Nitramine explosive and preparation method thereof

The technology of nitramine explosive and trinitro group is applied in the field of explosive synthesis, which can solve the problems of long reaction time and the like, and achieve the effects of less environmental damage, simple product post-processing and simple reaction steps.

Inactive Publication Date: 2013-07-10
NANJING UNIV OF SCI & TECH
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Problems solved by technology

However, researchers at home and abroad have seldom reported the synthesis of such compounds, and only a few literatures have reported 5-nitro-2,3-dihydro-1H-imidazo[4 ,5-b]pyridin-2-one and similar compounds, see (Smolyar N N, Troyan N N, Vasilechko A B, et al. Synthesis of 1-(1,3-Dialkyl-2-oxo-2,3-dihydro-1 H-imidazo-[4,5-b]pyri-din-5-yl)-5-oxopyrrolidine
[0004]-3-carboxylic Acids. Russian Journal of Organic Chemistry, 2007, 43: 1706–1709.), but its synthetic intermediate 2, The reaction time of 3-dihydro-1H-imidazo[4,5-b]pyridin-2-one is long, so the synthesis route and technology of pyridocyclic urea nitramine energetic compounds have also been exploring

Method used

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  • Nitramine explosive and preparation method thereof
  • Nitramine explosive and preparation method thereof
  • Nitramine explosive and preparation method thereof

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preparation example Construction

[0028] Nitramine explosive 1,3,5-trinitro-2,3-dihydro-1 of the present invention H -The preparation method of imidazo[4,5-b]pyridin-2-one, comprising the following steps:

[0029] In the first step, 2,3-diaminopyridine and urea are put into the reactor, and the ring-closing reaction of 2,3-diaminopyridine and urea is realized at high temperature. After the reaction, the mixture is extracted with boiling ethanol and filtered A dark brown solid was obtained;

[0030] In the second step, the black solid obtained in the first step is subjected to a nitration reaction in a nitration system. After the reaction, the mixture is poured into crushed ice, filtered with suction, and the filter cake is washed with water until it is neutral, and dried to obtain the product, which is identified as 1,3,5-Trinitro-2,3-dihydro-1 H - imidazo[4,5-b]pyridin-2-one.

[0031] Among them, in the first step, the molar ratio of 2,3-diaminopyridine to urea is 1:1~1:3.3, the ring closing temperatur...

Embodiment 1

[0035] Add 763.9 mg (7.0 mmol) of 2,3-diaminopyridine and 1.40 g (23.3 mmol) of urea into a 50 mL one-necked flask, mix well, and heat to 140 °C under reduced pressure for 1 h. The cooled reaction mixture was extracted with boiling ethanol (5*6 mL), and the crystals were collected by filtration. The filtrate was refrigerated in a refrigerator, and solids precipitated after overnight, filtered by suction, and dried to obtain 2,3-dihydro-1 H - Imidazo[4,5-b]pyridin-2-one, yield 95%.

[0036] m.p.273~275℃;

[0037] 1 H NMR (DMSO- d 6 , 500 MHz): δ 6.93(dd, 1H), 7.21(dd, 1H), 7.85(dd, 1H), 10.81(s, 1H), 11.28(s, 1H);

[0038] Elemental Analysis: C 6 h 5 N 3 O, Calculated: C, 53.33; H, 3.73; N, 31.10; Found: C, 53.26; H, 3.92; N, 31.15;

[0039] MS (ESI) m / z: 136.03(M+H).

Embodiment 2

[0041] Add 763.9 mg (7.0 mmol) of 2,3-diaminopyridine and 1.40 g (23.3 mmol) of urea into a 50 mL one-necked flask, mix well, and heat to 120 °C under reduced pressure for 0.2 h. The cooled reaction mixture was extracted with boiling ethanol (5*6 mL), and the crystals were collected by filtration. The filtrate was refrigerated in a refrigerator, and solids precipitated after overnight, filtered by suction, and dried to obtain 2,3-dihydro-1 H - Imidazo[4,5-b]pyridin-2-one, yield 36%.

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Abstract

The invention relates to a nitramine explosive 1,3,5-trinitro-2,3-dihydro-1H-imidazo [4,5-b] pyridine-2-ketone and a preparation method thereof. The method comprises the steps of achieving a reaction close loop of 2,3-diaminopyridine and urea at a high temperature, extracting the mixture by boiled ethanol after the reaction is finished, filtering to obtain dark brown solid; achieving nitrification reaction on 2,3-dihydro-1H-imidazo [4,5-b] pyridine-2-ketone in different nitrification systems; pouring the mixture into trash ice after the reaction is finished, filtering and washing a filter cake to become neutral, and drying to obtain light yellow solid. The compound containing energy synthetized by the method is novel in structure, mild in reaction condition, simple in technology, safe and reliable to produce, simple to carry out post-treatment on the product, small in damage to the environment, does not need a special device, and meets the basic requirements of industrial amplification production.

Description

technical field [0001] The invention belongs to the field of explosive synthesis, in particular to a nitramine explosive 1,3,5-trinitro-2,3-dihydro-1 H -imidazo[4,5-b]pyridin-2-one (1,3,5-trinitro-2,3-dihydro-1 H -imidazo-[4,5-b]pyridin-2-one) and a process for its preparation. Background technique [0002] High-energy density materials (HEDMs) play a vital role in both explosives and propellants. By introducing a cage structure or a group with more nitrogen atoms, oxygen atoms or fluorine atoms, such as azido (-N 3 ), Nitro (NO 2 ), nitramine (N-NO 2 ) and other functional groups, thereby changing the structure of the compound to achieve high energy and high density characteristics. Therefore, nitroamine compounds, especially cyclic nitroamines, such as 1,3,5-trinitro1,3,5-triazacyclohexane (RDX), 1,3,5,7-tetranitro -1,3,5,7-Tetraazacycloctane (HMX) has become a class of very potential high-energy density materials due to its structural characteristics, and has been d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C06B25/34C07D487/04
Inventor 刘祖亮马从明候可辉姚其正徐潇
Owner NANJING UNIV OF SCI & TECH
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