction, wash with diethyl ether (5mL), recrystallize from acetonitrile to give 206mg of yellow product in 75.2% yield. The structure of the single crystal of compound 4 is shown in FIG. 6, the DSC diagram is shown in FIG. 7A, the NMR spectrum is shown in FIG. 7B, and the NMR spectrum is shown in FIG. 7C.
Synthesis of Compound 5:
compound 4(274mg 1mmol) was dissolved in water (10mL) and AgNO was added in the dark3(680mg 4mmol) in 5mL of water. Reacting for 2h, filtering and collecting yellow precipitate obtained in the reaction, and drying to obtain 260mg of a product with the yield of 96.0%; the product was suspended in methanol (10mL) and NH was added dropwise3A solution of OHCL (67mg 0.96mmol) in methanol (10mL) showed a white precipitate during the dropwise addition, which was filtered off after 3h and dried in vacuo to give 245mg of a white product in 83.6% yield. The structure of the single crystal of compound 5 is shown in FIG. 8, the DSC diagram is shown in FIG. 9A, the NMR spectrum is shown in FIG. 9B, and the NMR spectrum is shown in FIG. 9C.
Synthesis of Compound 6:
compound 4(274mg 1mmol) was dissolved in water (10mL) and AgNO was added in the dark3(680mg 4mmol) in 5mL of water. Reacting for 2h, filtering and collecting yellow precipitate obtained in the reaction, and drying to obtain 260mg of a product with the yield of 96.0%; the product was suspended in water (10mL) and NH was added dropwise2NH3A solution of Cl (65mg 0.96mmol) in water (5mL) appeared white during the additionThe precipitate was filtered off after 6h and dried in vacuo to yield 250mg of white product in 83.1% yield. The DSC chart of the compound 6 is shown in figure 10A, the NMR spectrum is shown in figure 10B, and the NMR spectrum is shown in figure 10C.
< example 3>
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
dissolving the compound c (345mg 1mmol) in 10mL of methanol solution at normal temperature, dropwise adding ammonia water (0.74mL, 10mmol), reacting for 12h, gradually generating light yellow precipitate, filtering and collecting the precipitate, washing with methanol (3mL), and recrystallizing with acetonitrile to obtain 156mg of light yellow product with the yield of 54.0%. The structure of the single crystal of compound 7 is shown in FIG. 11, the DSC diagram is shown in FIG. 12A, the NMR spectrum is shown in FIG. 12B, and the NMR spectrum is shown in FIG. 12C.
< example 4>
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
step one, synthesis of compound f
Compound d (120mg, 0.5mmol) was added in one portion to 8mL of freshly prepared acetonitrile solution of HOF (0.2mmol/mL), reacted well and the solvent was removed to give viscous product e; and (3) cooling the round-bottom flask containing the e to-5 ℃ by using ice water, dropwise adding concentrated sulfuric acid (3mL), stirring for 30min until the solid is completely dissolved, dropwise adding 1.5mL fuming nitric acid, keeping the temperature lower than 0 ℃, reacting at a low temperature for 3h, wherein a large amount of white precipitate appears in the process, pouring the reaction solution into 20mL of ice water after the reaction is finished, filtering and collecting the precipitate, washing and drying the precipitate by using ice water (3mL) to obtain a white solid product 167mg, wherein the yield is 92.5%. The NMR spectrum of compound f is shown in FIG. 13A, and the NMR spectrum is shown in FIG. 13B.
Step two, synthesis of Compound 8
Dissolving f (361mg 1mmol) in acetonitrile (10mL) at normal temperature, slowly introducing ammonia gas into the reaction solution, gradually changing the solution from colorless to yellow to generate a small amount of precipitate, stopping introducing the ammonia gas after the reaction is completed, filtering the precipitate, and removing the solvent from the filtrate in vacuum to obtain 291mg of white solid product with the yield of 90.9%. The single crystal structure of the compound 8 is shown in FIG. 14, the DSC chart is shown in FIG. 15A, the nuclear magnetic resonance hydrogen spectrum chart is shown in FIG. 15B, and the nuclear magnetic resonance carbon spectrum chart is shown in FIG. 15C.
Step three
(1) Synthesis of Compound 9
Compound 8(320mg 1mmol) was dissolved in water (10mL) and AgNO was added in the dark3(680mg 4mmol) in 5mL of water. Reacting for 2h, filtering and collecting yellow precipitate obtained in the reaction, and drying to obtain 398mg of a product with the yield of 97.2%; the product was suspended in methanol (10mL) and NH was added dropwise3OHCl (68mg 0.97mmol) in methanol (10mL) and a white precipitate appeared during the dropwise addition, the precipitate was removed by filtration after 3h,drying in vacuo afforded 276mg of white product in 82.1% yield. The DSC chart of the compound 9 is shown in figure 16A, the NMR spectrum is shown in figure 16B, and the NMR spectrum is shown in figure 16C.
