skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution

Abstract

The present invention relates to a process to aminate electrophilic aromatic compounds by vicarious nucleophilic substitution of hydrogen using quaternary hydrazinium salts. The use of trialkylhydrazinium halide, e.g., trimethylhydrazinium iodide, as well as hydroxylamine, alkoxylamines, and 4-amino-1,2,4-triazole to produce aminated aromatic structures, such as 1,3-diamino-2,4,6-trinitrobenzene (DATB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and 3,5-diamino-2,4,6-trinitrotoluene (DATNT), is described. DATB and TATB are useful insensitive high 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).

Inventors:
; ;
Publication Date:
Research Org.:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
20050822
Application Number:
Int. Cl. C07C 209/02; US 6,069,277/A/; 8-967,914; TRN: IM200024%%333
Assignee:
LLNL; EDB-00:033428
DOE Contract Number:  
W-7405-ENG-48
Resource Type:
Patent
Resource Relation:
Other Information: PBD: 30 May 2000
Country of Publication:
United States
Language:
English
Subject:
45 MILITARY TECHNOLOGY, WEAPONRY, AND NATIONAL DEFENSE; AROMATICS; AMINATION; CHEMICAL PREPARATION; TATB; CHEMICAL EXPLOSIVES

Citation Formats

Mitchell, A.R., Pagoria, P.F., and Schmidt, R.D. Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution. United States: N. p., 2000. Web.
Mitchell, A.R., Pagoria, P.F., & Schmidt, R.D. Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution. United States.
Mitchell, A.R., Pagoria, P.F., and Schmidt, R.D. Tue . "Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution". United States.
@article{osti_20050822,
title = {Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution},
author = {Mitchell, A.R. and Pagoria, P.F. and Schmidt, R.D.},
abstractNote = {The present invention relates to a process to aminate electrophilic aromatic compounds by vicarious nucleophilic substitution of hydrogen using quaternary hydrazinium salts. The use of trialkylhydrazinium halide, e.g., trimethylhydrazinium iodide, as well as hydroxylamine, alkoxylamines, and 4-amino-1,2,4-triazole to produce aminated aromatic structures, such as 1,3-diamino-2,4,6-trinitrobenzene (DATB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and 3,5-diamino-2,4,6-trinitrotoluene (DATNT), is described. DATB and TATB are useful insensitive high 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 = {2000},
month = {5}
}