SBIR-STTR Award

New energetic materials are needed for use in explosives and propellants that have a very powerful energy release yet are insensitive to handling. Safer materials that also allow development of lighter weight, longer range missiles and higher performance explosives are needed. One class of such compounds is materials based on furazan heterocycles. While some furazans are too energetic, others have very attractive properties but are difficult or unsafe to make. To address this challenge, a synthetic method development program is proposed for the challenging selective oxidation of one amine of a diaminofurazan based compound called DAAzF to give the amino nitro compound ANAzF. New and current oxidants to such transformations will be trialed in a relatively high through put effort using microwave assisted organic synthesis with low to high temperature control. A much greater reaction space will thus be examined in terms of oxidant type, temperature, pressure, pH, reactant ratios and more to identify suitable conditions. Care will be taken to develop scalable methods, and LCMS will be used to follow progress of the reactions and determine mass balance. The end result will be a robust, general method that gives acceptable, reproducible yields in a scalable process that can be further scaled and expanded to other substrates in Phase II.

Benefit:
Successful completion of this program will provide a general method for preparing new, energetic materials of interest. The ability to prepare these new materials should be a useful tool in the development and testing of new, low sensitivity but high energy propellants and explosives. The method may also be useful in preparing pharmaceuticals and other chemicals.

Keywords:
Oxidation, Synthetic-Method, Safety, Energetic Materials

This proposal sets out a plan to continue the method development for selective chemical oxidization of one amine of a polyamino, multi-heterocyclic class of energetic materials. The approach is based on screening one substrate (DAAzF) with many different oxidants under a variety of conditions including microwave heating to find those conditions where one amine group has been oxidized to a nitro group to give ANAzF. The reaction mixtures are analyzed by liquid chromatography/mass spec (LC/MS) instrument with a refined method that separates, quantifies, and identifies more than 20 compounds within 15 min. Promising methods showing feasibility in Phase I will be optimized to give a scalable, robust method that delivers ANAzF in good yield with high purity. The method will be shown to effect selective oxidation of at least three other substrates of the same class. These are also known to be insensitive energetic materials but with higher explosive power than TNT. The developed method will be useful to provide the large quantities of new, promising energetic materials for further performance testing, formulation, and field tests to enable more rapid deployment of faster, longer range delivery systems and more powerful weapons.

Benefit:
The new synthetic method will facilitate the development of new energetic materials of interest to the Air Force and DoD. Such materials are key mission enablers that provide new and needed capabilities for propulsion systems, munitions, warheads, and military pyrotechnics. They can provide the increases in perfomance for increased pulse, range, ligher weight as well as safety and survivability of personal and munitions. The methods developed here will allow the production of new energetic materials at a scale where all development testing can be performed.

Keywords:
Energetic Materials, Insensitive Munitions, Furazans, Oxidation Heterocycle