121-14-2 Usage
Description
2,4-Dinitrotoluene is the most common of the six dinitrotoluene isomers. Dinitrotoluene (DNT) or Dinitro is an explosive with the formula C6H3(CH3)(NO2)2. At room temperature it is a pale yellow to orange crystalline solid. It is a high explosive and one of the precursors for trinitrotoluene (TNT), which is synthesized through three separate nitrations of toluene. The first product is mononitrotoluene, DNT is the second, and TNT is the third and final product. Dinitrotoluene induced sensitization in an employee of a manufacturers of explosives, also sensitized to nitroglycerin.
Chemical Properties
2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.
Physical properties
Both 2,4-Dinitrotoulene (2,4-DNT) and 2,6-Dinitrotoluene (2,6-DNT) are man-made solids that are pale yellow and have a slight odor. They are two of the six forms of a chemical called Dinitrotoluene (DNT). DNT is made by mixing toluene with nitric acid.
Uses
Different sources of media describe the Uses of 121-14-2 differently. You can refer to the following data:
1. 2,4-Dinitrotoluene is used largely, along with the 2,6-isomer,
to make toluene diisocyanate. The DNT mixture is hydrogenated
to yield the diamine that is reacted with phosgene to
form the diisocyanate that is reacted with polyols to make
polyurethane foams. DNT is also employed to some
extent in manufacturing explosives.
2. A metabolite of TNT (2,4,6-trinitrotoluene). The metabolites of TNT
Definition
ChEBI: 2,4-dinitrotoluene is a dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene.
General Description
Heated yellow liquid. Solidifies if allowed to cool. Insoluble in water and more dense than water. Toxic by skin absorption, inhalation and ingestion. Easily absorbed through the skin. Produces toxic oxides of nitrogen during combustion. Used to make dyes and other chemicals.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
DINITROTOLUENE is incompatible with strong oxidizing agents, caustics, active metals, tin and zinc . Decomposition occurs at 250°C. Prolonged heating below 250°C causes some decomposition, and the presence of impurities may decrease the decomposition temperatures. Decomposition is self-sustaining at 280°C. Containers may explode in a fire [USCG, 1999]. May react violently in the presence of a base or when heated to the boiling point. Attacks some forms of plastics, rubbers and coatings .
Health Hazard
Ingestion or overexposure to vapors from hot liquid can cause loss of color, nausea, headache, dizziness, drowsiness, collapse. Hot liquid can burn eyes and skin. Prolonged skin contact with solid can give same symptoms as after inhalation or ingestion.
Safety Profile
2,4-Dintirotoluene is used as an intermediate in the manufacture of polyurethanes. No information is available on the acute (short-term) effects of 2,4-dinitrotoluene in humans. Chronic (long-term) inhalation exposure to 2,4-dinitrotoluene affects the central nervous system (CNS) and blood in humans. A significant reduction in sperm count and normal sperm morphology was observed in one study of chronically exposed workers, while other studies have not reported this effect. No significant increase in cancer mortality was observed in a study of workers occupationally exposed to 2,4-dinitrotoluene by inhalation. Kidney, liver, and mammary gland tumors were observed in animals orally exposed to 2,4- dinitrotoluene. EPA has not classified 2,4-dinitrotoluene for potential carcinogenicity.
Environmental fate
Biological. When 2,4-dinitrotoluene was statically incubated in the dark at 25 °C with yeast
extract and settled domestic wastewater inoculum, significant biodegradation with gradual
acclimation was followed by deadaptive process in subsequent subcultures. At a concentration of 5
mg/L, 77, 61, 50, and 27% losses were observed after 7, 14, 21, and 28-d incubation periods,
respectively. At a concentration of 10 mg/L, only 50, 49, 44, and 23% were observed after 7, 14,
21, and 28-d incubation periods, respectively (Tabak et al., 1981).
Photolytic. Low et al. (1991) reported that nitro-containing compounds (e.g., 2,4-dinitrophenol)
degrade via UV light in the presence of titanium dioxide yielding ammonium, carbonate, and
nitrate ions. By analogy, 2,4-dinitrotoluene should degrade forming identical ions.
Chemical/Physical. Wet oxidation of 2,4-dinitrotoluene at 320 °C yielded formic and acetic
acids (Randall and Knopp, 1980).
Metabolic pathway
The major biliary metabolite of 2,4-dinitrotoluene (2,4-
DNT) in the rat is the glucuronide conjugate of 2,4-
dinitrobenzyl alcohol and the minor metabolites are
2,4-dinitrobenzyl alcohol, 2,4-dinitrobenzaldehyde, 2-
acetylamino-4-nitrotoluene, 4-amino-2-nitro or 2-
amino-4-nitrobenzyl alcohol sulfate, 2,4-dinitrobenzoic
acid, 2,4-diacetylaminobenzoic acid, and 2-amino-4-
nitrobenzoic acid.
