A New Synthetic Route to 1,3,5-Triamino-2,4,6-Trinitrobenzene (TATB)

• Published in: Propellants, explosives, pyrotechnics Vol. 27; no. 2; pp. 49 - 58
• Main Authors: Bellamy, Anthony J., Ward, Simon J., Golding, Peter
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 01.04.2002; WILEY‐VCH Verlag GmbH
• ISSN: 0721-3115; 1521-4087
• DOI: 10.1002/1521-4087(200204)27:2<49::AID-PREP49>3.0.CO;2-4

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.