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N-Nitropyridinium Nitrate: An Efficient Nitrating Agent for the Synthesis of 2-[Butyl(nitro)amino]ethyl Nitrate (n-BuNENA)

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The present investigation focused on the synthesis of 2-[butyl(nitro)amino]ethyl nitrate (n-BuNENA), by the nitration of N-butylethanolamine. For this purpose, various nitrating agents were studied and N-nitropyridinium nitrate was found to be a good nitrating agent. Short reaction time, ease of handling, performance of the reaction in one step and good yield are the main aspects of the present method. It also lead to 75% yield, which is a higher yield than by other methods. The purity of the product was evaluated by HPLC analysis, and its identity was confirmed by IR and 1H NMR spectroscopy.
Rocznik
Strony
838--844
Opis fizyczny
Bibliogr. 23 poz., rys., tab.
Twórcy
autor
  • Department of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, Tehran, Iran
  • Department of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, Tehran, Iran
Bibliografia
  • [1] Urbanski T., Chemistry and Technology of Explosives, Pergamon Press, PWN Polish Scientific Publishers, Warsaw, 1964.
  • [2] Agrawal J., Percent Trends in High Energy Materials, Prog. Energy Combust. Sci., 1998, 24, 1.
  • [3] Davenas A., Solid Propellants for Future Space Applications, European Space Agency, Special Publication, 2001, 484 (SP-484), 105.
  • [4] Agrawal J.P., Some New High Energy Materials and Their Formulations for Specialized Applications, Propellants Explos., Pyrotech., 2005, 30, 316.
  • [5] Schack C.J., Flanagan J.E., Alkyl, Azido, Nitro Ethers and Method of Preparation, tent US 4,522,756, 1985.
  • [6] Ou Y., Chen B., Yan H., Jia H., Li J., Dong S., Development of Energetic Additives for Propellants in China, J. Propul. Power, 1995, 11, 838.
  • [7] Wright G.F., Chute W.J., Nitramines and Their Preparation, Patent US 2,461,582, 1959.
  • [8] Chakraborthy T.K., Raha K.C., Omprakash B., Singh A., A Study on Gun Propellants Based on Butyl-NENA, J. Energ. Mater., 2004, 21, 41.
  • [9] Rao K.P.C. Sikder A.K. Kulkarni M.A. Bhalerao M.M. Gandhe B.R. Studies on n-Butyl Nitroxyethylnitramine (n-BuNENA): Synthesis, Characterization and Propellant Evaluations, Propellants Explos. Pyrotech., 2004, 29, 93.
  • [10] Blomquist A.T., Fiedorek F.T., Nitramines, Patent US 2,485,855, 1949.
  • [11] Blomquist A.T., Fiedorek F.T., Process of Preparing Nitroxy Alkyl Nitramines, Patent US 2,678,946, 1954.
  • [12] Chute W.J., Herring K.G., Toombs L.E., Wright G.F., Catalyzed Nitration of Amines: I. Dinitroxydiethylnitramine, Can. J. Res., 1948, 26B, 89.
  • [13] Frankel M.B., Vanneman C.R., Preparation of Aliphatic Secondary Nitramines, J. Org. Chem., 1958, 23, 1810.
  • [14] Olah G.A., Malhotra R., Narang S.C., Nitration: Methods and Mechanisms, Wiley VCH, 1989; ISBN 978-0-471-18695-3.
  • [15] Golding P., Millar R.W. Paul N.C., Richards D.H., Preparation of Nitraminenitrates by Ring-opening Nitration of Aziridines by Dinitrogen Pentoxide (N2O5), Tetrahedron, 1993, 49, 7063.
  • [16] Brown T.A., Watt J.A.C., Chemistry in Britain, 1967, 3, 504.
  • [17] Sitzmann M.E., Trivedi N.J., Skahan P.B., Kenar J.A., Nock L.A., Stern A.G., Investigation of an N-Butyl-N-(2-Nitroxyethyl)nitramine (BuNENA) Process: Identification of Process Intermediates, By-products and Reaction Pathways, Propellants Explos. Pyrotech., 2006, 31(2), 124–130.
  • [18] Olah G.A., Olah J.A., Overchuk N.A., Aromatic Substitution. XXIII. 1 Nitration and Nitrosation of Pyridine with Nitronium and Nitrosonium Tetrafluoroborate. Isolation of N-Nitro- and N-Nitrosopyridinium Tetrafluoroborates, J. Org. Chem., 1965, 30, 3373.
  • [19] Cupas C.A., Pearson R.L., Transfer Nitration via N-Nitropyridinium Salts, J. Am. Chem. Soc., 1968, 90, 4742.
  • [20] Bayat Y., Zolfigol M.A., Khazaei A., Mokhlesi M., Daraei M., Heydari Nezhad Tehrani A., Chehardoli G., Synthesis of 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12- hexaazaisowurtzitane Using Melaminium-tris-(hydrogensulfate) by a Simple One-pot Nitration Procedure, Propellants Explos. Pyrotech., 2013, 38, 745.
  • [21] Gruenhut N.S., Goldfrank M., Cushing M.L., Caesar P.D., Shoemaker C., Inorganic Synthesis., Vol. III, Ch. V, McGraw-Hill Book Company Inc., 1950, pp. 78-81.
  • [22] Tao D.J., Wu J., Wang Z.Z., Lu Z.H., Yang Z., Chen X.S., SO3H-Functionalized Brønsted Acidic Ionic Liquids as Efficient Catalysts for the Synthesis of Isoamyl Salicylate, RSC Adv., 2014, 4, 1.
  • [23] Bakke J.M., Riha J., Nitration of Pyridine Compounds. The Reaction of N-Nitro-1,4-dihydro-4-pyridinesulfonic Acid, Acta Chem. Scand., 1999, 53, 356.
Uwagi
Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę (zadania 2017).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-8cff27f0-ebc1-4ef7-8483-abb609cd4a62
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