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• W2051208668 abstract "The demilitarization of TNT, DNT and ammonium picrate in Russia and the West is producing million pounds of surplus energetic materials. These have been disposed by open burning/detonation. The use of open burning/ detonation is becoming unacceptable due to public concern and environmental regulations. Therefore, the chemical conversion study of surplus energetic materials to higher value products would be highly desirable. The West have used TNT as a versatile starting material for the design of different types of valuable products. During our research on conversion of TNT and DNT into high valuable raw materials in fine chemical industry, we reported synthesis of Phloroglucinol from TNT. Herein we describe a synthesis of nitroaryl halides from TNB by substitution of nitro group with halogen atom. The introduction of halogen atoms into aromatic compounds is one of the difficult operations in organic chemistry. The conventional methods proceeded by the Sandmeyer reaction are unsatisfactory from the point of view of industrial application. Another substitution method promoted by potassium fluoride from nitroaryl compound showed the unsatisfactory result (Figure 1). On the other hand, the acid halide-aided substitution reactions of nitroaryl compounds with KF have been received great attention in the field of fluorine chemistry due to relatively easy introduction of fluorine atom. However, only KF have been utilized for this transformation and this conversion method is still required to improve the yield of product. We examined the reactions of TNB prepared from TNT with LiF, NaF, KF and CsF in the presence of phthaloyl chloride and sulfolane. As expected, the use of CsF gave good yield of the 1-fluoro-3,5-dinitrobenzene (1) and 1,3difluoro-5-nitrobenzene (2), while the use of KF, NaF and LiF gave poor yield or no products (Table 1, Figure 2). In case of X− (X: halogens) in the protic solvents, nucleophilicity increases going down the periodic table; for example, nucleophilicity decreases in the order I− > Br− > Cl− > F−. However, in case of X− in the aprotic solvents such as DMSO, DMF and sulfolane, nucleophilicity decreases in the order F− > Cl− > Br− > I−. Because the cations associated with nucleophilic anions are strongly solvated in aprotic solvents, the anions are dissociated from the cations, which further enhance their nucleophilicity. In the presence of protic solvent, presumed intermediate was decomposed by protic solvent (Figure 3). Therefore, we got fluorobenzene compounds easier than other aromatic halogen compounds. To evaluate the scope of this system, the range of metal salts was extended to various metal halides. Among the different metal halides, chlorides and bromides were found to afford a only 1-chloro-3,5-dinitrobenzene (3) and 1bromo-3,5-dinitrobenzene (4) respectively with poor yield (Table 1, Figure 2). It was also observed that reaction of iodine metal salts did not give any product. Therefore, the aryl fluoride is more easily prepared than other aryl halides. In the presence of protic solvent, the" @default.
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• W2051208668 date "2011-08-20" @default.
• W2051208668 modified "2023-10-01" @default.
• W2051208668 title "The Phthaloyl chloride-Induced Conversion Reactions of Trinitrobenzene into Nitroaryl Halides" @default.
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• W2051208668 doi "https://doi.org/10.5012/bkcs.2011.32.8.2820" @default.
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