3-(4-azidofurazan-3-yloxymethyl)-3-azidomethyloxetane, synthetic method and application

Abstract

This invention provides a method for synthesizing 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane, its structural formula is shown below: The method includes the following steps: Step 1, 3-nitro-4-hydroxyfurazan, 3,3-dibromomethyloxetane, a basic donor and a phase transfer catalyst are added to a polar aprotic solvent, and the mixture is stirred at 45-85°C for 0.5-2 hours. Then, the mixture is extracted, washed with water, dried, filtered, the solvent is evaporated, and recrystallized to obtain 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane. 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane; the 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane obtained in steps 2 and 1 and the azidating agent are added to a polar aprotic solvent and stirred at room temperature for 0.5-1.5 h. Then, the mixture is extracted, washed with water, dried, filtered, and the solvent is evaporated to obtain the final product. The 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane prepared by this invention can be used as an energetic binder or an energetic initiator.

Description

Technical Field

[0001] This invention belongs to the field of energetic materials technology, specifically relating to a 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane, its synthesis method, and its application. Background Technology

[0002] Due to the inability of existing production capacity for high-precision munitions to meet the sudden surge in demand, modular energetic materials have emerged. These materials can be combined with other units through various processing methods to form products, possessing relatively independent functions and being decomposable, combinable, and interchangeable. Modular energetic materials can be mass-produced and manufactured in series based on standardization. Research on the design, customization, and synthesis of modular energetic materials has recently gained attention.

[0003] Oxycyclobutane, as a saturated four-membered ring ether monomer with dual active sites, can simultaneously load two energetic groups to form a polymer backbone, representing an important branch of energetic polymers with broad application prospects. Furazan compounds differ from traditional energetic compounds. On one hand, their molecular structure contains numerous CN, C=N, and N=N bonds, resulting in a high enthalpy of formation. Furthermore, the aromaticity of the furazan ring enhances the thermal stability of furazan derivatives, and the coplanarity of the furazan ring contributes to their high density. On the other hand, due to the high electronegativity of nitrogen and oxygen atoms, furazan compounds' nitrogen-heteroaromatic ring system can form benzene-like large π bonds, exhibiting insensitive and thermally stable properties. Therefore, many furazan energetic derivatives possess advantages such as high energy density, high standard enthalpy of formation (ΔHf), high nitrogen content, and excellent heat resistance. The excellent mechanical properties of oxycyclobutane polymers and the stable furazan-based energetic groups perfectly match the application requirements of modular energetic materials.

[0004] The prior art discloses a 3,3-bis(4-nitrofurazan-3-oxomethyl)oxetane monomer. This energetic monomer contains a furazan group and an oxetane monomer, has a high energy density, and can be polymerized as an energetic polymer, showing promise as a precursor for multifunctional modular energetic materials. However, its oxetane ring carries two large side groups that are symmetrically distributed, which leads to a sharp increase in the monomer's crystallization tendency and seriously affects the subsequent polymerization process, making it impossible to obtain a polymer that meets the application standards and thus difficult to apply in practice.

[0005] Therefore, it is promising to design an energetic furazan-substituted oxetane compound that can retain the high-energy insensitivity of 3,3-bis(4-azidofurazan-3-oxomethyl)oxetane while overcoming the performance defects caused by its highly symmetrical structure. Summary of the Invention

[0006] To address the shortcomings of existing technologies, the present invention aims to provide a 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane, its synthesis method, and its applications. This material possesses excellent detonation performance and desensitizing properties, and functions as a liquid-phase carrier for cast explosives, a monomeric plasticizer, and a single-element explosive.

[0007] To solve the above-mentioned technical problems, the present invention adopts the following technical solution:

[0008] A 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane has the following structural formula:

[0009]

[0010] The present invention also has the following technical features:

[0011] This invention also protects a method for synthesizing 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane, the method comprising the following steps:

[0012] Step 1: 3-nitro-4-hydroxyfurazan, 3,3-dibromomethyloxetane, a basic donor and a phase transfer catalyst are added to a polar aprotic solvent and stirred at 45-85°C for 0.5-2 hours. Then, the mixture is extracted, washed with water, dried, filtered, the solvent is evaporated and recrystallized to obtain 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane.

