Synthesis of Cubane Based Energetic Molecules

• Main Authors: Schmitt, Robert J, Botaro, Jeffrey C, Penwell, Paul E
• Format: Report
• Language: English
• Subjects: Ammunition and Explosives; CARBOXYLIC ACID(TETRA)/CUBANE-1-2-4-7; CARBOXYLIC ACIDS; CUBANES; CYCLIC COMPOUNDS; DIOL/1-4-CUBANE; DIOLS; EFFICIENCY; ENERGETIC PROPERTIES; ENVIRONMENTS; EXPLOSIVES; Fuels; HEAT OF FORMATION; HYDROCARBONS; Industrial Chemistry and Chemical Processing; LPN-SRI-2723; MATERIALS; MOLECULES; OCTYL RADICALS; ORGANIC CHEMISTRY; OXIDATION; PROPELLANTS; Solid Rocket Propellants; STABILITY; SYNTHESIS(CHEMISTRY); TEST AND EVALUATION; WEAPONS

The need to pack more power with less weight into less space in tomorrow's weapons drives this program for the synthesis of new generations of super energetic materials based on cubane. Cubane's heat of formation (+161 kcal/mol), density (1.29 g/cm3), and strain energy (+159 kcal/mol) make a combination not exceeded by any other stable hydrocarbon available in reasonable quantities. The addition of energy-rich and/or oxidizing groups will create exceptionally dense and powerful explosives, propellants, and fuels. The cubane system is geometrically very different from ordinary compounds and thus requires the development of innovative methods to prepare substituted cubanes. This SDI/ IST project provides the first extended testing of the theories of organic chemistry regarding highly strained compounds. The first energetic cubanes have been synthesized including the only cubanes sufficiently oxidized to be considered as explosives or propellants. The objective has been to develop new methods for the functionalization of the cubane nucleus and to synthesize energetic cubanes for the SDI/IST program. This program has developed new methods of cubane functionalization that have resulted in a more efficient, environmentally sound method for the synthesis of the intermediate cubane-1,2,4, 7-tetracarboxylic acid and an improved synthesis of 1,4-cubane diol. (aw)