US 5,633,406 A · 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

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 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.

Claims20

Dependent claims

A process to produce 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB), which process comprises:

(a) reacting at ambient pressure and a temperature of between about 0.degree. and 30.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic starting material compound of the structure:
##STR6## 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 of X, Y, and Z is hydrogen;
with an effective amount of 4-amino-1,2,4-triazole;
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, or combinations thereof;
in a solvent selected from the group consisting of dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformamide, dimethylacetamide and mixtures thereof;
and
(b) isolating the TATB produced.

4 more elements

A process to produce 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB), which process comprises:

(a) obtaining an aromatic starting material compound of the structure:
##STR7## mixtures thereof from commercial sources or by:
(i) reacting
ph--NO.sub.2
with an amount of 4-amino-1,2,4-triazole effective to produce 4-nitroaniline;
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 dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformamide, dimethylacetamide, or mixtures thereof, or isolating the product which is III;
(ii) or nitrating aniline using a mixture of nitric acid and sulfuric acid to produce compounds III and IV;
or
(iii) nitrating acetanilide using a mixture of nitric acid and sulfuric acid to produce 4-nitroacetanilide and nitrating further using a mixture of nitric acid and sulfuric acid to produce compound VI;
(b) reacting 2-nitroaniline, 4-nitroaniline or combinations thereof with a nitric acid and sulfuric acid mixture under conditions to produce 2,4,6-trinitroaniline;
(A) reacting at temperature of between about 0.degree. and 30.degree. C. for between about 0.1 and 24 hr a trinitroaromatic starting material compound:
##STR8## 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 of X, Y, and Z is hydrogen;
with an effective amount of 4-amino-1,2,4-triazole;
in the presence of a strong base selected from the group consisting of sodium butoxide, potassium butoxide, potassium propoxide, sodium propoxide, sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, and mixtures thereof;
in a solvent selected from the group consisting of dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformamide, dimethylacetamide, and mixtures thereof;
and
(B) isolating the 1,3,5-triamino-2,4,6-trinitrobenzene produced.

15 more elements

Dependencies are inferred from the claim text.

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

Life of this patent

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

Life of this patent

Abstract

Claims20