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Statistical Optimization of a Novel Approach for the Reductive Debenzylation of 2,4,6,8,10,12-Hexabenzyl-2,4,6,8,10,12-hexaazaisowurtzitane Using Pd@SiO2 Nano Catalyst

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The synthesis of 2,6,8,12-tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12-hexaazaisowurtzitane (TADB), from 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazaisowurtzitane(HBIW) is a key step in the preparation of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW or CL-20). In this study, a novel highly efficient nano catalyst based on Pd@SiO2 was used for the reductive debenzylation of HBIW. It is notable that an orthogonal array design OA9 was applied as a statistical optimization method for the synthesis of TADB. The current application of the Taguchi method in optimizing the experimental parameters of the TADB synthetic procedure was successful. TADB was synthesized by investigating the effect of the reaction conditions, such as catalyst percentage, time (h) and temperature (°C). The effects of these factors on the yield of TADB were evaluated quantitavely by the analysis of variance (ANOVA). The Pd@SiO2 nano catalyst, consisting of a palladium core with SiO2 monolayer shells, was synthesized and characterized by SEM, TEM and IR spectroscopy. The optimum condition indicated that the use of fresh Pd@SiO2 nano catalyst provides a high yield (90%). The use of Pd@SiO2 nano catalyst after recovery gave a yield of 65%.
Słowa kluczowe
Rocznik
Strony
984--995
Opis fizyczny
Bibliogr. 30 poz., rys., tab.
Twórcy
autor
  • Young Researchers and Elite Club, Qom Branch, Islamic Azad University, Qom, Iran
autor
  • Department of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, P.O. Box 16765-3454, Tehran, Iran
  • Department of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, P.O. Box 16765-3454, Tehran, Iran
  • Department of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, P.O. Box 16765-3454, Tehran, Iran
Bibliografia
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  • [2] Deraedt, C.; Salmon, L.; Etienne, L.; Ruiza, J.; Astruc, D. “Click” Dendrimers as Efficient Nanoreactors in Aqueous Solvent: Pd Nanoparticle Stabilization for Sub-ppm Pd Catalysis of Suzuki-Miyaura Reactions of Aryl Bromides. Chem. Commun. 2013, 49: 8169-8171.
  • [3] Tsui, G. C.; Tsoung, J.; Dougan, P.; Lautens, M. One-Pot Synthesis of Chiral Dihydrobenzofuran Framework via Rh/Pd Catalysis. Org. Lett. 2012, 14(21):5542-5545.
  • [4] Stevens, P. D.; Fan, J.; Gardimalla, H. M. R.; Yen, M.; Gao, Y. Superparamagnetic Nanoparticle-supported Catalysis of Suzuki Cross-coupling Reactions. Org. Lett. 2005, 7(11): 2085-2088.
  • [5] Mazumder, V.; Sun, S. Oleylamine-mediated Synthesis of Pd Nanoparticles for Catalytic Formic Acid Oxidation. J. Am. Chem. Soc. 2009, 131(13): 4588-4.
  • [6] Ge, J.; Zhang, Q.; Zhang, T.; Yin, Y. Core-satellite Nanocomposite Catalysts Protected by a Porous Silica Shell: Controllable Reactivity, High Stability, and Magnetic Recyclability Angew. Chem., Int. Ed. 2008, 47: 8924.
  • [7] Joo, S. H.; Park, J. Y.; Tsung, C.; Yamada, Y.; Yang, P.; Somorjai, G. A. Thermally Stable Pt/Mesoporous Silica Core-shell Nanocatalysts for High-temperature Reactions. Nat. Mater. 2009, 8: 126.
  • [8] Shokouhimehr, M.; Piao, Y.; Kim, J.; Jang, Y.; Hyeon, T. A Magnetically Recyclable Nanocomposite Catalyst for Olefin Epoxidation. Angew. Chem., Int. Ed. 2007, 46(37): 7039.
  • [9] Yang, P.; Zhao, D.; Margolese, D. I.; Chmelka, B. F.; Stucky, G. D. Block Copolymer Templating Syntheses of Mesoporous Metal Oxides with Large Ordering Lengths and Semicrystalline Framework. Chem. Mater. 1999, 11: 2813-2826.
  • [10] Jun, S.; Joo, S. H.; Ryoo, R.; Kruk, M.; Jaroniec, M.; Liu, Z.; Ohsuna, T.; Terasaki, O. Synthesis of New, Nanoporous Carbon with Hexagonally Ordered Mesostructure. J. Am. Chem. Soc. 2000, 122: 10712-10713.