[0013] Step 2: The 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane and the azide reagent obtained in Step 1 are added to a polar aprotic solvent and stirred at room temperature for 0.5-1.5 h. Then, the mixture is extracted, washed with water, dried, filtered, and the solvent is evaporated to obtain the final product.

[0014] Specifically, the alkaline donors mentioned in step 1 include anhydrous potassium carbonate, cesium carbonate, and iron hydroxide.

[0015] Furthermore, the phase transfer catalyst described in step 1 includes tetrabutylammonium bromide, benzyltriethylammonium chloride, methyltrialkylammonium chloride, and 18-crown ether-6.

[0016] Furthermore, in step 1, the molar ratio of 3,3-dibromomethyloxetane to 3-nitro-4-hydroxyfurazan is 1:(0.8–1.5).

[0017] Furthermore, in step 1, the molar ratio of 3-nitro-4-hydroxyfurazan to the basic donor is 1:(1-3).

[0018] Furthermore, the azide reagent in step 2 includes sodium azide, trimethyl azidosilane, p-toluenesulfonyl azide, ethyl azide, tetrabutylammonium azide, and tri-n-butyltin azide.

[0019] Furthermore, in step 2, the molar ratio of 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane to the azide reagent is 1:(2-2.5).

[0020] Furthermore, the polar aprotic solvent includes N,N-dimethylformamide, acetonitrile, acetone, and dimethyl sulfoxide.

[0021] The present invention also protects the use of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane as an energetic adhesive or an energetic initiator.

[0022] Compared with the prior art, the present invention has the following technical effects:

[0023] (I) The 3-(4-azidofuzan-3-oxomethyl)-3-azidomethyloxetane provided by this invention has good detonation performance and desensitizing characteristics, and also functions as a liquid phase carrier for cast explosives, a monomer plasticizer, a single explosive, and an energetic initiator. At the same time, the oxetane structure introduced into it endows it with good polymerization ability, which greatly expands its application field. It can be polymerized as a structural energetic material or an energetic adhesive, and can also be used as an energetic initiator / chain extender. It is a multifunctional desensitizing energetic material with great application prospects.

[0024] (2) The synthetic method of this invention uses readily available and inexpensive 3-nitro-4-hydroxyfurazan and commercially available 3,3-dibromomethyloxetane as raw materials. Heating in an alkaline solvent system in the presence of a catalytic amount of phase transfer catalyst yields the intermediate 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane. This intermediate is then reacted with an azide reagent in a polar aprotic solvent to obtain the final product 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane. This synthetic route utilizes readily available raw materials, simple reaction conditions, and minimal environmental pollution, exhibiting atom economy and aligning with the strategic concept of green development.

[0025] (3) The synthesis method of the present invention controls the reaction conditions to completely convert the intermediate into the azide-substituted product 3-(4-azidofuzan-3-oxomethyl)-3-azidomethyloxetane. The purity of the final product is not less than 98%, the yield is high, the reaction route is efficient and time-saving, and it is convenient for continuous industrial production.

[0026] The specific content of the present invention will be further explained in detail below with reference to the embodiments. Attached Figure Description

[0027] Figure 1 The 1H NMR spectrum of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane;

[0028] Figure 2 The carbon NMR spectrum of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane;

[0029] Figure 3 The FTIR spectrum of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane;

[0030] Figure 4 High-resolution mass spectrum of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane;

[0031] Figure 5 The DSC diagram of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane;

[0032] Figure 6 The GPC spectrum of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane.

[0033] The specific content of the present invention will be further explained in detail below with reference to the embodiments. Detailed Implementation

[0034] It should be noted that, unless otherwise specified, all raw materials used in this invention are those known in the prior art.

