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A group of polycyclic and aliphatic azido-esters (as energetic plasticizers) have been synthesized by simple synthetic routes and their molecular structures were confirmed by spectroscopic techniques. In addition, their thermal and rheological properties have been determined utilizing DSC, TGA, viscosity, and contact angle. Computational studies of these plasticizers have been performed by means of DFT (B3LYP/6-31G*) to estimate possible stable structures, energies, heat of formation, bond dissociation energies, IR and NMR spectra etc. Their compatibility with glycidyl azide polymer (GAP) binder was studied to explore their applicability in propellants. All of these molecules are novel and have been synthesized with the possibility of scale up.
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Tom
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844--860
Opis fizyczny
Bibliogr. 15 poz., rys., tab.
Twórcy
autor
- Organic Synthesis Laboratory, Defence Institute of Advanced Technology, Department of Applied Chemistry Girinagar, 411025 Pune (Maharashtra), India
autor
- Organic Synthesis Laboratory, Defence Institute of Advanced Technology, Department of Applied Chemistry Girinagar, 411025 Pune (Maharashtra), India
autor
- Organic Synthesis Laboratory, Defence Institute of Advanced Technology, Department of Applied Chemistry Girinagar, 411025 Pune (Maharashtra), India
autor
- Organic Synthesis Laboratory, Defence Institute of Advanced Technology, Department of Applied Chemistry Girinagar, 411025 Pune (Maharashtra), India
autor
- Organic Synthesis Laboratory, Defence Institute of Advanced Technology, Department of Applied Chemistry Girinagar, 411025 Pune (Maharashtra), India
autor
- Organic Synthesis Laboratory, Defence Institute of Advanced Technology, Department of Applied Chemistry Girinagar, 411025 Pune (Maharashtra), India
Bibliografia
- [1] Kumari, D.; Balakshe, R.; Banerjee, S.; Singh, H. Energetic Plasticizers for Gun and Rocket Propellants. Rev. J. Chem. 2012, 2: 240-262.
- [2] Schedlbauer, F. LOVA Gun Propellants with GAP Binder. Propellants Explos. Pyrotech. 1992, 17: 164-170.
- [3] (a) Klapötke, T. M. Chemistry of High Energy Materials. 3rd ed. Walter de Gruyter, Berlin 2015, ISBN 978-3-11-037375-2; (b) Kumari, D.; Yamajala, K. D. B.; Singh, H.; Sanghavi, R. R.; Asthana, S. N.; Raju, K.; Banerjee, S. Application of Azido Esters as Energetic Plasticizers for LOVA Propellant Formulations. Propellants Explos. Pyrotech. 2013, 38: 805-809.
- [4] Agrawal, J. P.; Hodgson, R. D. Organic Chemistry of Explosives. John Wiley & Sons, UK 2007; ISBN 9780470029671.
- [5] Talawar, M. B.; Sivabalan, R.; Mukundan, T.; Muthurajan, H.; Sikder, A. K.; Gandhe, B. R.; Rao, A. S. Environmentally Compatible Next Generation GreenEnergetic Materials (GEMs). J. Hazard. Mater. 2009, 161: 589-607.
- [6] Badgujar, D. M.; Talawar, M. B.; Asthana, S. N.; Mahulikar, P. P. Advances in Science and Technology of Modern Energetic Materials: An Overview. J. Hazard. Mater. 2008, 151: 289-305.
- [7] Kumari, D., Anjitha, S. G., Pant, C. S.; Patil, M.; Singh, H.; Banerjee, S. Synthetic Approach to Novel Azido Esters and Their Utility as Energetic Plasticizers. RSC Adv. 2014, 4: 39924-39933.
- [8] Wypych, G. Effect of Plasticizers on Properties of Plasticized Materials. In: Handbook of Plasticizers. Ch. 10, William Andrew Publishing, 2012; ISBN 978-1-895198-97-3.
- [9] Drees, D.; Loffel, D.; Messmer, A.; Schmid, K. Synthesis and Characterization of Azido Plasticizer. Propellants Explos. Pyrotech. 1999, 24: 159-162.
- [10] (a) Gao, H.; Shreeve, J. M. Azole-based Energetic Salts. Chem. Rev., 2011, 111:7377-7436; (b) Kumari, D.; Singh, H.; Patil, M.; Thiel, W.; Pant, C. S.; Banerjee, S. Synthesis, Characterization, Thermal and Computational Studies of Novel Tetraazido Esters as Energetic Plasticizers. Thermochim. Acta 2013, 562: 96-104; (c) Garg, S.; Shreeve, J. M. Trifluoromethyl- or Pentafluorosulfanyl-substituted Poly-1,2,3-triazole Compounds as Dense Stable Energetic Materials. J. Mater. Chem. 2011, 21: 4787-4795; (d) Wang, R.; Xu, H.; Guo, Y.; Sa, R.; Shreeve, J. M. Bis [3-(5-nitroimino-1,2,4-triazolate)]-based Energetic Salts: Synthesis and Promising Properties of a New Family of High-density Insensitive Materials. J. Am. Chem. Soc. 2010, 132: 11904-11905.
- [11] (a) Shaojun, Q.; Huiqing, F.; Chao, G.; Xiaodong, Z.; Xiaoxian, G. An Azido Ester Plasticizer, 1,3‐Di(azidoacetoxy)‐2,2‐di(azidomethyl) Propane (PEAA): Synthesis, Characterization and Thermal Properties. Propellants Explos. Pyrotech. 2006, 31: 205-208; (b) Klapötke, T. M.; Stierstorfer, J. The CN7− Anion. J. Am. Chem. Soc. 2009, 131: 1122-1134.
- [12] Pant, C. S.; Wagh, R. M.; Nair, J. K.; Gore, G. M.; Thekkekara, M.; Venugopalan, S. Synthesis and Characterization of First Generation Dendritic Azidoesters. Propellants Explos. Pyrotech. 2007, 32: 461-467.
- [13] Yuan, Y.; Randall Lee, T. Contact Angle and Wetting Properties. Surface Science Techniques 2013, 3-34.
- [14] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A. Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.;Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Orokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT, 2010.
- [15] Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-class Functionals and 12 Other Functionals. Theor. Chem. Acc. 2008, 120: 215-241. Handbook of Plasticizers. Ch. 10, William Andrew Publishing, 2012; ISBN 978-1-895198-97-3.
Uwagi
Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2018).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-bd6ae57d-e792-4c1b-833e-3bec2abe4ae1