  • [11] Xu, X.; Li, Y.; Gong, Y.; Zhang, P.; Li, H.; Wang, Y. Synthesis of Palladium Nanoparticles Supported on Mesoporous N-Doped Carbon and Their Catalytic Ability for Biofuel Upgrade. J. Am. Chem. Soc. 2012, 134(41): 16987-16990.
  • [12] Ebitani, K.; Fujie, Y.; Kaneda, K. Immobilization of a Ligand-preserved Giant Palladium Cluster on a Metal Oxide Surface and its Nobel Heterogeneous Catalysis for Oxidation of Allylic Alcohols in the Presence of Molecular Oxygen. Langmuir 1999, 15(10): 3557-3562.
  • [13] Nielsen, A. T. Patent US Application No. 253,106,30 September 1988; Patent US 5,693,794.
  • [14] Gore, G. M.; Sivabalan, R.; Nair, U. R.; Saikia, A.; Venugopalan, S.; Gandhe, B. R. Synthesis of CL-20: by Oxidative Debenzylation with Cerium(IV) Ammonium Nitrate (CAN). Ind. J. Chem. 2007, 46(3): 505-508.
  • [15] Nair, U.; Sivabalan, R. R.; Gore, G. M.; Geetha, M.; Asthana, S. N.; Singh, H. Hexanitrohexaazaisowurtzitane (CL-20) and CL-20-based Formulations (Review). Combust., Explos. Shock Wave 2005, 41(2): 121-132.
  • [16] Hvalec, M.; Gorsek, A.; Glavic, P. Experimental Design of Crystallization Processes. Acta Chim. Slov. 2004, 51: 245-256.
  • [17] Box, G.; Hunter, W. G. Statistics for Experimenters: an Introduction to Design, Data Analysis and Model Building. John Wiley & Sons, New York 1978, pp. 75-100; ISBN 978-0471093152.
  • [18] Roy, K. R. A Primer on Taguchi Method. Van Nostrand Reinhold, New York 1990, pp. 50-105; ISBN 04422372949780442237295.
  • [19] Ross, P. J. Taguchi Techniques for Quality Engineering. McGraw-Hill, New York 1988; ISBN 978-0070539587.
  • [20] Montgomery, D. C. Design and Analysis of Experiments. 3rd ed., John Wiley & Sons, New York 1991; ISBN 978-1-119-32093-7.
  • [21] Roy, R. K. Design of Experiments Using the Taguchi Approach. John Wiley & Sons, New York 2001; ISBN 978-0471361015.
  • [22] Hsiao, Y. F.; Tarng, Y. S.; Huang, W. Optimization of Plasma Arc Welding Parameters by Using the Taguchi Method with the Grey Relational Analysis. J. Mater. Manuf. Process 2008, 23(1): 51-58.
  • [23] Pourmortazavi, S. M.; Hajimirsadeghi, S. S.; Kohsari, I.; Hosseini, S. G. Orthogonal Array Design for the Optimization of Supercritical Carbon Dioxide Extraction of Different Metals from a Solid Matrix with Cyanex 301 as a Ligand. J. Chem.Eng. Data 2004, 49(6): 1530-1534.
  • [24] Carino, C. Structural Layout Assessment by Orthogonal Array Based Simulation. Mech. Res. Commun. 2006, 33(3): 292-301.
  • [25] 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.
  • [26] Ghammamy, S.; Baghy, M. Using of Taguchi Method for Experimental Design of Crystallization Processes of an Oxidant: Tetraethylammonium Chlorochromate(VI). J. Chem. Crystallogr. 2008, 38(12): 907-912.
  • [27] Matin Tehrani, 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.
  • [28] Bayat, Y.; Malmir, S.; Hajighasemalie, F.; Dehghani, H. Reductive Debenzylation of Hexabenzylhexaazaisowurtzitane using Multi-walled Carbon Nanotube-supported Palladium Catalysts: an Optimization Approach. Cent. Eur. J. Energ. Mater. 2015, 12(3): 439-458.
  • [29] Bayat, Y.; Zarandi, M.; Khadiv-parsi, P.; Salimi-beni, A. Statistical Optimization of the Preparation of HNIW Nanoparticles via Oil in Water Microemulsions. Cent. Eur. J. Energ. Mater. 2015, 12(3): 459-472.
  • [30] Azimi, S.; Sadeghi Moghadam, M. R. Synthesis and Characterization of the Pd/SiO2 Nanocomposite by the Sol-Gel Method. Nanosci. Nanoeng. 2013, 1(2): 94-97.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-c9e9401c-3d69-4001-9e74-6a2dac7cb32a
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