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-11566009-B1
Publication Date
2023-01-31
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
The invention disclosed herein relates to embodiments of an energetic compound and methods of making and using the same. The energetic compound exhibits physical and chemical properties suited for various applications, including high energy propellant plasticizers and melt-castable explosives. The patent also details efficient and safe methods to synthesize these energetic compounds.
The core innovation includes compounds with specific structural formulas involving bis-oxadiazole moieties functionalized with nitrate ester groups. The compounds exhibit high decomposition temperatures, suitable melting points for melt casting, high densities, and detonation velocities superior to traditional explosives like TNT. These properties support their utility as energetic materials and/or energetic plasticizers.
The problem being addressed arises from the limitations in existing high-energy-density melt-castable explosives. Current materials such as TNT have toxicity and environmental concerns, while alternatives like DNAN have lower performance metrics. There is a need in the art for new energetic materials and plasticizer ingredients that offer higher performance, better safety profiles, and environmental compatibility along with scalable, safe manufacturing methods.
Claims Coverage
The patent contains multiple claims including both compound and method claims, encompassing compositions of energetic compounds and methods for making and using them. The main inventive features cover the novel compound structures, the specific physical and energetic properties, and methods of synthesis and use.
Energetic compound having a bis-oxadiazole structure
A compound having a structure of Formula I with each five-membered ring independently selected from carbon, CH, nitrogen, NH, or oxygen; each Y independently selected from aliphatic-ONO2, aliphatic-OH, or aliphatic-OPG where PG is a hydroxyl protecting group; and each n independently an integer 0 to 4, with further specific embodiments where the rings are oxadiazoles and Y is —CH2ONO2.
Compound properties within defined thermal and explosive parameters
The compound exhibits decomposition temperatures ranging from 140° C. to 195° C., onset melting temperatures from greater than 80° C. to 85° C., explosive densities from greater than 1.75 g/cm3 to 2 g/cm3, and detonation velocities greater than 8000 m/s to 8200 m/s.
Method of synthesis involving nitration of bis-oxadiazole products
A method comprising exposing a bis-oxadiazole product, having aliphatic-OH or aliphatic-OPG groups, to a nitrating agent such as HNO3 to provide a bis-oxadiazole dinitrate.
Stepwise synthesis including formation of diaminoglyoxime and its combination with carbonyl-containing reagent
The method further includes making the bis-oxadiazole product by combining a diaminoglyoxime compound with a carbonyl-containing reagent and heating above room temperature, with the diaminoglyoxime produced by reacting a di-aldehyde precursor with hydroxylamine.
Use of the energetic compound in making melt-castable explosive or propellant plasticizer compositions
A method of using the compound of Formula I in making melt-castable explosive compositions and/or propellant plasticizer compositions.
The claims cover novel energetic compounds based on bis-oxadiazole structures bearing nitrate esters, their favorable energetic and thermal properties, efficient synthetic routes involving nitration and intermediate steps, and the use of these compounds in energetic material formulations specifically for melt-cast explosives and propellant plasticizers.
Stated Advantages
Higher energy performance than conventional materials such as TNT and DNAN, including higher density, detonation velocity, and detonation pressure.
Reduced toxicity and environmental impact compared to TNT, addressing health and waste disposal concerns.
Suitable melting point for melt-cast applications, enabling efficient and scalable manufacturing processes.
Improved safety profile with lower sensitivity to impact and friction compared to conventional explosives like RDX.
Versatility as both stand-alone energetic materials and as energetic plasticizers that enhance physical properties and energetic output of propellant formulations.
Stability including high decomposition temperatures and low volatility, facilitating longer shelf life and safer handling.
Documented Applications
Use as high-energy melt-castable explosives that can replace TNT-based, RDX-based, furazan-based, furoxan-based, and DNAN-based formulations.
Use as energetic plasticizers to replace diethylene glycol dinitrate (DEGDN), triethylene glycol dinitrate (TEGDN), and non-energetic plasticizer ingredients in double-base propellants, rocket and gun propellants.
Use as energetic ingredients to improve wetting and plasticization of nitrocellulose in propellant formulations, enabling improved mechanical properties.
Use in pressed and extruded dynamite formulations to improve manufacturing, transportation, and storage safety.
Applications in underground mining and deep petroleum fracking due to thermal stability, low vapor pressure, and slow aging characteristics.
Use in tactical platforms exposed to thermal extremes to reduce migration of propellants within liners and into the environment.
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