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5, 5 '-bistetrazole-1, 1'-dioxo hydroxylammonium salt synthetic method

A technology of dioxanthamine salt and synthesis method, which is applied in the field of organic synthesis, can solve the problems of complex reaction process, low utilization rate of raw materials, insufficient optimization of TKX-50 synthesis process route, low yield, short reaction time, easy The effect of industrial scale-up production

Inactive Publication Date: 2015-08-12
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis process route of TKX-50 reported in the literature is not optimized enough, the utilization rate of raw materials is low, and the reaction process is complicated

Method used

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  • 5, 5 '-bistetrazole-1, 1'-dioxo hydroxylammonium salt synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A kind of synthetic method of 5,5'-tetrazole-1,1'-dioxanolamine salt of the present invention, concrete steps are as follows:

[0022] 1) Dissolve 70g NaOH in 150mL water, add 139g hydroxylamine hydrochloride at 0°C, stir to dissolve, add 128g 40% glyoxal solution dropwise, react for 20min, remove the ice-water bath, and react overnight at room temperature. After filtering, washing with water and drying, 75.2 g of glyoxime was obtained with a yield of 86% and a melting point of 175-176°C.

[0023] 2) Add 50g of glyoxime obtained in step 1) into a container containing 500mL of DMF solvent, add 150g of N-chlorosuccinimide in batches at 0°C under constant stirring, remove the ice-water bath after adding , slowly rose to room temperature for 1h. Then put the container into ice water again, slowly add 74g of sodium azide at 0°C, and react for 3h to obtain 87.8g of diazideglyoxime. Yield 91%, melting point: 182-184°C.

[0024] 3) Put the diazideglyoxime solution obtained i...

Embodiment 2

[0026] A kind of synthetic method of 5,5'-tetrazole-1,1'-dioxanolamine salt of the present invention, concrete steps are as follows:

[0027] 1) Dissolve 80g of KOH in 150mL of water, add 139g of hydroxylamine hydrochloride at 0°C, stir to dissolve, add 128g of 40% glyoxal solution dropwise, react for 20min, remove the ice-water bath, and react overnight at room temperature. After filtering, washing with water and drying, 74.3 g of glyoxime was obtained with a yield of 85% and a melting point of 175-177°C.

[0028] 2) Add 50g of glyoxime obtained in step 1) into a container containing 500mL of DMF solvent, add 202g of N-bromosuccinimide in batches at 0°C under constant stirring, and remove the ice-water bath after adding , slowly rose to room temperature for 1h. Then put the container into ice water again, slowly add 74g of sodium azide at 0°C, and react for 3h to obtain 83.9g of diazideglyoxime. Yield 87%, melting point: 182-183°C.

[0029] 3) Put the diazideglyoxime solut...

Embodiment 3

[0031] A kind of synthetic method of 5,5'-tetrazole-1,1'-dioxanolamine salt of the present invention, concrete steps are as follows:

[0032] 1) 150g Ba(OH) 2 Dissolve in 150mL of water, add 139g of hydroxylamine hydrochloride at 0°C, stir to dissolve, add 152g of 40% glyoxal solution dropwise, react for 20min, remove the ice-water bath, and react overnight at room temperature. After filtering, washing with water and drying, 69.9 g of glyoxime was obtained with a yield of 80% and a melting point of 175-177°C.

[0033] 2) Add 50 g of glyoxime obtained in step 1) into a container containing 500 mL of DMF solvent, add 73.8 g of NaClO aqueous solution in batches at 0°C under constant stirring, remove the ice-water bath after the addition, and slowly rise to Reaction at room temperature for 1h. Then put the container into ice water again, slowly add 74g of sodium azide at 0°C, and react for 3h to obtain 64.2g of diazideglyoxime. Yield 65%, melting point: 182-185°C.

[0034] 3) ...

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Abstract

The invention relates to a 5, 5 '-bistetrazole-1, 1'-dioxo hydroxylammonium salt synthetic method, and belongs to organic synthesis technical field. According to the method, glyoxal is used as a raw material, and TKX-50 is obtained by changing of intermediate raw materials, a reaction solvent and technological conditions; the second step is direct preparation of diazido glyoxime by use of one pot method, reaction conditions are mild, the intermediate links are reduced, and the product yield is improved. The third step is direct introduction of HCl gas for preparation of BTO without separation of the high sensitivity diazido glyoxime, BTO salt can be obtained by use of an alkaline solution, later period control of TKX-50 purity is facilitated, product quality can be improved, and the whole reaction overall yield is more than 72%. According to the method, a lot of intermediate operation links can be reduced, the product yield is improved, and the method helps to achieve industrial production.

Description

technical field [0001] The invention relates to a synthesis method of 5,5'-bitetrazole-1,1'-dioxanolamine salt (TKX-50), which belongs to the technical field of organic synthesis. Background technique [0002] 5,5'-tetrazole-1,1'-dioxanolamine salt (TKX-50) is a new type of high energy density compound synthesized by Niko Fischer et al. at the University of Munich in 2012, with a density of 1.918 g / cm 3 , the theoretical detonation velocity can reach 9698m / s, the impact sensitivity is greater than 20J, the friction sensitivity is greater than 120N, and has high nitrogen content, positive enthalpy of formation, insensitivity to heat and mechanical action, and does not contain halogen. It is a high-energy, Low-sensitivity, economical, green, energetic compound with excellent comprehensive performance. It has excellent application prospects in the field of mixed explosives and propellants. At present, the synthesis process route of TKX-50 reported in the literature is not op...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/04
CPCC07D257/04
Inventor 张春园金韶华束庆海王小军张晓鹏陈树森魏晓春代元权
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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