Amination of electrophilic aromatic compounds by vicarious nucleophilic substitution
- Livermore, CA
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).
- 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 6069277
- OSTI ID:
- 873015
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
3-diamino-2
4-amino-1
4-triazole
5-diamino-2
5-triamino-2
6-trinitrobenzene
6-trinitrotoluene
alkoxylamines
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