USA As Represented by Secretary of the Navy

Alfred G Stern

Craig J Diamond

Horst G Adolph

Patrick A Caruana

R Jason Jouet

Michael E Sitzmann

William M Koppes

Gregory S Lee

Philip F Pagoria

Lori A Nock

Jesse Stuart Moran

Donna M Cason-Smith

David M Rosenberg

Michael E Sitzman

Thao Vo

Alex J Zaita

A synthesis for an azo intermediate, 5,5'-azobis(4-chloropyrimidine) is disclosed. 5,5&#x2032;-azobis(4-chloropyrimidine) is a relatively stable azo compound in that decomposition does not occur until about 194&#xb0; C. 5,5&#x2032;-azobis(4-chloropyrimidine) is a product of oxidative dimerization of 5-amino-4-pyrimidine, which a water soluble compound. The azo intermediate is formed in an aqueous solution, but the azo intermediate is substantially insoluble in water; and as it forms it separates producing a reaction mixture that is a slurry. The azo intermediate is isolated by filtration. The azo intermediate is marginally soluble in acetone. The yield is at least 18%, and the oxidizing agent (bleach) is inexpensive, reaction conditions do not require extreme heat or cold, which taken together make the azo intermediate suitable for scaling up.

Synthesis of AZO intermediate

The present invention relates to methods for synthesizing energetic compounds and intermediates thereof. Specifically, the present invention relates to methods for synthesizing adamantanes and intermediates that are useful in such synthesis. Synthesized intermediates are useful in the synthesis of bicyclic and tricyclic substituted adamantanes. Examples of various intermediates are: acyclic 2-nitromalonaldehyde intermediates, 2,6,9-tri-substituted-4,8-dinitro-2,6,9-triazabicyclo[3.3.1]nona-3,7-dienes and 2,6-dinitro-4,8,9,10-tetra-aza-4,8,9,10-tetra-substituted adamantanes. Intermediates synthesized according to the methods of the present invention are useful toward the synthesis of tetraaza-adamantanes, which can serve as precursors to potentially superior new high-energy-density compounds (HEDCs).

Synthesis of 2,6-dinitro-4,8,9,10-tetraaza-4,8,9,10-tetra-substituted adamantanes

Synthesis of substituted 2-nitromalonaldehyde intermediates toward the preparation of polyaza-adamantanes

The present invention relates to methods for synthesizing energetic compounds and intermediates thereof. Specifically, the present invention relates to methods for synthesizing adamantanes and intermediates that are useful in such synthesis. Synthesized intermediates are useful in the synthesis of bicyclic and tricyclic substituted adamantanes. Examples of various intermediates are: acyclic 2-nitromalonaldehyde intermediates, 2,6,9-tri-substituted-4,8-dinitro-2,6,9-triazabicyclo[3.3.1]nona-3,7-dienes and 2,6-dinitro-4,8,9,10-tetra-aza-4,8,9,10-tetra-substituted adamantanes. Intermediates synthesized according to the methods of the present invention are useful toward the synthesis of tetraaza-adamantanes, which can serve as precursors to potentially superior new high-energy-density compounds (HEDCs). The tricyclic intermediate compound has a structure of Formula III: 

Synthesis of 2,6,9-tri-substituted-4,8-dinitro-2,6,9-triazabicyclo[3.3.1]nona-3,7-diene intermediates toward the preparation of polyaza-adamantanes

Substituted tetraazapentalenes have two benzenoid rings and eight substitutable positions. Substitutions are made of hydrogen or C&#x2014;H groups in favor of amino groups, nitro groups or nitrogen atoms. The tetraazapentalenes are synthesized through an intermediate azo, which is made from a 1:1:1 molar ratio of a nitroaniline, sodium nitrite and an amine.

Substituted tetraazapentalenes

A protective passivation layer is formed on the surface of an aluminum mass, such as bare aluminum particles, creating a protected aluminum mass. Formation of the protective layer onto the aluminum mass may occur from an in-situ process.

Passivation layer on aluminum surface and method thereof

A process for synthesizing 1,5-Dinosyl-3,3,7,7-tetrakis(difluoramino) octahydro-1,5-diazocine (DNTDFD) by reacting tetrahydro-1,5-bis(4-nitrobenzenesulfonyl)-1,5-diazocine-3,7-(2H, 6H) dione with HNF2/oleum initially approximately between &#x2212;5 and 0 degrees C., and allowing the temperature to rise to between 10 degrees C. and ambient temperature during said reaction to initiate difluoramination producing product DNTDFD. A 2:1 mixture of FREON&#xae; 11 refrigerant and pentane or cyclopentane, or pentane alone is used as a diluent and absorbent for the reagent difluoramine. The present invention reduces the time required to produce DNTDFD from about two weeks to one to three days and reduces the need to use relatively large quantities of FREON&#xae; 11, a compound which is damaging to the environment.

Process for synthesizing 1,5 dinosyl-3,3,7,7-tetrakis(difluoramino)octahydro-1,5-diazocine (DNTDFD)

Dinitropyrazolopyrazole-amine salts are used as burn modifier ingredients in gun propellant compositions.

Dinitropyrazolopyrazole-amine salts useful in gun propellants

The present invention provides energetic thermoplastic elastomers which may be used as binders in propellant, explosive and pyrotechnic applications. The elastomers of the present invention are all hydrolyzable, allowing recycling of the elastomer's constituents and/or facilitating other constituents of the propellant, explosive or pyrotechnic. The elastomers of the present invention contain a first polymer, a second polymer having a repeating unit different from that of the first polymer, and a bridging group. Methods of preparing elastomers of the present invention include reaction of the first and second polymers with a dioic acid, or with an organic diisocyanate and a diol containing a formal linkage.

Hydrolyzable, energetic thermoplastic elastomers and methods of preparation thereof

A process for preparing ammonium dinitramide by:

Growing community of inventors

Upper Marlboro, MD, United States of America

Alfred G Stern