N1, N3-bis (2, 4-dinitrophenyl)-2-fluoro-1, 3-diamino-4, 6-dinitrobenzene and preparation method thereof

Abstract

The invention discloses N1, N3-bis (2, 4-dinitrophenyl)-2-fluoro-1, 3-diamino-4, 6-dinitrobenzene and a preparation method thereof, and relates to the technical field of compound preparation, the chemical structural formula of the compound is as follows: # imgabs0 #; the preparation method comprises the following steps: under ice-water bath magnetic stirring, adding 65% nitric acid into a 100ml reaction flask, slowly adding a compound 3 into the reaction flask in batches, continuously stirring until the reaction is complete, and filtering to obtain a yellow solid. The prepared novel multi-nitro energetic compound has the advantages of higher energy density, higher thermal stability, lower sensitivity and better adjustability, the used raw materials are safe, the required equipment is simple, the preparation method is simple and feasible, and the yield is higher.

Description

Technical Field

[0001] The present invention belongs to the technical field of compound preparation, and particularly relates to N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene and a preparation method thereof. Background Art

[0002] Heat-resistant explosives are explosives with high stability against thermal energy. Their main feature is that they can still maintain high explosive performance in high-temperature environments and will not fail due to high temperature. This makes these heat-resistant explosives play an important role in some special environments. For example, in the aerospace field, rocket engines, and propellants, etc., which need to work under extremely high temperatures, so heat-resistant explosives are required to ensure their reliability and safety.

[0003] Conventionally, such as triaminotrinitrobenzene, hexanitrostilbene, etc. are all monomer heat-resistant explosives, but most heat-resistant explosives are polymer-bonded explosives. The synthesis and development of heat-resistant explosives with novel structures have attracted people's interest in modern military and civilian fields. They have important uses in aerospace and unconventional oil and gas extraction, and with the continuous development of the aerospace and energy development fields, the demand for heat-resistant explosives will also continue to increase. For example, 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), with a density of 1.94 g cm -3 ³, and a thermal decomposition temperature of 360 °C, it has been used as a benchmark for comparing thermally stable and insensitive explosives, but the demand for new heat-resistant explosives with enhanced thermal stability, explosive performance, and lower sensitivity is still very high.

[0004] Based on this, the present invention proposes a new type of polynitro energetic compound, which has a high energy density, high thermal stability, low sensitivity, and better tunability, making it have broad application prospects in the fields of military, aerospace, civilian explosives, etc. Summary of the Invention

[0005] In view of the above-mentioned existing defects and problems, the present invention provides N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene and a preparation method thereof.

[0006] The solution adopted by the present invention to solve its technical problems is: a kind of N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene, and the chemical structural formula of this compound is as follows: .

[0007] The present invention also provides a preparation method of N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene, comprising the following steps: Under magnetic stirring in an ice-water bath, after adding 65% nitric acid to a 100 mL reaction flask, compound 3 was slowly added to the reaction flask in batches, and stirring was continued until the reaction was complete. After filtration, N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene in the form of a yellow solid was obtained; the chemical structural formula of compound 3 is as follows: .

[0008] Furthermore, the preparation process of compound 3 includes the following steps: Under magnetic stirring at room temperature, 2,3,4-trifluoro-1,5-dinitrobenzene and aniline were successively added to a 100 mL reaction flask, and the system was heated to 100 °C and reacted until complete; Work-up: After the reaction was complete, it was cooled, and the reaction solution was slowly poured into acidic ice water to produce a precipitate. After filtration, the solid part was washed to neutrality and then dried. Then the solid part was added to a single-necked flask, and anhydrous methanol was added to the flask. It was heated for 4 - 6 hours, and after cooling and filtration, compound 3 could be obtained.

[0009] Furthermore, compound 3 is in the form of a red powder.

[0010] Compared with the prior art, the beneficial effects of the present invention are: The N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene and its preparation method provided by the present invention produce a novel polynitro energetic compound with high energy density, high thermal stability, low sensitivity, and good tunability. Moreover, the raw materials used are safe, the required equipment is simple, the preparation method is simple and feasible, and the yield is relatively high, having broad application prospects in the fields of military, aerospace, civilian explosives, etc.

