606-20-2 Usage
Description
2,6-Dinitrotoluene is an organic compound that is a derivative of toluene, with two nitro groups (-NO2) attached to the benzene ring at the 2nd and 6th positions. It is a yellow crystalline solid and is known for its explosive properties.
Uses
Used in Organic Synthesis:
2,6-Dinitrotoluene is used as a chemical intermediate in the synthesis of various organic compounds, including dyes, pharmaceuticals, and agrochemicals. Its reactivity and functional groups make it a versatile building block for the production of a wide range of chemicals.
Used in Propellant Additive Industry:
2,6-Dinitrotoluene is used as a propellant additive in the manufacturing of solid rocket propellants. Its high energy content and compatibility with other propellant ingredients make it a valuable component in enhancing the performance of rocket fuels.
Used in Explosives Industry:
2,6-Dinitrotoluene is used in the manufacture of explosives, such as dynamite and blasting agents, due to its high energy release and sensitivity to shock and friction. Its properties make it suitable for various applications in mining, construction, and demolition.
Used in Polyurethane Industry:
2,6-Dinitrotoluene is used as an intermediate in the production of toluene diisocyanate, a key component in the synthesis of polyurethanes. The annual production of toluene diisocyanate ranges from 100 million to almost a billion pounds, highlighting the importance of 2,6-dinitrotoluene in the polyurethane industry.
Preparation
2,6-Dinitrotoluene is synthesized from o-nitrotoluene by nitration with mixed acid.
Air & Water Reactions
Mixes slowly with water. Insoluble in water.
Reactivity Profile
2,6-Dinitrotoluene is sensitive to heat. 2,6-Dinitrotoluene may explode when exposed to heat or flame. 2,6-Dinitrotoluene can be detonated only by a very strong initiator. 2,6-Dinitrotoluene is incompatible with strong oxidizers. 2,6-Dinitrotoluene is also incompatible with caustics and metals such as tin and zinc. 2,6-Dinitrotoluene may react with reducing agents. 2,6-Dinitrotoluene will attack some forms of plastics, rubber and coatings.
Health Hazard
INHALATION, INGESTION OR SKIN ABSORPTION: Headache, weakness, nausea or dizziness, cyanosis, drowsiness, shortness of breath and collapse. Can burn eyes and skin.
Safety Profile
Poison by ingestion. A
skin irritant. Questionable carcinogen with
experimental tumorigenic data. Mutation
data reported. When heated to
decomposition it emits toxic fumes of NOx.
See also 2,4-DINITROTOLUENE
Environmental fate
Biological. When 2,6-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, 82, 55, 47, and 29% losses were observed after 7, 14, 21, and 28-d incubation periods,
respectively. At a concentration of 10 mg/L, only 57, 49, 35, and 13% were observed after 7, 14,
21, and 28-d incubation periods, respectively (Tabak et al., 1981). Under anaerobic and aerobic
conditions, a sewage inoculum degraded 2,6-dinitrotoluene to aminonitrotoluene (Hallas and
Alexander, 1983).
Photolytic. Simmons and Zepp (1986) estimated the photolytic half-life of 2,6-dinitrotoluene in
surface water to range from 2 to 17 h.
Low et al. (1991) reported that the nitro-containing compounds (e.g., 2,4-dinitrophenol) undergo
degradation by UV light in the presence of titanium dioxide yielding ammonium, carbonate, and
nitrate ions. By analogy, 2,6-dinitrotoluene should degrade forming identical ions.
Chemical/Physical. 2,6-Dinitrotoluene will not hydrolyze (Kollig, 1993).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities
were 145, 70, 33, and 16 mg/g, respectively (Dobbs and Cohen, 1980).
Metabolic pathway
2-Amino-6-nitrotoluene, 2,6-dinitrobenzyl alcohol, 2-
amino-6-nitrobenzyl alcohol, and the conjugates of the
latter two alcohols are detected in the urine of male
Wistar rats as metabolites of 2,6-dinitrotoluene (2,6-
DNT). In addition to the metabolites identified in the
urine, 2,6-dinitrobenzaldehyde is detected in the rat
bile. Incubation of 2,6-DNT with a hepatic microsomal
preparation gives 2,6-dinitrobenzyl alcohol. Incubation
of benzyl alcohol with a microsomal plus cytosol
preparation gives 2,6-dinitrobenzaldehyde, and
incubation of 2,6-dinitrobenzaldehyde with cytosol
preparations gives 2,6-dinitrobenzyl alcohol and 2,6-
dinitrobenzoic acid.
Purification Methods
Crystallise it from acetone. EXPLOSIVE when dry.[Beilstein 5 III 761, 5 IV 866.]
Check Digit Verification of cas no
The CAS Registry Mumber 606-20-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 6 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 606-20:
(5*6)+(4*0)+(3*6)+(2*2)+(1*0)=52
52 % 10 = 2
So 606-20-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N2O4/c1-5-6(8(10)11)3-2-4-7(5)9(12)13/h2-4H,1H3
606-20-2Relevant articles and documents
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.
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.
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.