[0035] The concept of this invention is as follows: 3,3-diazidomethyloxetane containing two azidomethyl substituents has a high energy density, but its low density seriously affects its reliability in practical applications; 3,3-di(4-nitrofurazan-3-oxomethyl)oxetane containing two nitrofurazan substituents has a high energy density and relatively low sensitivity, and also has the potential to be used as a precursor for multifunctional modular energetic materials. However, its oxetane ring carries two large side groups that are symmetrically distributed, which leads to a sharp increase in the tendency of monomer crystallization, which also seriously affects the subsequent polymerization process of the monomer, making it impossible to obtain polymers that meet the application standards and making it difficult to apply in practice. A simple and feasible solution is to reduce its crystallinity by introducing asymmetric side groups. In addition, by designing the molecular structure, introducing multiple energetic groups into the same energetic monomer can also improve the compatibility of energetic materials, making them more conducive to practical applications.

[0036] Furazan is combined with an oxacyclobutane body via a Williamson etherification reaction under alkaline conditions through nucleophilic attack by oxonium anions. By controlling the reaction conditions to ensure that the reaction product is predominantly a monosubstituted product, a subsequent azidation reaction yields the target product. This route can successfully synthesize the target compound, but the first step in preparing the intermediate has a long reaction time (1-2 h) and a low yield (60%). Therefore, the inventors explored using readily available and inexpensive solvents such as N,N-dimethylformamide (DMF), acetonitrile (MeCN), acetone, and dimethyl sulfoxide (DMSO) as solvents and phase transfer catalysts to accelerate the reaction.

[0037] A 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane has the following structural formula:

[0038]

[0039] The synthetic route for 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane is as follows:

[0040]

[0041] The method includes the following steps:

[0042] Step 1: 3-nitro-4-hydroxyfurazan, 3,3-dibromomethyloxetane, a basic donor and a phase transfer catalyst are added to a polar aprotic solvent and stirred at 45-85°C for 0.5-2 hours. Then, the mixture is extracted, washed with water, dried, filtered, the solvent is evaporated and recrystallized to obtain 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane.

[0043] The alkaline donors include anhydrous potassium carbonate, cesium carbonate, and ferric hydroxide.

[0044] The phase transfer catalysts include tetrabutylammonium bromide, benzyltriethylammonium chloride, methyltrialkylammonium chloride, and 18-crown ether-6.

[0045] Preferably, the molar ratio of 3,3-dibromomethyloxetane to 3-nitro-4-hydroxyfurazan is 1:(0.8-1.5).

[0046] Preferably, the molar ratio of 3-nitro-4-hydroxyfurazan to the basic donor is 1:(1-3).

[0047] Preferred polar aprotic solvents include DMF, MeCN, Acetone, and DMSO.

[0048] Step 2: The 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane and the azide reagent obtained in Step 1 are added to a polar aprotic solvent, including N,N-dimethylformamide (DMF), acetonitrile (MeCN), acetone (Acetone), and dimethyl sulfoxide (DMSO). The mixture is stirred at room temperature for 0.5–1.5 h, and then extracted, washed with water, dried, filtered, and the solvent is evaporated to obtain the final product.

[0049] Furthermore, the azide reagent includes sodium azide, trimethyl azidosilane, p-toluenesulfonyl azide, ethyl azide, tetrabutylammonium azide, and tri-n-butyltin azide.

[0050] Furthermore, the molar ratio of 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane to the azide reagent is 1:(2-2.5).

[0051] The following are specific embodiments of the present invention. It should be noted that the present invention is not limited to the following specific embodiments. All equivalent modifications made based on the technical solutions of this application fall within the protection scope of the present invention.

[0052] Example 1

[0053] This embodiment provides a method for synthesizing 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane, comprising the following steps:

[0054] Step 1: 3-nitro-4-hydroxyfurazan (1.31 g, 0.01 mol), 3,3-dibromomethyloxetane (2.44 g, 0.01 mol), anhydrous potassium carbonate (1.88 g, 0.01 mol), and phase transfer catalyst 18-crown ether-6 (0.05 g, 0.0002 mol) were added to dimethylformamide DMF (10 ml) at room temperature and stirred thoroughly. The mixture was reacted at 65 °C for 1.5 h. After the reaction was completed, water and dichloromethane were added for extraction. The mixture was then washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated. Recrystallization yielded white crystals of 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane (2.3 g, yield 83.5%) as an intermediate.

