New synthesis of TATB. Process development studies

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We have discovered that 1,1,1-trialkylhydrazinium salts are highly reactive reagents which aminate nitroaromatic compounds through vicarious nucleophilic substitution (VNS) of hydrogen. When applied to picramide, these reagents produce TATB in high yield. Traditionally, TATB has been manufactured in the USA by nitration of the relatively expensive and domestically unavailable 1,3,5- trichlorobenzene (TCB) to give 2,4,6-trichloro- 1,3,5- trinitrobenzene (TCTNB) which is then aminated to yield TATB. Elevated temperatures (1500 C) are required for both reactions. Our new VNS synthesis potentially affords an inexpensive and a more environmentally benign preparation of TATB. We describe in this report our progress in scaling up ... continued below

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14 p.

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Schmidt, R. D., LLNL May 1, 1998.

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Description

We have discovered that 1,1,1-trialkylhydrazinium salts are highly reactive reagents which aminate nitroaromatic compounds through vicarious nucleophilic substitution (VNS) of hydrogen. When applied to picramide, these reagents produce TATB in high yield. Traditionally, TATB has been manufactured in the USA by nitration of the relatively expensive and domestically unavailable 1,3,5- trichlorobenzene (TCB) to give 2,4,6-trichloro- 1,3,5- trinitrobenzene (TCTNB) which is then aminated to yield TATB. Elevated temperatures (1500 C) are required for both reactions. Our new VNS synthesis potentially affords an inexpensive and a more environmentally benign preparation of TATB. We describe in this report our progress in scaling up the synthesis of TATB from the laboratory to the pilot plant. We will discuss structure and control of impurities, changes in yield/quality with reaction conditions, choice of solvents, workup and product isolation, safety, and environmental considerations. Particle size characterizations as well as small-scale safety and performance testing will also be discussed.

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14 p.

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OSTI as DE98058880

Other: FDE: PDF; PL:

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  • Joint Working Group (JOWOG) 9, Aldermaston (United Kingdom), 22-26 Jun 1998

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  • Other: DE98058880
  • Report No.: UCRL-JC--130089-Rev.1
  • Report No.: CONF-9806105--
  • Grant Number: W-7405-ENG-48
  • Office of Scientific & Technical Information Report Number: 675084
  • Archival Resource Key: ark:/67531/metadc710254

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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.

Office of Scientific and Technical Information (OSTI) is the Department of Energy (DOE) office that collects, preserves, and disseminates DOE-sponsored research and development (R&D) results that are the outcomes of R&D projects or other funded activities at DOE labs and facilities nationwide and grantees at universities and other institutions.

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  • May 1, 1998

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  • Sept. 12, 2015, 6:31 a.m.

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  • April 10, 2017, 1:39 p.m.

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Schmidt, R. D., LLNL. New synthesis of TATB. Process development studies, article, May 1, 1998; California. (digital.library.unt.edu/ark:/67531/metadc710254/: accessed June 20, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.