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In this study, the nitration reactions of imidazole and its nitro derivatives with a mixture of 98% HNO₃ and 98% H₂SO₄ (or 15% SO₃ in H₂SO₄) were reinvestigated. When imidazole or 4(5)-nitroimidazole was nitrated with a mixture of 98% HNO₃ and 98% H₂SO₄ (or 15% SO₃ in H₂SO₄), only 4,5-dinitroimidazole was obtained. Imidazolium 2,4,5-trinitroimidazolate was prepared from 2-nitroimidazole or 2,4(5)-dinitroimidazole with a mixture of 98% HNO₃ and 98% H₂SO₄ (or 15% SO₃ in H₂SO₄); the highest yields were 57.8 and 62.8%, respectively. However, on increasing the reaction temperature, duration, amount of H₂SO₄ or HNO₃, the by-product ethanedioic acid was produced. A possible reaction mechanism for the formation of ethanedioic acid from 2,4,5-trinitroimidazole is suggested. The compounds 4,5-dinitroimidazole, imidazolium 2,4,5-trinitroimidazolate and ethanedioic acid were characterized by infrared spectroscopy, multinuclear ¹H and ¹³C NMR spectroscopy, and elemental analysis. The structures of 4,5-dinitroimidazole and ethanedioic acid were further confirmed by single-crystal X-ray diffraction.
Rocznik
Tom
Strony
379--392
Opis fizyczny
Bibliogr. 25 poz., rys., tab.
Twórcy
autor
- Shanxi North Xingan Chemical Industry Co., Ltd., China
- School of Chemical Engineering and Technology, North University of China, Taiyuan 030051, China
autor
- School of Chemical Engineering and Technology, North University of China, Taiyuan 030051, China
autor
- School of Chemical Engineering and Technology, North University of China, Taiyuan 030051, China
autor
- Gansu Yinguang Cherical Industry Group Co., Ltd., Baiyin 730900, China
autor
- Gansu Yinguang Cherical Industry Group Co., Ltd., Baiyin 730900, China
autor
- School of Chemical Engineering and Technology, North University of China, Taiyuan 030051, China
Bibliografia
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- [3] Cho, J.R.; Kim, K.J.; Cho, S.G.; Kim, J.K. Synthesis and Characterization of 1-Methyl-2,4,5-trinitroimidazole (MTNI). J. Heterocycl. Chem. 2002, 39(1): 141-147; DOI: 10.1002/jhet.5570390121.
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- [7] Coburn, M.D. Ammonium 2,4,5-Trinitroimidazole. Patent US 4028154, 1977.
- [8] Chen, J.; Lian, P.; Chen, L.; Wang, J.; Chen, J. Crystal Structure and Thermal Behaviour of Imidazolium 2,4,5-Trinitroimidazolate. Cent. Eur. J. Energ. Mater. 2019, 16(5): 547-563; DOI: 10.22211/cejem/113123.
- [9] Lian, P.; Chen, J.; Yuan, Y.; Chen, L.; Wang, J. The Nitration of 2,4,5-Triiodoimidazole and Its Oxidation Under Nitration Conditions. J. Energ. Mater. 2020, 39(3): 333-343; DOI: 10.1080/07370652.2020.1797928.
- [10] Katritzky, A.R.; Cundy, D.J.; Chen, J. Polyiodoimidazoles and Their Nitration Products. J. Energ. Mater. 1993, 11(4-5): 345-352.
- [11] Grimmett, M.R.; Hua, S.-T.; Channg, K.-C.; Foley, S.A.; Simpson, J. 1,4-Dinitroimidazole and Derivatives. Structure and Thermal Rearrangement. Aust. J. Chem. 1989, 43(8): 1281-1289.
- [12] Fargher, R.G.; Pyman, F.L. Nitro-, Arylazo-, and Amino-glyoxalines. J. Chem. Soc., Trans. 1919, 115(2).
- [13] Zhao, X.X.; Zhang, J.C.; Li, S.H.; Yang, Q.P.; Li, Y.C.; Pang, S.P. A Green and Facile Approach for Synthesis of Nitro Heteroaromatics in Water. Org. Process Res. Dev. 2014, 18(7): 886-890: 217-260; DOI: 10.1021/op5000754.
- [14] Sheldrick, G.M. SHELXT ‒ Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. Sect. A Found. Crystallogr. 2015, A71(1): 3-8.
- [15] Sheldrick, G.M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. Sect. C Struct. Chem. 2015, C71(1): 3-8; DOI: 10.1107/S2053229614024218.
- [16] Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H. OLEX2: a Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42(2): 339-341; DOI: 10.1107/S0021889808042726.
- [17] Latypov, N.V.; Bergman, J. Synthesis and Reactions of 1,1-Diamino-2,2-dinitroethylene. Tetrahedron 1998, 54(38): 11525-11536.
- [18] Cai, H.-Q.; Shu, Y.-J.; Yu, W.-F.; Li, J.-S.; Cheng, B.-B. Study on Synthesis of FOX-7 and Its Reaction Mechanism. Acta Chim. Sinica 2004, 64(3): 295-301.
- [19] Marlin, J.E.; Killpack, M. Nitroimidazolones. Synthesis of Deaza Analogues of 3-Nitro-1,2,4- triazol-5-one. Heterocycles 1992, 34(7): 1385-1393.
- [20] Cady, H.H.; Coburn, M.D.; Harris, B.W.; Rogers, R.N. Synthesis and Thermochemistry of Ammonium 2,4,5-Trinitroimidazole. Los Alamos Scientific Laboratory, Report No. LA-6802-MS, 1977.
- [21] Lian, P.; Chen, L.; Chen, J.; Wang, J.; Wang, J.; Chen, J. The Nitration of 1-Methyl2,4,5-triiodoimidazole and Its Oxidation by-Product Under Nitration Conditions. J. Energ. Mater. 2020, 40(1): 46-60; DOI: 10.1080/07370652.2020.1827313.
- [22] Lian, P.-B.; Chen, J.; Chen, L.-Z.; Zhao, C.-Y.; Wang, J.-L.; Shen, F.-F. Preparation of 1-Methyl-2,4,5-trinitroimidazole from Derivatives of 1-Methylimidazole and Its Oxidation Under Nitration Conditions. Chem. Heterocycl. Compd. 2020, 56(1): 55-59; DOI: 10.1007/s10593-020-02622-7.
- [23] Lian, P.-B.; Yuan, Y.; Chen, J.; Chen, L.-Z.; Wang, J.-L. Study of the Methylation Reaction of 2,4-Dinitroimidazole and Potassium 2,4,5-Trinitroimidazol-1-ide with Dimethyl Sulfate. Chem. Heterocycl. Compd. 2020, 56(8): 1010-1014; DOI: 10.1007/s10593-020-02767-5.
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Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-1657fb31-fcd5-4349-8e05-5100e9615728