Insensitive plasticizer and melt-castable energetic material
Inventors
Sabatini, Jesse J. • Drake, Gregory W. • Wingard, Leah A. • Johnson, Eric C.
Assignees
United States Department of the Army
Publication Number
US-10246428-B2
Publication Date
2019-04-02
Expiration Date
2037-08-25
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Abstract
A method and compound includes mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol to create a mixture; adding a salt compound and water to the mixture to create bis-isoxazole diol; and nitrating the bis-isoxazole diol to create 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate, which has the structural formula: The alcohol containing an alkyne functional group may include propargyl alcohol. The salt compound may include sodium bicarbonate. The method may include nitrating the bis-isoxazole diol with nitric acid. The nitric acid may include at least a concentration of 90% nitric acid in water. Alternatively, the method may include nitrating the bis-isoxazole diol with 100% nitric acid and acetic anhydride. The salt compound and the water may be added to the mixture over at least a six-hour period. The method may include mixing the mixture after adding the salt compound and the water for at least ten hours.
Core Innovation
The invention provides a method and compound related to energetic materials, specifically focusing on the synthesis of 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate, an energetic material with favorable sensitivity and energetic properties. The method involves mixing dichloroglyoxime with an alcohol containing an alkyne functional group, such as propargyl alcohol, in methanol, adding a salt compound like sodium bicarbonate and water, to create bis-isoxazole diol, which is then nitrated to form the energetic dinitrate compound.
The problem solved by this invention addresses the limitations of current melt-castable explosives and energetic plasticizers, which include high sensitivity, thermal instability, volatility, and environmental concerns. Traditional materials like TNT and nitroglycerin (NG) suffer from issues such as toxicity, lower performance, or thermal decomposition and volatility leading to premature decomposition and detonable materials. This invention aims to provide a material that has low sensitivity, high melting point distinct from decomposition temperature, and better performance characteristics, potentially replacing TNT in melt-cast formulations and serving as an improved energetic plasticizer in propellants.
Claims Coverage
The patent discloses two independent claims focused on a method of synthesizing an energetic material and the compound itself, outlining multiple inventive features.
Method for synthesizing a 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate compound
A method comprising mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol, adding a salt compound and water to create bis-isoxazole diol, and nitrating the bis-isoxazole diol to produce 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate.
Compound of 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate formed by defined synthesis
A compound having the structural formula of 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate, formed by the method involving mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol, adding a salt compound and water to create bis-isoxazole diol, and nitrating the bis-isoxazole diol.
The claims focus on both the novel method of synthesizing the energetic plasticizer compound and the compound itself, highlighting the use of specific reactants (dichloroglyoxime, propargyl alcohol), reaction conditions (use of sodium bicarbonate and nitric acid at specified concentrations), and resulting in a compound with advantageous energetic and sensitivity properties.
Stated Advantages
The material exhibits low sensitivity to impact, friction, and electrostatic discharge compared to RDX, indicating improved safety.
The compound has a melting point significantly below its decomposition temperature, making it suitable as a melt-castable material.
It possesses energetic properties that indicate potential to replace TNT in melt-castable explosive formulations.
It can serve as an energetic plasticizer enhancing the mechanical and energetic performance of propellant formulations with reduced volatility and migration during thermal and mechanical shock.
Enhanced handling, processing safety, reduced aging, longer shelf-life, and lower vapor pressure in propellant applications compared to existing nitrate ester plasticizers due to primary nitrate functionality.
Documented Applications
Use as an ingredient in melt-castable explosive formulations, including as a replacement for TNT-based formulations such as Composition B and DNAN-based formulations.
Use as an energetic plasticizer to replace or supplement diethylene glycol dinitrate (DEGDN) and triethylene glycol dinitrate (TEGDN) in double-base propellant formulations.
Use as an energetic plasticizer to replace or supplement non-energetic plasticizers like phthalate-based, adipate-based, and triacetin-based plasticizers in rocket and gun propellant applications.
Use as a plasticizing ingredient in general double-base propellant formulations to improve formulation performance.
Enhanced handling, processing, and detooling during manufacture of insensitive, energetic castable rocket propellants, allowing higher nitrogen content nitrocellulose with improved mechanical properties.
Use in pressed and/or extruded dynamite formulations to provide energetic plasticizer with reduced volatility, improving manufacture, transport, storage, thermal stability, and safety.
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