Tetrazole cyano boric acid ionic liquid and preparation method thereof

A technology of tetrazolium cyanoboronic acid and ionic liquid, applied in chemical instruments and methods, offensive equipment, generation of compressed gas, etc., can solve problems such as unfavorable large-scale synthesis, cumbersome synthesis steps, gaps in density, energy and specific impulse, etc. , to achieve the effect of wide liquid range, safe operation and short ignition delay

Active Publication Date: 2017-09-08
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the high carbon content of most spontaneously combustible ionic liquids, there is still a gap in terms of density, energy and specific impulse from the requirements of practical engineering applications.
[0003] At present, there is only one case report on the synthesis of tetrazolium cyanoborate, which is obtained through the ring-forming reaction of sodium isocyanoborohydride and sodium azide, and the synthesis steps of sodium isocyanoborohydride are cumbersome, and the reaction process involves highly toxic Silver cyanide reagent is not conducive to large-scale synthesis (B. Z.Berente, I, Lázár, Synthesis and characterization of cyanohydroisocyanoborates. Reactivity of the isocyano group towards nucleophiles, Polyhedron, 1998, 17, 3175)

Method used

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  • Tetrazole cyano boric acid ionic liquid and preparation method thereof
  • Tetrazole cyano boric acid ionic liquid and preparation method thereof
  • Tetrazole cyano boric acid ionic liquid and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0048] The preparation steps of 1-allyl-3-methyl-1H-imidazole tetrazolium cyanoborate are as follows:

[0049] (1) Under the protection of argon, first add 100mmol sodium cyanoborohydride to 70mL toluene, then add 100mmol 1H-tetrazole, then reflux and stir at 120°C for 6h, cool to room temperature, filter and collect the solid Substance; then mixed solution of tetrahydrofuran and dioxane (V 四氢呋喃 :V 二氧六环 =10:1) recrystallize the collected solid matter, filter to obtain the recrystallized solid, and vacuum-dry to obtain sodium tetrazolium cyanoborate;

[0050] (2) After adding 20mmol 1-allyl-3-methyl-1H-imidazolium chloride salt and 24mmol sodium tetrazolium cyanoborate into 30mL acetonitrile, stir the reaction at 25°C for 7 days, filter and collect the filtrate ; After the acetonitrile solvent in the filtrate was removed by rotary evaporation, dissolve with 50mL dichloromethane, then wash with water three times, then dry with anhydrous sodium sulfate, then carry out vacuum di...

Embodiment 2

[0060] Synthesis of 1-ethyl-3-methyl-1H-imidazolium tetrazolium cyanoborate

[0061] (1) Under the protection of argon, first add 100mmol sodium cyanoborohydride to 70mL toluene, then add 100mmol 1H-tetrazole, then reflux and stir at 120°C for 6h, cool to room temperature, filter and collect the solid Substance; then mixed solution of tetrahydrofuran and dioxane (V 四氢呋喃 :V 二氧六环 =10:1) recrystallize the collected solid matter, filter to obtain the recrystallized solid, and vacuum-dry to obtain sodium tetrazolium cyanoborate;

[0062] (2) Add 20mmol 1-ethyl-3-methyl-1H-imidazolium chloride salt and 24mmol sodium tetrazolium cyanoborate to 30mL acetonitrile, stir and react at 25°C for 7 days, filter and collect the filtrate; After the acetonitrile solvent in the filtrate was removed by rotary evaporation, it was first dissolved with 50 mL of dichloromethane, then washed with water three times, then dried with anhydrous sodium sulfate, then subjected to vacuum distillation, and ...

Embodiment 3

[0072] Synthesis of 1-ethyl-pyridine tetrazolium cyanoborate

[0073] (1) Under the protection of argon, first add 100mmol sodium cyanoborohydride to 70mL toluene, then add 100mmol 1H-tetrazole, then reflux and stir at 120°C for 6h, cool to room temperature, filter and collect the solid Substance; then mixed solution of tetrahydrofuran and dioxane (V 四氢呋喃 :V 二氧六环 =10:1) recrystallize the collected solid matter, filter to obtain the recrystallized solid, and vacuum-dry to obtain sodium tetrazolium cyanoborate;

[0074] (2) Add 20mmol 1-ethyl-pyridinium bromide and 24mmol sodium tetrazolium cyanoborate to 30mL of acetonitrile, stir and react at 25°C for 7 days, filter and collect the filtrate; remove the acetonitrile in the filtrate by rotary evaporation After the solvent was dissolved, it was first dissolved with 50 mL of dichloromethane, then washed with water three times, then dried with anhydrous sodium sulfate, then subjected to vacuum distillation, and finally vacuum-dri...

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Abstract

The invention relates to tetrazole cyano boric acid ionic liquid and a preparation method thereof, and belongs to the fields of organic synthesis and pyrophoric liquid propellants. The tetrazole cyano boric acid ionic liquid is prepared by carrying out replacement reaction in an organic solvent by utilizing sodium tetrazole cyano borate and corresponding imidazole, pyrrolidine or pyridine halogeno salt; the tetrazole cyano boric acid ionic liquid has very high nitrogen content, positive formation enthalpy, high density, wide liquid range, lower viscosity, good heat stability and ultrashort ignition delay time, and has a potential application value in the field of the pyrophoric liquid propellants. In addition, the invention also provides the preparation method of the sodium tetrazole cyano borate. According to the preparation method, the sodium tetrazole cyano borate is prepared from sodium cyanoborohydride and 1H-tetrazole through one step under a heating condition, the step is simple, and no virulent raw materials are involved.

Description

technical field [0001] The invention relates to a tetrazolium cyanoboric acid ionic liquid and a preparation method thereof, belonging to the field of organic synthesis and spontaneous combustion liquid propellants. Background technique [0002] Ionic liquids have extremely low vapor pressure, wide liquid range, high energy capacity, and design versatility. Pyrophoric ionic liquids can spontaneously combust when in contact with strong oxidants such as nitric acid and nitrogen tetroxide, and can be used as a substitute for traditional hydrazine fuels that are volatile and toxic. Compared with traditional hydrazine derivative fuels (highly toxic, highly carcinogenic, and highly volatile), energetic ionic liquids are more environmentally friendly as propellant fuels (almost no vapor pressure at room temperature and pressure). The non-volatility and low toxicity of ionic liquids make them very safe as propellant fuels, which are convenient for transportation, storage and practi...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07D233/58C07D213/20C06D5/00
CPCC06D5/00C07D213/20C07D233/58C07F5/022
Inventor 陈甫雪李兴业
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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