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 »
- Inventors:
-
- Livermore, CA
- Issue Date:
- Research Org.:
- Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
- OSTI Identifier:
- 870667
- Patent Number(s):
- 5569783
- Assignee:
- Regents of University of California (Oakland, CA)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y10 - TECHNICAL SUBJECTS COVERED BY FORMER USPC Y10T - TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- 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. Mon .
"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 = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1996},
month = {1}
}
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