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118-96-7Relevant articles and documents
Synthesis of 2,4,6-trinitrotoluene (TNT) using flow chemistry
Anderson, David,Berglund, Michael,Diaconu, Gabriela,Emma, Giovanni,Exarchou, Vassiliki,Kyprianou, Dimitris,Rarata, Grzegorz
, (2020)
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.
Aromatic nitration using nitroguanidine and EGDN
Oxley, Jimmie C.,Smith, James L.,Moran, Jesse S.,Canino, Jonathan N.,Almog, Joseph
, p. 4449 - 4451 (2008)
Acid catalyzed nitration has been examined using a variety of novel nitration agents: guanidine nitrate (GN) and nitroguanidine (NQ) as well as the simple nitrate ester, ethylene glycol dinitrate (EGDN). Reactions with either activated or deactivated aromatic substrates proceed rapidly and in high yield. Regioselectivity was similar for all nitrating agents examined. The synthetic advantages of liquid EGDN include high solubility in organic solvents, strong nitration activity and ease of preparation.
Photocatalytic degradation of trinitrotoluene and other nitroaromatic compounds
Dillert, Ralf,Brandt, Matthias,Fornefett, Iris,Siebers, Ulrike,Bahnemann, Detlef
, p. 2333 - 2341 (1995)
The photocatalytic degradation of 2,4,6-trinitrotoluene and ten other nitroaromatic compounds in aerated TiO2 suspensions has been studied. The following order of reactivity was observed: nitrotoluenes > nitrobenzene > dinitrotoluenes > dinitrobenzenes > 2,4,6-trinitrotoluene > 1,3,5-trinitrobenzene, which reflects the known influence of nitro groups towards the attack of electrophilic reagents on the aromatic molecule.
Biotransformation of 2,4,6-trinitrotoluene (TNT) by ectomycorrhizal basidiomycetes
Meharg,Dennis,Cairney
, p. 513 - 521 (1997)
The ability of four ectomycorrhizal basidiomycetes to biotransform 2,4,6-trinitrotoluene (TNT) in axenic culture was tested. All species were capable of TNT biotransformation to a greater or lesser extent. When biotransformation was expressed on a biomass basis 4 out of the 5 isolates tested were equally efficient at transforming TNT. The factors regulating TNT biotransformation were investigated in detail for one fungus, Suillus variegatus. When the fungus was grown under nitrogen limiting conditions the rate of biotransformation decreased relative to nitrogen sufficient conditions, but no decrease was observed under short term carbon starvation. Extracellular enzymes of S. variegatus could transform TNT, but transformation was greater in intact cells. The mycelial cell wall fraction did not degrade TNT. The TNT concentration that caused 50% reduction in biomass (EC50) for S. variegatus was within the range observed for other basidiomycete fungi being between 2-10 μg mL-1. The potential use of ectomycorrhizal basidiomycetes as in-situ bioremediation agents for TNT contaminated soils is discussed.
The Stabilities of Meisenheimer Complexes. Part 21. Sulphite Additions to 2,4,6-Trinitrotoluene and 2,4,6-Trinitrobenzyl Chloride
Brooke, David N.,Crampton, Michael R.
, p. 1850 - 1853 (1980)
In aqueous sodium sulphite solutions, 2,4,6-trinitrotoluene and 2,4,6-trinitrobenzyl chloride give 1:1 and 1:2 adducts by addition at unsubstituted ring positions.Rate and equilibrium data for these reactions have been obtained by the stopped-flow method and are compared with similar data for other nitro-compounds.
Kinetics and Tunneling in the Proton- and Deuteron-Transfer Reaction between 2,4,6-Trinitrotoluene and 1,8-Diazabicycloundec-7-ene in Some Aprotic Solvents
Sugimoto, Naoki,Sasaki, Muneo,Osugi, Jiro
, p. 3418 - 3423 (1982)
The proton/deuteron-transfer reactions of 2,4,6-trinitrotoluene with 1,8-diazabicycloundec-7-ene in acetonitrile, 1,2-dichloroethane, and dichloromethane have been found to produce an ion pair.The reaction rates at 5-35 deg C of the proton- and deuteron-transfer reactions have been followed by a stopped-flow method.The reaction rate ratio kH/kD diminishes from 24.0 at 10 deg C to 18.3 at 30 deg C in acetonitrile and from 35.0 at 15 deg C to 27.1 at 30 deg C in 1,2-dichloroethane.The difference in the activation energies EaD - EaH is 2.3 and 2.1 kcal mol-1 in acetonitrile and 1,2-dichloroethane, respectively.The ratio of Arrhenius preexponential factors is 2.5 in acetonitrile and 2.0 in 1,2-dichloroethane.All these values are greater than the semiclassical limits which can be predicted since the primary kinetic isotope effect is brought about by loss of the zero-point energy difference between C-H and C-D bond at transition state.This remarkable isotope effect, when fitted to Bell's equation, indicates that there is a considerable contribution from proton tunneling.These results are discussed in comparison with those of other proton/deuteron-transfer reactions.