(2) Synthesis of Compound 10
Compound 8(320mg 1mmol) was dissolved in water (10mL) and AgNO was added in the dark3(680mg 4mmol) in 5mL of water. Reacting for 2h, filtering and collecting yellow precipitate obtained in the reaction, and drying to obtain 398mg of a product with the yield of 97.2%; the product was suspended in water (10mL) and NH was added dropwise2NH3A solution of Cl (66mg 0.97mmol) in water (5mL) gave a white precipitate upon dropwise addition, which was filtered off after 6h and dried in vacuo to give 280mg of white product in 83.5% yield. The DSC chart of the compound 2 is shown in figure 17A, the NMR spectrum is shown in figure 17B, and the NMR spectrum is shown in figure 17C.
< example 5>
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
synthesis of compound 11:
compound f (361mg 1mmol) was dissolved in 20mL acetonitrile solution at room temperature, ammonia (0.74mL, 10mmol) was added dropwise, reaction was carried out for 6h, after completion of the reaction the solvent was removed in vacuo, washed with diethyl ether (5mL) and recrystallized from acetonitrile to give 231mg of yellow product in 79.6% yield. The single crystal structure of compound 11 is shown in FIG. 18, the DSC graph is shown in FIG. 19A, the NMR spectrum is shown in FIG. 19B, and the NMR spectrum is shown in FIG. 19C.
Synthesis of compound 12:
compound 11(290mg 1mmol) was dissolved in water (10mL) and AgNO was added in the dark3(680mg 4mmol) in 5mL of water. Reacting for 2h, filtering and collecting yellow precipitate obtained by the reaction, and drying to obtain 345mg of a product with the yield of 90.7%; the product was suspended in methanol (10mL) and NH was added dropwise3A solution of OHCl (63mg 0.90mmol) in methanol (10mL) gave a white precipitate upon addition which was filtered off after 3h and dried in vacuo to give 267mg of yellow product in 87.3% yield. The single crystal structure of compound 12 is shown in FIG. 20, the DSC chart is shown in FIG. 21A, the NMR spectrum is shown in FIG. 21B, and the NMR spectrum is shown in FIG. 21C.
Synthesis of compound 13:
compound 11(290mg 1mmol) was dissolved in water (10mL) and AgNO was added in the dark3(680mg 4mmol) in 5mL of water. Reacting for 2h, filtering and collecting yellow precipitate obtained by the reaction, and drying to obtain 345mg of a product with the yield of 90.7%; the product was suspended in water (10mL) and NH was added dropwise2NH3A solution of Cl (63mg 0.90mmol) in water (5mL) appeared as a white precipitate over the course of dropwise addition, which was removed by filtration after 6h and dried under vacuum to give 275mg of the bright yellow product in 90.1% yield. The DSC chart of the compound 13 is shown in figure 22A, the NMR spectrum chart is shown in figure 22B, and the NMR spectrum chart is shown in figure 22C.
< example 6>
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
f (361mg 1mmol) is dissolved in 10mL of methanol solution at normal temperature, ammonia water (0.74mL, 10mmol) is added dropwise, reaction is carried out for 12h, white precipitate gradually appears in the reaction, the precipitate is collected by filtration, washed by methanol (3mL) and recrystallized by acetonitrile to obtain 213mg of white product with the yield of 69.8%. The structure of the single crystal of compound 14 is shown in FIG. 23, the DSC is shown in FIG. 24A, the NMR spectrum is shown in FIG. 24B, and the NMR spectrum is shown in FIG. 24C.
< example 7>
The performances of the compounds 1 to 14 synthesized in the example of the invention are compared with those of the existing explosives, hexogen (RDX) and octogen (HMX):
the performance of compounds 1-14 and RDX, HMX are compared in table 1 below.
Table 1: testing and evaluation of Compounds 1-14, RDX and HMX
The properties of the 14 kinds of energetic salts are compared with those of the existing high-performance energetic materials. From the comparison of detonation velocity D and detonation pressure P, the properties of 14 energetic salts are known: the energetic salt 2, 8, 9, 10, 12 and 13 are superior to RDX and are close to HMX; is a good high explosive. 3.5, 6 are close to RDX, and the sensitivity of the energetic salt 5, 6, 12, 13 is far better than that of RDX and HMX.
The formation enthalpy and the density jointly determine the detonation velocity and the detonation pressure, the detonation velocity and the detonation pressure are the key of the performance of the energetic material, and the higher the detonation velocity and the detonation pressure, the better the detonation velocity and the detonation pressure; the impact sensitivity and the friction sensitivity are the key for using, the higher the bluntness, the better the stability of the bluntness energetic material, and the safer the use and the storage.
