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International Journal of Energetic Materials and Chemical Propulsion
ESCI SJR: 0.149 SNIP: 0.16 CiteScore™: 0.29

ISSN Imprimer: 2150-766X
ISSN En ligne: 2150-7678

International Journal of Energetic Materials and Chemical Propulsion

DOI: 10.1615/IntJEnergeticMaterialsChemProp.v9.i4.60
pages 365-375

REDUCTIVE DEBENZYLATION OF 2,4,6,8,10,12-HEXAAZAISQWURTZITANE

Sergey V. Sysolyatin
Institute for Problems of Chemical and Energetic Technologies of the Siberian Branch of the Russian Academy of Sciences, Biysk
Alexander I. Kalashnikov
Institute for Problems of Chemical and Energetic Technologies of the Siberian Branch of the Russian Academy of Sciences, Biysk
Valeriy Malykhin
Institute for Problems of Chemical and Energetic Technologies of the Siberian Branch of the Russian Academy of Sciences, Biysk
Irina A. Surmacheva
Institute for Problems of Chemical and Energetic Technologies of the Siberian Branch of the Russian Academy of Sciences, Biysk
Gennady V. Sakovich
Institute for Problems of Chemical and Energetic Technologies of the Siberian Branch of the Russian Academy of Sciences, Biysk

RÉSUMÉ

A high-pressure liquid chromatography-mass spectroscopy (HPLC-MS) study of the product composition from the catalytic hydrogenolysis of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazaisowurtzitane (HBIW) and 4,10-dibenzyl-2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (DBTA) was undertaken. The hydrogenolysis of HBIW is observed in all possible directions. Debenzylation of DBTA in formic acid results in forming the mixture of 4,10-diformyl-2,6,8,12- tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (DFTA), 4-formyl-2,6,8,12-tetraacetyl-2,4,6,8,10,12- hexaazaisowurtzitane (FTA), and 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane (TA), the contents of which depend on the CHOOH concentration. In aqueous solutions of formic acid the process is complicated by hydrolysis of the amide groups. Some of the hydrolysis products keep the structure of 2,4,6,8,10,12-hexaazaisowurtzitane. Debenzylation of DBTA in mixtures of formic/acetic, formic/propionic, or formic/iso-butyric acids leads to the same mixed products. The procedure of palladium catalyst reuse in the two-stage reductive debenzylation of HBIW was developed and is presented.

RÉFÉRENCES

  1. Bellamy, A. J., Reductive debenzylation of hexabenzylhexaazaisowurtzitane.

  2. Nair, U. R., SivabalanR., Gore, R. G., Geetha, M., Asthana, S. N., and Singh, H., Hexanitrohexaazaisowurtzitane (CL-20) and CL-20-based formulations.

  3. Nielsen, A. T., Caged polynitramine compound.

  4. Nielsen, A. T., Chafin, A. P., Christian, S. L., Moore, D. W., Nadler, M. P., Nissan, R. A., and Vanderah, D. J., Synthesis of polyazapolycyclic caged polynitramins.

  5. Nielsen, A. T., Nissan, R. A., and Vanderah, D. J., Polyazapolycyclics by condensation of aldegides with amines, 2. Formation of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12- hexaazatetracyclo [5,5,0,05,9,03,11] dodecanes from glyoxal and benzylamines.

  6. Sysolyatin, S. V, Lobanova, A. A., Chernikova, Yu. T., and Sakovich, G. V., Methods of synthesis and properties of hexanitrohexaazaisowurtzitane.


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