Nitrobenzene 1,3,5-trinitrobenzene

Picric Acid compared with Trinitrobenzene is probably the result of the former s greater ability to detonate. The ease of detonation of Picric and Styphnic acids as compared with Trinitrobenzene is well known. D. Smolefiski and W. Czuba (Ref 8) recently pointed out that Dinitrophenol detonates more readily than Di-nitrobenzene... 

OS 31] ]R 4] ]P 23] Under electroosmotic flow conditions, the reactant benzene was mobilized as a microemulsion using sodium dodecyl sulfate (SDS) as surfactant [103] (see also [14]). The nitronium ions, generated in situ from sulfuric and nitric acid, were moved by electrophoretic forces. By this means, a 65% yield of a nitrobenzene was obtained consecutive nitration products such as 1,3-dinitrobenzene (8% yield) and 1,3,5-trinitrobenzene (5% yield) were also produced. 

The difficulty of nitration increases progressively with the number of nitro-groups introduced. Already the introduction of a second nitro-group into nitrobenzene requires much more powerful reagents than the nitration of benzene itself. Symmetrical trinitrobenzene is formed only after several days boiling of the dinitro-compound with fuming nitric add and even then only in poor yield. 

TRINITROBENZENE m-DIBROMOBENZENE m-CHLORONITROBENZENE o-CHLORONITROBENZENE p-CHLORONITROBENZENE tn-D I CHLOROBENZENE o-DICHLOROBENZENE p-DI CHLOROBENZENE m-DIFLUOROBENZENE o-DIFLUOROBENZENE p-DIFLUOROBENZENE m-DI NITROBENZENE o-DINITROBENZENE p-DINITROBENZENE BROMOBENZENE MONOCHLOROBENZENE m-CHLOROPHENOL o-CHLOROPHENOL p-CHLOROPHENOL... 

The nitration of l,3,5-trichloro-2-nitrobenzene (8) to l,3,5-trichloro-2,4-dinitrobenzene (9) with dinitrogen pentoxide in absolute nitric acid goes to completion in only 2-4 minutes at 32-35 °C. Further nitration of (9) would yield l,3,5-trichloro-2,4,6-trinitrobenzene (10) which undergoes ammonolysis on treatment with ammonia in toluene to give the thermally stable explosive 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) (11). The same sequence of reactions with l,3-dichloro-2-nitrobenzene provides a route to l,3-diamino-2,4,6-trinitrobenzene (DATE). Such reactions are clean and occur in essentially quantitative yield. 

Ethy 1-2,4,6-tri nitrobenzene or 2,4,6-Trinitro-1-ethylbenzene (TNEtB) listed in some papers as 2-Ethy 1-1,3,5-trinitrobenzene,... 

M,N -Dimethy 1-2,4,6-trinitro-N,N dinitro-phenylenedi amine N N -Bistmethyl) -N,N -d initramino-2,4,6-tri nitrobenzene 1,3-Bis(methylnitramino)-2,4,6 trinitrobenzene or N,Ni-Dimethyl-H,N,2,4,6-pentanitropHenyl-ene-1,3-diamine called by the British Ditetryl. This must not be confused with American Ditetryl, called.hy the British Octyl, which is l,2-Bis(2(4,6,-trinitro-anilino)-ethane (See Vo I 2 of Encycl, p... 

Ethanolbenzene and derivs 6 El81—El82 ethanol-2,4-dinitrobenzene 6 El81 ethanol-2,4-dinitrobenzene nitrate 6 E182 ethanolnitrate-nitrobenzene 6 E182 ethanol-2,4,6-trinitrobenzene 6 E181-E182 ethanol-2,4,6-trinitrobenzene nitrate 6 El 82... 

It has been established experimentally (T. Urbanski, Kwiatkowski, Miladowski [22]) that the addition to pentaerythritol tetranitrate of such nitro compounds as nitrobenzene, nitrotoluene, dinitrobenzene, dinitrotoluene, trinitrobenzene, and trinitrotoluene, decreases its stability as determined by heating to 120-135°C. The degree of decomposition of PETN, heated alone or in mixtures, can be estimated in terms of the pH-values determining the acidity of the decomposition products (Table 32, Fig. 72). 

Tetracyanoethylene (TONE), 1,3,5-trinitrobenzene (TNB), ra-dinitro-benzene, nitrobenzene, naphthalene, and anthracene were all laboratory chemical grade reagents and were purified by standard procedures. Pery-lene from Rutgerswerke-Aktiengesellschaft was used as received. Benzene (AR) was stored over active silica-alumina and filtered before use. Solutions of the adsorbates in benzene were 10 XM for TONE and TNB and 5 X 10 3M for naphthalene, anthracene, and perylene. 

Figure 9.19 shows the Hammett s equation for degradation rates of substituted nitrobenzenes from experimental data. Photocatalytic degradation of the nitro aromatic compounds by UV/Ti02 from the experimental data reported by Dillert et al. (1995) are used to construct the model. The degradation of nitrobenzenes can be described according to the number of nitro substituents nitrobenzene > dinitrobenzene > 1,3,5-trinitrobenzene (Dillert et al., 1995). 

BTT and BTN, butane-1,2,4-triol-trinitrate DNT, dinitrotoluene EGDN, ethylene glycol dinitrate HPLC, high-performance liquid chromatography LOD, limits of detection MDQ, minimum detectable quantities NB, nitrobenzene NG, nitroglycerine NN, nitronaphthalene NT, nitrotoluene PETN, pentaerythritol tetranitrate RDX, cyclotrimethylene trinitramine SFE, supercritical fluid extraction SGC, solvating gas chromatography TDM, thermal desorption modulator TNB, trinitrobenzene and TNT, trinitrotoluene. 

Changes occurring on the conversion of nitrobenzene to trinitrobenzene have been the subject of investigations of a number of authors (Radulescu Mid Elexa [3], Kortiim [4], Fielding and Le Fevre [5]). All of them obtained similar results. Fielding and Le Fevre give the following data for compounds in mi alcoholic solution (Table 19). 

Phthalic anhydride Nitrobenzene 2,6-dini trotoluene Maleic anhydride m-dinitrobenzene s-trinitrobenzene... 

Three isomers of trinitrobenzene are known 1,3,5-trinitrobenzene (sym-tri-nitrobenzene), 1,2,4-trinitrobenzene and 1,2,3-trinitrobenzene ... 

Kovache and Thibon also found that similar inflammable metal products were formed by lower nitrated toluene derivatives, e.g. p- nitrotoluene and 2,4-dinitroto-luene, and also by trinitrobenzene. Nitrobenzene and trinitroxylene did not react... 

Of the trimtro derivatives of chlorobenzene, l-chloro-2,4,6-nitrobenzene (m. p. 81.5-83°C), known also as picryl chloride, is the most important. Next in importance is l-chloro-2,4,5-trinitrobenzene (m. p. 116°C) ... 

Polynitropolyphenylene is obtained from the reaction of a solution of 1,3-dichloro-2,4,6-trinitrobenzene in nitrobenzene at 150°-180 °C with copper powder (Ullmann reaction). 

The largest group of organic molecular compounds, in which hydrogen bond formation plays no part, are the compounds, usually in the ratio 1 1, between on the one hand aliphatic and aromatic nitro compounds (nitromethane, tetranitro-methane, chloropicrin CC13N02, nitrobenzene, s-trinitrobenzene, picric acid), quinones, anhydrides (phthalic acid-and maleic acid anhydride) and ketones with on the other hand especially aliphatic and aromatic amines (aniline, pyridine), unsaturated aliphatic and aromatic hydrocarbons, ethers etc. 

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