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A kind of synthetic method of 3-cyano-4-nitrofuroxan

A technology of nitrofuran and aminofuran oxide, applied in the direction of organic chemistry, can solve the problems of low reaction yield, cumbersome post-treatment, long reaction steps, etc., and achieve the effect of simple reaction steps

Inactive Publication Date: 2018-12-11
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method has long reaction steps, cumbersome post-treatment, and low reaction yield

Method used

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  • A kind of synthetic method of 3-cyano-4-nitrofuroxan
  • A kind of synthetic method of 3-cyano-4-nitrofuroxan
  • A kind of synthetic method of 3-cyano-4-nitrofuroxan

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Under stirring, add 30g (454mmol) malononitrile and 37g (536mmol) sodium nitrite into 50mL water at a temperature of 0°C, then add 4mL (70mmol) of glacial acetic acid dropwise, and heat up to 20°C after the addition After reacting for 4 hours, the reaction liquid was extracted with ethyl acetate (100 mL×4) and dried. After filtration, the filtrate was distilled under reduced pressure to obtain 47.0 g of malononitrile oxime sodium salt, with a yield of 88.6% and a purity of 98.1%;

[0026] Structure Identification:

[0027] Infrared Spectrum: IR(KBr,cm -1 )ν: 2229, 1633, 1347;

[0028] NMR spectrum: 13 CNMR (CDCl 3 ,125MHz), δ:115.76,110.59,109.54;

[0029] Elemental Analysis: Structural Formula C 3 N 3 ONa

[0030] Theoretical value: C 30.79, N 35.90

[0031] Measured value: C 30.56, N 35.79;

[0032] The above-mentioned structural identification data confirm that the material obtained in this step is indeed malononitrile oxime sodium salt;

[0033] (2) Un...

Embodiment 2

[0062] (1) Under stirring, add 30g (454mmol) malononitrile and 35g (550mmol) sodium nitrite into 50mL water at a temperature of 0°C, then add 5mL (87mmol) of glacial acetic acid dropwise, and heat up to 20°C after the addition After reacting for 5 hours, the reaction liquid was extracted with ethyl acetate (100 mL×4) and dried. After filtration, the filtrate was distilled under reduced pressure to obtain 43.0 g of malononitrile oxime sodium salt, with a yield of 80.1% and a purity of 99.2%;

[0063] (2) Under stirring, add 13g (131.5mmol) of malononitrile oxime sodium salt to 250mL of absolute ethanol, then add 8.70g (125mmol) of hydroxylamine hydrochloride, heat up to reflux reaction for 4h after the addition, remove the solid by filtration, reduce Pressure distillation yielded 12.1 g of white solid 1-amino-2-cyanodioxime, yield 71.8%, purity 98.5%, m.p.: 99°C-100°C;

[0064] (3) Under stirring, dissolve 5.3 g (42 mmol) of 1-amino-2-cyanodioxime in 125 mL of ether, slowly add...

Embodiment 3

[0068] (1) Under stirring, add 30g (454mmol) malononitrile and 38g (507mmol) sodium nitrite into 50mL water at a temperature of 0°C, then add 3mL (52mmol) of glacial acetic acid dropwise, and heat up to 20°C after the addition After reacting for 4 hours, the reaction solution was extracted with ethyl acetate (100 mL×4) and dried. After filtration, the filtrate was distilled under reduced pressure to obtain 32.0 g of malononitrile oxime sodium salt, with a yield of 59.9% and a purity of 98.6%;

[0069] (2) Under stirring, add 13g (131.5mmol) of malononitrile oxime sodium salt to 320mL of absolute ethanol, then add 9.39g (135mmol) of hydroxylamine hydrochloride, heat up to reflux reaction for 5h after the addition, remove the solid by filtration, reduce Pressure distillation yielded 13.2 g of white solid 1-amino-2-cyanodioxime, yield 78.5%, purity 98.4%, m.p.: 99°C-100°C;

[0070] (3) Under stirring, 1-amino-2-cyanodioxime 5.3g (42mmol) was dissolved in 140mL ether, slowly added...

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Abstract

The invention discloses a method for synthesizing 3-cyano-4-nitrofuroxan.The method includes the following steps that firstly, malononitrile and sodium nitrite are added into water under stirring and at the temperature of -5-0 DEG C, then glacial acetic acid is added dropwise, the temperature is increased to 10-25 DEG C, reaction is conducted for 3-5 h, and malononitrile oxime sodium salt is obtained; secondly, under stirring, the malononitrile oxime sodium salt is added into anhydrous ethanol, then hydroxylamine hydrochloride is added, heating is conducted after addition till reflux reaction is conducted for 3-6 h, and 1-amino-2-cyano dioxime is obtained; thirdly, under stirring, 1-amino-2-cyano dioxime is dissolved in diethyl ether, glacial acetic acid and lead dioxide are added, reaction is conducted for 3-5 h at the temperature of 10-25 DEG C, and 3-cyano-4-aminofuroxan is obtained; fourthly, under stirring, concentrated sulfuric acid is slowly added into a sodium tungstate dehydrate and 30% hydrogen peroxide slowly at the temperature of -10-0 DEG C, the temperature is increased to 20-35 DEG C after addition, then 3-cyano-4-aminofuroxan is added in batches, the temperature of 25-35 DEG C is preserved after addition, reaction is conducted for 2-3 h, and 3-cyano-4-nitrofuroxan is obtained.The method is mainly used for synthesizing 3-cyano-4-nitrofuroxan.

Description

technical field [0001] The invention relates to a synthesis method of 3-cyano-4-nitrofuroxan, which belongs to the field of energetic materials. Background technique [0002] The furoxan ring is a useful structural unit for designing and synthesizing high-energy-density compounds containing C, H, N, and O atoms. It has a nitrogen-oxygen five-membered ring that coordinates an oxygen atom. group" and become an explosive group. Furazan oxide ring has high nitrogen content, "active oxygen" and positive standard enthalpy of formation, and high density. Unlike high-nitrogen compounds such as tetrazole and tetrazine, it can form a "latent nitro" inner ring structure, which is quite Due to the role of the two nitro groups, it is suitable for high-energy explosives and has become a field of general concern for researchers of energetic materials around the world. 3-cyano-4-nitrofuroxan is a high-energy compound formed by introducing energetic groups cyano and nitro into furoxan stru...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/08
CPCC07D271/08
Inventor 翟连杰樊学忠王伯周毕福强李亚南周诚
Owner XIAN MODERN CHEM RES INST
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