Synthesis of 4,4'-Dimethyl-3,3',5,5'-Tetranitroazoxybenzene by Selective Reduction of Trinitrotolune

  • U.S. Prasad High Energy Materials Research Laboratory, Pune
  • Mehi Lal High Energy Materials Research Laboratory, Pune
  • R.N. Surve High Energy Materials Research Laboratory, Pune
  • J.P. Agarwal High Energy Materials Research Laboratory, Pune
Keywords: Explosives

Abstract

Selective reduction of trinitrotoluene in dioxane solution by H/sub 2/S/NH/sub 3/ yields a mixture containing 4-amino-2,6-dinitrotoluene, 4-hydroxylamino-2,6-dinitrotoluene and 4,4'-dimethyl- 3,3',5,5'-tetranitroazoxybenzene. Treatment of crude mixture with KI/HCl converts 4-hydroxylamino-2,6-dinitrotoluene into 4-amino-2,6-dinitrotoluene as well as increases the percentage of 4,4'-dimethyl-3,3,5,5'-tetranitroazoxybenzene. The resulting compound 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) was isolated and characterised by IR, NMR and elemental analysis. Its thermal decomposition as well as explosive properties have been studied. The data indicate that TATB is stable up to 294 °c and is also insensitive to impact and friction.

Author Biographies

U.S. Prasad, High Energy Materials Research Laboratory, Pune
Mr US Prasad received his MSc (Organic Chemistry) from the University of Poona in 1984. He joined High Energy Materials Research Laboratory (HEMRL), Pune, in 1987 and since then, he has been working in the field of synthesis of high energy and allied materials.
Mehi Lal, High Energy Materials Research Laboratory, Pune
Dr Mebi Lal joined DRDO at HEMRL in 1985 and made significant contributions in the development of plastic-bonded explosives (PBXs). He is working in the field of high energy materials and has developed a process for the synthesis of TATB.
R.N. Surve, High Energy Materials Research Laboratory, Pune
Dr RN Surve has been working as Scientist at HEMRL, Pune, since 1965. He has made significant contributions in the field of initiatory explosives and high explosives. With his sincere efforts, developed and introduced safe initiatory explosive, basic lead azide (BLA), TOT for basic lead azide has been successfully transferred to ordnance factories. A number of detonators have been developed using BLA, which are in production at ordnance factories. He has developed a number of processes for various thermally-stable high explosives. He was given DRDO Cash Award (1989) with citation for successful development of technology for BLA tubular detonators.
J.P. Agarwal, High Energy Materials Research Laboratory, Pune
Dr JP Agrawal, Joint Director, HEMRAL has a background of brilliant academic career and valuable professional experience. He obtained his PhD for his work on explosive nature of metal picrates and picramates' from Gorakhpur University in 1971. His areas of interest are cost-effective polymeric materials, such as unsaturated polyesters, chloropolyesters, epoxy resins, epoxy flexibilizers, silicons and polyurethanes which find applications as inhibitors for rocket propellants and binders for explosives/pyrotechnics etc. At present, He is active in the field of thermally stable explosives, high performance explosives, insensitive explosives and energetic additives for explosives/propellants and has contributed immensely in this area. He has made significant contributions in the field of inhibition of rocket proellants. The development of filament winding technology and inhibitor sleeve technology are some of his major achievements for inhibition of composite rocket propellants. He was given DRDO Cash Award and Commendation Certificate for his significant contributions to the integrated guided missile development programme. He also given , DRDO Technology Award (1996) for the development of mine antipersonnal inflammable (MAPI).
Published
2013-01-01
How to Cite
PrasadU., LalM., SurveR., & AgarwalJ. (2013). Synthesis of 4,4’-Dimethyl-3,3’,5,5’-Tetranitroazoxybenzene by Selective Reduction of Trinitrotolune. Defence Science Journal, 48(3), 323-328. https://doi.org/10.14429/dsj.48.3955
Section
Armaments & Explosives