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
- Livermore, CA
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.
- Research Organization:
- Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
- DOE Contract Number:
- W-7405-ENG-48
- Assignee:
- Regents of University of California (Oakland, CA)
- Patent Number(s):
- US 5633406
- OSTI ID:
- 870969
- Country of Publication:
- United States
- Language:
- English
Similar Records
Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene
Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene
Related Subjects
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/