Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

Title: Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

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Abstract

The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by: (a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from --H, or --NH.sub.2, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen, with an amount effective to produce DATB or TATB of 1,1,1-trialkylhydrazinium halide wherein alkyl is selected from methyl, ethyl, propyl or butyl and halide is selected from chloride, bromide or iodide. in the presence of a strong base selected from sodium butoxide, potassium butoxide, potassium propoxide, sodium propoxide, sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, and combinations thereof; in a solvent selected from the group consisting of methanol, ethanol, propanol, butanol, dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformide, dimethylacetamide and mixtures thereof, provided that when alcohols are present primarily DATB and picramide is formed; and (b) isolating the DATB or TATB produced. DATB and TATB are useful specialty explosives. TATB is also used for the preparation of benzenehexamine, a starting material for the synthesis of novel materials (optical imagingmore »« less

Inventors:

Mitchell, Alexander R ^[1]; Pagoria, Philip F ^[1]; Schmidt, Robert D ^[1]

Livermore, CA

Issue Date:: 1996-01-01

Research Org.:: Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)

OSTI Identifier:: 870667

Patent Number(s):: 5569783

Assignee:: Regents of University of California (Oakland, CA)

DOE Contract Number:: W-7405-ENG-48

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: vicarious; nucleophilic; substitution; prepare; 3-diamino-2; 6-trinitrobenzene; 5-triamino-2; relates; process; produce; datb; -trinitrobenzene; tatb; reacting; ambient; pressure; temperature; degree; 50; 24; trinitroaromatic; compound; structure; str1; z; independently; selected; -h; -nh; proviso; hydrogen; amount; effective; 1-trialkylhydrazinium; halide; alkyl; methyl; ethyl; propyl; butyl; chloride; bromide; iodide; presence; strong; base; sodium; butoxide; potassium; propoxide; ethoxide; methoxide; combinations; solvent; consisting; methanol; ethanol; propanol; butanol; dimethylsulphoxide; n-methylpyrrolidone; hexamethylphosphoramide; dimethylformide; dimethylacetamide; mixtures; provided; alcohols; primarily; picramide; formed; isolating; produced; useful; specialty; explosives; preparation; benzenehexamine; starting; material; synthesis; novel; materials; optical; imaging; devices; liquid; crystals; ferromagnetic; compounds; aromatic compound; liquid crystals; imaging devices; independently selected; optical imaging; imaging device; starting material; liquid crystal; amount effective; novel materials; nucleophilic substitution; strong base; ambient pressure; base selected; solvent selected; vicarious nucleophilic; /74/999/

Citation Formats


                    Mitchell, Alexander R, Pagoria, Philip F, and Schmidt, Robert D. Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene.  United States: N. p., 1996. 
        Web.

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                    Mitchell, Alexander R, Pagoria, Philip F, & Schmidt, Robert D. Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene.  United States.

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                    Mitchell, Alexander R, Pagoria, Philip F, and Schmidt, Robert D. Mon .  
        "Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene".  United States.  https://www.osti.gov/servlets/purl/870667.

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@article{osti_870667,

  title        = {Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene},

  author       = {Mitchell, Alexander R and Pagoria, Philip F and Schmidt, Robert D},

  abstractNote = {The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by: (a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from --H, or --NH.sub.2, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen, with an amount effective to produce DATB or TATB of 1,1,1-trialkylhydrazinium halide wherein alkyl is selected from methyl, ethyl, propyl or butyl and halide is selected from chloride, bromide or iodide. in the presence of a strong base selected from sodium butoxide, potassium butoxide, potassium propoxide, sodium propoxide, sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, and combinations thereof; in a solvent selected from the group consisting of methanol, ethanol, propanol, butanol, dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformide, dimethylacetamide and mixtures thereof, provided that when alcohols are present primarily DATB and picramide is formed; and (b) isolating the DATB or TATB produced. DATB and TATB are useful specialty explosives. TATB is also used for the preparation of benzenehexamine, a starting material for the synthesis of novel materials (optical imaging devices, liquid crystals, ferromagnetic compounds).},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {1996},

  month        = {1}

}

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