Toluene dinitro

Dinitro- Aryloxy- AW-diphenyl 1-Naphthyl Toluene-/)- 2,4-Dinitro- 0-Aryl... 

AI3-15342 Benzene, 1-methyl-2,4-dinitro- CCRIS 268 Dinitrotoluene 2,4-Dinitrotoluene Z4-Dinitrotoluol DNT 2,4-DNT EINECS 204-450-0 HSDB 1144 NCI-C01865 NSC 7194 RCRA waste number U105 Toluene, 2,4-dinitro-. Used in synthesis of tduidines, dyes and explosives. Yellow needles mp = 71° bp = 300° (dec) d = 1.3208 km = 234 nm (cyclohexane), insoluble in H2O, soluble in EtOH, Et20, CeHe, CHCI3, C7H8, CS2, EtOAc very soluble in MezCO, CsHsN LD50 (rat orl) = 268 mg/kg. 

CAS 121-14-2 EINECS/ELINCS 204-450-0 Synonyms Dinitrotoluol 2,4-Dinitrotoluol DNT 2,4-DNT 1-Methyl-2,4-dinitrobenzene 4-Methyl-1,3-dinitrobenzene Toluene, 2,4-dinitro... 

Benzene, methyidinitro- Binitrotoluene Dinitrophenyl-methane Dinitrotoluene Dinitrotoluene (mixed isomers) Dinitrotoluenes Dinitrotoluol DNT EINECS 246-836-1 HSDB 3907 Methyidinitrobenzene Toluene, ar,ar-dinitro- Toluene, dinitro- UN1600 UN2038. Mixture of 0, m and p-isomers. 

The TDI mixtures are produced by a series of reactions starting from toluene. The first stage is the nitration of the toluene to yield 2-nitrotoluene and 4-nitrotoluene in roughly equal proportions. These can be further nitrated, the 4-isomer yielding only 2,4-dinitrotoluene and 2-nitrotoluene both the 2,4- and the 2,6-dinitro compound Figure 27.1). 

Formation of diamines from dinitro compounds, which are unable to interact intramolecularly, presents no problem. Very large volumes of diaminotoluene, a precursor to toluene diisocyanate, are produced by hydrogenation of dinitrotoluene over either nickel or palladium-on-carbon. Selective hydrogenation of one or the other of two nitro groups is much more of a challenge, but a number of outstanding successes have been recorded. A case in point is the hydrogenation of 2,4-dinitroaniline (11) to 4-nitro-l,2-benzenediamine (12) (2) or to 2-nitro-l,4-benzenediamine (10). 

Diisocyanates generally employed with polyols to produce polyurethanes are 2,4-and 2,6-toluene diisocyanates prepared from dinitro-toluenes (Chapter 10) ... 

Toluidine, nitrotoluene isomers, diaminotoluene, and dinitro-toluene isomers... 

Lendemann U, 1C Spain, BE Smets (1998) Simnltaneous biodegradation of 2,4-dinitrotolnene and 2,6-dinitro-toluene in an anerobic flnidized-bed biofibn reactor. Environ Sci Technol 32 82-87. 

Titanium dioxide suspended in an aqueous solution and irradiated with UV light X = 365 nm) converted benzene to carbon dioxide at a significant rate (Matthews, 1986). Irradiation of benzene in an aqueous solution yields mucondialdehyde. Photolysis of benzene vapor at 1849-2000 A yields ethylene, hydrogen, methane, ethane, toluene, and a polymer resembling cuprene. Other photolysis products reported under different conditions include fulvene, acetylene, substituted trienes (Howard, 1990), phenol, 2-nitrophenol, 4-nitrophenol, 2,4-dinitrophenol, 2,6-dinitro-phenol, nitrobenzene, formic acid, and peroxyacetyl nitrate (Calvert and Pitts, 1966). Under atmospheric conditions, the gas-phase reaction with OH radicals and nitrogen oxides resulted in the formation of phenol and nitrobenzene (Atkinson, 1990). Schwarz and Wasik (1976) reported a fluorescence quantum yield of 5.3 x 10" for benzene in water. 

Haidour and Ramos (1996) analyzed the degradation products of 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, and 2,6-dinitrotoluene by the bacterium Pseudomonas sp. clone A under aerobic conditions. The bacterium utilized 2,6-dinitrotoluene as a source of nitrogen yielding two compounds 2-amino-6-toluene and 6,6 -dinitro-2,2 -azoxytoluene. 2-Hydroxylamino-6-nitro-toluene and subsequent formation of 2,6-dihydroxyaminotoluene were reported as intermediate products of 2,6-dinitrotoluene metabolism by Clostridium acetobutylicum. 2,6-Diaminotoluene was reported as the end product (Hughes et al., 1999). 

Plant. Trifluralin was absorbed by carrot roots in greenhouse soils pretreated with the herbicide (0.75 Ib/acre). The major metabolite formed was a,a,a-trifluoro-2,6-dinitro-7V-(/i-propyl-toluene)-p-toluidine (Golab et al., 1967). Two metabolites of trifluralin that were reported in goosegrass Eleucine indica) were 3-methoxy-2,6-dinitro-A7A-dipropyl-4-(trifluoromethyl)benz-enamine and A-(2,6-dinitro-4-(trifluoromethyl)phenyl)-jV-propylpropanamide (Duke et al., 1991). 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

The presence of two methyl groups in m-xylene makes it a more reactive substrate than toluene, but as a consequence, this substrate is more susceptible to oxidation. Therefore, the nitration of m-xylene requires lower temperatures and the use of less concentrated mixed acid. In fact, the nitration of either 2,4- or 2,6-dinitro-m-xylenes to 2,4,6-trinitroxylene (TNX) can be achieved with mixed acid containing up to 10 % water. TNX is a less powerful explosive than TNT and has a poor oxygen balance (—78.4 %). 

Nitration via diazotisation has been extensively used for the synthesis of isomeric dinitronaphthalenes. Ward and co-workers used nitration via diazotisation to prepare 3,3, 4,4 -tetranitrobiphenyl from 3,3 -dinitrobenzidine, and 3,4,5-trinitrotoluene from 3,5-dinitro-4-toluidine. Ward and Hardy " prepared 1,4,6-trinitronaphthalene from 4,7-dinitro-1-naphthylamine. Korner and Contardi used the nitrate salts of aryldiazonium compounds for the synthesis of polynitro derivatives of benzene " and toluene. " " Accordingly,... 

Beilstein Kuhlberg investigated nitration of toluene with mixed nitric-sulfuric acid of various concns and isolated for the first time several isomers of mono- and dinitro-toluene. They also prepd in 1870 TNT, but did not prepare Trinitrobenzene. At about the same time, mono-, di-, tri- and tetra-nitronaphthalenes were prepd (Ref 12, p 18). Trinitrobenzenes were prepd in 1882 by P. Hepp... 

C3Hs.N(N02).CeH(N02)4 mw 346.17, N 24.28% ctysts, mp 96° sol in benz toluene may be prepd by Creating 3,4-dinitro-N,N-diethylaniline and sodium nitrate in dilute nitric acid and nitrating the resulting product with nitric acid (d 1.49) and sulfuric acid Refs 1) Beil 12, (372) 2) P. van Romburgh... 

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