Preparation of 3,3′-diamino-4,4′-azofurazan

Details Preparation of 3,3′-diamino-4,4′-azofurazan Preparation of 3,3′-diamino-4,4′-azofurazan

2001-10-30

2003-04-22

Miller, Edward A. (Department: 3641)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C149S036000

Reexamination Certificate

active

06552201

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to derivatives of 3,4-diaminofurazan useful as insensitive high explosive materials. This invention was made with government support under a contract with the Department of Energy (Contract No. W-7405-ENG-36).
BACKGROUND OF THE INVENTION
The synthesis of 3,4-diaminofurazan was first reported by Coburn in J. Heterocyclic Chem., vol. 5, pp. 83-87 (1968). Since then a large body of work has been accumulated on the oxidation of 3,4-diaminofurazan, especially by Russian scientists, e.g., Solodyuk et al., in Zh. Org. Khim., vol. 17(4), pp. 756-759 (1981) wherein the compounds 3,3′-diamino-4,4′-azoxyfurazan (DAAF) and 3,3′-diamino-4,4′-azofurazan (DAAzF) were described. They used a variety of peroxide reagents on 3,4-diaminofurazan to prepare 3,3′-diamino-4,4′-azoxyfurazan (DAAF), 3,3′-diamino-4,4′-azofurazan (DAAzF) and 3-amino-4-nitrofurazan usually as mixtures which were separated by differing solubilities. However, no characterization of the explosive properties of these compounds was reported.
One previously known explosive formulation included a combination of 2,2′,4,4′,6,6′-hexanitrostilbene (HNS) and 1,3,5-triamino-2,4,6-trinitrobenzene (TATB). While this formulation has been useful, it suffers some drawbacks in terms of performance and safety. Improved formulations including TATB have been sought.
The present inventors undertook a study of the compounds 3,3′-diamino-4,4′-azoxyfurazan (DAAF) and 3,3′-diamino-4,4′-azofurazan (DAAzF). Through their efforts, it was found that the compounds 3,3′-diamino-4,4′-azoxyfurazan (DAAF) and 3,3′-diamino-4,4′-azofurazan (DAAzF) were both useful as insensitive high explosive materials. In addition, an improved synthesis of 3,3′-diamino-4,4′-azofurazan (DAAzF) was developed. Also, formulations of 3,3′-diamino-4,4′-azofurazan (DAAzF) and 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) should overcome the drawbacks of TATB/HNS formulations.
It is an object of this invention to provide an improved process for preparation of 3,3′-diamino-4,4′-azofurazan (DAAzF).
Another object of the present invention is to provide for use of 3,3′-diamino-4,4′-azoxyfurazan (DAAF) and 3,3′-diamino-4,4′-azofurazan (DAAzF) as insensitive high explosive materials.
Still another object of the present invention is to provide formulations including 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and 3,3′-diamino-4,4′-azofurazan (DAAzF).
SUMMARY OF THE INVENTION
To achieve the foregoing and other objects, and in accordance with the purposes of the present invention, as embodied and broadly described herein, the present invention provides for the use of 3,3′-diamino-4,4′-azoxyfurazan (DAAF) and 3,3′-diamino-4,4′-azofurazan (DAAzF) as insensitive, high explosive materials.
The present invention further provides a process for the preparation of 3,3′-diamino-4,4′-azofurazan (DAAzF) from 3,4-diaminofurazan.
The present invention further provides a composition including 3,3′-diamino-4,4′-azofurazan and 1,3,5-triamino-2,4,6-trinitrobenzene (TATB).


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