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A kind of safe synthetic method of 1,3,5-triamino-2,4,6-trinitrobenzene

A technology of triaminobenzene and trinitrobenzene, applied in the field of safe synthesis of 1,3,5-triamino-2,4,6-trinitrobenzene, which can solve the impact of chlorine-containing by-products and harsh reaction conditions , cost reduction and other issues, to achieve the effect of avoiding separation, purification and collection, simplifying the operation process and improving safety

Active Publication Date: 2022-04-15
BEIJING INSTITUTE OF TECHNOLOGYGY
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Problems solved by technology

Among them, the cost of raw material TCB used in method (1) is relatively high, and the chlorine atoms are often not completely replaced in the amination step, and the residual chlorine-containing by-products will significantly reduce the quality of the final product, which is harmful to the safety and compatibility of explosives. Performance parameters such as all have adverse effects; Method (2) is starting raw material with phloroglucinol, compares method (1) and cost declines to some extent, has avoided the residue of chlorinated by-product simultaneously, but these two kinds of methods The amination steps are all carried out under high temperature and pressure, and there are safety problems such as harsh reaction conditions and difficult operation; method (3) uses 4-nitroaniline as a raw material, and its amination steps are different from the previous two methods, but utilize 4 -Amino-1,2-triazole attacks 2,4,6-trinitroaniline, and removes neutral molecules by introducing nucleophilic species to carry out heavy aromatization process to obtain the target product TATB, so method (3) is more advanced than the first two The method is milder and safer, but this method mostly uses dimethyl sulfoxide as a solvent, which increases the cost of wastewater post-treatment
[0004] In summary, for the synthetic method of TATB, there are still the following problems: (1) higher raw material cost, especially the synthetic method with 1,3,5-trichlorobenzene as the starting material; (2) harsh reaction Conditions often require high temperature and high pressure for amination reaction; (3) the impact of chlorine-containing by-products and environmental pollution problems

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  • A kind of safe synthetic method of 1,3,5-triamino-2,4,6-trinitrobenzene
  • A kind of safe synthetic method of 1,3,5-triamino-2,4,6-trinitrobenzene
  • A kind of safe synthetic method of 1,3,5-triamino-2,4,6-trinitrobenzene

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preparation example Construction

[0035] The embodiment of the present invention provides a safe synthesis method of 1,3,5-triamino-2,4,6-trinitrobenzene shown in structural formula I, refer to figure 1 Shown, this synthesis method comprises:

[0036] Step 1 (S101), based on the isomerism characteristics of 1,3,5-cyclohexanetriketone imine shown in structural formula VI and 1,3,5-triaminobenzene shown in structural formula V, with structural formula VIII 1,3,5-Cyclohexanetrione is used as the reaction raw material, and the N,N',N"-three Acetyl-1,3,5-triaminobenzene.

[0037] In this implementation step, first, 1,3,5-cyclohexanone oxime reacts with hydroxylamine under alkaline conditions to obtain 1,3,5-tricyclohexanone oxime represented by structural formula VII in high yield; Then, the 1,3,5-tricyclohexanone oxime shown in the structural formula VII cuts the N-O bond under the catalysis of Raney nickel and other catalysts to obtain the 1,3,5-triaminobenzene shown in the structural formula V; finally, the st...

Embodiment 1

[0063] Step 1: Preparation of N,N,N-triacetyl-1,3,5-triaminobenzene represented by structural formula IV.

[0064] Take hydroxylamine hydrochloride (500.4g, 7.2mol, 6eq) and dissolve it in concentrated ammonia water (25%, 540ml, 7.2mol, 6eq), add 2250ml of water to make it fully dissolved, then weigh 1,3,5-cyclohexanetrione ( 194.4g, 1.2mol, 1eq), continued to stir vigorously at 5°C for 5 hours, and the suspension was filtered, washed and dried to obtain a powder solid 1,3,5-cyclohexanetrione oxime (192.7g, yield 94 %).

[0065] It should be noted that when hydroxylamine hydrochloride is fully dissolved and 1,3,5-cyclohexanetrione is directly added, the degree of dissolution of 1,3,5-cyclohexanetrione is low, resulting in low reaction efficiency and difficult identification of the reaction End point and low yield, etc., therefore, in order to solve these problems, in this implementation step, after hydroxylamine hydrochloride is fully dissolved, deionized water is added, so t...

Embodiment 2

[0090] Step 1: Preparation of N,N,N-triacetyl-1,3,5-triaminobenzene represented by structural formula IV.

[0091] Dissolve hydroxylamine hydrochloride (500.4g, 7.2mol, 6eq) in concentrated ammonia water (25%, 1620ml, 21.6mol, 18eq), add 1000ml of water to fully dissolve it, and weigh 1,3,5-cyclohexanetrione Glycinol (194.4g, 1.2mol, 1eq), under ice bath (-5°C), continued to react with vigorous stirring for 5 hours, the obtained suspension was suction filtered, washed and dried to obtain powder solid 1,3,5-tris Cyclohexanone oxime (135.4 g, 66% yield).

[0092] The proton nuclear magnetic resonance spectrum of the 1,3,5-tricyclohexanone oxime shown in the structural formula VII of the embodiment of the present invention 2, the carbon nuclear magnetic resonance spectrum and the infrared spectrum are respectively with figure 2 , image 3 and Figure 4Same, not repeated.

[0093] Place the prepared 1,3,5-tricyclohexanone oxime (200g, 1.2mol, 1eq) and the Raney nickel catalys...

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Abstract

The invention provides a safe synthesis method of 1,3,5-triamino-2,4,6-trinitrobenzene. The method comprises: based on the isomerization characteristics of 1,3,5-cyclohexanetrione imine and 1,3,5-triaminobenzene, using 1,3,5-cyclohexanetrione as a reaction raw material, passing trioxime N-O bond cleavage-isomerization reaction and N-acylation reaction to obtain N,N',N"-triacetyl-1,3,5-triaminobenzene; N,N',N" ‑Triacetyl‑1,3,5‑triaminobenzene was used as raw material, and TATB was prepared by a multi-stage one-pot trinitration reaction. The method is characterized by the multi-stage one-pot trinitration reaction, which not only avoids the amination step of explosive polynitro compounds, but greatly improves the safety, and the reactants or catalysts used are commonly used in the chemical industry. The product avoids the use of refractory organic solvents and realizes the theme of green and safe synthesis. At the same time, based on the characteristics of the one-pot method, it simplifies the operation process and avoids the separation, purification and collection of intermediate products, which is conducive to the realization of 1,3 , Large-scale preparation of 5-triamino-2,4,6-trinitrobenzene.

Description

technical field [0001] The invention relates to the fields of chemical industry and new materials, and mainly relates to a safe synthesis method of 1,3,5-triamino-2,4,6-trinitrobenzene. Background technique [0002] 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB) is one of the most excellent insensitivity explosives at present. It is extremely insensitivity to friction, flame and impact, and has good Stability and thermal stability (its thermal decomposition temperature is 350°C, impact sensitivity (H 50 ) is 170cm, friction sensitivity is 36kg, and has considerable detonation performance (detonation velocity is 8159m / s, detonation pressure is 30.5GPa). Therefore, it can be widely used in special environments that require high explosive insensitivity, such as nuclear weapons, and is currently one of the most important high-performance insensitive explosives. [0003] At present, TATB can be mainly prepared by the following chemical synthesis methods: (1) using 1,3,5-trichlorob...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/76C07C211/52C07C231/02C07C233/43
CPCC07C209/76C07C231/02C07C211/52C07C233/43
Inventor 黄木华邓汉林贾琼彭山青罗贤升
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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