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New synthesis of TATB. Process development studies
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Abstract
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.
- Authors:
- Publication Date:
- Research Org.:
- Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
- Sponsoring Org.:
- USDOE, Washington, DC (United States)
- OSTI Identifier:
- 675084
- Report Number(s):
- UCRL-JC-130089-Rev.1; CONF-9806105-
ON: DE98058880; BR: DP0401047; CNN: W-7405-Eng-48
- DOE Contract Number:
- W-7405-ENG-48
- Resource Type:
- Conference
- Resource Relation:
- Conference: Joint Working Group (JOWOG) 9, Aldermaston (United Kingdom), 22-26 Jun 1998; Other Information: PBD: 1 May 1998
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 45 MILITARY TECHNOLOGY, WEAPONRY, AND NATIONAL DEFENSE; 40 CHEMISTRY; SYNTHESIS; TATB; REACTION KINETICS; PERFORMANCE TESTING; PARTICLE SIZE; HYDROGEN
Citation Formats
Schmidt, R. D., LLNL. New synthesis of TATB. Process development studies. United States: N. p., 1998.
Web.
Schmidt, R. D., LLNL. New synthesis of TATB. Process development studies. United States.
Schmidt, R. D., LLNL. 1998.
"New synthesis of TATB. Process development studies". United States. https://www.osti.gov/servlets/purl/675084.
@article{osti_675084,
title = {New synthesis of TATB. Process development studies},
author = {Schmidt, R. D., LLNL},
abstractNote = {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.},
doi = {},
url = {https://www.osti.gov/biblio/675084},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Fri May 01 00:00:00 EDT 1998},
month = {Fri May 01 00:00:00 EDT 1998}
}