P- Dinitrotoluene

The fluorination reaction of o,p-dinitrotoluene in formic acid can also be carried out in a continuous three-channel microreactor using 10% F2 in N2 to give the corresponding fluorinated product in 70% conversion yield (Scheme 8.5). 

Further nitration of the 2- and 4- isomers yields 2,4-dinitrotoluene, yellow crystals, m.p. 71 "C. This material is reduced to 2,4-di-aminotoluene and treated with phosgene to give 2,4-diisocyanatotoluene, a precursor of polyurethanes. 

Toluene, Proceed as for Benzene but use 0-5 ml. of toluene and a mixture of 3 ml. of concentrated sulphuric acid and 2 ml. of fuming nitric acid. Gently warm the mixture over a free flame for 1-2 minutes, cool, and pour into 20 ml. of ice water. Recrystalhse the product from dilute alcohol. 2 4-Dinitrotoluene, m.p. 71°, is obtained. 

Place 18 g. (12 ml.) of fuming nitric acid, sp. gr. 1 5, and 30 g. (16-5 ml.) of concentrated sulphuric acid and a few fragments of broken glass in a 250 or 500 ml. round-bottomed flask. Add gradually, in small portions, 14 g. of p-nitrotoluene do not allow the temperature to rise above 50 and cool the flask, if necessary, by immersion in cold water. Place a small funnel in the mouth of the flask and heat on a water bath at 90-95° for 30 minutes. Allow to cool almost to the laboratory temperature and pour the reaction mixture slowly into about 500 ml. of ice water containing a few small pieces of ice. Filter the crude dinitrotoluene through a Buchner funnel at the pump, wash it thoroughly with cold water, and drain as completely as possible. RecrystalUse from the minimum volume of hot methyl alcohol (flask, reflux condenser, and water bath experimental details as in Section IV,12). The yield of pure 2 4-dinitrotoluene, m.p. 71°, is 12 -5 g. 

Nitroxyl radicals, p-benzoquinone, and dinitrotoluene terminate chains only by the reaction with alkyl macroradicals. They form the following series according to their activity nitroxyl radical > quinone > nitro compound. 

The most important raw material is toluene diisocyanate. Nitration of toluene produces o-nitrotoluene (60%) and p-nitrotoluene (40%) which on further nitration gives 2, 4-dinitrotoluene (80%) and 2, 6-dinitrotoluene (20%). Nitration of pure 2-nitrotoluene yields 65 per cent 2,4 and 35 per cent 2, 6-... 

The 60 still base was a 45.5 m3 horizontal, cylindrical, mild steel tank 7.9 m long and 2.7 m diameter. The still was used to separate a mixture of the isomers of mononitrotoluene (MNT), two of which (o-nitrotoluene and m-nitrotoluene) are liquids at room temperature and third (p-nitrotoluene) a solid. Other byproducts were also present, principally dinitrotoluene and nitrocresols. It is well known in the industry that these nitro compounds can be explosive in the presence of strong alkali or strong acid, but in addition explosions can be triggered if they are heated to high temperatures or held at moderate temperatures for a long period. 

Hz for the ortho, meta and/or para coupling constants of p-nitroanisole, two dinitrotoluenes and 2,4-dinitrochlorobenzene. Both reports indicate that other aromatic compounds investigated showed even less solvent dependence. 

BRN 1912585, see Hexachlorobenzene BRN 1912384, see 2,4-Dinitrotoluene BRN 1913355, seep,p -DDE BRN 1914064, see Di-fl-butyl phthalate BRN 1914072, see p,p -DDD BRN 1915474, see Chlordane BRN 1915994, see Di-fl-octyl phthalate BRN 2049930, see Naled BRN 2051258, see Pindone BRN 2052046, see 2,6-Dinitrotoluene BRN 2054389, see 4,6-Dinitro-o-cresol BRN 2055620, see 2,4,5-T BRN 2057367, see Methoxychlor BRN 2059093, see Parathion BRN 2062204, see Benzyl butyl phthalate BRN 2215168, see Diuron BRN 2542580, see EPN BRN 2807677, see 2-Acetylaminofluorene BRN 3195880, see a-BHC BRN 3196099, see Camphor BRN 3910347, see cis-Chlordane, frans-Chlordane Brocide, see 1,2-Dichloroethane Brodan, see Chlorpyrifos Bromchlophos, see Naled Bromex, see Naled Bromic ether, see Ethyl bromide Bromobenzol, see bromobenzene 4-Bromobiphenyl ether, see 4-Bromophenyl phenyl ether 4-Bromodiphenyl ether, see 4-Bromophenyl phenyl ether p-Bromodiphenyl ether, see 4-Bromophenyl phenyl ether Bromoethane, see Ethyl bromide Bromofluoroform, see Bromotrifluoromethane Bromofume, see Ethylene dibromide Brom-o-gaz, see Methyl bromide Bromomethane, see Methyl bromide Bromomethyl chloride, see Bromochloromethane... 