[0055] Step 2: Add 1.39 g (0.05 mol) of 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane obtained in Step 1 and sodium azide (0.65 g, 0.01 mol) to 3 ml of DMF, stir and react at room temperature for 0.5 h, then extract with ethyl acetate, wash with water, dry with anhydrous magnesium sulfate, filter, and evaporate to dryness to obtain the oily product 3-(4-azidofuran-3-oxomethyl)-3-azidomethyloxetane (1.13 g, yield 96%).

[0056] Structural assessment:

[0057] (1) Carbon nuclear magnetic resonance spectroscopy analysis

[0058] like Figure 1 and Figure 2 As shown, the characteristic peaks of 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane at 158.79 ppm and 152.79 ppm shifted to lower and higher fields, moving to 159.28 ppm and 145.19 ppm, respectively. Furthermore, the peak shape changed from the high-low peak pattern characteristic of nitrofuran to an approximately equal peak pattern characteristic of azidofuran, indicating the disappearance of the furazan nitro group and the formation of azidofuran. The characteristic peaks of methyloxetane at 74.94 ppm, 74.15 ppm, and 43.37 ppm showed little change, indicating that the main body of methyloxetane remained unchanged. Correspondingly, the carbon spectrum peak of bromomethyl at 36.44 ppm shifted to a lower field, moving to 52.85 ppm, indicating that bromomethyl was converted into the more electronegative (weaker shielding effect) azidomethyl. The area obtained by integrating the corresponding peaks in the proton spectrum is 1:2:1, which also confirms the successful synthesis of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane.

[0059] (2) Infrared spectral analysis

[0060] like Figure 3 As shown, comparing the infrared spectrum of the product obtained in this embodiment with that of the starting material 3,3-dibromomethyloxetane, the intermediate 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane, and the byproduct 3,3-di(4-nitrofurazan-3-oxomethyl)oxetane, it can be seen that the product obtained in this embodiment is located at 835 cm⁻¹. -1 The characteristic peak of 3,3-dibromomethyloxetane is still present, indicating that the oxetane structure still exists in the pure monomer, and the peak at 1624 cm⁻¹ is... -1 The disappearance of the nitro infrared absorption peak at 2100 cm⁻¹ indicates that the product no longer contains nitro groups; while the nitro infrared absorption peak at 2100 cm⁻¹... -1 With 2150cm -1 The appearance of the characteristic absorption peak of the azido group indicates the successful synthesis of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane.

[0061] (3) High-resolution mass spectrometry analysis

[0062] like Figure 4 As shown, the highest peak m / z in the high-resolution mass spectrum is 253.08677, which is in good agreement with the predicted hydrogenation peak of 253.0798, indicating the successful synthesis of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane.

[0063] (4) DSC chart

[0064] The DSC results show that 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane exhibits distinct decomposition peaks at 193℃ and 246℃, corresponding to the stepwise decomposition of the azido group and the furazan group, respectively, demonstrating good thermal stability.

[0065] The performance parameters of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane prepared in this embodiment were compared with those of the existing BAMO, and the results are shown in the table below:

[0066]

[0067] As can be seen from the table, this invention, by introducing furazan groups into oxetane, successfully improves the stability of BAMO while maintaining its excellent energy characteristics, and overcomes the drawback of poor post-polymerization performance caused by the highly symmetrical structure of BAMO. It is liquid at room temperature, possesses excellent detonation performance and extremely high stability, and functions as both a single-element explosive and an energetic initiator. Simultaneously, the introduced oxetane structure endows it with good polymerization ability, greatly expanding its application fields. It can be polymerized as a structural energetic material or energetic binder, and can also be used as an energetic initiator / chain extender, making it a highly promising multifunctional insensitive energetic material.

[0068] The polymerization ability of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane prepared in this example was verified. Polymerization was carried out at room temperature using boron trifluoride diethyl ether catalyst and BDO as initiator, and the polymer was successfully obtained, as shown below. Figure 6 The GPC spectrum of the polymer shown in the figure indicates that the molecular weight after polymerization is 1560 and the PDI is 1.32179, proving that the product has completed polymerization and the polymerization is well controllable, which meets the design requirements.

[0069] In summary, 3-(4-azidofuzan-3-oxomethyl)-3-azidomethyloxetane has good polymerization ability and can be used as an energetic binder or energetic initiator to participate in polymerization reactions at room temperature to obtain polymers.

