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Title: Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

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 and 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 the group consisting of --H and --NH.sub.2, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen; with an effective amount of 1-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxamine to produce DATB or TATB; 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 or when hydroxylamine or its O-alkyl derivatives replace ATA primarily DATB is formed; and (b) isolating the DATB or TATB produced. DATB and TATB are important and useful specialty explosives and intermediates for other materials.
 [1];  [1];  [1]
  1. (Livermore, CA)
Issue Date:
OSTI Identifier:
Regents of University of California (Oakland, CA) LLNL
Patent Number(s):
US 5633406
Contract Number:
Research Org:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Country of Publication:
United States
vicarious; nucleophilic; substitution; 4-amino-1; 4-triazole; hydroxylamine; o-alkylhydroxylamine; 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; consisting; -h; -nh; proviso; hydrogen; effective; amount; 1-amino-1; o-alkylhydroxamine; presence; strong; base; sodium; butoxide; potassium; propoxide; ethoxide; methoxide; combinations; solvent; methanol; ethanol; propanol; butanol; dimethylsulphoxide; n-methylpyrrolidone; hexamethylphosphoramide; dimethylformide; dimethylacetamide; mixtures; provided; alcohols; o-alkyl; derivatives; replace; ata; primarily; formed; isolating; produced; useful; specialty; explosives; intermediates; materials; aromatic compound; independently selected; effective amount; nucleophilic substitution; strong base; ambient pressure; base selected; solvent selected; vicarious nucleophilic; /999/