Mechanochemical Nitration of Aromatic Compounds

Lagoviyer, Oleg S.; Krishtopa, Larisa G.; Schoenitz, Mirko; Trivedi, Nirupam J.; Dreizin, Edward L.

doi:10.1080/07370652.2017.1343407

Cited by 10 publications

(3 citation statements)

References 22 publications

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“…C▬N bond forming reactions were paid larger attention to. Mechanochemical nitration reactions of aromatics are extended to various reagents: NaNO 3 in conjunction with MoO 3 as an additive [43], BiNO 3 with MgSO 4 [44], as well as BiNO 3 alone was applied for nitration of fullerene C 60 [45]. Amine guanylation with N,N′-Di-Boc-1H-pyrazole-1-carboxamidine [46] and facile Boc deprotection was achieved with TsOH [47].…”

Section: Synthesismentioning

confidence: 99%

Recent Advances in Mechanochemical Organic Synthesis

Margetić¹,

Štrukil²

2020

Organic Synthesis [Working Title]

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Section: Synthesismentioning

confidence: 99%

Recent Advances in Mechanochemical Organic Synthesis

Margetić¹,

Štrukil²

2020

Organic Synthesis [Working Title]

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“…By applying a conventional synthesis, highly concentrated nitric acid (100%) and oleum (sulfuric acid containing up to 60% SO 3 ) are required to achieve a conversion rate higher than 98% as required for military grade TNT [ 7 , 8 ]. This way of synthesis presents safety concerns since the handling, mixing, and disposal of oleum with anhydrous nitric acid is particularly dangerous [ 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

“…They focus mainly on improving the process by achieving higher purity, faster reaction times, and more environmentally friendly approaches. Some examples include the methods developed by Millar et al, who performed the nitration of DNT in batch mode by using N 2 O 5 /H 2 SO 4 98% as the nitrating mixture, Lagoviyer et al that used sodium nitrate/molybdenum oxide for nitration of toluene, and Kyler et al that patented the use of 98–99% nitric acid with trifluoromethanesulfonic acid for the conversion of DNT to TNT [ 7 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,4,6-Trinitrotoluene (TNT) Using Flow Chemistry

et al. 2020

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This paper describes the nitration of 2,4-dinitrotoluene (DNT) and its conversion to 2,4,6-trinitrotoluene (TNT) at a gram scale with the use of a fully automated flow chemistry system. The conversion of DNT to TNT traditionally requires the use of highly hazardous reagents like fuming sulfuric acid (oleum), fuming nitric acid (90–100%), and elevated temperatures. Flow chemistry offers advantages compared to conventional syntheses including a high degree of safety and simpler multistep automation. The configuration and development of this automated process based on a commercially available flow chemistry system is described. A high conversion rate (>99%) was achieved. Unlike established synthetic methods, ordinary nitrating mixture (65% HNO3/98% H2SO4) and shorter reaction times (10–30 min) were applied. The viability of flow nitration as a means of safe and continuous synthesis of TNT was investigated. The method was optimized using an experimental design approach, and the resulting process is safer, faster, and more efficient than previously reported TNT synthesis procedures. We compared the flow chemistry and batch approaches, including a provisional cost calculation for laboratory-scale production (a thorough economic analysis is, however, beyond the scope of this article). The method is considered fit for purpose for the safe production of high-purity explosives standards at a gram scale, which are used to verify that the performance of explosive trace detection equipment complies with EU regulatory requirements.

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