Oxidation of 4-alkylfurazan-3-amines to the corresponding nitrofurazans was achieved using mixtures of hydrogen peroxide. The volatility of the products as a function of the size of substituent R, has been studied. The phase and relaxation transitions were characterized and the thermodynamic compatibility with polyester urethane was established. The melting points and melting enthalpies of alkylnitrofurazans were determined.
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(a) Pivina, T. S.; Sukhachev, D. V.; Evtushenko, A. V.; Khmelnitskii, L. I. Propellants, Explos., Pyrotech. 1995, 20, 5. (b) Sheremetev, A. B.; Pivina, T. S. In Energetic Materials. Technology, Manufacturing and Processing. 27th International Annual Conference of ICT, June 25 – June 28, 1996, Karlsruhe, Federal Republic of Germany; Karlsruhe, 1996, pp. 30-1. (c) Sheremetev, A. B. Mendeleev Chem. J. 1997, 41(2), 62. [Ros. Khim. Zh. 1997, 41(2), 43.] (d) Sheremetev, A. B.; Kulagina, V. O.; Aleksandrova, N. S.; Dmitriev, D. E.; Strelenko, Yu. A.; Lebedev, V. P.; Matyushin, Yu. N. Propellants, Explos., Pyrotech. 1998, 23, 142. (e) Stepanov, A. I.;Dashko, D. V.; Astrat'ev, A. A. Cent. Eur. J. Energ. Mater. 2012, 9, 329. (f) Sheremetev, A. B.; Aleksandrova, N. S.; Palysaeva, N. V.; Struchkova, M. I.; Tartakovsky, V. A.; Suponitsky, K. Yu. Chem.–Eur. J. 2013, 19, 12446. (g) Ilyushin, M. A.; Shugaley, I. V.; Tselinskii, I. V.; Garabadzhiu, A. V. Russ. J. Gen. Chem. 2013, 83, 2624. [Ekologicheskaya khimiya 2012, 21(3), 154.] (h) Zhang, Y.; Zhou, C.; Wang, B.; Zhou, Y.; Xu, K.; Jia, S.; Zhao, F. Propellants, Explos., Pyrotech. 2014, 39, 809. (i) Wu, X.; Chu, Y.; Zheng, C.; Wang, T.; Lei, W.; Wang, F.; Xia, M. Chem. Heterocycl. Compd. 2015, 51, 760. [Khim. Geterotsikl. Soedin. 2015, 51, 760.] (j) Luk'yanov, O. A.; Pokhvisneva, G. V.; Ternikova, T. V. Russ. Chem. Bull., Int. Ed. 2015, 64, 83. [Izv. Akad. Nauk, Ser. Khim. 2015, 83.] (k) Liu, N.; Zeman, S.; Shu, Y.-J.; Wu, Z.-K.; Wang, B.-Z.; Yin, S.-W. RSC Adv. 2016, 6, 59141. (l) Sinditskii, V. P.; Burzhava, A. V.; Chernyi, A. N.; Shmelev, D. S.; Apalkova, V. N.; Palysaeva, N. V.; Sheremetev, A. B. J. Therm. Anal. Calorim. 2016, 123, 1431. (m) Yi, Q.; Liang, D.; Ma, Q.; Huang, M.; Tan, B.; Liu, Y.; Chi, Y. Propellants, Explos., Pyrotech. 2016, 41, 906. (n) Li, X.; Wang, B.-L.; Lin, Q.-H.; Chen, L.-P. J. Energ. Mater. 2016, 34, 409. (o) Wang, X.; Wang, B.; Bi, F.; Zhai, L.; Ma, L.; Huo, H. Patent CN105601581. (p) Wang, X.; Bi, F.; Wang, B.; Li, X.; Zhang, J.; Zhou, C.; Huo, H. Patent CN105646388. (q) Li, Y.; Xue, M.; Wang, J.; Cao, D.; Ma, Z. Chin. J. Org. Chem. 2016, 36, 1528.
(a) Shen, H.-P.; Lu, Y.-H.; Cao, Y.-L.; He, J.-X. Hanneng Cailiao 2011, 19, 735. (b) Lempert, D. B.; Sheremetev, A. B. Chem. Heterocycl. Compd. 2016, 52, 1070. [Khim. Geterotsikl. Soedin. 2016, 52, 1070.]
(a) Chernaya, V. V.; Vol'chenko, R. L. Russ. Chem. Rev. 1962, 31, 167. [Usp. Khim. 1962, 31, 336.] (b) Rogov, N. G.; Ischenko, M. A. Composite Solid Rocket Propellants: Components, Requirements, Properties [in Russian]; Izd-vo SPbGTI (TU): St. Petersburg, 2005, p. 195. (b) Pavlovets, G. Ya.; Tsutsuran, V. I. Physicochemical Properties of Powders and Rocket Propellants [in Russian]; Izd-vo Min-va Oboroni RF: Moscow, 2009, 408 pp. (c) Kumari, D.; Balakshe, R.; Banerjee, S.; Singh, H. Rev. J. Chem. 2012, 2, 240. (d) Yan, Q.-L.; Zeman, S.; Elbeih, A. Thermochim. Acta 2012, 537, 1. (e) Kostochko, A. V.; Kazban, B. M. Powders, Solid Rocket Propellants and their Properties [in Russian]; INFRA-M: Moscow, 2015, 400 pp.
Sheremetev, A. B.; Shamshina, Yu. L.; Dmitriev, D. E. Russ. Chem. Bull., Int. Ed. 2005, 54, 1032. [Izv. Akad. Nauk, Ser. Khim. 2005, 1007.]
