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Synthetic method of bis(2,2,2-trinitro ethyl)-3-6-diamino tetrazine

A technology of trinitroethyl and diaminotetrazine, applied in the direction of organic chemistry, etc., can solve the problems of unspecified reaction yield and low reaction yield

Inactive Publication Date: 2012-09-12
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method does not specifically provide the reaction yield, and the reaction yield calculated with diaminotetrazine is about 19%, but the reaction yield of this method is relatively low

Method used

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  • Synthetic method of bis(2,2,2-trinitro ethyl)-3-6-diamino tetrazine
  • Synthetic method of bis(2,2,2-trinitro ethyl)-3-6-diamino tetrazine
  • Synthetic method of bis(2,2,2-trinitro ethyl)-3-6-diamino tetrazine

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Experimental program
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Effect test

preparation example Construction

[0017] Preparation of trinitroethanol:

[0018] Under an ice-water bath, add 33.6g (0.3mol) of 4,6-dihydroxypyrimidine to concentrated sulfuric acid in batches, and after it is completely dissolved, add 96.3g (1.5mol) of concentrated nitric acid dropwise, react at 42°C for 2h, and pour the reaction solution into Put into ice water, extract with dichloromethane, dry over anhydrous magnesium sulfate, and distill off dichloromethane under atmospheric pressure to obtain trinitromethane solution containing a small amount of dichloromethane.

[0019] Add 15 g of the above-mentioned trinitromethane solution containing dichloromethane into carbon tetrachloride, then add paraformaldehyde, and stir under reflux for 3 h. Dichloromethane and part of carbon tetrachloride were distilled off under reduced pressure, cooled, filtered, and dried to obtain 12.4 g of trinitroethanol.

Embodiment 1

[0021] Dissolve 11.2g (0.1mol) of 3,6-diaminotetrazine in 200mL of dimethyl sulfoxide, and add the above solution to 180.9g of 22% (mass) trinitrate under stirring at 0°C to 5°C In the aqueous solution of base ethanol, and while adding the aqueous solution of trinitroethanol, adjust the pH of the reaction system to 2 with sulfuric acid, after adding the dimethyl sulfoxide solution of 3,6-diaminotetrazine, the After reacting at ℃ for 3 hours, the reaction solution was poured into 300 mL of ice water, and a large amount of solids were precipitated. After filtering and drying the filter cake, 27.4 g of BTAT was obtained with a yield of 62.6%.

[0022] Structure Identification:

[0023] Infrared (KBr, cm -1 ): 3285 (-NH-), 1612, 1587 (tetrazine ring), 1532, 1313 (-NO 2 ), 2964 (-CH 2 -).

[0024] NMR (DMSO, δ, ppm): 6.8(-NH-), 2.5(-CH 2 -).

[0025] Mass spectrum: 438[m, 13.5%], 392[m-NO 2 , 1.4%], 346[m-2NO 2 , 1.5%], 300[m-3NO 2 , 2.0%], 206[N-C-NH-CH 2 -C(NO 2 ) 3 ...

Embodiment 2

[0031] Dissolve 11.2g (0.1mol) of 3,6-diaminotetrazine in 200mL of dimethyl sulfoxide, add the above solution to 181g of trinitroethanol with a mass fraction of 20% under stirring at 0°C to 5°C In the aqueous solution, the pH of the reaction system can be kept at 1 with 36% hydrochloric acid during the dropping process. After adding the dimethyl sulfoxide solution of 3,6-diaminotetrazine, react at 20°C to 25°C for 2 hours , the reaction solution was poured into 500 mL of ice water, a large amount of solids were precipitated, filtered and dried to obtain 22.7 g of the target compound BTAT, with a yield of 51.8%.

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Abstract

The invention discloses a synthetic method of bis(2,2,2-trinitro ethyl)-3-6-diamino tetrazine of the following formula. The method is characterized by using 3,6-diamino tetrazine and trinitro ethanol as raw materials, adding dimethyl sulfoxide of 3,6-diamino tetrazine in an aqueous solution of trinitro ethanol at low temperature under acidic conditions, and reacting at room temperature to obtain bis(2,2,2-trinitro ethyl)-3-6-diamino tetrazine. The invention is mainly used for synthesizing bis(2,2,2-trinitro ethyl)-3-6-diamino tetrazine.

Description

technical field [0001] The invention relates to a method for synthesizing bis(2,2,2-trinitroethyl)-3,6-diaminotetrazine. Background technique [0002] With the continuous progress of a new generation of high-energy-density materials, designing and synthesizing compounds with higher energy density, better explosive performance, better chemical stability and thermal stability, and environmental friendliness is the field of research and development of energetic materials. main goal of . Bis(2,2,2-trinitroethyl)-3,6-diaminotetrazine (BTAT), as an isomer of CL-20, is a new type of energetic compound, and its intramolecular tetrazine Ring is a typical energetic structural unit with high nitrogen and low carbon and hydrogen content, which has high positive enthalpy of formation, high density, low sensitivity, good thermal stability and easier to reach oxygen balance. [0003] At present, the main synthesis method of bis(2,2,2-trinitroethyl)-3,6-diaminotetrazine (BTAT) is to synth...

Claims

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Application Information

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IPC IPC(8): C07D257/08
Inventor 郭涛刘敏李普瑞姜俊唐望郑晓东李洪丽秦明娜石强吕英迪陈志强张彦邱少君
Owner XIAN MODERN CHEM RES INST
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