Toluene nitro

Physical Properties. Nitrobenzene, C HjNOj pale yellow liquid, insoluble in and heavier than water, characteristic odour of bitter almonds, (similar to that of benzaldehyde and benzonitrile). /> Nitro toluene, C,H4(CH3)N02, usually pale yellow solid, insoluble in water, m-Dinitrobenzene, C8H4(N02)g, colourless solid when pure, but often pale yellow insoluble in water. 

Three products are possible from nitration of toluene o mtrotoluene m nitro toluene and p mtrotoluene All are formed but not m equal amounts Together the ortho and para substituted isomers make up 97% of the product mixture the meta only 3%... 

In mononitration the hazard is due to the extremely violent reaction of the unreacted hydrocarbon with the MA, and to the fact that nitro derivatives of cresols are formed in the process, along with nitro toluenes. The last stage — trinitration — is dangerous due to the drastic conditions of the reaction which requires coned acids and a high temp. The earlier method of trinitration at which temps up to 120° were applied was particularly hazardous. If the mono-nitre toluene hns not b n freed from nitro-cresols, trinitration is still more dangerous, due to the high reactivity of nitrocresols, and their liability to undergo oxidation... 

Morrison and Migdalof (Ref 14) irradiated o-nitrotoluene and p-nitrotoluene with a Pyrex-filtered mercury lamp using D20 and p-dioxane as solvents. C-D bonds formed with o-nitrotoluene, with no C-D formation for p-nitro-toluene - ... 

After drying for 10 min in a stream of cold air 1,4-phenylenediamine (h/Jj 5-10), 2-amino-4-chlorophenol (h/ f 15-20), 4-nitroaniline (h/ f 25-30) and l,4-amino-3-nitro-toluene (h/ f 50-55) appeared as blue-violet chromatogram zones on a blue background. These could be recognized without difficulty for several days from the back of the chromatogram. 

XfjT Conversion m-nitro toluene Conversion bromine Selectivity benzyl bromide Selectivity benzal bromide Selectivity side product... 

Fig. 6 High p,T operation for the radical side-chain bromination of m-nitro toluene in a micro-mixer-reactor setup. The large increase in operational temperature increases conversion at good selectivities, which tend to decline slightly with temperature. The two-fold substituted product, m-nitro toluene benzal bromide, is formed in larger amounts at temperatures above 200°C (IMM, unpublished results)...

James KD, PA Williams (1998) ntn genes determining the early steps in the divergent catabolism of 4-nitro-toluene and toluene in Pseudomonas sp. strain TW3. J Bacterial 180 2043-2049. 

In contrast to the parent substance of the series, p-tolylhydroxyl amine, which is prepared by the reduction with zinc dust of p-nitro-toluene in boiling alcohol, is a quite stable compound. 

The above procedure differs from that recorded in the literature, mainly in the use of a fairly large excess of sulfuric acid. This shortens the reaction time from forty hours to about one hour, which is especially convenient in the preparation of the acid on a laboratory scale. Because of the use of this large excess of sulfuric acid, the reaction is apt to be rather violent if the directions given are not carefully followed. The oxidation should be carried out under a hood. Small amounts of nitro-toluene are lost by volatilization, but this loss is not serious, as can be seen from the yield of product obtained. 

Ten or 20 g. of unchanged nitro toluene can be recovered from the reaction mixture by steam distillation, but the value of the by-product would not pay for the time spent in recovery. 

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). 

Chemical/Physical. Products identified from the reaction of toluene with nitric oxide and OH radicals include benzaldehyde, benzyl alcohol, 3-nitrotoluene, p-methylbenzoquinone, and o, m, and p-cresol (Kenley et ah, 1978). Gaseous toluene reacted with nitrate radicals in purified air forming the following products benzaldehyde, benzyl alcohol, benzyl nitrate, and 2-, 3-, and 4-nitro-toluene (Chiodini et al., 1993). Under atmospheric conditions, the gas-phase reaction with OH radicals and nitrogen oxides resulted in the formation of benzaldehyde, benzyl nitrate, 3-nitrotoluene, and o-, m-, and p-cresol (Finlayson-Pitts and Pitts, 1986 Atkinson, 1990). 

UN 1662, see Nitrobenzene UN 1663, see 2-Nitrophenol, 4-Nitrophenol UN 1664, see 2-Nitrotoluene, 3-Nitrotoluene, 4-Nitro-toluene... 

Metabolism and genetic toxicity have been reported to differ with the isomer of nitro-toluene. p-Nitrotoluene was not mutagenic in bacterial assays, but it did increase sister chromatid exchange frequencies and chromosomal aberrations in vitro-, in vivo it did not increase the frequency of micronuclei in bone marrow of treated rodents. Similar findings were reported for the ortho isomer, except that it did not induce chromosomal aberrations in vitro. Only the ortho isomer induces DNA excision repair in the in vivo-in vitro hepatocyte unscheduled DNA synthesis assay. Furthermore, ort/jo-nitrotoluene binds to hepatic DNA to a much greater extent than meta- or para-nitrotoluene, and investigators suggest that it may act similarly to the rodent hepatocarcino-gen 2,6-dinitrotoluene. ... 

The 2003 ACGIH threshold limit value-time-weighted average (TLV-TWA) for nitro-toluene is 2 ppm (11 mg/m ) with a notation for skin absorption. 

Ciss M et al Toxicological study of nitro-toluenes Long-term toxicity. Dakar Med 25 293, 1980... 

The method of preparation adopted is substantially that of Buchka,3 as this is the only one of practical value. fw-Nitro-toluene has been obtained by a similar process from s-nitro-2-aminotoluene 4 (obtained by nitration of acetyl-0-toluidine), but this compound is not commercially available, and gives a poor product unless carefully purified. 

Explosive Nitric Esters, Liquid. Spout wash water formed in the mfg of liquid expl nitric esters is created with a non expl aromatic nitro hydrocarbon e. g. 0-Nitro toluene (1), to extract the expl esters and render the wash water safe for disposal. Wash water from a Nitro glycerine (II) plant contg 0-35% II was treated at a rate of 25000 lbs/8 hrs with 1000 pounds of (I) which was continuous ly recycled so as to give a 2 1 wash water I vol ratio Ref W.G.Allan et al, Brit P7345 2 3 (1955)... 

Toluene, like benzene, undergoes electrophilic substitutions, where the substitutions take place in ortho and para positions. As the —CH3 group is an activating group, the reaction rate is much faster than usually observed with benzene. For example, the nitration of toluene produces ortho-nitro-toluene (61%) and para-nitrotoluene (39%). 

The methods of measuring the liquid phase properties were described previously [1], It was observed that heat was evolved during the preparation of all these mixtures. It should be mentioned that the electrical conductivities of the sulphuric acid-nitromethane mixtures were not constant, but were found to increase with time. Reliable data could therefore not be obtained. This is due to the fact that nitromethane reacts with sulphuric acid in dilute solutions, as has been recently discussed by Gillespie and Solomons [6]. All other properties of these mixtures were constant at 25° and measurements were restricted to this temperature. For the other four systems the viscosity, electrical conductivity and density were investigated at two temperatures 25° and 40°), because of the importance of the temperature coefficients of viscosity and electrical conductivity. The refractive indexes were measured only at 25°. The investigation of the liquid phase properties of the system with p-nitro toluene at these temperatures was possible only up to 50 mole % of p-nitrotoluene, i.e. until the solutions became saturated with respect to p-nitrotoluene. The refractive indexes of these solutions were not measured. 

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