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

Patent ·
OSTI ID:870667
 [1];  [1];  [1]
  1. Livermore, CA
+ Show Author Affiliations

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).

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 5569783
OSTI ID:
870667
Country of Publication:
United States
Language:
English

References (10)

Preparation of Picramide journal September 1946
The Reaction of Chloramine with Tertiary Amines. 1 1,1,1-Trisubstituted Hydrazinium Salts 2 journal March 1956
Direct amination of nitrobenzenes by vicarious nucleophilic substitution journal December 1986
Identification of 1,3,5-triamino-2,4-6-trinitrobenzene impurities by two-dimensional thin-layer chromatography journal September 1972
Synthesis of polynitro compounds. Hexasubstituted benzenes journal August 1986
Reactions of organic anions. 194. Amination of nitroarenes with sulfenamides via vicarious nucleophilic substitution of hydrogen journal August 1992
Vicarious nucleophilic substitution of hydrogen journal August 1987
Shock Sensitivity of Explosives Clarified journal August 1987
Alkylaminonitrobenzenes by vicarious nucleophilic amination with 4-(alkylamino)-1,2,4-triazoles journal August 1988
Über die Alkylierung des Hydrazins journal May 1941

Similar Records

Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene
Patent · Tue Oct 29 00:00:00 EST 1996 · OSTI ID:870667
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
Patent · Wed Jan 01 00:00:00 EST 1997 · OSTI ID:870667
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
Patent · Tue May 27 00:00:00 EDT 1997 · OSTI ID:870667

Related Subjects

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
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