The introduction of the nitro group into the oxadiazole ring bridged dinitromethyl energetic salt is very helpful to improve the density and the enthalpy of formation, which is beneficial to the detonation performance of energetic materials. The introduction of amino groups can effectively construct a hydrogen bond system among molecules, so that the arrangement of molecular crystals is more regular, the sensitivity of the energetic material is reduced, and the method has positive significance for the research and development of insensitive explosives. According to the invention, the nitro compound is obtained by adopting an amino oxidation method, and then different energetic compounds with nitro and amino are obtained by adopting different ammoniation methods, so that the simultaneous development of the two energetic compounds is realized, the nitro compound has the characteristic of high detonation, and the amino compound has the characteristic of high stability. The furoxan ring has higher oxygen balance, and the introduction of the coordinated oxygen can effectively improve the density, so that the furoxan ring has more advantages in the application of energetic materials.
While embodiments of the invention have been disclosed above, it is not intended to be limited to the uses set forth in the specification and examples. It can be applied to all kinds of fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. It is therefore intended that the invention not be limited to the exact details and illustrations described and illustrated herein, but fall within the scope of the appended claims and equivalents thereof.
Claims (8)
1. An oxadiazole-containing ring bridged dinitromethyl energetic salt, wherein the energetic salt has a structure as shown in formula (I):
wherein R is an oxadiazole ring or a furoxan ring containing a substituent;
are nitrogen-containing cations.
2. The bridged dinitromethyl energetic salt containing an oxadiazole ring of claim 1 wherein R is
3. The bridged dinitromethyl energetic salt containing an oxadiazole ring according to claim 1,
is composed of
4. A method for preparing the oxadiazole ring-bridged dinitromethyl energetic salt of any one of claims 1 to 3, comprising the steps of:
step one, synthesis of compound of formula (III)
Obtaining a compound of a formula (II) under the action of a compound of the formula (II), concentrated sulfuric acid and fuming nitric acid;
step two, synthesis of compound of formula (I)
Reacting the compound of the formula (III) obtained in the first step with a basic compound to obtain a compound of the formula (I);
5. the method of claim 4, wherein in step one, the volume ratio of concentrated sulfuric acid to fuming nitric acid is 2: 1.
6. The method of claim 4, wherein the first step specifically comprises: and (3) dropwise adding concentrated sulfuric acid into the compound of the formula (II), stirring for 30min until the concentrated sulfuric acid is completely dissolved, dropwise adding fuming nitric acid, keeping the temperature below 0 ℃, reacting for 3h at a low temperature, pouring the reaction solution into 20mL of ice water after the reaction is finished, filtering, collecting the precipitate, washing and drying the precipitate with ice water to obtain the compound of the formula (III).
7. The method according to claim 4, wherein in the second step, the alkaline compound is ammonia gas, ammonia water, an aqueous hydroxylamine solution or hydrazine hydrate.
8. The method of claim 5, wherein in the first step, the concentrated sulfuric acid is 98% sulfuric acid by mass.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210401189.XA CN114605345B (en) | 2022-04-15 | 2022-04-15 | Oxadiazole ring-containing bridged dinitromethyl energetic salt and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210401189.XA CN114605345B (en) | 2022-04-15 | 2022-04-15 | Oxadiazole ring-containing bridged dinitromethyl energetic salt and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114605345A true CN114605345A (en) | 2022-06-10 |
| CN114605345B CN114605345B (en) | 2023-09-15 |
Family
ID=81868557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210401189.XA Active CN114605345B (en) | 2022-04-15 | 2022-04-15 | Oxadiazole ring-containing bridged dinitromethyl energetic salt and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114605345B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114874154A (en) * | 2022-06-16 | 2022-08-09 | 北京理工大学 | 3,3 '-disubstituted-5, 5' -bis (1,2, 4-oxadiazole) compound and preparation method thereof |