C-07100,see2,4,5-T C-07101, see 2,4,5-Trichlorophenol C-07328, see Isoamyl alcohol C-07557, see TCDD C-08374, see Dodecane C-08380, see 2-Heptanone C-11043, see Methoxychlor C-11088, see 2,6-Dinitrotoluene C-11142, see Phenanthrene C-11160, see Thiram C-11233, see Dimethylphthalate C-14098, see 2-Methylnaphthalene C-10998, see 4-Aminobiphenyl C-11249, see Cyclohexane C-2292-52A, see Carbofuran CAF, see a-Chloroacetophenone Calmathion, see Malathion 2-Camphanone, see Camphor Camphechlor, see Toxaphene Camphochlor, see Toxaphene Camphoclor, see Toxaphene DL-Camphor, see Camphor Camphor-natural, see Camphor Camphor-synthetic, see Camphor Camphor tar, see Naphthalene Candaseptic, see p-Chloro-m-cresol Canogard, see Dichlorvos CAP, see a-Chloroacetophenone Caprolin, see Carbaryl... 

Diaminotoluene, see 2,6-Dinitrotoluene Diazoxon, see Diazinon Dibenzodioxin, see TCDD p,//-DDT Dibenzo[6,e][l,4]dioxin, see TCDD Dibenzophenone, see p,p -DDT Dibromoaniline, see o-Bromoaniline... 

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. ... 

Two other derivatives of toluene are the important explosive trinitrotoluene (TNT) and the polyurethane monomer toluene diisocyanate (TDI). TNT requires complete nitration of toluene. TDI is derived from a mixture of dinitrotoluenes (usually 80% o,p and 20% o,o) by reduction to the diamine and reaction with phosgene to the diisocyanate. TDI is made into flexible foam polyurethanes for cushioning in furniture (35%), transportation (25%), carpet underlay (20%), and bedding (10%). A small amount is used in polyurethane coatings, rigid foams, and elastomers. 

Cost data has also been generated from the pilot-scale testing of the treatment of trinitrotoluene- (TNT-) and dinitrotoluene-contaminated water. Treatment costs range from 0.60 per 1000 gal for mildly contaminated water [<70 parts per billion (ppb) TNT], to 3.88 per 1000 gal for more contaminated water (2000 ppb TNT) (D14344C, p. 204). 

Entoyaku. A light-yellow expl mixture of K chlorate 80, DNT (Dinitrotoluene) 16 castor oil 4% used for the same items as Ennayaku (Ref 1, p 28)... 

The systematic studies of T. Urbanski, Kwiatkowski and Miladowski [76] proved that the addition of an aromatic nitro compound distinctly enhances the stability of nitrocellulose and nitrocellulose powder. Thus, nitrocellulose containing 13.4% N which on heating for 5 hr at 120°C had pH=2.28 showed pH=2.89 on addition of 9 1% p-nitrotoluene, pH=3.17 on addition of 9.1 % 2,4-dinitrotoluene and pH=3.34 on addition of the same amount of a-trinitrotoluene. The same samples when heated in a constant volume (Tagliani test) gave at 134.5°C a pressure of decomposition... 

In addition to the synthesis of saccharin, also a number of other side-chain oxidations have been studied leading to aromatic carboxylic acids by indirect electrochemical oxidation using chromic acid as oxidizing agent. They include the oxidation of p-nitrotoluene 2,4-dinitrotoluene toluene, p-xylene, and p-tolualdehyde... 

P 11.6 Estimating the Arrival of 2,6-Dinitrotoluene at a Water Supply Well... 

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