(a) Novikova, T. S.; Mel'nikova, T. M.; Kharitonova, O. V.; Kulagina, V. O.; Aleksandrova, N. S.; Sheremetev, A. B.; Pivina, T. S.; Khmel'nitskii, L. I.; Novikov, S. S. Mendeleev Commun. 1994, 4, 138. (b) Sheremetev, A. B.; Kozeev, A. M.; Aleksandrova, N. S.; Struchkova, M. I.; Suponitsky, K. Yu. Chem. Heterocycl. Compd. 2013, 1358. [Khim. Geterotsikl. Soedin. 2013, 1457.]
Dmitriev, D. E.; Strelenko, Yu. A.; Sheremetev, A. B. Russ. Chem. Bull., Int. Ed. 2013, 62, 504. [Izv. Akad. Nauk, Ser. Khim. 2013, 503.]
Stepanov, R. S.; Kruglyakova, L. A.; Astakhov A. M. Russ. J. Gen. Chem. 2009, 79, 1047. [Zh. Obshch. Khim. 2009, 79, 874.]
Physics of Explosion [in Russian]; Orlenko, L. P., Ed.; Fizmatlit: Moscow, 2002, 3rd ed., Vol. 1, p. 204.
(a) Konkova, T. S.; Miroshnichenko, E. A.; Matyushin, Y. N.; Prokhorova, S. V.; Inozemtsev, J. O.; Inozemtsev, A. V.; Sheremetev, A. B.; Kozeev, A. M.; Pashchenko, L. L. In Energetic Materials: Synthesis, Characterization, Processing. 43rd International Annual Conference of the Fraunhofer ICT, June 26–29, 2012, Karlsruhe, Germany; Karlsruhe, 2012, p. 76.1–12. (b) Miroshnichenko, E. A.; Kon'kova, T. S.; Matyushin, Yu. N.; Berlin, A. A. Dokl. Phys. Chem. 2014, 456(2), 94. [Dokl. Akad. Nauk 2014, 456, 673.]
(a) Lebedev, Yu. A.; Miroshnichenko, E. A.; Knobel', Yu. K. Thermochemistry of Nitro Compounds [in Russian]; Nauka: Moscow, 1970, p. 64. (b) Kustova, L. V.; Kirpichev, E. P.; Rubtsov, Yu. I.; Avdonin, V. V.; Korepin, A. G.; Eremenko, L. T. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1981, 30, 1830. [Izv. Akad. Nauk SSSR, Ser. Khim. 1981, 2232.] (c) Kizin, A. N.; Dvorkin, P. L.; Ryzhova, G. L.; Lebedev, Yu. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1986, 35, 343. [Izv. Akad. Nauk SSSR, Ser. Khim. 1986, 372.] (d) Sagadeev, E. V.; Gimadeev, A. A.; Barabanov, V. P. Theor. Found. Chem. Eng. 2009, 43, 108. [Teoret. Osnovy Khim. Tekhnologii 2009, 43, 114.] (e) Holmes, J. L.; Aubry, C. J. Phys. Chem. A 2012, 116, 7196.
Price, D. M. Thermochim. Acta 2001, 367-368, 253.
Lotmentsev, Yu. M.; Pleshakov, D. V.; Ermakova, T. D.; Kryukov V. N. Methods for Evaluation of Thermodynamic Stability of Plasticized Polymers [in Russian]; Izd-vo RKhTU im. D. I. Mendeleeva: Moscow, 2000, p. 60.
(a) Engels, H.-W.; Pirkl, H.-G.; Albers, R.; Albach, R. W.; Krause, J.; Hoffmann, A.; Casselmann, H.; Dormish, J. Angew. Chem., Int. Ed. 2013, 52, 9422. (b) Madyakin, F. P.; Tikhonova, N. A. Components and Combustion Products of Pyrotechnic Compositions. Polymers and Oligomers [in Russian]; Izd-vo KGTU: Kazan, 2008, Vol. 2, 492 pp. (с) Ang, H. G., Pisharath, S. Energetic Polymers: Binders and Plasticizers for Enhancing Performance; Wiley-VCH: Weinheim, 2012, 218 pp.
Malkin, A. Ya.; Chakikh, A. E. Diffusion and Viscosity of Polymers. Methods for Measurement [in Russian]; Khimiya: Moscow, 1979, p. 201. 15. (a) Meyer, R.; Köhler J.; Homburg A. Explosives; Wiley-VCH: Weinheim, 2007, 6th completely revised ed., p. 94, 224. (b) Braak, E. C. J. Energ. Mater. 1990, 8, 21.
Specific parts of this work were performed with financial support from OKhNM-04 programs of the Russian Academy of Sciences.
The authors would like to express their gratitude to Dr. M. I. Struchkova (Institute of Organic Chemistry, Russian Academy of Sciences) for acquisition of NMR spectra and to the leading engineer N. N. Il'icheva (D. I. Mendeleev Russian Chemical Technology University) for her assistance with performing calorimetric measurements.
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Supplementary information file containing thermograms of compounds 1а–f is available from the journal website at http://link.springer.com/journal/10593.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 740–745
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Lotmentsev, Y.M., Kondakova, N.N., Bakeshko, A.V. et al. 3-Alkyl-4-nitrofurazans – plasticizers for polymers. Chem Heterocycl Comp 53, 740–745 (2017). https://doi.org/10.1007/s10593-017-2120-y
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DOI: https://doi.org/10.1007/s10593-017-2120-y