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Nitration of γ-Cyclodextrin

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A number of γ-cyclodextrin (γ-CD) nitration reactions were conducted with different times, temperatures and types of nitrating mixtures. The degree and yield of γ-CD nitration (γ-CDN) depended on the HNO3 concentration, the type of nitrating mixture, the nitration time and, to a lesser extent, the temperature. 100% HNO3 proved to be the finest nitrating agent. By nitrating γ-CD in this system, a degree of nitration of 1, as well as a yield of 90-99% were obtained. An examination of the properties of the resulting γ-CDN served to conclude that the density and sensitivity to mechanical stimuli (friction and impact) depend on the degree of substitution of the –OH groups with –ONO2 groups. The higher the degree of γ-CD nitration, the greater the density and sensitivity to external stimuli. Thermal analysis of the γ-CDN obtained at various nitration levels demonstrated that γ-CDN with a high degree of substitution decomposes in one exothermic stage, at temperatures of approximately 184-250 °C. The lower the degree of γ-CDN nitration, the lower is the thermal effect of decomposition, with the maximum exothermic peak being shifted increasingly towards a higher temperature.
Słowa kluczowe
Rocznik
Strony
362--383
Opis fizyczny
Bibliogr. 21 poz., rys., tab.
Twórcy
  • Warsaw University of Technology, Faculty of Chemistry, The Division of High Energetic Materials, 3 Noakowskiego Street, 00-664 Warsaw, Poland
  • Warsaw University of Technology, Faculty of Chemistry, The Division of High Energetic Materials, 3 Noakowskiego Street, 00-664 Warsaw, Poland
Bibliografia
  • [1] Del Valle, E.M.M. Cyclodextrins and Their Uses: A Review. Process Biochem. 2004, 39(9): 1033-1046.
  • [2] Szejtli, J. Introduction and General Overview of Cyclodextrin Chemistry. Chem. Rev. 1998, 98(5): 1743-1754.
  • [3] Szejtli, J. Cyclodextrin Technology. Kluwer Academic Publishers, Dordrecht/Boston/London, 1988, pp. 6-7; ISBN 978-90-481-8427-9.
  • [4] Bender, M.L.; Komiyama, M. Cyclodextrin Chemistry. Springer-Verlag, Berlin/Heidelberg/New York, 1978; ISBN 978-3-642-66844-9.
  • [5] Śliwa, W.; Girek, T. Cyclodextrin, Properties and Applications. Wiley-VCH Verlag GmbH & Co. KGaA, Germany, 2017; ISBN: 978-3-527-33980-8.
  • [6] Singh, R.; Bharti, N.; Madan, J. Characterization of Cyclodextrin Inclusion Complexes – A Review. J. Pharm. Sci. Technol. 2010, 2(3): 171-183.
  • [7] Szejtli, J. Past, Present, and Future of Cyclodextrin Research. Pure Appl. Chem. 2004, 76(10): 1825-1845.
  • [8] Deshmukh, M.B.; Wagh, N.D.; Sikder, A.K.; Borse, A.U. Cyclodextrin Nitrate Ester/H2SO4 as a Novel Nitrating System for Efficient Synthesis of Insensitive High Explosive 3-Nitro-1,2,4-triazol-5-one. Ind. Eng. Chem. Res. 2014, 53: 19375-19379.
  • [9] Luppi, F.; Cavaye, H.; Dossi, E. Nitrated Cross-linked β-Cyclodextrin Binders Exhibiting Low Glass Transition Temperatures. Propellants, Explos., Pyrotech. 2018, 43(10): 1023-1031.
  • [10] Consaga, J.P.; Gill, R.C. Synthesis and Use of Cyclodextrin Nitrate. Int. Annual Conf. ICT, Proc., 29th, Karlsruhe, 1998, V5/1-V5/6.
  • [11] Statton, G.L.; Kosowski, B.M. Synthesis of Cyclodextrin Polymer (Poly CD), a Raw Material for Insensitive, High Energy and Shock Survivable Explosives. Int. Annual Conf. ICT, Proc., 29th, Karlsruhe, 1998, P46/1-P46/12.
  • [12] Ruebner, A.; Statton, G.L.; Meyers, C.; Kosowski, B.M.; Robitelle, D. Cyclodextrin Polymer Nitrate. Int. Annual Conf. ICT, Proc., 31st, Karlsruhe, 2000, V12/1-V12/10.
  • [13] Consaga, J.P.; Collignon, S.L. Energetic Composites of Cyclodextrin Nitrate Esters and Nitrate Ester Plasticizers. Patent US 5114506, 1992.
  • [14] Ruebner, A.; Statton, G.L.; Consaga, J.P. Polymeric Cyclodextrin Nitrate Esters. Patent US 6527887B1, 2003.
  • [15] Consaga, J.P. Complexed Liquid Fuel Compositions. Patent US 6110306, 1992.
  • [16] Consaga, J.P. Chemically Reactive Fragmentation Warhead. Patent US 6293201, 2001.
  • [17] Akito, E.; Nakajima, Y.; Horioka, M. Nitroglycerine Inclusion Compounds with Cyclodextrin and Composition Containing the Same. Patent US 4073931, 1978.
  • [18] Maksimowski, P.; Rumianowski, T. Properties of the Gamma-Cyclodextrin/CL-20 System. Cent. Eur. J. Energ. Mater. 2016, 13(1): 217-229.
  • [19] Maksimowski, P.; Grzegorczyk, A.; Cieślak, K.; Gołofit, T.; Chmielarek, M.; Tomaszewski, W.; Pawłowski, W. γ-Cyclodextrin Nitrate/CL-20 Complex: Preparation and Properties. Propellants, Explos., Pyrotech. 2019, 44(2): 207-216.
  • [20] Nauflett, W.G.; Farncomb, E.R. Nitration of Organics in Carbon Dioxide. Patent US 6177033, 2001.
  • [21] Romanova, L.B.; Barinova, L.S.; Lagodzinskaya, G.V.; Kazakov, A.I.; Mikhailov, Yu.M. Preparation and NMR Analysis of β-Cyclodextrin Nitrates. Russ. J. Appl. Chem. 2014, 87(12): 1884-1889.
Uwagi
Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2021).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-5d0f2427-b978-45af-b844-7b82a9fa2d6f
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