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3,4-bis(1-hydro-5-tetrazolyl)furoxan ionic salt containing energy and preparation method thereof

A technology for oxidizing furoxan and tetrazolium, which is applied in 3 fields and achieves the effects of easy industrialization, low impact sensitivity and simple synthesis method

Inactive Publication Date: 2013-03-06
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no acidic hydrogen in the furoxan ring, which makes them unable to be directly used as Bronsted acids, that is, they cannot react with Lewis bases, therefore, they cannot be directly used as anions of energetic ion salts

Method used

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  • 3,4-bis(1-hydro-5-tetrazolyl)furoxan ionic salt containing energy and preparation method thereof
  • 3,4-bis(1-hydro-5-tetrazolyl)furoxan ionic salt containing energy and preparation method thereof
  • 3,4-bis(1-hydro-5-tetrazolyl)furoxan ionic salt containing energy and preparation method thereof

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Experimental program
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Embodiment 13

[0021] Embodiment 13, the preparation of 4-bis (1-hydrogen-5-tetrazolyl) furazan oxide (2)

[0022] Its structural formula is as follows:

[0023]

[0024] Dissolve 1.000 g (7.3 mmol) of 3,4-dicyanofuroxan in 4 mL of DMF in a 25 mL one-necked flask, and then add 1.147 g (17.6 mmol) of NaN 3 and 0.786g (14.7mmol). The resulting reaction mixture was stirred at 80°C for 4 h and then cooled to room temperature. After adding 4 mL of deionized water, the pH was adjusted to 1-2 with 2% hydrochloric acid, extracted with ethyl acetate (10 mL×4), and the organic phases were combined and saturated. washed several times with saline, and the organic phase was washed with anhydrous MgSO 4 After drying, it was concentrated to give a pale yellow solid. Yield: 60%.

[0025] Decomposition temperature: 229°C (DSC). Density is 1.62g cm -3 . 13 C NMR: δ=149.0, 146.3, 144.5, 106.8ppm; IR (neat): 3135, 2908, 2446, 1620, 1579, 1457, 1418, 1386, 1282, 1232, 1203, 1181, 1128, 1093, 1069, 1025...

Embodiment 23

[0026] Example 23, 4-bis(5-tetrazolyl) furazan barium salt 8H 2 Preparation of O(3)

[0027] Its structural formula is as follows:

[0028]

[0029] Add 2.000g (9.0mmol) 2 to 2.839g Ba(OH) 2 ·8H 2 In a suspension of O (9.0 mmol) in water (20 mL), the reaction mixture was stirred at 80° C. for 2 h, then the insoluble matter was filtered, and the filtrate was concentrated. The resulting solid was recrystallized in water as yellow crystals, yield: 80%.

[0030] Decomposition temperature: 297°C (DSC). Density is 2.07g cm -3 . 13 C NMR: δ=152.4, 150.5, 147.0, 111.0ppm; IR (neat): 3566, 3329, 3172, 1602, 1574, 1532, 1440, 1387, 1367, 1394, 1238, 1203, 1188, 1148, 1110, 1095 , 1064, 1044, 1003, 971, 827, 763, 534, 481cm -1 .

Embodiment 33

[0031] Embodiment 33, the preparation of 4-bis(5-tetrazolyl) oxide furazan diammonium salt (4)

[0032] Add excess 25% ammonia water to 222mg (1.0mmol) methanol (3mL) solution, stir at room temperature for 2h, then evaporate the solvent under reduced pressure, the yield is 95%, and the obtained solid is washed with EtOH / H 2 O Recrystallized colorless needle crystals.

[0033] Its structural formula is as follows:

[0034]

[0035] Decomposition temperature: 262°C (DSC). Density is 1.71g cm -3 . 1 H NMR (400MHz, d 6 -DMSO): δ = 7.29 (s, 8H) ppm; 13 C NMR (100MHz, d 6 -DMSO): δ=152.1, 150.5, 147.0, 110.8ppm; IR (neat): 3137.8, 3012.5, 2804.1, 1680.6, 1611.8, 1579.4, 1527.3, 1501.8, 1405.0, 993.8, 966.1, 824.3cm -1;elemental analysis(%) calcd for C 4 h 8 N 12 o 2 (256.19): C 18.75, H 3.15, N 65.61; found: C 18.81, H 3.02, N 65.05.

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Abstract

The invention provides a 3,4-bis(1-hydro-5-tetrazolyl)furoxan ionic salt containing energy and a preparation method thereof, which belongs to the technical field of energy materials. A synthetic method for the 3,4-bis(1-hydro-5-tetrazolyl)furoxan ionic salt comprises the following steps: subjecting 3,4-bis(1-hydro-5-tetrazolyl)furoxan and equimolar organic base to an acid-base neutralization reaction to obtain corresponding ionic salts or 3,4-bis(5-tetrazolyl)furoxan barium salt and equimolar sulfate of corresponding cations (wherein a part of sulfate is prepared through a reaction of a chlorine salt or an iodine salt and silver sulfate); filtering a precipitate; and removing a solvent in a filtrate through steaming so as to obtain a target product. The synthetic method provided by the invention is simple and is easy for industrialization. 16 energy-containing salts prepared in the invention have good heat stability, calculated detonation performances of all the energy-containing salts are much better than those of TNT, and a part of the energy-containing salts have detonation performances close to those of RDX, but have a degree of percussion sensitivity lower than that of RDX and can be used as a green substitute for RDX.

Description

technical field [0001] The present invention relates to 3,4-bis(1-hydrogen-5-tetrazolyl)furazan oxide, 3,4-bis(1-hydrogen-5-tetrazolyl)furazan oxide energetic ion salt and a preparation method thereof , belonging to the technical field of energetic materials. Background technique [0002] High energy density materials (HEDMs) have been receiving great attention, and nitrogen-rich energetic ion salts have become one of the hotspots in the field of high energy density materials research in recent years. Energetic materials based on ionic salts have the advantages of low vapor pressure (less toxic vapors generated during processing), high density, and good thermal stability compared with their molecular analogues. The use of anions and cations with high nitrogen content can lead to energetic ionic salts with high formation enthalpy and density because they contain a large number of energetic N-N and C-N bonds. Moreover, the decomposition of nitrogen-rich compounds mainly gene...

Claims

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Application Information

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IPC IPC(8): C07D413/14C06B25/00C06D3/00C06D5/04
Inventor 周智明黄海丰梁丽轩宋靳红王凯曹丹卞成明
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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