[0070] Example 2

[0071] The synthesis method and steps used in this embodiment are the same as those in Example 1, except that: in step 1, 3,3-dibromomethyloxetane is used in an amount of 3.66 g (0.015 mol), yielding 2.5 g of product (90.8% yield) as an intermediate; in step 2, the component amounts and reaction conditions are the same as in Example 1, finally yielding 1.13 g of the oily product 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane (96% yield).

[0072] The structural identification results in this embodiment are the same as those in Embodiment 1.

[0073] Example 3

[0074] The synthesis method and steps used in this embodiment are the same as those in Example 1, except that sodium azide (0.975 g, 0.015 mol) is added in step 2; the final product is 1.15 g, with a yield of 98%.

[0075] The structural identification results in this embodiment are the same as those in Embodiment 1.

[0076] Example 4

[0077] The synthesis method and steps used in this embodiment are the same as those in Example 1, except that in step 1, the reaction is carried out at 65°C for 1 hour to obtain white crystals (yield 1.5 g, yield 54.5%); the component amounts and reaction conditions in step 2 are the same as those in Example 1, and the final product is an oily product 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane (yield 1.13 g, yield 96%).

[0078] The structural identification results in this embodiment are the same as those in Embodiment 1.

[0079] Example 5

[0080] The synthesis method and steps used in this embodiment are the same as those in Example 1, except that: in step 1, the reaction is carried out at 65°C for 2.5 h to obtain white crystals (yield 2.4 g, 87.1%); the component amounts and reaction conditions in step 2 are the same as those in Example 1, and the final product is an oily product 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane (yield 1.13 g, 96%).

[0081] The structural identification results in this embodiment are the same as those in Embodiment 1.

[0082] Example 6

[0083] The synthesis method and steps used in this embodiment are the same as those in Example 1, except that the polar aprotic solvent used in both steps 1 and 2 is dimethyl sulfoxide (10 mL), which yields white crystals (yield 1.9 g, 69.0%); and finally, the oily product 3-(4-azidofuzan-3-oxomethyl)-3-azidomethyloxetane (yield 1.13 g, 96%) is obtained.

[0084] The structural identification results in this embodiment are the same as those in Embodiment 1.

[0085] Example 7

[0086] The synthesis method and steps used in this embodiment are the same as those in Example 1, except that: in step 1, the phase transfer catalyst is tetrabutylammonium bromide (TBAB), and white crystals are obtained (yield 2.0 g, yield 72.6%). The component amounts and reaction conditions in step 2 are the same as those in Example 1, and the final product is an oily product 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane (yield 1.13 g, yield 96%).

[0087] The structural identification results in this embodiment are the same as those in Embodiment 1.

[0088] Example 8

[0089] The synthesis method and steps used in this embodiment are the same as those in Example 1, except that: in step 1, the phase transfer catalyst is benzyltriethylammonium chloride, and white crystals (2.0 g, yield 72.5%) are obtained; the component amounts and reaction conditions in step 2 are the same as those in Example 1, and the final product is an oily product 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane (1.13 g, yield 96%).

[0090] The structural identification results in this embodiment are the same as those in Embodiment 1.

[0091] Comparative Example 1

[0092] The synthesis method used in this comparative example is the same as that in Example 1, except that no phase transfer catalyst was added in step 1; the final product was 1.03 g, with a yield of 37.6%.

[0093] The structural identification results of this comparative example are the same as those of Example 1.

[0094] As can be seen from Examples 1 to 8, and Comparative Example 1:

[0095] In step 1, the product yield increases with increasing reaction temperature, but the increase is not significant after 65°C. Considering the safety implications, 65°C is the optimal temperature for this reaction. Polar aprotic solvents, especially DMF, have a significant solvation effect on this reaction and can promote its progress. The product yield increases with increasing ratio of 3-nitro-4-hydroxyfuran to dibromomethyloxocyclic ring, but the increase is not significant after 1:1. Therefore, 1:1 is the optimal feed ratio.

[0096] In step 2, the reaction efficiency is extremely high. The azide reagent and the intermediate 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane are fed in a 2:1 ratio to achieve complete reaction without heating for 1 hour, which has the characteristics of atom economy.

