Synthesis of Cubane Based Energetic Molecules

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...

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Bibliographic Details
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
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Summary: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)