3,3′-Dinitro-4,4′-hydrazofurazan and methods of...

Details 3,3′-Dinitro-4,4′-hydrazofurazan and methods of... 3,3′-Dinitro-4,4′-hydrazofurazan and methods of...

2000-11-21

2002-05-14

Gerstl, Robert (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06388087

ABSTRACT:

BACKGROUND OF INVENTION
Furazan derivatives have been of interest for the construction of rocket propellants and explosives ingredients because the compounds are relatively insensitive and yet provide favorable oxygen balance. The starting point is usually diaminofurazan, and oxidation converts amino groups to nitro groups, and also to azo and azoxy groups. The azo and azoxy groups serve as energetic linking groups that link two or more furazan rings: Solidyuk, G. D.; Boldyrev, M. D.; Gidaspov, B. V.; Nikolaev. V. D.
Zhur.Org.Khim.
1981 17(4), 861-5. Kulagina, V. O.; Novikova, T. S.; Mel'nikova, T. M.; Khmelnitskii, L. I.
Chem. Heterocyclic Comp.
1994, 30(5), 631-5. Kulagina, V. O.; Novikova, T. M.; Khmelnitskii, L. I.
Chem.HeterocyclicComp.
1994, 30(5), 629-30. Sheremetev, A. B.; Kulgina, V. O.; Aleksandrova, N. S.; Dmitriev, D. E.; Strelenko, Y. A.; Lebedev, V. P.; Matyushin, Y. N.
Propellants, Explosives, Pyrotechnics
1998, 23,142-9.
The use of reduction chemistry to modify the structures of furazans has been little studied. It has recently been reported that the reduction of 3,3′-diamino-4,4′-azoxyfurazan with zinc in acetic acid gave 3,3′-diamino-4,4′hydrazofurazan, which could be oxidized to the desired 3,3′-diamino-4,4′-azofurazan with air. Chavez, D.; Hill, L.; Hiskey, M.;
Kinkead,S. J. of Energetic
Materials, Vol.18, p. 219-236(2000). Selective reductions of azoxy groups in the presence of nitro groups are not trivial. Thus, March J., “Advanced Organic Chemistry”, McGraw-Hill Book Co., New York, N.Y., 1977, p. 1125-1132 reported that nitro groups and azoxy groups are both reduced by zinc/acid.
SUMMARY OF INVENTION
This invention relates to the novel compound 3,3-Dinitro-4,4′-hydrazofurazan and the methods of preparation.
One method of preparing 3,3-Dinitro-4,4′-hydrazofurazan comprises partially reducing 3,3′-Dinitro-4,4′-azoxyfurazan.
Another method of preparing 3,3′-Dinitro-4,4′-hydrazofurazan according to this invention is by the partial reduction of 3,3′-Dinitro-4,4′-azofurazan.
UTILITY
3,3′-Dinitro-4,4′-hydrazofurazan is valuable as an ingredient for rocket propellants and explosives because of its combination of high oxygen balance, high melting point, and low sensitivity to impact and friction.


REFERENCES:
Beal, Propellonts, Explosives, pyrotechnics 25, 241-6 2000.*
Solidyuk, G.D.; Boldyrev, M.D.; Gidaspov, B.V.; Nikolaev, V.D. Zhur. Org. Khim. 1981 17(4), 861-5.
Kulagina, V.O.; Novikova, T.S.; Mel'nikova, T.M.; Khmelnitskii, L.I. Chem. Heterocyclic Comp. 1994, 30(5), 631-5.
Kulagina, V.O.; Novikova T.M,; Khmelnitskii, L.I. Chem. Heterocyclic Comp. 1994, 30(5), 629-30.
Sheremetev, A.B.; Kulgna, V.O.; Aleksandrova, N.S.; Dmitriev, D.E.; Strelenko, Y.A.; Lebedev, V.P.; Matyushin, Y.N. Propellants, Explosives, Pyrotechnics, 1998, 23, 142-9.
Chavez, D.; Hill, L.; Hiskey, M.; Kinkead, S.J. of Energetic Materials, vol. 18, p. 219-236 (2000).
March, J., “Advanced Organic Chemistry”, McGraw-Hill Book Co., New York, N.Y., 1977, p 1125-1132.
pGunasedavan, A.; Trudell, M.L.; Boyer, J.H. Heteroatom Chem. 1994, 516, 441.
Zelenin, A.K.; Stevens, E.D. Trudell, M.L.; Structural Chemistry 1997, 8(5), 373.

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