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International Journal of Energetic Materials and Chemical Propulsion
ESCI SJR: 0.149 SNIP: 0.16 CiteScore™: 0.29

ISSN Imprimir: 2150-766X
ISSN On-line: 2150-7678

International Journal of Energetic Materials and Chemical Propulsion

DOI: 10.1615/IntJEnergeticMaterialsChemProp.2014011184
pages 309-318

EXPERIMENTAL INVESTIGATIONS OF 1,4-DI(AZIDOMETHYL)-1',4'-DIMETHYL-2-TETRAZENE AND 1-AZIDOMETHYL-1',4,4'-TRIMETHYL-2-TETRAZENE FOR THE REPLACEMENT OF HYDRAZINES IN BIPROPELLANT SYSTEMS−SYNTHESIS AND OPTIMIZATION

Teddy Gilloux
Universite Claude Bernard Lyon 1, Laboratoire Hydrazines et Composes Energetiques Polyazotes, UMR 5278, UCBL/CNRS/CNES/Herakles (Safran)
Chaza Darwich
Universite Claude Bernard Lyon 1, Laboratoire Hydrazines et Composes Energetiques Polyazotes, UMR 5278, UCBL/CNRS/CNES/Herakles (Safran), 22 avenue Gaston Berger, 69622 Villeurbanne, France
Lionel Joucla
Universite Claude Bernard Lyon 1, Laboratoire Hydrazines et Composes Energetiques Polyazotes, UMR 5278, UCBL/CNRS/CNES/Herakles (Safran), 22 avenue Gaston Berger, 69622 Villeurbanne, France
Guy Jacob
Universite Claude Bernard Lyon 1, Laboratoire Hydrazines et Composes Energetiques Polyazotes, UMR 5278, UCBL/CNRS/CNES/Herakles (Safran), 22 avenue Gaston Berger, 69622 Villeurbanne, France; Direction Recherche et Technologie, Herakles (Safran)
Emilie Labarthe
CNES, Direction des Lanceurs, SDT Equipements Propulsifs et Mecanismes, 52 rue Jacques Hillairet, 75012 Paris, France
Henri Delalu
Universite Claude Bernard Lyon 1, Laboratoire Hydrazines et Composes Energetiques Polyazotes, UMR 5278, UCBL/CNRS/CNES/Herakles (Safran), 22 avenue Gaston Berger, 69622 Villeurbanne, France

RESUMO

A new azidonation reaction has been realized on 1,1',4,4'-tetramethyl-2-tetrazene (TMTZ) using iodosylbenzene/trimethylsilyl azide couple (PhIO/TMSN3). This one-step synthesis has led to two azido derivatives: 1-azidomethyl-1',4,4'-trimethyl-2-tetrazene (MATMTZ) and 1,4-di(azidomethyl)-Y,4'-dimethyl-2-tetrazene (DADMTZ). Several conditions were tested such as TMTZ concentration, temperature, and reagent number of equivalents in order to increase the yield of the reaction and to optimize the MATMTZ/DADMTZ ratio. Due to the low thermal stability in solution of these two molecules, we decided to study their decomposition in solution at different temperatures using proton NMR analysis and quantitative NMR. Results showed that DADMTZ is more stable than MATMTZ.

Referências

  1. Magnus, P. and Lacour, J., New Trialkylsilyl Enol Ether Chemistry. Direct β-Azido Functionalization of Triisopropylsilyl Enol Ethers.

  2. Magnus, P., Lacour, J., and Weber, W., Direct N-Alkyl Azidonation of N,N-Dialkylarylamines with the Iodosylbenzene/Trimethylsilylazide Reagent Combination.

  3. Magnus, P., Hulme, C., and Weber, W. , α-Azidonation of Amides, Carbamates, and Ureas with the Iodosylbenzene/Trimethylsilyl Azide Reagent Combination: N-Acyliminium Ion Precursors.

  4. Sabate, C. M., Delalu, H., Guelou, Y., Dhenain, A., and Perut, C., Process for Preparing Alkyltetrazenes.

  5. Varvoglis, A., Hypervalent Iodine In Organic Synthesis.

  6. Zefirov, N. S., Safromov, S. O., Kaznacheev, A. A., and Zdhankin, V. V. , General synthetic approach to aryliodoso compounds under aprotic conditions by the reaction of iodosobenzene with substituted trimethyl silanes.


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