Prior Art
M. B. Frankel, J. Org. Chem., 26, 4709 (1961).
Reference shows the reaction of 2,2-dinitro-1,3-propanediol with polynitroaliphatic primary amines and formaldehyde to give 1,3-bis(3',3',3'-trinitropropyl) and 1,3-bis(3,3-dinitrobutyl)-5,5-dinitrohexahydropyrimidine. PA1 Reference shows thorough investigation of the products of the reaction described in the previous reference as well as the nitration of 1,3-bis(3',3',3'-trinitropropyl)-5,5-dinitrohexahydropyrimidine to give 1,1,3,6,6-hexanitro-3-azaheptane. PA1 Reference describes the nitration of 7-nitro-1,3,5-triazaadamantane. Seven 1,3,5-trinitrohexahydropyrimidines, each with a different additional substituent at the 5-position were obtained.
R. G. Gafurov, S. I. Sviridov and L. T. Eremenko, Izv. Akad. Nauk. SSSR, Ser. Khim., 6, 1366 (1973).
A. F. Farminer and G. A. Webb, J.C.S. Perkin I, 940 (1976).
Mention may also be made of two compounds which find widespread usage as rocket fuel oxidants. The first of these compounds, commonly termed HMX, is 1,3,5,7-tetranitro-1,3,5,7-octahydrotetrazocine. This compound has the structure ##STR2##
The other compound, commonly termed RDX, is 1,3,5-trinitro-1,3,5-hexahydrotriazine. This compound has the structure ##STR3##
As compared to the DNNC compound of the present invention, the compounds of the prior art are relatively lean in oxygen in the sense of containing little if any oxygen over and above that required to burn the compound to CO and H.sub.2 O. In expressing the available oxygen value of a given oxidant compound, reference can be made to its "oxygen balance". This characteristic is determined by first calculating the number of oxygen atoms theoretically left in the compound after burning the same to CO, H.sub.2 O and N.sub.2 in the absence of any external oxygen source. The number so obtained is then divided by the molecular weight of the oxygen compound under test, with the value so obtained being multiplied by 1,000. Using this method all the prior art compounds mentioned above are found to have an oxygen balance equal to, or less than 0%, while DNNC has the relatively high oxygen balance of 6%.