[0011] The N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene provided by the present invention has a high energy density, can store more energy in a small volume, thereby improving the explosion power of explosives; it also has high thermal stability and can remain stable in a high-temperature environment; and this compound has low sensitivity and is not easily affected by external factors such as impact, friction, or static electricity, thus improving safety. Description of the Drawings

[0012] Figure 1 is the crystal structure diagram of N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene; Figure 2 is the 1H NMR spectrum of compound 3; Figure 3It is the carbon spectrum of Compound 3; Figure 4 It is the hydrogen spectrum of the target Compound 4. Embodiment

[0013] The present invention will be further described below in conjunction with the accompanying drawings and embodiments.

[0014] Please refer to Figures 1-3 , the present invention provides a technical solution for N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene and its preparation method: Example

[0015] This example provides a preparation method of N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene, which specifically includes the following steps: S1. Under magnetic stirring at room temperature, 6.66 g of 2,3,4-trifluoro-1,5-dinitrobenzene and 30 ml of aniline are successively added to a 100-ml reaction flask, and the system is heated to 100 °C and reacted until complete; Post-treatment: After the reaction is complete, cool it down. Slowly pour the reaction solution into acidic ice water to produce a precipitate. Filter it, wash the solid part until neutral and then dry it. Then add the solid part to a 100-ml single-necked flask, and then add 60 ml of anhydrous methanol to the flask. Heat it for 5 hours, cool and filter to obtain Compound 3 in the form of a red powder, with a yield of 97.45%.

[0016] The nuclear magnetic hydrogen spectrum characterization of Compound 3 is as follows: 1 HNMR: δ=9.32(s, 2H), 8.71(s, 1H), 7.24-7.26(t, 4H), 7.07-7.08 (d, 4H), 6.99-7.02(t, 2H); 13 CNMR: δ=144.67, 142.04,141.10, 133.79, 133.87, 129.96-130.01, 124.14, 122.49, 120.52. S2. Under magnetic stirring in an ice-water bath, add 30 ml of 65% nitric acid to a 100-ml reaction flask, and then slowly add 7.36 g of Compound 3 in batches. After adding, continue to stir until the reaction is complete, filter to obtain a yellow solid, which is Compound 4 N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene, and its crystal structure is as Figure 1 shown, with a yield of 92.75%.

[0017] The nuclear magnetic hydrogen spectrum characterization of Compound 4 is as follows:1 HNMR: δ = 7.35 - 7.36 (d, 2H), 8.53 - 8.54 (d, 2H), 8.85 - 8.86 (d, 2H), 8.87 (s, 1H), 10.49 (s, 2H). The synthetic route of N1,N3 - bis(2,4 - dinitrophenyl) - 2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene is as follows:

[0018] The N1,N3 - bis(2,4 - dinitrophenyl) - 2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene provided by the present invention and its preparation method result in a novel polynitro energetic compound with high energy density, high thermal stability, low sensitivity, and good tunability. Moreover, the raw materials used are safe, the required equipment is simple, the preparation method is simple and feasible, and the yield is relatively high, showing broad application prospects in the fields of military, aerospace, and civilian explosives, etc. Example

[0019] This example provides a preparation method of N1,N3 - bis(2,4 - dinitrophenyl) - 2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene, which specifically includes the following steps: S1. Under magnetic stirring at room temperature, 6.70 g of 2,3,4 - trifluoro - 1,5 - dinitrobenzene and 30 ml of aniline are successively added to a 100 - ml reaction flask, and the system is heated to 100 °C and reacted until complete; Post - treatment: After the reaction is complete, it is cooled, and the reaction solution is slowly poured into acidic ice water to produce a precipitate. After filtration, the solid part is washed to neutrality and then dried. Then, the solid part is added to a 100 - ml single - necked flask, and 60 ml of anhydrous methanol is added to the flask. After heating for 5.5 hours, after cooling and filtration, a red - powder - like compound 3 can be obtained, with a yield of 97.79%.

