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International Journal of Energetic Materials and Chemical Propulsion
ESCI SJR: 0.142 SNIP: 0.16 CiteScore™: 0.29

ISSN Imprimer: 2150-766X
ISSN En ligne: 2150-7678

International Journal of Energetic Materials and Chemical Propulsion

DOI: 10.1615/IntJEnergeticMaterialsChemProp.v5.i1-6.1060
pages 1031-1047

CHEMICAL CONVERSION OF 2.4.6-TRINITROTOLUENE (TNT) TO NEW HIGH PERFORMANCE POLYMERS

A. L. Rusanov
A.N. Nesmeyanov bstitute of Organo-Element Compounds, Russian Academy of Sciences, 117813, 28 Vavilov Str., Moscow, Russia
L. G. Komarova
A.N.Nesmeyanov institute of Organo-Element Compounds, Russian Academy of Sciences, 117813, 28 Vavilov St., Moscow, Russia
M. P. Prigozhina
A.N.Nesmeyanov institute of Organo-Element Compounds, Russian Academy of Sciences, 117813, 28 Vavilov St., Moscow, Russia
V. A. Tartakovsky
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 117913, Leninsky prospekt 47, Moscow, Russia
S. A. Shevelev
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 117913, Leninsky prospekt 47, Moscow, Russia
M. D. Dutov
N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 117013, 47 Leninsky Prospect, Moscow, Russia

RÉSUMÉ

2,4,6-Trinitrotoluene (TNT) is a well-known military explosive. For chemists, however, TNT represents a polyfunctional molecule that could serve as a source for various higher value products. We have systematically investigated numerous chemical transformations of TNT with the goal of producing useful materials for civilian applications. We have developed techniques for the selective conversion of the nitro and methyl groups in TNT, which has allowed the subsequent production of new high performance polymers.
We initially converted TNT to 1,3,5-trinitrobenzene (TNB). TNB was then transformed into a variety of dinitro-and diaminoarenes containing phenoxy, thiophenoxy, phenylsulfoxide and phenylsulfone substituents. The substituted dinitroarenes were used for the preparation of aromatic polyethers. The substituted diaminoarenes were used for the preparation of aromatic polyamides and polyimides having improved processibilities combined with good thermal and mechanical properties.