A New Synthetic Route to 1,3,5-Triamino-2,4,6-Trinitrobenzene (TATB)
A new, three‐stage synthesis of 1,3,5‐triamino‐2,4,6‐trinitrobenzene (TATB) has been developed which avoids the use of halogenated precursors or reagents. The starting material, 1,3,5‐trihydroxy‐benzene, is converted via the sequence nitration‐alkylation‐amination to TATB in an overall yield of 87%....
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| Published in | Propellants, explosives, pyrotechnics Vol. 27; no. 2; pp. 49 - 58 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag GmbH
01.04.2002
WILEY‐VCH Verlag GmbH |
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| Abstract | A new, three‐stage synthesis of 1,3,5‐triamino‐2,4,6‐trinitrobenzene (TATB) has been developed which avoids the use of halogenated precursors or reagents. The starting material, 1,3,5‐trihydroxy‐benzene, is converted via the sequence nitration‐alkylation‐amination to TATB in an overall yield of 87%. The product, when 1,3,5‐tripropoxy‐2,4,6‐trinitrobenzene is the intermediate subjected to amination, is directly comparable, in terms of purity and thermal stability, to TATB synthesized from trichlorobenzene. An analogous route has been used to convert 1,3‐dihydroxybenzene to 1,3‐diamino‐2,4,6‐trinitrobenzene (DATB), and phenol to picramide via picric acid. |
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| AbstractList | A new, three‐stage synthesis of 1,3,5‐triamino‐2,4,6‐trinitrobenzene (TATB) has been developed which avoids the use of halogenated precursors or reagents. The starting material, 1,3,5‐trihydroxy‐benzene, is converted via the sequence nitration‐alkylation‐amination to TATB in an overall yield of 87%. The product, when 1,3,5‐tripropoxy‐2,4,6‐trinitrobenzene is the intermediate subjected to amination, is directly comparable, in terms of purity and thermal stability, to TATB synthesized from trichlorobenzene. An analogous route has been used to convert 1,3‐dihydroxybenzene to 1,3‐diamino‐2,4,6‐trinitrobenzene (DATB), and phenol to picramide via picric acid. |
| Author | Golding, Peter Bellamy, Anthony J. Ward, Simon J. |
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| References | J. J. Wolff and H.-H. Limbach , Liebigs Ann. Chem., 691 (1991). A. J. Bellamy , P. Golding , and S. J. Ward , J. Chem. Res., 2002, in press. S. V. Dubiel and S. Zuffanti , J. Org. Chem. 19, 1359 (1954). A. J. Bellamy , P. Golding , and S. J. Ward , Propellants, Explosives, Pyrotechnics, 27, 57 (2002). A. P. Marchand and G. M. Reddy , Synthesis, 261 (1992). B. Smith , Acta Chem. Scand. 10, 1006 (1956). 1954 1992 1956 1991 2002 |
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| Snippet | A new, three‐stage synthesis of 1,3,5‐triamino‐2,4,6‐trinitrobenzene (TATB) has been developed which avoids the use of halogenated precursors or reagents. The... |
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| Title | A New Synthetic Route to 1,3,5-Triamino-2,4,6-Trinitrobenzene (TATB) |
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