Skip to main content
OSTI.GOVU.S. Department of Energy Office of Scientific and Technical Information
U.S. Department of Energy
Office of Scientific and Technical Information
 

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
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)

Reactions of organic anions. 194. Amination of nitroarenes with sulfenamides via vicarious nucleophilic substitution of hydrogen journal August 1992
Alkylaminonitrobenzenes by vicarious nucleophilic amination with 4-(alkylamino)-1,2,4-triazoles journal August 1988
Über die Alkylierung des Hydrazins journal May 1941
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
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
Vicarious nucleophilic substitution of hydrogen journal August 1987
Shock Sensitivity of Explosives Clarified journal August 1987

Similar Records

Related Subjects

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