New aminating reagents forthe synthesis of 1,3,5-Triamino-2,4,6-Trinitrobenzene (TATB) and other insensitive energetic materials

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We are investigating the amination of electrophilic aromatic systems through the use of Vicarious Nucleophilic Substitution (VNS) chemistry. This research has led to a new synthesis of 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB) and 1,3-diamino-2,4,6-trinitrobenzene (DATB) which uses 2,4,6-trinitroaniline (picramide) or 1,3,5-trinitrobenzene as starting materials. We also describe the development of a new class of VNS aminating reagents based on quarternary hydrazinium halides. 1,1,1-Trimethylhydrazinium iodide (TMHI), available from the methylation of the surplus propellant uns-dimethylhydrazine (UDMH), was used in a new synthesis of TATB. The advantages, scope and limitations of the VNS approach to the synthesis of TATB and other amino-substituted nitroarenes are discussed.

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6 p.

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Pagoria, P.F.; Mitchell, A.R. & Schmidt, R.D. September 19, 1995.

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We are investigating the amination of electrophilic aromatic systems through the use of Vicarious Nucleophilic Substitution (VNS) chemistry. This research has led to a new synthesis of 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB) and 1,3-diamino-2,4,6-trinitrobenzene (DATB) which uses 2,4,6-trinitroaniline (picramide) or 1,3,5-trinitrobenzene as starting materials. We also describe the development of a new class of VNS aminating reagents based on quarternary hydrazinium halides. 1,1,1-Trimethylhydrazinium iodide (TMHI), available from the methylation of the surplus propellant uns-dimethylhydrazine (UDMH), was used in a new synthesis of TATB. The advantages, scope and limitations of the VNS approach to the synthesis of TATB and other amino-substituted nitroarenes are discussed.

Physical Description

6 p.

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OSTI as DE96007550

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  • American Defense Preparedness Association (ADPA) international symposium on energetic material technology, Phoenix, AZ (United States), 24-27 Sep 1995

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  • Other: DE96007550
  • Report No.: UCRL-JC--121967
  • Report No.: CONF-9509213--3
  • Grant Number: W-7405-ENG-48
  • Office of Scientific & Technical Information Report Number: 205208
  • Archival Resource Key: ark:/67531/metadc669778

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  • September 19, 1995

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  • June 29, 2015, 9:42 p.m.

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  • Feb. 19, 2016, 8:23 p.m.

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Pagoria, P.F.; Mitchell, A.R. & Schmidt, R.D. New aminating reagents forthe synthesis of 1,3,5-Triamino-2,4,6-Trinitrobenzene (TATB) and other insensitive energetic materials, article, September 19, 1995; California. (https://digital.library.unt.edu/ark:/67531/metadc669778/: accessed May 22, 2019), University of North Texas Libraries, Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.