Aromatic Nitrocompounds

Almost insoluble in cold water. Higher alcohols (including benzyl alcohol), higher phenols (e.g., naphthols), metaformaldehyde, paraldehyde, aromatic aldehydes, higher ketones (including acetophenone), aromatic acids, most esters, ethers, oxamide and domatic amides, sulphonamides, aromatic imides, aromatic nitriles, aromatic acid anhydrides, aromatic acid chlorides, sulphonyl chlorides, starch, aromatic amines, anilides, tyrosine, cystine, nitrocompounds, uric acid, halogeno-hydrocarbons, hydrocarbons. 

Investigations of the solubilities of aromatic compounds in concentrated and aqueous sulphuric acids showed the activity coefficients of nitrocompounds to behave unusually when the nitro-compound was dissolved in acid much more dilute than required to effect protonation. This behaviour is thought to arise from changes in the hydrogenbonding of the nitro group with the solvent. 

Aromatic nitrocompounds 7.182 - 0.236N -213.14-1- 18.330N For aromatic correction, see- ... 

As stated above under TNMe, in Ger during WWII, the prepn of TeNMe by this process was scaled up for use as an intermediate and as a substitute for nitric acid in the V-2 rocket (Ref 26). A pilot plant was built at Newark, NJ for prodn using this procedure. It was destroyed by an expln in 1953 and not rebuilt (Refs 33 44). Other prepns of lesser importance are by the action of Ag nitrite on iodotrinitro-methane (Ref 3) by the action of 90% nitric acid and 25% oleum on malononitrile, yield 45% (Ref 40) by the action of mixed acid on a number of aromatic nitrocompounds, of which nitrobenzene, dinitrobenzene, and nitronaphtha-lene gave the best yields (Ref 13a) and by the action of nitryl chloride on salts of TNMe. 

Aromatic Amine and Nitrocompounds, Their Toxicity and Potential Dangers , US Public Health Bull No 271, Washington, DC (1941), 105 6) Davis (1943), 140... 

Thermal Stability. Satisfactory Refs 1) Beil—not found 2) L.F. Fieser, Aromatic, Aliphatic Nitrocompounds and Nitrate Esters , OSRD 176 (1941) 3) R. 

Debnath AK, Lopez de Compadre RL, Debnath G, Shusterman AJ, Hansch C. Structure-activity relationship of mutagenic aromatic and heteroaromatic nitrocompounds—correlation with molecular orbital energies and hydrophobicity. I Med Chem 1991 34 786-97. 

Aromatic nitrocompounds (see Fig. 21) such as nitrobenzene and the dinitrobenzenes diminish the rate of polymerization of styrene without suppressing it altogether and without introducing an induction periodi.e., they are typical retarders. Larger quantities are required to produce significant reductions in the rate, and the retardation persists throughout the polymerization, suggests... 

It is worth noting, however, that up until fairly recently the reduction of aromatic nitrocompounds to the corresponding amines was commonly performed on an industrial scale, e.g. in the synthesis of azo dyes, with a mixture of iron and hydrochloric acid. This so-called Bechamp reduction has an E factor of ca. 15 compared to 1 for catalytic hydrogenation. 

J. Heyrovsky and K. Holleck and B. Kastening pointed out that the reduction of aromatic nitrocompounds is characterized by a fast one-electron step, e.g. 

HTC (2) [Hydrogen transfer catalysis] A catalytic process for reducing aromatic nitrocompounds. Developed by Rohner in 1993. 

Bendova, M., Rehak, K.. Matous, J., and Novak, J.P. Liquid + liquid equilibrium in the ternary systems water + ethanol + dialkyl phthalate (dimethyl, diethyl, and dibutyl phthalate) at 298.15 K, /. Chem. Eng. Data, 46(6) 1605-1609, 2001. Benes M. andDohnal, V. Limiting activity coefficients ofsome aromatic and aliphatic nitrocompounds in water, / Chem. Eng. Data, 44(5) 1097-1102, 1999. 

The behaviour of other aromatic nitrocompounds (e.g. m-nitroanisole, 3,5-dimethoxynitrobenzene and 4-nitrobiphenyl) follows the same pattern the same short-lived absorption is produced upon exciting an aromatic compound in the presence of a variety of nucleophilic agents, whereas the lifetime of the species formed depends on the nature of the reagent. 

Electron Spin Resonance Coupling Constants (Gauss) of Radicals of Some Aromatic Nitrocompounds, Produced Electrochemically and Photochemically, in Protic and Aprotic Media... 

Reduction of aromatic nitrocompounds takes place in three overall stages. The first two steps proceed in sequence because nitrosocompounds produced in the first step have a much less negative reduction potential than nitrocompounds. Arylhy-... 

High Density Explosives. Explosives of high density are prepd by heating AN with freezing point depressants such as urea to effect only partial liquefaction of AN and adding to the mixture Ca-Si, Fe-Si, Al, or aromatic nitrocompounds... 

Kaystonite. See under Alkalies, Action on Aromatic Nitrocompounds in Vol 1, p A126-R... 

Na chloride 14, paraffin 8, MNN 5 wood meal 1%. OB -2.6% Trauzl test value, 195cc Refs 1) Naoum, Expl (1927), 147 2) PATR 2510 (1958), Ger 101-R Kohlen-Salit. NG (gelatinized with NC) 12.5, vegetable meal 2.5, aromatic nitrocompounds 7.0, AN 41.0 alkali chlorides 37.0%. OB -2.6%, Trauzl test value 260cc Refs 1) Naoum, NG (1928), 411 2) Fedoroff Clift 4 (1946), 49 3) PATR 2510... 

Most dangerous group Black Powder and colloidal propellants, in bulk placed in boxes, and chlorate explosives, not cartridged. Dynamites with attached caps fuses, detonators, nonelectric at electric and Nitroceiiuioses wetted with at least 25% water. Aromatic nitrocompounds, packed in double containers the inner ones from leather, cardboard, heavy paper envelope., while the outer ones nf wood or copper. The fulminates must be transported in vessels filled with water... 

Any of these expls may be rendered low-freezing by incorporating NGc (Nirroglycol), DNG (Dinitroglycerin) or DNClH (Dinitro-chlorohydrin). Aromatic nitrocompounds, such as DNT and TNT, can be used for the same purpose... 

Due to the acute shortage in Germany of TNT and other aromatic nitrocompounds, several substitute explosive mixtures were developed and used during WWII. 

Esplosivi al 20-26%, di NGL, with 1% NC, about 10% aromatic nitrocompounds or organic combustible materials, Amm nitrate (with or without Na nitrate.) To these belongs the gelignite S A... 

Refractive indexes of these systems are given in Fig. 3 and in Tables 10-13, They all show positive deviations from additivity in volume fractions of the components, which increase in the order nitrobenzene < m-nitroi oluene < o-nitrotoluene. This confirms that the addition compounds formed by these aromatic nitrocompounds with sulphuric acid are more and more stable in this order, which is the order of increasing basicities. Rathex unexpectedly, however, the system with nitromethane shows high positive deviations from additivity, which equal those in the system with. o-nitrotoluene, This fact might be due to the small dimensions of the nitromethane molecules, which are therefore Jess likely to cause the disruption of the structure of sulphuric acid and thus U lower the Tefractive indexes of the mixtures, than the larger molecules of the aromatic nitrocompounds. 

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