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Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution

United States Patent

6,069,277
May 30, 2000
View the Complete Patent at the US Patent & Trademark Office
Lawrence Livermore National Laboratory - Visit the Industrial Partnerships Office Website
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).
Mitchell; Alexander R. (Livermore, CA), Pagoria; Philip F. (Livermore, CA), Schmidt; Robert D. (Livermore, CA)
The Regents of the University of California (Oakland, CA)
08/ 967,914
November 12, 1997
ORIGIN OF THE INVENTION The United States Government has rights in this invention pursuant to Contract No. W-7405-ENG-48 between the U.S. Department of Energy and the University of California, for the operation of Lawrence Livermore National Laboratory, Livermore, Calif.