Purification Methods
Crystallise it from Me2CO, isopropanol or MeOH. Dry it in a vacuum over H2SO4. It has also been purified by zone melting. It could be EXPLOSIVE when dry.[Beilstein 5 H339, 5 IV 865, 5 III 759.]
Check Digit Verification of cas no
The CAS Registry Mumber 121-14-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 121-14:
(5*1)+(4*2)+(3*1)+(2*1)+(1*4)=22
22 % 10 = 2
So 121-14-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N2O4/c1-5-3-2-4-6(8(10)11)7(5)9(12)13/h2-4H,1H3
121-14-2Relevant articles and documents
Okamoto,Attarwala
, p. 3269,3271 (1979)
Fluoropolymer-Coated PDMS Microfluidic Devices for Application in Organic Synthesis
Yang, Tianjin,Choo, Jaebum,Stavrakis, Stavros,de Mello, Andrew
, p. 12078 - 12083 (2018)
In recent years there has been huge interest in the development of microfluidic reactors for the synthesis of small molecules and nanomaterials. Such reaction platforms represent a powerful and versatile alternative to traditional formats since they allow for the precise, controlled, and flexible management of reactive processes. To date, the majority of microfluidic reactors used in small-molecule synthesis have been manufactured using conventional lithographic techniques from materials such as glasses, ceramics, stainless steel, and silicon. Surprisingly, the fabrication of microfluidic devices from such rigid materials remains ill-defined, complex, and expensive. Accordingly, the microfluidic toolkit for chemical synthesis would significantly benefit from the development of solvent-resistant microfluidic devices that can be manufactured using soft-lithographic prototyping methods. Whilst significant advances in the development of solvent-resistant polymers have been made, only modest steps have been taken towards simplifying their use as microfluidic reactors. Herein, we emphasize the benefits of using a commercially available, amorphous perfluorinated polymer, CYTOP, as a coating with which to transform PDMS into a chemically inert material for use in organic synthesis applications. Its efficacy is demonstrated through the subsequent performance of photooxidation reactions and reactions under extremely acidic or basic conditions.
Control over m-nitrotoluene concentration in products of heterogeneous mononitration of toluene
Artemov,Tselinskii,Kukushkin,Filatova,Ashikhin
, p. 2063 - 2072 (2007)
Heterogeneous mononitration of toluene with sulfuric-nitric acid mixtures, occurring in the charged interfacial monolayer with high para selectivity, was studied. Ways to suppress the meta substitution in the toluene mononitration stage by controlling the nitrating mixture composition, process parameters, and catalytic additives were found.
Regioselective double Kyodai nitration of toluene and chlorobenzene over zeolites. High preference for the 2,4-dinitro isomer at the second nitration stage
Peng, Xinhua,Suzuki, Hitomi
, p. 3431 - 3434 (2001)
(matrix presented) The Kyodai nitration of toluene and chlorobenzene has been examined in the presence of a solid inorganic catalyst (montmorillonite K10, zeolite HZSM-5, or HBEA-25). Regioselection was quite low at the mononitration stage, but a considerably high preference for the 2,4-isomer was observed at the dinitration stage.
Eisen,Siskind
, p. 996,997 (1964)
Hafnium(IV) and zirconium(IV) triflates as superior recyclable catalysts for the atom economic nitration of o-nitrotoluene
Waller, Francis J.,Barrett, Anthony G. M.,Braddock, D. Christopher,Ramprasad, Dorai
, p. 1641 - 1642 (1998)
The hydrated group 4 metal triflates, Hf(OTf)4 and Zr(OTf)4, were found to be excellent catalysts (10 mol%) for the mononitration of o-nitrotoluene using a single equivalent of concentrated (69%) nitric acid. The only side product is water and the catalysts are readily recycled from the aqueous phase and re-used.
Tris(trifluoromethanesulfonyl)methide ('triflide') anion: Convenient preparation, X-ray crystal structures, and exceptional catalytic activity as a counterion with ytterbium(III) and scandium(III)
Waller, Francis J.,Barrett, Anthony G. M.,Braddock, D. Christopher,Ramprasad, Dorai,McKinnell, R. Murray,White, Andrew J. P.,Williams, David J.,Ducray, Richard
, p. 2910 - 2913 (1999)
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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 deactivated aromatic compounds via mechanochemical reaction
Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin
supporting information, (2021/05/05)
A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.