| CN115340506A (en) * | 2022-08-10 | 2022-11-15 | 北京理工大学 | 4-amino-3-nitro-amino oxadiazole copper energetic compound and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108689959A (en) * | 2017-04-11 | 2018-10-23 | 南京理工大学 | Compound and its ion salt containing energy |
| CN112661749A (en) * | 2021-01-18 | 2021-04-16 | 北京理工大学 | Oxadiazole-containing cyclic gem-dinitro energetic salt and preparation method thereof |
-
2022
- 2022-04-15 CN CN202210401189.XA patent/CN114605345B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108689959A (en) * | 2017-04-11 | 2018-10-23 | 南京理工大学 | Compound and its ion salt containing energy |
| CN112661749A (en) * | 2021-01-18 | 2021-04-16 | 北京理工大学 | Oxadiazole-containing cyclic gem-dinitro energetic salt and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| CHUNLIN HE ET AL: "Energetic salts of 4-nitramino-3-(5-dinitromethyl-1,2,4-oxadiazolyl)-furazan: powerful alliance towards good thermal stability and high performance", JOURNAL OF MATERIALS CHEMISTRY A, vol. 6, no. 35, pages 16833 - 16837 * |
| PENG CHEN ET AL: "Unraveling the reactivity of the azo bridge in 3,3 0 -(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4 0 -azofurazanate in the synthesis of energetic compounds", CHEM. COMMUN., vol. 58, no. 17, pages 2874 - 2877 * |
| 廖思丞: "基于噁二唑骨架的新型含能化合物的合成及性能研究", 中国优秀硕士学位论文全文数据库, no. 1, pages 3 - 16 * |
| 张珣 等: "偕二硝基含能盐的合成研究进展", 含能材料, vol. 29, no. 8, pages 759 - 770 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114874154A (en) * | 2022-06-16 | 2022-08-09 | 北京理工大学 | 3,3 '-disubstituted-5, 5' -bis (1,2, 4-oxadiazole) compound and preparation method thereof |
| CN114874154B (en) * | 2022-06-16 | 2024-06-11 | 北京理工大学 | 3,3 '-Disubstituted-5, 5' -bis (1, 2, 4-oxadiazole) compound and preparation method thereof |
| CN115340506A (en) * | 2022-08-10 | 2022-11-15 | 北京理工大学 | 4-amino-3-nitro-amino oxadiazole copper energetic compound and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114605345B (en) | 2023-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114605345B (en) | Oxadiazole ring-containing bridged dinitromethyl energetic salt and preparation method thereof | |
| CN112661749B (en) | Oxadiazole-containing cyclic gem-dinitro energetic salt and preparation method thereof | |
| Lei et al. | New pyrazole energetic materials and their energetic salts: combining the dinitromethyl group with nitropyrazole | |
| CN109096215B (en) | Nitrogen-rich energetic material 3-amino-3 '-nitro-amino-5, 5' -bi-1, 2, 4-triazole and preparation method thereof | |
| CN114149372A (en) | Nitropyrazole energetic compound and synthesis method thereof | |
| CN114634462B (en) | Furazan-containing cyclonitrate simulated energetic compound or usable salt thereof and preparation method thereof | |
| CN110526909B (en) | 5,5 '-bis (3, 5-dinitropyrazolyl) -2,2' -bis (1,3,4 oxadiazole) and synthesis method thereof | |
| CN115108990A (en) | Synthesis method of 3-nitro-amino-4-nitro-2H-pyrazole energetic compound | |
| CN115322153B (en) | Bipyrazole energetic compound or energetic salt and preparation method thereof | |
| CN115611903B (en) | Gem-dinitro energetic compound or salt thereof and preparation method thereof | |
| CN104672156B (en) | 2-methyl-4-nitro-1,2,3-triazolyl-5-ammonia, and preparation method and application thereof | |
| CN112778377A (en) | Ferrocene burning-rate catalyst containing bis (imidazole or pyrazole-1, 2, 3-triazole) group and preparation method thereof | |
| CN115368314A (en) | Nitro-imitation energetic compound containing oxadiazole ring and preparation method thereof | |
| US5405971A (en) | Preparation of hydroxylammonium salts of 5-nitro-1,2,4-triazol-3-one | |
| CN115340501B (en) | Energetic ionic salt based on bitriazole compounds and synthesis method thereof | |
| CN110590669B (en) | 4,4' -bis (3, 5-dinitropyrazolyl) methane compound and synthesis method thereof | |
| US3006957A (en) | Process for preparation of bis(trinitroethyl)amine | |
| CN109020910B (en) | 2-amino-4-nitramine-6-formazanolamine-1, 3, 5-triazine nitrogen oxide and preparation method thereof | |
| CN115448879B (en) | Polynitro nitrogen-rich energy-containing compound and preparation method thereof | |
| CN115141190B (en) | 1,2, 4-triazolyl-1, 3, 4-oxadiazole energetic compound and preparation method thereof | |
| CN114644601A (en) | High nitrogen compound and synthesis method thereof | |
| CN107266376B (en) | LLM-105 nitramine derivatives and preparation method thereof | |
| US3544640A (en) | Aromatic nitro compounds | |
| JP4384726B2 (en) | Novel polycyclic polyamides as precursors of energy generating polycyclic polynitramine oxidants | |
| CN117777145A (en) | Pyrazinopyridazine fused ring compounds and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |