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606-20-2Relevant academic research and scientific papers
Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium
Fauziev, Ruslan V.,Kharchenko, Alexandr K.,Kuchurov, Ilya V.,Zharkov, Mikhail N.,Zlotin, Sergei G.
, p. 25841 - 25847 (2021/08/09)
Regardless of the sustainable development path, today, there are highly demanded chemical productions still operating that bear environmental and technological risks inherited from the previous century. The fabrication of nitro compounds, and nitroarenes in particular, is traditionally associated with acidic wastes formed in nitration reactions exploiting mixed acids. However, nitroarenes are indispensable for industrial and military applications. We faced the challenge and developed a greener, safer, and yet effective method for the production of nitroaromatics. The proposed approach comprises the application of an eco-friendly nitrating agent, namely dinitrogen pentoxide (DNP), in the medium of liquefied 1,1,1,2-tetrafluoroethane (TFE) - one of the most non-hazardous Freons. Importantly, the used TFE is not emitted into the atmosphere but is effortlessly recondensed and returned into the process. DNP is obtainedviathe oxidation of dinitrogen tetroxide with ozone. The elaborated method is characterized by high yields of the targeted nitro arenes, mild reaction conditions, and minimal amount of easy-to-utilize wastes.
NITRATION OF AROMATIC COMPOUNDS
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Paragraph 0049; 0050, (2016/08/17)
The present invention provides a process for nitrating aromatic compounds without the need for a solid catalyst and/or any organic solvents and/or any other additives. A typical process includes combining or admixing a nitric acid and an anhydride compound under conditions sufficient to produce a reactive intermediate. The aromatic compound to be nitrated is then added to this reactive intermediate to produce a nitroaromatic compound. The nitroaromatic compound can be substituted with one or more, typically, one to three, and often one or two nitrate (-NO2) groups.
Competition between electron-donor and electron-acceptor substituents in nitrotoluene isomers: A photoelectron spectroscopy and ab initio investigation
Rondino, Flaminia,Catone, Daniele,Mattioli, Giuseppe,Bonapasta, Aldo Amore,Bolognesi, Paola,Casavola, Anna Rita,Coreno, Marcello,O'Keeffe, Patrick,Avaldi, Lorenzo
, p. 5272 - 5282 (2014/01/23)
We present an investigation of the close relationship between chemical structure, physical properties and reactivity of the three nitrotoluene isomers: a joint experimental and theoretical study, based on X-ray photoelectron spectroscopy (XPS) measurements and ab initio calculations, addressing the complex interplay between the competing electron-donor and electron-acceptor effects of the nitro- and methyl-substituents on the chemical properties of the nitrotoluene isomers. As the main results of the investigation we: (i) point out that accurate ab initio calculations play a key role in the complete assignment of photoemission measurements, as well as in the estimate of proton affinities in the case of all the eligible sites; (ii) revisit, at a more quantitative level, textbook models based on inductive and resonant effects of different substituents of the aromatic ring, as well as on the hyper-conjugative connection of the methyl group to the π-conjugated system; (iii) provide an accurate analysis of correlation patterns between calculated proton affinities and core-ionization energies, which represent a powerful tool, capable of predicting site-specific reactivities of polysubstituted molecules in the case of electrophilic aromatic substitution reactions.
Regioselective nitration of 2- and 4-nitrotoluenes over systems comprising nitric acid, an acid anhydride and a zeolite
Smith, Keith,Alotaibi, Mohammad Hayal,El-Hiti, Gamal A.
, p. 301 - 309 (2014/10/16)
Nitration of 2-nitrotoluene using nitric acid, acetic anhydride and Hβ zeolite produces a 97% yield of 2,4-dinitotoluene along with 3% of 2,6-dinitrotoluene. Nitration of 4-nitrotoluene under similar reaction conditions produces 2,4-dinitrotoluene in 89% yield. When chloroacetic anhydride was used instead of acetic anhydride, nitration of 4-nitotoluene produced a quantitative yield (>99%) of 2,4-nitrotoluene. ARKAT-USA, Inc.
Regioselective dinitration of simple aromatics over zeolite Hβ/nitric acid/acid anhydride systems
Smith, Keith,Alotaibi, Mohammad Hayal,El-Hiti, Gamal A.
, p. 107 - 123 (2014/04/17)
Various nitration systems comprising nitric acid, acid anhydride and zeolite H￡] in the absence of solvent are described. Direct double nitration of toluene with a nitric acid, propanoic anhydride and zeolite Hβ system has been developed to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of 123:1. This system also nitrates activated mono-substituted benzenes (anisole and phenetole) and moderately activated mono-substituted benzenes (ethylbenzene and propylbenzene) to give mainly 2,4-dinitro derivatives. The zeolite can be recovered, regenerated and reused to give almost the same yield as that given when fresh zeolite is used. ARKAT-USA, Inc.
Oxidation of aromatic amines into nitroarenes with m-CPBA
Liu, Jia,Li, Jue,Ren, Jiangmeng,Zeng, Bu-Bing
, p. 1581 - 1584 (2014/03/21)
A versatile and highly efficient approach for the synthesis of nitroarenes from aromatic amine using m-CPBA has been developed. This oxidation reaction was operationally straightforward and proceeded to afford products in good isolated yields.
Preparation of heteropoly acid based amphiphilic salts supported by nano oxides and their catalytic performance in the nitration of aromatics
Wang, Peng-Cheng,Yao, Kai,Lu, Ming
, p. 2197 - 2202 (2013/03/14)
A series of Keggin heteropoly acid anion based amphiphilic salts supported by nano oxides were synthesized and used as catalysts in the nitration of aromatic compounds with HNO3. The reaction conditions in the nitration of toluene were optimized and both 92.6% conversion and good para selectivity (ortho:para = 1.09) were obtained.
Preparation, catalytic performance and theoretical study of porous sulfated binary metal oxides shell (SO42 -/M1xO y-M2xOy) using pollen grain templates
Wang, Peng Cheng,Yao, Kai,Zhu, Jie,Liu, Xiang,Lu, Ting Ting,Lu, Ming
, p. 90 - 95 (2013/07/26)
Porous micro-sized particles of binary metal oxide (SO4 2 -/M1xOy-M2xOy) shell were prepared by template-directed synthesis method employing HCl-treated pollen grains. With 150 m2/g high surface area, these solid acids could provide more acid sites and thus obtain better catalytic activity. Using aromatic nitration as the typical reaction, their catalytic performances were evaluated and showed a significant improvement in both conversion and regioselectivity. Then, with chlorobenzene as substrate, theoretical studies were performed to investigate the interaction between transition metals and chlorobenzene. The results showed that the excellent para-selectivity was closely relative to the metal ion in these solid acids.
METHODS FOR THE NITRATION OF AROMATIC COMPOUNDS
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Page/Page column 14-15, (2012/05/04)
According to the invention there is provided a method for the nitration of an aromatic compound including the step of reacting the aromatic compound with nitric acid in the presence of an acid anhydride and an aluminosilicate catalyst, in which the acid anhydride is at least one of: ((CnH2n+1)CO)20, where n is 1 to 4 and the moiety CnH2n+1 can be straight or branched chain; ((CHpClq)CO)20, where p is 0 to 2, q is 1 to 3, and p+q = 3; and oxoiane -2, 5-dione, with the proviso that when the acid anhydride is (CH3CO)20, the aromatic compound is toluene, 2-nitrotoluene or 4-nitrotoluene, and the nitration is performed to produce 2,4-dinitrotoluene.
PROCESS FOR THE PREPARATION OF NITRATED AROMATICS AND MIXTURES THEREOF
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Page/Page column 4-5, (2012/01/03)
A process for the preparation of mononitroaromatics and dinitroaromatics, in which a hydrate melt of at least one metal nitrate M(NO3)3 is used as a nitrating medium, it being possible for M to be the metals Fe, Cr, Y, La, Ce, Al, Bi and In, and the metal nitrate having a water content of from 4 to 9 mol of water per M(NO3)3, leads to simplifications of the process and improved yields.