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Języki publikacji
Abstrakty
This paper describes a method for increasing the yield of glycidyl nitrate from chloro-epoxypropane and dilute nitric acid, in the presence of 5-aminotetrazolium nitrate. The presence of 5-aminotetrazolium nitrate as catalyst and co-nitrating agent, enabled glycidyl nitrate to be produced smoothly and in excellent yield under mild condition. The optimal reaction conditions were obtained by the Taguchi method, increasing the yield from 66 to 81%. The product was characterized by FTIR and 1H NMR spectroscopy.
Rocznik
Tom
Strony
579--591
Opis fizyczny
Bibliogr. 25 poz., rys., tab.
Twórcy
autor
- Department of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology, P.O. Box 16765-3454, Tehran, Iran
autor
- Department of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology, P.O. Box 16765-3454, Tehran, Iran
Bibliografia
- [1] Hinshaw C.J., Wardle R.B., Highsmith T.K., Propellant Formulations Based on Dinitramide Salts and Energetic Binders, Patent US 5 741 998, 1998.
- [2] Willer R., Stern A.G., Day R.S., Polyglycidyl Nitrate Plasticizers, Patent US 5 380 777, 1995.
- [3] Ang H.G., Pisharath S., Energetic Polymers, Wiley, New York, 2012, p. 8; ISBN 9783527331550.
- [4] Provatas A., Energetic Polymers and Plasticizers for Explosive Formulations − a Review of Recent Advances, Defence Science and Technology Organization, DTIC Document, Report No. DSTO-TR-0966, Melbourne, Australia, 2000, 13.
- [5] Ingham J.D., Nichols P.L., High Performance PGN-polyurethane Propellants, Jet Propulsion Laboratory, Publication No. 93, 1959.
- [6] Bednarski M.D., Oehler L.M., Knox S., Cannizzo L., Warner K., Wardle R., Velarde S., Ning S., O-Nitro Compounds, Pharmaceutical Compositions Thereof and Uses Thereof, Patent US 0,135,380, 2007.
- [7] Liu J., Liquid Explosives, Springer, Berlin, 2015, p. 211; ISBN 978-3-662-45847-1.
- [8] Cannizzo L.F., Hajik R.M., Highsmith T.K., Sander A.J., Martins L., Wardle R.B., A New Low-cost Synthesis of PGN, 31st Int. Conf. ICT, Karlsruhe, Germany, 2000, 1-36.
- [9] Highsmith T.K., Sanderson A.J., Cannizzo L.F., Hajik R.M., Polymerization of Poly(Glycidyl Nitrate) from High Purity Glycidyl Nitrate Synthesized from Glycerol, Patent US 6 362 311, 2002.
- [10] Sanderson A.J., Martins L.J., Dewey M.A., Process for Making Stable Cured Poly(Glycidyl Nitrate) and Energetic Compositions Comprising Same, Patent US 6 861 501, 2005.
- [11] Sanderson A.J., Martins L.L., Method for Making Stable Cured Poly(Glycidyl Nitrate), Patent US 0,133,128, 2005.
- [12] Wang Q., Shi F., Zhang X., Wang L., Mi Z., Green Synthesis of Glycidyl Nitrate (in Chinese), Chinese J. Explos. Propellants, 2009, 32(2), 14-16.
- [13] Desai H.J., Cunliffe A.V., Lewis T., Millar R.W., Paul N.C., Stewart M.J., Amass A.J., Synthesis of Narrow Molecular Weight α, ω-Hydroxy Telechelic Poly(Glycidyl Nitrate) and Estimation of Theoretical Heat of Explosion, Polymer, 1996, 37(15), 3471-3476.
- [14] Ochoa-Gómez J.R., Blanco-Gómez J.J., A Safe Two-step Process for Manufacturing Glycidyl Nitrate from Glycidol Involving Solid-Liquid Phase-transfer Catalysis, Org. Process Res. Dev., 2011, 15(6), 1454-1457.
- [15] Hong-Chang M., Xiao-Xian G., Xian-Ming L., Shao-jun Q., Qing L., Synthesis and Characterization of Glycidyl Nitrate (in Chinese), Chinese J. Energ. Mater., 2009, 17(4), 396-398.
- [16] Young-Gu Ch., Jae-Kyung K., Derk-Soon H., Young-Hwan K., Jin-Seuk K., A Study on the Polymerization of Energetic Poly(Glycidyl Nitrate) (in Korean), Polymer (Korea), 1993, 17(3), 233-241.
- [17] Qiu S., Gan X., Fan. H., One-pot Synthesis of Glycidyl Nitrate, Energ. Mater., 2005, 13(4), 211-213.
- [18] Tehrani Matin K., Bastani D., Kazemian H., Applying the Taguchi Method to Develop an Optimized Synthesis Procedure for Nanocrystals of T-type Zeolite, Chem. Eng. Technol., 2009, 32(7), 1042-1048.
- [19] Yu X., Li Y., Wu D., Microencapsulation of Tannase by Chitosan-alginate Complex Coacervate Membrane: Synthesis of Antioxidant Propyl Gallate in Biphasic Media, J. Chem. Technol. Biotechnol., 79(5), 475-479.
- [20] Ata O.N., Yeşilyurt M., Çolak S., Beşe A.V., Determination of the Optimum Conditions for Zinc Extraction from Ore Containing Sphalerite by HCl Solutions, Can. J. Chem. Eng., 2002, 80(4), 1-11.
- [21] Montgomery D.C., Design and Analysis of Experiments, Wiley, New York, 2008, pp. 1-22; ISBN 9780470128664.
- [22] Zhou J., Wu D., Guo D., Optimization of the Production of Thiocarbohydrazide Using the Taguchi Method, J. Chem. Technol. Biotechnol., 2010, 85(10), 1402-1406.
- [23] Highsmith T.K., Lund G.K., Method for Synthesizing 5-Aminotetrazole, Patent US 5,451,682, 1994.
- [24] Von Denffer M., Klapötke T.M., Kramer G., Spieß G., Welch J.M., Heeb G., Improved Synthesis and X-ray Structure of 5-Aminotetrazolium Nitrate, Propellants Explos. Pyrotech., 2005, 30(3), 191-195.
- [25] Iranpoor N., Salehi P., Ceric Ammonium Nitrate: a Mild and Efficient Reagent for Conversion of Epoxides to β-Nitrato Alcohols, Tetrahedron, 1995, 51(3), 909-912.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-de5eae82-4294-49ce-a518-ae9d6706f7bc