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A kind of synthetic method of hexaaminobenzene hydrochloride

A technology of hexaaminobenzene hydrochloride and synthesis method, which is applied in the field of synthesis of hexaaminobenzene hydrochloride, can solve the problems of difficult synthesis of HAB, expensive raw materials, easy deterioration of HAB, etc., and achieve reaction safety, green environmental protection, Easy separation and purification, low cost of raw materials

Active Publication Date: 2021-02-02
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, the method of preparing TAB using TATB as a starting material has disadvantages: (1) TATB is a common inert explosive, which has certain dangers; (2) there are cumbersome steps in the synthesis and reduction process of TATB, The conditions are harsh and the operation is extremely difficult, and it is difficult to synthesize in large quantities; (3) the raw materials used in the synthesis process are expensive and costly; (4) the synthesized HAB is easily deteriorated, and the shelf life is extremely short, and the purity will decrease or even fail due to oxidation
[0007] Considering that the synthesis of HAB is relatively difficult at present, a technical problem that needs to be urgently solved by those skilled in the art is: provide a simple, efficient, safe, environmentally friendly and low-cost method to prepare HAB

Method used

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  • A kind of synthetic method of hexaaminobenzene hydrochloride
  • A kind of synthetic method of hexaaminobenzene hydrochloride
  • A kind of synthetic method of hexaaminobenzene hydrochloride

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preparation example Construction

[0069] figure 1 A method flow chart of the preparation method of hexaaminobenzene hydrochloride provided by the embodiment of the present invention is shown. refer to figure 1 , the invention provides a kind of synthetic method of hexaaminobenzene hydrochloride, described method comprises:

[0070] Using the 1,3,5-triaminobenzene shown in structural formula I as the reaction raw material, carry out coupling reaction with the diazonium salt shown in structural formula III under alkaline conditions, and obtain the hexaamine shown in structural formula IV after filtering and drying. Substituted aromatic azo compounds;

[0071]

[0072] The hexa-substituted aromatic azo compound is reduced, and hydrochloric acid reagent is added to obtain the hexaaminobenzene hydrochloride represented by structural formula V.

[0073] Preferably, the method further includes: using nitrite or isoamyl nitrite and an aromatic amine shown in structural formula II to prepare the diazonium salt sh...

Embodiment 1

[0105] Embodiment 1: the easy synthesis of hexaaminobenzene hydrochloride.

[0106] Step 1: Synthesis of aniline diazonium fluoroborate.

[0107] Sodium nitrite (1.4096g, 21mmol, 1.05eq) was dissolved in 5ml deionized water, and placed in an ice bath for pre-cooling for 10min; after mixing 50wt% tetrafluoroboric acid aqueous solution (6ml) with deionized water (6ml), Place in ice-water mixture for precooling, add aniline (1.8ml, 20mmol, 1eq) dropwise, mix well by magnetic stirring, then add 5ml NaNO dropwise 2 aqueous solution, and reacted for 10 min under magnetic stirring. After the reaction, a white needle-like solid was obtained by filtration, washed with ice water and dried to obtain aniline diazonium fluoroborate (3.3302 g, yield 86.7%).

[0108] refer to figure 2 , image 3 with Figure 4 , shows the proton nuclear magnetic resonance spectrum, carbon nuclear magnetic resonance spectrum and fluorine nuclear magnetic resonance spectrum of the intermediate product an...

Embodiment 2

[0133] Embodiment 2: the easy synthesis of hexaaminobenzene hydrochloride.

[0134] Step 1: Synthesis of 4-methylaniline diazonium fluoborate.

[0135] Sodium nitrite (704mg, 1.01mmol, 1.01eq) was dissolved in 3ml deionized water, and placed in an ice bath for pre-cooling for 10min; after mixing 50wt% tetrafluoroboric acid aqueous solution (3ml) with deionized water (3ml), Pre-cool in an ice-water mixture, add quantitative 4-methylaniline (1.074g, 10mmol, 1eq), stir the mixture uniformly by magnetic stirring, then add 3ml NaNO 2 aqueous solution, and reacted for 10 min under magnetic stirring. After the reaction, a white needle-like solid was obtained by filtration, washed with ice water and dried to obtain 4-methylaniline diazonium fluoroborate (1.8722 g, yield 90.9%).

[0136] refer to Figure 14 with Figure 15 , shows the proton nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum of the intermediate product 4-methylaniline diazonium f...

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Abstract

The embodiment of the present invention provides a synthesis method of hexaaminobenzene hydrochloride. The method comprises: using 1,3,5-triaminobenzene shown in structural formula I as a reaction raw material, performing a coupling reaction with a diazonium salt shown in structural formula III under alkaline conditions, and obtaining the structural formula after filtering and drying The hexa-substituted aromatic azo compound shown in IV; reducing the hexa-substituted aromatic azo compound and adding hydrochloric acid reagent to prepare the hexaaminobenzene hydrochloride shown in structural formula V. The synthesis method provided by the invention has the advantages of simple process, wide sources of raw materials, low cost of raw materials, fast reaction speed, high yield, easy separation and purification of products, and the like.

Description

technical field [0001] The invention relates to a synthesis method of hexaaminobenzene hydrochloride, which belongs to the field of chemical materials. Background technique [0002] Hexaaminobenzene (HAB, CAS#:4444-26-2) is a very important chemical raw material, which can be used to synthesize many novel compounds and functional materials, such as hexaazatriphenylene (HAT) derivatives, hexaazatriphenylene (HAT) derivatives, Azacarbazoles, fused-ring benzotriazoles, benzotriimidazoles, and porous polymer materials (C 2 N-h2D) [Nature Communication, 2015, 6, 6486] and so on. Among them, the porous polymer material (C 2 N-h2D) Compared with the existing nitrogen-doped graphite-type materials, graphitic carbon nitride (g-C 3 N 4 ), has higher nitrogen content, specific surface area and hole distribution, and its unique planar conjugated structure makes the polymer more stable, and the higher hole distribution endows it with unique electromagnetic properties. It has semicon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/42C07C211/50C07C245/08C07C245/20
CPCC07C209/42C07C245/08C07C245/20C07C211/50
Inventor 黄木华罗贤升邓汉林刘向向
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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