Journal of the Korea Institute of Military Science and Technology (한국군사과학기술학회지)

The Korea Institute of Military Science and Technology (한국군사과학기술학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of 2,6-Diamino-4-Nitrotoluene using Gas Chromatography Monitoring in the Reduction of Trinitrotoulene

Trinitrotoluene의 환원반응에서 가스크로마토그래피 모니터링을 이용한 2,6-diamino-4-nitrotoluene의 합성

  • Received : 2013.12.29
  • Accepted : 2014.03.29
  • Published : 2014.04.05
Download PDF
⟨ Previous Next ⟩

Abstract

In this research, we investigated synthetic method of 2,6-DANT that can be used as a chain extender of urethane/urea and epoxy materials in a demilitarization method via chemical transformations considering environmental, economical aspects and stability of process. We was able to identify through GC monitoring that 2,4-DANT and 2,6-DANT were produced when we inject 'hydrazine monohydrate 3.3 eq. by TNT 1 eq.' with a fine metering pump for 30 minutes and then, reflux for an additional 2 hours. We was able to isolate only 2,6-DANT(99.3% purity and 45.0% yield) from mixture of 2,4-DANT and 2,6-DANT through the separating and refining methods using 2,6-DANT solubility in methanol and crystallinity of 2,6-DANT.

Keywords

References

  1. P. Bayman, V. R. Gauri, "Ttansformation and Tolerance of TNT(2,4,6-trinitrotoluene) by Fungi," International Biodegradation & Biodegradation, 39, pp. 45-53, 1996.
  2. W. D. Won, L. H. Disalvo, and I. Ng, "Toxicity and Mutagenecity of 2,4,6-Trinitro-Toluene and Its Microbial Metabolites," Appl. Environ. Microbiol., 31, pp. 576-580, 1976.
  3. R. Boopathy, "Bioremediation of Explosives Contaminated Soil," International Biodegradation & Biodegradation, 46, pp. 29-36, 2000. https://doi.org/10.1016/S0964-8305(00)00051-2
  4. D. Juck, B. T. Driscoll, T. C. Charles and C. W. Greer, "Effect of Experimental Contamination with the Explosive Hexahydro-1,3,5-Trinitro-1,3,5-Triazine on Soil Bacterial Communities", Microbiology Ecology, 1453, pp. 1-8, 2002.
  5. S. E. George, G. Huggins-clark and L. R. Brooks, "Use of a Salmonella Microsuspension Bioassay to Detect the Mutagenicity of Munitions Compounds at Low Concentrations," Mutation Research., 490, pp. 45-46, 2001. https://doi.org/10.1016/S1383-5718(00)00150-9
  6. E. P. Best, S. L. Sprecher, S. L. Larson, H. L. Fredrickson and D. F. Bader, "Environmental Behavior of Explosives in Groundwater from the Milan Army Ammunition Plant in Aquatic and Wetland Plant Treatment. Removal, Mass Balances and Fate in Groundwater of TNT and RDX," Chemosphere, 38, pp. 3383-3396, 1999. https://doi.org/10.1016/S0045-6535(98)00550-5
  7. R. Bhrada, "Characterization of Oxidation Products of TNT Metabolism in Aquatic Phytoremediation Systems of Myriophyllum Aquaticum," Environ. Sci Technol., 33, pp. 3354-3461, 1999. https://doi.org/10.1021/es990436i
  8. Edval Lab., "Preparation of Symmetrical Triamino- Benzene Compounds," Patent, US2461498.
  9. A. Burger, M. L. Stein and J. B. Clements, "Some Pyridylnitroalkens, Nitroalkanols, and Alkylamines," J. Org. Chem., 22, pp. 143-144, 1957. https://doi.org/10.1021/jo01353a010
  10. A. T. Nielsen, "The Isomeric Dinitrocyclo-hexanes. II. Stereochemistry," J. Org. Chem., 27, pp. 1998- 2001, 1962. https://doi.org/10.1021/jo01053a019
  11. O. Temme, T. Dickner, S. Laschat, R. Frohlich, S. Kotila and K. Bergander, "Synthesis of Azapolycyclic Systems Based on the Indolizino [3,4-b] Quinoline Skeleton - A Diastereo-Selective Entry to Portential Oligodentate Artificial Receptors," Eur. J. Org. Chem., 4, p. 651, 1998.
  12. Hirashima T, Manabe O., "Catalytic Reduction of Aromatic Nitro Compound with Hydrazine in the Presence of Iron(III) Chloride and Active Carbon," Chem Lrtt, 4, pp. 259-260, 1975.
  13. John W. Larsen, Michael Freund, Kwang Y. Kim, Matthew Sidovar, "Mechanism of the Carbon Catalyzed Reduction of Nitrobenzene by Hydrazine," Carbon, 38, pp. 655-661, 2000. https://doi.org/10.1016/S0008-6223(99)00155-4