Rockwell International Corporation

United States of America as Represented by the Secretary of the Air Force

USA as Represented by Secretary of the Navy

US Government as Represented by the Secretary of the Army

Milton B Frankel

Edward F Witucki

Joseph E Flanagan

Edgar R Wilson

Dean O Woolery, Ii

James F Weber

George A Lo

Louis R Grant

Michael A Cunningham

Glen D Artz

Vernon E Haury

Frederick D Raniere

John C Gray

Harry A Arbit

Lionel A Dickinson

Frank C Gunderloy, Jr

Naomi N Ogimachi

Wallace W Thompson

High-energetic explosive and propellant compositions having decreased detonation sensitivity are provided. To enhance the specific impulse of these formulations and ensure detonation desensitization, the highly-energetic oxidizer 1,9-dinitrato-2,4,6,8-tetranitrazanonane is utilized.

High-energy explosive or propellant

1,5-Diazido-3-Nitrazapentane is disclosed as an energetic plasticizer, together with a method for producing same.

1,5-diazido-3-nitrazapentane and method of preparation thereof

A castable smoke-producing pyrotechnic composition comprising a hydroxy-terminated azido polymer binder with a polyisocyanate curative, an energetic plasticizer, and a dye in an amount sufficient to generate colored smoke.

Castable smoke-producing pyrotechnic compositions

Energetic azido curing agents are provided for curing hydroxy-terminated aliphatic polymers having pendant alkyl azide groups.

Energetic azido curing agents

Provided herein are the compounds 4,4-dinitro-1-butanol, 4-azido-4,4-dinitro-1-butyl acetate and methods for preparing each compound. 4,4-dinitro-1-butanol is prepared by reacting trinitromethane with acrolein, reducing the resulting trinitroaldehyde to provide the corresponding alcohol and reducing the alcohol. 4-azido-4,4-dinitro-1-butyl acetate is prepared by reacting 4,4-dinitro-1-butanol with acetyl chloride to yield the corresponding acetate and reacting the acetate with an alkali metal azide in an electrolysis cell.

Synthesis of azidodinitro compounds

There is provided the compound 4-azido-4,4-dinitro-1-butanol (ADNBOH) and a method for making same which comprises reacting trinitromethane and acrolein at a reduced temperature to provide 4,4,4-trinitro-butyraldehyde (TNBAl), reducing the TNBSl to provide 4,4-trinitro-1-butanol (TNBOH) which is further reduced to provide 4,4-dinitro-1-butanol (DNBOH), reacting the DNBOH with acetyl chloride to provide 4,4-dinitro-1-butyl acetate (DNBAc), reacting the DNBAc with an alkali metal azide in an electrolysis cell to provide 4-azido-4,4-dinitro-1-butyl acetate (ADNBAc) and reacting the ADNBAc with a lower alcohol and recovering the 4-azido-4,4-dinitro-1-butanol (ADNBOH). Also provided are several azidodinitro derivatives of 4-azido-4,4-dinitro-1-butanol and methods for making same.

4-azido-4,4-dinitro-1-butanol and derivatives thereof

An energetic azide-terminated azido compound and a method for producing same is disclosed.

Azide-terminated azido compound

A process for producing 1,5-diazido-3-nitrazapentane (DANPE) which comprises the steps of nitrating diethanolamine with nitric acid in a halogenated solvent such as methylene chloride to form 1,5-dinitrato-3-nitrazapentane (DINA) as intermediate, solvent transferring such intermediate from the halogenated solvent to dimethylsulfoxide, adding sodium azide to the resulting solution to form DANPE as product, and solvent transferring such product from the dimethylsulfoxide to another halogenated solvent, e.g. methylene chloride. Thus, both DINA intermediate and DANPE product are prepared in solution, and both can also be purified in solution, eliminating the necessity for isolating the neat, hazardous compounds. The DANPE product can be further solvent transferred from the halogenated solvent to ethyl acetate to form an ethyl acetate solution of DANPE, which can be used to furnish the DANPE as an energetic plasticizer, e.g. in the production of gun propellants.

Process for preparing 1,5-diazido-3-nitrazapentane

1,9-Difluoro-1,1,3,5,5,7,9,9-octanitro-3,7-diazanonane, C.sub.7 H.sub.8 F.sub.2 N.sub.10 O.sub.16, is disclosed as a new energetic oxidizer for solid propellants. A method for producing the new oxidizer is also disclosed.

1,9-difluoro-1,1,3,5,7,9,9-octanitro-3,7-diazanonane and method of

Diazido derivatives of pentaerythritol are prepared by reacting 3,3-bis(azidomethyl) oxetane with inorganic acids such as hydrobromic or nitric acid. The resulting diazido monobromide can be reacted with sodium azide to produce pentaerythritol triazide which can be subsequently nitrated to pentaerythritol triazido mononitrate. The pentaerythritol diazido mononitrate produced by the reaction of nitric acid with the above oxetane can be further nitrated with nitric acid to produce pentaerythritol diazido dinitrate. These diazido and triazido derivatives of pentaerythritol can be utilized as energetic azido plasticizers per se or can serve as intermediates for the production of such plasticizers.

Azido derivatives of pentaerythritol

Energetic plasticizers comprising 4,4,4-trinitrobutyryl and 1,3,5-benzene tricarboxylic acid esters of pentaerythritol triazide and pentaerythritol diazido mononitrate, prepared by reacting the appropriate acid chloride, e.g. 4,4,4-trinitrobutyryl chloride, with pentaerythritol triazide or pentaerythritol diazido mononitrate.

Polyazido esters

A method of introducing N-azido alkyls into cyclic nitramines comprises reacting under non-basic conditions in an inert organic solvent a N-halo alkyl cyclic nitramine with the novel azidation agent acetyl azide to form the corresponding N-azido alkyl cyclic nitramine.

1-Azidomethyl-3,5,7-trinitro-1,3,5,7-tetrazacyclooctane and synthesis

A new compound tris(2-azidoethyl)amine, N-(CH.sub.2 CH.sub.2 N.sub.3).sub.3, and its method of preparation is disclosed. The subject azido derivative of a tertiary amine has the empirical formula C.sub.6 H.sub.12 N.sub.10.

Tris(2-azidoethyl)amine and method of preparation thereof

1,1,1-azidodinitro compounds such as 1,1,1-azidodinitroethane are prepared by reacting the corresponding 1,1,1-trinitromethyl compound with lithium azide in the presence of a dipolar aprotic solvent. 1,1,1-azidodinitro compounds are also known as 1-azido-1,1-dinitro compounds.

Method of preparing 1,1,1-azidodinitro compounds

This invention involves the synthesis of a novel family of azido fluorodinitro amines and their utilization as energetic plasticizers for advanced solid propellant compositions.

Growing community of inventors

Tarzana, CA, United States of America

Milton B Frankel