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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

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 --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 imagingmore » devices, liquid crystals, ferromagnetic compounds).« less

Inventors:
 [1];  [1];  [1]
  1. Livermore, CA
Publication Date:
Research Org.:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
OSTI Identifier:
870667
Patent Number(s):
US 5569783
Assignee:
Regents of University of California (Oakland, CA)
DOE Contract Number:  
W-7405-ENG-48
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
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; /74/999/

Citation Formats

Mitchell, Alexander R, Pagoria, Philip F, and Schmidt, Robert D. Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene. United States: N. p., 1996. Web.
Mitchell, Alexander R, Pagoria, Philip F, & Schmidt, Robert D. Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene. United States.
Mitchell, Alexander R, Pagoria, Philip F, and Schmidt, Robert D. 1996. "Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene". United States. https://www.osti.gov/servlets/purl/870667.
@article{osti_870667,
title = {Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene},
author = {Mitchell, Alexander R and Pagoria, Philip F and Schmidt, Robert D},
abstractNote = {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).},
doi = {},
url = {https://www.osti.gov/biblio/870667}, journal = {},
number = ,
volume = ,
place = {United States},
year = {1996},
month = {1}
}

Works referenced in this record:

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


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