[0097] There is a high energy barrier when a monosubstituted product is further substituted into a disubstituted product. Under the same starting material composition, using a high-boiling-point polar aprotic solvent can not only provide energy through heating to help the reaction overcome the energy barrier, but also the special solvation effect of the polar aprotic solvent can greatly improve the reaction rate and yield. The addition of a phase transfer catalyst can catalyze this type of reaction.

[0098] In summary, the synthetic method of this invention uses readily available and inexpensive 3-nitro-4-hydroxyfurazan and commercially available 3,3-dibromomethyloxetane as raw materials. Heating in an alkaline solvent system in the presence of a catalytic amount of phase transfer catalyst yields the intermediate 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane. Subsequently, reaction with an azide reagent in a polar aprotic solvent yields the final product 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane. This synthetic route utilizes readily available raw materials, simple reaction conditions, and minimal environmental pollution, exhibiting atom economy and aligning with the strategic concept of green development.

[0099] The synthesis method of this invention, by controlling the reaction conditions, completely converts the intermediate into the azide-substituted product 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane, with the final product having a purity of not less than 98%, high yield, efficient and time-saving reaction route, and is convenient for continuous industrial production.

[0100] The preferred embodiments of this disclosure have been described in detail above with reference to the accompanying drawings. However, this disclosure is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this disclosure, various simple modifications can be made to the technical solutions of this disclosure, and these simple modifications all fall within the protection scope of this disclosure.

[0101] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, this disclosure will not describe the various possible combinations separately.

[0102] Furthermore, various different embodiments of this disclosure can be combined in any way, as long as they do not violate the spirit of this disclosure, they should also be regarded as the content disclosed in this disclosure.

Claims

1. A 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane, characterized in that, Its structural formula is shown below: 。 2. A method for synthesizing 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane as described in claim 1, characterized in that, The method includes the following steps: Step 1: 3-nitro-4-hydroxyfurazan, 3,3-dibromomethyloxetane, base and phase transfer catalyst are added to a polar aprotic solvent and stirred at 45~85℃ for 0.5~2 h. Then, after extraction, washing with water, drying, filtration, evaporation of solvent and recrystallization, 3-(4-nitrofurazan-3-oxomethyl)-3-bromomethyloxetane is obtained. Step 2: The 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane and the azide reagent obtained in Step 1 are added to a polar aprotic solvent and stirred at room temperature for 0.5-1.5 h. Then, the mixture is extracted, washed with water, dried, filtered, and the solvent is evaporated to obtain the final product.

3. The synthesis method as described in claim 2, characterized in that, The alkali mentioned in step 1 is selected from either anhydrous potassium carbonate or cesium carbonate.

4. The synthesis method according to claim 2, characterized in that, The phase transfer catalyst mentioned in step 1 is selected from any one of tetrabutylammonium bromide, benzyltriethylammonium chloride, methyltrialkylammonium chloride and 18-crown ether-6.

5. The synthesis method as described in claim 2, characterized in that, In step 1, the molar ratio of 3,3-dibromomethyloxetane to 3-nitro-4-hydroxyfurazan is 1:(0.8~1.5).

6. The synthesis method according to claim 2, characterized in that, In step 1, the molar ratio of 3-nitro-4-hydroxyfurazan to the base is 1:(1~3).

7. The synthesis method according to claim 2, characterized in that, In step 2, the azide reagent is selected from any one of sodium azide, trimethyl azidosilane, p-toluenesulfonyl azide, ethyl azide, tetrabutylammonium azide, and tri-n-butyltin azide.

8. The synthesis method according to claim 2, characterized in that, In step 2, the molar ratio of 3-(4-nitrofuran-3-oxomethyl)-3-bromomethyloxetane to the azide reagent is 1:(2~2.5).

9. The synthesis method according to claim 2, characterized in that, The polar aprotic solvent is selected from any one of N,N-dimethylformamide, acetonitrile, acetone, and dimethyl sulfoxide.

10. The application of 3-(4-azidofurazan-3-oxomethyl)-3-azidomethyloxetane as described in claim 1 as an energetic binder or energetic initiator.

Images