Conversion of the rocket propellant UDMH to a reagent useful in vicarious nucleophilic substitution reactions

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The objective of our program is to develop novel, innovative solutions for the disposal of surplus energetic materials resulting from the demilitarization of conventional and nuclear munitions. In this report we describe the use of surplus propellant (UDMH) and explosives (TNT, Explosive D) as chemical precursors for higher value products. The conversion of UDMH to 1,1,1-trimethylhydrazinium iodide (TMHI) provides a new aminating reagent for use in Vicarious Nucleophilic Substitution (VNS) reactions. When TMHI is reacted with various nitroarenes the amino functionality is introduced in good to excellent yields. Thus, 2,4,6-trinitroaniline (picramide) reacts with TMHI to give 1,3,5-triamino-2,4,6-trinitroaniline (TATB) while 2,4,6-trinitrotoluene ... continued below

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8 p.

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Mitchell, A.R.; Pagoria, P.F. & Schmidt, R.D. November 10, 1995.

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Description

The objective of our program is to develop novel, innovative solutions for the disposal of surplus energetic materials resulting from the demilitarization of conventional and nuclear munitions. In this report we describe the use of surplus propellant (UDMH) and explosives (TNT, Explosive D) as chemical precursors for higher value products. The conversion of UDMH to 1,1,1-trimethylhydrazinium iodide (TMHI) provides a new aminating reagent for use in Vicarious Nucleophilic Substitution (VNS) reactions. When TMHI is reacted with various nitroarenes the amino functionality is introduced in good to excellent yields. Thus, 2,4,6-trinitroaniline (picramide) reacts with TMHI to give 1,3,5-triamino-2,4,6-trinitroaniline (TATB) while 2,4,6-trinitrotoluene (TNT) reacts with TMHI to give 3,5-diamino-2,4,6-trinitrotoluene (DATNT). The advantages, scope and limitations of the VNS approach and the use of TMHI are discussed.

Physical Description

8 p.

Notes

OSTI as DE96009322

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  • Joint Army-Navy-NASA-Air Force safety and environmental protection subcommittee meeting, Tampa, FL (United States), 5-8 Dec 1995

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  • Other: DE96009322
  • Report No.: UCRL-JC--122489
  • Report No.: CONF-951262--7
  • Grant Number: W-7405-ENG-48
  • Office of Scientific & Technical Information Report Number: 226422
  • Archival Resource Key: ark:/67531/metadc670413

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Office of Scientific & Technical Information Technical Reports

Reports, articles and other documents harvested from the Office of Scientific and Technical Information.

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  • November 10, 1995

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  • June 29, 2015, 9:42 p.m.

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  • Feb. 16, 2016, 6:09 p.m.

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Mitchell, A.R.; Pagoria, P.F. & Schmidt, R.D. Conversion of the rocket propellant UDMH to a reagent useful in vicarious nucleophilic substitution reactions, article, November 10, 1995; California. (digital.library.unt.edu/ark:/67531/metadc670413/: accessed October 15, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.