Application of [PVI-SO3H]NO3as a novel polymeric nitrating agent with ionic tags in preparation of high-energetic materials
Sepehrmansourie, Hassan,Zarei, Mahmoud,Zolfigol, Mohammad Ali,Mehrzad, Amin,Hafizi-Atabak, Hamid Reza
, p. 8367 - 8374 (2021)
In this paper, poly(vinyl imidazole) sulfonic acid nitrate [PVI-SO3H]NO3was synthesized and fully characterized. Then, [PVI-SO3H]NO3was applied for the preparation of energetic materials such as 1,1-diamino-2,2-dinitroethene (FOX-7), pentaerythritol tetranitrate (PETN), 1,3,5-trinitro-1,3,5-triazinane (RDX) and trinitrotoluene (TNT). The major advantages of the presented methodology are mild, facile workup, high yields and short reaction times. [PVI-SO3H]NO3is a suitable nitrating agent forin situgeneration of NO2and without using any co-catalysts of the described nitrating reagent.
Method for preparing TNT (Trinitrotoluene) by taking nitrotoluene as raw material through one-step method
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Paragraph 0026; 0027, (2018/11/22)
The invention discloses a method for preparing TNT (Trinitrotoluene) by taking nitrotoluene as a raw material through a one-step method. According to the method disclosed by the invention, p-nitrotoluene or o-nitrotoluene is used as the raw material and a mixed system of fuming HNO3/concentrated H2SO4 is used as a nitrating agent, and 2,4,6-trinitrotoluene TNT is prepared through one-step nitrification reaction; the 2,4,6-trinitrotoluene TNT is subjected to structure characterization by adopting a melting point, thin-layer chromatography, mass spectrometry and liquid chromatography. Influences, caused by a ratio, a feeding manner and a dosage of the mixed system of the fuming HNO3/concentrated H2SO4, to the yield of a product are explored and reaction conditions are optimized. The TNT is synthesized by taking the nitrotoluene as the raw material through one-step nitrification, so that environment pollution caused by the fact that a lot of waste acid and red water are generated is avoided, and energy source and power consumption caused by reaction steps and nitrification equipment are reduced.
Process For Preparing High Purity TNT
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Page/Page column 1-2, (2009/12/27)
A process for preparing trinitrololuene (TNT) in which toluene is treated with nitric acid having a concentration of about 90% to about 99%, and preferably about 98% to about 99%, by weight at a temperature of less than about 60° C., and preferably less than 30° C., to produce high purity dinitrotoluene. The resulting dinitrotoluene is then treated with nitric acid having a concentration of about 98% to about 99% by weight and trifluoromethane sulfuric acid to produce high purity TNT.
METHOD FOR PRODUCING DINITROTOLUENE
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Page/Page column 9-11, (2008/06/13)
The invention relates to a method for producing dinitrotoluene, comprising the steps of a) reacting toluene with nitric acid in the presence of sulphuric acid to give mononitrotoluene, b) separating the reaction product of step a) into a mononitrotoluene-containing organic phase and a sulphuric acid-containing aqueous phase, c) reacting the mononitrotoluene-containing organic phase with nitric acid in the presence of sulphuric acid to give dinitrotoluene, d) separating the reaction product of step c) into a dinitrotoluene-containing organic phase and a sulphuric-acid containing aqueous phase, whereby the reaction product of step a) contains 3.0 to 8 wt. % of toluene, in relation to the organic phase, and 0.1 to 1.2 wt. % of nitric acid, in relation to the aqueous phase and the phase separation of step b) is carried out in such a manner that further reaction of toluene with nitric acid is prevented.