- Igneous rock powder as a heterogeneous multi-oxide nano-catalyst for the synthesis of 5-substituted-1H-tetrazoles in polyethylene glycol
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The use of igneous rock nano-powder as a heterogeneous and recyclable multi-oxide nano-catalyst synthesizing of 5-substituted-1H-tetrazoles is reported. The igneous rock nano-powder was initially prepared by using the ball-milling method. Then, the structure, morphology, and magnetic properties of the prepared igneous rock nano-powder were characterized with some different spectroscopic, microscopic, and thermogravimetric techniques, such as FTIR, FESEM, XRF, XRD, Histogram, and EDS. The instrumental analyses showed that the prepared igneous rock powder is a mixture of metal oxides, such as Si, Al, Ca, Mg, Fe, Na, Mn, and Sr. It showed an excellent catalytic performance in synthesizing of 5-substituted-1H-tetrazoles through [3 + 2] cycloaddition reaction between sodium azide and nitrile compounds. Various aliphatic and aromatic nitriles and sodium azide were reacted in the presence of a catalytic amount of igneous rock nano-powder at 80 o C temperature in PEG-400. The protocol was simple and rapid, with suitable yields of the obtained tetrazoles. The igneous rock nano-powder is readily accessible, reusable, and holds potential for further application in acid-catalyzed organic syntheses and industrial requirements. Graphic abstract: [Figure not available: see fulltext.]
- Javaherian, Mohammad,Movaheditabar, Parviz,Nobakht, Valiollah
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- New energetic polynitrotetrazoles
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This combined experimental, theoretical and comparative study details the syntheses and chemical characterisation of two new energetic polynitromethyl tetrazole derivatives, namely, 2-(2-nitro-2-azapropyl)-5-(trinitromethyl)-2H-tetrazole and its fluorine-containing analogue 2-(2-nitro-2-azapropyl)-5-(fluorodinitromethyl)-2H-tetrazole. Their crystal structures and energetic behaviour are compared to those of their starting materials, the ammonium salts of the corresponding 5-(polynitromethyl)-2H-tetrazoles. Additionally, the crystal structures of two further related polynitrotetrazoles are presented.
- Kettner, Marcos A.,Klap?tke, Thomas M.
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p. 3755 - 3765
(2015/03/04)
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- Energetic high-nitrogen compounds: 5-(trinitromethyl)-2 H -tetrazole and -tetrazolates, preparation, characterization, and conversion into 5-(dinitromethyl)tetrazoles
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A convenient access to 5-(trinitromethyl)-2H-tetrazole (HTNTz) has been developed, based on the exhaustive nitration of 1H-tetrazole-5-acetic acid, which was prepared from ethyl cyanoacetate and HN3 in a 1,3-dipolar cycloaddition reaction, followed by basic hydrolysis. HTNTz was converted into the ammonium, guanidinium, rubidium, cesium, copper, and silver 5-(trinitromethyl)-2H-tetrazolates. In addition, the ammonia adducts of the copper and silver salts were isolated. The reaction of HTNTz with hydrazine and hydroxylamine resulted in the formation of hydrazinium 5-(dinitromethyl) tetrazolate and hydroxylammonium 5-(dinitromethyl)-1H-tetrazolate, respectively. Acid treatment of both 5-(dinitromethyl)tetrazolates resulted in the isolation of 5-(dinitromethylene)-4,5-dihydro-1H-tetrazole, which was converted into potassium 5-(dinitromethyl)-1H-tetrazolate by reaction with K2CO 3. All prepared compounds were fully characterized by 1H, 13C, 14N, and 15N NMR spectroscopy and X-ray crystal structure determination. Initial safety testing (impact, friction, and electrostatic sensitivity) and thermal stability measurements (differential thermal analysis, DTA) were also carried out. The 5-(trinitromethyl) and 5-(dinitromethyl)tetrazoles are highly energetic materials that explode upon impact or heating.
- Haiges, Ralf,Christe, Karl O.
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p. 7249 - 7260
(2013/07/25)
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