[0020] S2. Under magnetic stirring in an ice - water bath, 35 ml of 65% nitric acid is added to a 100 - ml reaction flask, and then 7.4 g of compound 3 is slowly added in batches. After addition, continue stirring until the reaction is complete. After filtration, a yellow solid, namely compound 4 N1,N3 - bis(2,4 - dinitrophenyl) - 2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene, is obtained, with a yield of 93.37%. Example

[0021] This example provides a preparation method of N1,N3 - bis(2,4 - dinitrophenyl) - 2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene, which specifically includes the following steps: S1. Under magnetic stirring at room temperature, 7.2 g of 2,3,4-trifluoro-1,5-dinitrobenzene and 35 ml of aniline were successively added to a 100-ml reaction flask, and the system was heated to 100 °C and reacted until complete. Work-up: After the reaction was complete, it was cooled, and the reaction solution was slowly poured into acidic ice water to produce a precipitate. After filtration, the solid part was washed to neutrality and then dried. Then the solid part was added to a 100-ml single-necked flask, and 65 ml of anhydrous methanol was added to the flask. After heating for 4 hours and cooling and filtering, the compound 3 in the form of a red powder could be obtained, with a yield of 98.63%.

[0022] S2. Under magnetic stirring in an ice-water bath, 35 ml of 65% nitric acid was added to a 100-ml reaction flask, and then 7.5 g of compound 3 was slowly added in batches. After addition, stirring was continued until the reaction was complete. After filtration, a yellow solid, namely compound 4 N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene, was obtained, with a yield of 94.63%. Example

[0023] This example provides a preparation method of N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene, which specifically includes the following steps: S1. Under magnetic stirring at room temperature, 7.5 g of 2,3,4-trifluoro-1,5-dinitrobenzene and 40 ml of aniline were successively added to a 100-ml reaction flask, and the system was heated to 100 °C and reacted until complete. Work-up: After the reaction was complete, it was cooled, and the reaction solution was slowly poured into acidic ice water to produce a precipitate. After filtration, the solid part was washed to neutrality and then dried. Then the solid part was added to a 100-ml single-necked flask, and 70 ml of anhydrous methanol was added to the flask. After heating for 6 hours and cooling and filtering, the compound 3 in the form of a red powder could be obtained, with a yield of 99.57%.

[0024] S2. Under magnetic stirring in an ice-water bath, 40 ml of 65% nitric acid was added to a 100-ml reaction flask, and then 8.1 g of compound 3 was slowly added in batches. After addition, stirring was continued until the reaction was complete. After filtration, a yellow solid, namely compound 4 N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene, was obtained, with a yield of 96.78%.

[0025] The above are only the preferred embodiments of the present invention and do not limit the present invention. Any modifications, equivalent substitutions, and improvements made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.

Claims

1. N1,N3 - bis(2,4 - dinitrophenyl)-2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene, characterized in that: The chemical structural formula of the compound is as follows: 。 2. A method for preparing N1,N3 - bis(2,4 - dinitrophenyl)-2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene according to claim 1, characterized in that: It includes the following steps: Under magnetic stirring in an ice-water bath, after adding 65% nitric acid to a 100 mL reaction flask, compound 3 is slowly added to the reaction flask in batches, and stirring is continued until the reaction is complete. After filtration, N1,N3-bis(2,4-dinitrophenyl)-2-fluoro-1,3-diamino-4,6-dinitrobenzene in the form of a yellow solid is obtained. The chemical structural formula of compound 3 is as follows: 。 3. The method for preparing N1,N3 - bis(2,4 - dinitrophenyl)-2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene according to claim 2, characterized in that: The preparation process of compound 3 includes the following steps: Under magnetic stirring at room temperature, 2,3,4-trifluoro-1,5-dinitrobenzene and aniline are successively added to a 100 mL reaction flask, and the system is heated to 100 °C and reacted until complete. Post-treatment: After the reaction is complete, it is cooled, and the reaction solution is slowly poured into acidic ice water to produce a precipitate. After filtration, the solid part is washed to neutral and then dried. Then the solid part is added to a single-neck flask, and anhydrous methanol is added to the flask. After heating for 4 - 6 hours, after cooling and filtration, compound 3 can be obtained.

4. The method for preparing N1,N3 - bis(2,4 - dinitrophenyl)-2 - fluoro - 1,3 - diamino - 4,6 - dinitrobenzene according to claim 3, characterized in that: Compound 3 is in the form of a red powder.

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