Energetic compound embodiments and methods of making and using the same
Inventors
Chavez, David • Sabatini, Jesse • Guzmán, Pablo • Wingard, Leah • Johnson, Eric
Assignees
Triad National Security LLC • United States Department of the Army
Publication Number
US-12215089-B1
Publication Date
2025-02-04
Expiration Date
2040-05-15
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Abstract
Disclosed herein are embodiments of an energetic compound and methods of making and using the same. Energetic compound embodiments disclosed herein exhibit physical and chemical properties that facilitate their use in various applications, such as high energy propellant plasticizers, melt-castable explosives, and the like. Efficient and safe method embodiments for making the disclosed energetic compound embodiments are described herein.
Core Innovation
Disclosed herein are embodiments of an energetic compound and methods of making and using the same. The energetic compound embodiments exhibit physical and chemical properties that facilitate their use in various applications, including high-energy propellant plasticizers and melt-castable explosives. The methods describe efficient and safe production of these compounds, involving exposing a bis-oxadiazole product to a nitrating agent to produce a bis-oxadiazole dinitrate.
The problem being solved is the need for new high-energy-density materials with excellent performance and reasonable sensitivity, particularly melt-castable explosives that are scalable and efficient to manufacture. Existing materials such as TNT have toxicity and environmental concerns and other alternatives like DNAN underperform in density and detonation velocity. Moreover, previously studied materials suffer from stability issues, so there is a need for new energetic compounds and methods of making them that are safe, scalable, and produce materials with favorable energetic and physical properties.
Claims Coverage
The claims include one independent claim directed to a method of making an energetic compound, supported by multiple dependent claims expanding on the method steps and reagents. The main inventive features involve the synthesis process using specific intermediates and nitrating conditions.
Method for nitrating bis-oxadiazole to bis-oxadiazole dinitrate
The method comprises exposing a bis-oxadiazole product of a defined structure to a nitrating agent to provide a bis-oxadiazole dinitrate.
Formation of bis-oxadiazole product from diaminoglyoxime and carbonyl-containing reagent
The method further comprises making the bis-oxadiazole product by combining a diaminoglyoxime intermediate with a carbonyl-containing reagent and a solvent, then heating the reaction mixture above room temperature.
Preparation of diaminoglyoxime intermediate from di-aldehyde and hydroxylamine
The method includes making the diaminoglyoxime product by combining a di-aldehyde precursor compound with a hydroxylamine.
Specific reagents identified for intermediates and solvents
The di-aldehyde precursor is oxalaldehyde and the hydroxylamine is NH2OH or its aqueous composition; solvents include DMF/toluene, dioxane, acetonitrile; nitrating agent includes concentrated nitric acid in various purities or mixed acid systems.
The claims collectively cover a multi-step method for synthesizing energetic bis-oxadiazole dinitrate compounds emphasizing safe, scalable steps including intermediate formation, cyclization, and nitration using specific reagents and conditions.
Stated Advantages
The energetic compound embodiments outperform traditional TNT by having higher density, detonation velocity, and detonation pressure.
They exhibit lower sensitivities to impact and friction and equivalent electrostatic discharge sensitivity compared to conventional explosives like RDX, indicating enhanced handling safety.
The compounds offer good thermal stability with decomposition temperatures suitable for melt-cast explosives, accompanied by favorable melting points allowing efficient processing.
The Lewis basic character of the compounds enables them to serve as effective energetic plasticizers and wetting agents, improving the plasticization and performance of propellant formulations.
Documented Applications
The energetic compounds are used as high-energy propellant plasticizers, replacing traditional plasticizers such as diethylene glycol dinitrate and triethylene glycol dinitrate in double-base propellants.
They serve as melt-castable explosives, offering replacements for TNT-based, RDX-based, furazan-based, furoxan-based, and DNAN-based formulations with improved energetic performance and reduced toxicity.
The compounds improve the wetting and plasticization of nitrocellulose in propellant compositions, allowing use of higher nitrogen content nitrocellulose to enhance mechanical properties.
They are used in pressed and extruded dynamite formulations to provide energetic plasticizers with reduced volatility and enhanced manufacture, transportation, and storage safety.
They are applicable in underground mining and deep petroleum fracking operations due to their thermal stability, low vapor pressure, and slow aging properties, making them suitable for tactical platforms exposed to thermal extremes and extended thermal stress.
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