Dinitro-m-xylene

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 %). 

Azi do-5 -(tert-butyl)4,6 -dinitro-m-xylene 2 B390 Azidobutyramide 2 B390—B391 Azidobutyric acid 2 B391 4-Azido-butyronitrile 2 B393... 

N 11.11%. Two isomers are known 5-(tert-Butyl) 2,4 dinitro-m-xylene, yel ndls(from ale), mp 68° readily sol in org solvs(Refs 1,3 4) and 5-(tert-Butyl-4,6 dinitro-m-xylene, plates(from ligroin) or ndls(from ale), mp 84°(Refs 2 3)-Other props methods of prepn are given in the Refs listed... 

The following three isomers of dinitro-m-xylene are known ... 

The composition of the nitrating mixture depends on whether m- xylene, nitro-or dinitro-m-xylene is to be nitrated. Usually more dilute mixtures are applied than for the nitration of toluene to trinitrotoluene. 

The constitution of 2,4,6-trinitro-m-xylene was determined by Grevingk [13], He nitrated both 2,4- and 4,6-dinitro-m-xylene and obtained the same product. 

The wet product is separated into two fractions - liquid (oily) and solid. Usually 20% of liquid Mid 80% of solid dinitro-m-xylene is obtained. 

Titanium ions can also he used as redox catalysts for the indirect cathodic reduction of nitro compounds (417). The electroreduction is carried out in an H20-H2S04/Ti(S04)2-(Pb/Cu) system at 45 80°C under 5 20Am . Nitrobenzene, dinitrobenzene, nitrotoluene, 2,4-dinitrotoluene, 2-nitro-m-xylene, nitro-phenol, 2,4-dinitrophenol, nitrophenetole, o-nitroanisole, 4-nitrochlorotoluene, ni-trobenzenesulfonic acid, and 4,4 -dinitro-stilbene-2,2 -disulfonic acid can all be reduced by this procedure to the corresponding amino compounds (418) in good yields (Scheme 146) [513-516]. Tin... 

The isomers of xylene offer one of the most practical starting points for organic synthesis for the preparation of valuable products for argicultural pest control. o-Xylene is a starting material in making dioctylphthalate, which is an important solvent for para-thion. 3,6-Dinitro-<>-xylene is also made from o-xylene. m-Xylene is the starting material... 

Nitro-2,4-diamino-l, 3-dimetbylbenzene, or-yel nds (from w), mp 151-52° readily sol in ale diffc sol in w was prepd by reduction of 4,6-dinitro-2-amino-m-xylene with Aram hydrosulfide (Ref 1) ... 

Dinitro-l, 3-dime tbylbenzene, col prisms (from ale), mp 92—94°, bp—explodes prepd by nitrating m-xylene with coned nitric acid at RT (Ref 1, P380 Ref 2, pl84 Ref 3, p295 Ref 4, p844)... 

For example, for the conversion of dinitro- to trinitro-m-xylene, a mixture containing 9-10% of water at a temperature up to 100°C is used. 

DNB — Dinitrobenzene DNCB — Dinitrochlorobenzene DNCr — Dinitrocresole DNPh — Dinitro phenol DNT — 2,4,-Dinitrotoluene ErN — Erythritol Tetranitrate HNDPhA — Hexanitro-diphenylamine MHeN — Mannitol Hexanitrate MNPh — Mononitrophenol MNT — Mononitrotoluene PA — Picric Acid PETN — Pentaerythritol Tetranitrate TNAn — Trinitroaniline TNAns — Tri-nitroanisole TNB — Trinitrobenzene TNCr — Trinitrocresole TNPh — Trinitrophenol TNT — 2,4,6- Trinitrotoluene TNX — Trinitro m xylene... 

Of the xylenes, the meta compound yields a trinitro derivative more readily than toluene does, but trinitro-m-xylene (TNX) melts somewhat higher than is desirable and is not quite powerful enough when used alone. It has been used in shells in mixtures with TNT and with ammonium nitrate. The other xylenes yield only dinitro derivatives by direct nitration. A mixture of o- and p-xylene may be converted into an explosive—an oily mixture of a large number of isomers, which has been used in the composition of non-freezing dynamites—by chlorinating at an elevated CH,... 

Dinitro 6 Chloro m- xylene, CHgCNO L. CgH.(Cl)CH3, wh crysts(from ale), mp 61, bp 290-91° 178° at 27mm was prepd from 5,6-dinitro-4 amino l,3-dimethyIbenzene thru diazotization treatment with cuprous chloride (Refs 1 2)... 

The condensation reactions of di- and trinitro mesitylene and m-xylene also indicate that nitro groups lose their characteristic activating influence when they are flanked by two methyl groups. In the presence of piperidine, 4,6-dinitro-ra-xylene (XLVII) and 2,4,6-trinitro-m-xylene (XLVIII) will condense with benzaldehyde 22 (equations 4 and 5). When... 

G-Dinitro-S terf.-butyl-d-aceto-m-xylene (2 4- Dinitro - 6 - tert.- tyl - 6 - acetyl - m-xylene, " Ketone Musk )... 

European Commission. 2008. Commission Communication on the Results of the Risk Evaluation and Risk Reduction Strategies for the Substances Piperazine Cyclohexane Methylenediphenyl diisocyanate But-2yne-l,4-diol Methyloxirane Aniline 2-Ethylhexylacrylate 1,4-Dichlorobenzene 3,5-dinitro-2,6-dimethyl-4-tert-butylace-tophenone Di-(2ethylhexyl)phthalate Phenol 5-tert-butyl-2,4,6-trinitro-m-xylene. (2008/C 34/01) Available at http //esis.jrc.ec.europa.eu/doc/risk assess-ment/OJ RECOMMENDATION/ojrecl06467.pdf (accessed December 8,2013. 

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