Mono nitro benzene

This group covers aromatic nuclei bearing one nitro group most mono-nitro benzenes can be persuaded to detonate by a tetryl booster few are an immediate danger in tbe absence of other sources of energy. Calorimetric studies [1] suggest tbat nitroaiyl compounds decompose by an autocatalytic mechanism, and thus stability may depend upon thermal history. Individually indexed compounds are ... 

Mono-nitro Benzene.—When benzene is treated with concentrated nitric and sulphuric acids at ordinary temperatures, or only moderate heat, only one nitro group is substituted and mono-nitro benzene is the product. If different proportions of the two acids be used, or if fuming nitric acid be added and the mixture boiled, then two nitro groups are substituted, and di-nitro benzene results. 

Mono-nitro benzene is a pale yellow liquid heavier than water sp. gr. 1.2 boiling point 209.4 melting point +3 . It distils with water vapor and is soluble in alcohol. It is known as oil of mirhane, but because of its resemblance in odor to oil of bitter almonds it is used as a substitute for the latter in perfumes. The chief importance of the compound is due to its easy preparation and its transformation by reduction into amino benzene or aniline, through which it becomes the starting point in the manufacture of dyes. 

Fuchsin, Magenta.—In 1859 Verguin in France found that crude aniline oxidized by means of stannic chloride yielded a red dye which was named fuchsin and also magenta. Other oxidizing agents were used later, e.g., mercuric chloride, arsenic acid, mono-nitro benzene. 

The simplest derivatives of this mixed character which yield dyes are the nitro naphthols, i.e., mixed nitro and hydroxyl substitution products. Recalling well-known compounds of the benzene series it will be remembered that whereas mono-nitro benzene has practically no color, and di-nitro-benzene only a faint yellow color, the mixed tri-nitro phenol or picric acid has an intense yellow color and was one of the first yellow dyes used. 

Mono-nitro-benzene—Nitro-benzol—Nitro-benzene—Essence of Mirbane—CeH((NOa)—133—is obtained by the moderated action f fuming HNOa, or of a mixture of HNOa and HaSOa on benzene. 

Nitro Compounds of Benzene and Toluene.—The preparation of the nitro derivatives of the hydrocarbons of the benzene series is very simple. It is only necessary to bring the hydrocarbon into contact with strong nitric acid, when the reaction takes place, and one or more of the hydrogen atoms of the hydrocarbon are replaced by the nitryl group (NO 2 ). Thus by the action of nitric acid on benzene (or benzol), mono-nitro-benzene is formed —... 

Potassium Chlorate 79 parts. Mono-nitro-Benzene 21 "... 

The H-NMR spectra of amino, nitro and nitroso compounds have been reviewed16,17, and the effects of these substituents on the proton chemical shifts have been investigated16. Table 4 gives these substituent effects for mono-substituted benzenes. 

There is a continual tendency for the values of cr/ and aR (and other substituent chemical shifts for a series of mono-substituted benzenes in very dilute solution in cyclohexane, carbon tetrachloride or deuteriochloroform were the basis for a redefinition of the aR scale and some amendment of a R values. However, the value for the nitro group was confirmed as 0.15. 

Reaction LH. (a) Action of Copper Powder on 2- and 4-mono-nitro-and 2 4-di-nitro-chloro- and -bromo-benzenes and their Homologues... 

Submarine Fuel, Winand s. Patented by P. Winant in the USA in 1909, it was intended to detonate without direct access to the atm. It consisted of a mixt of tetranitroethane and mono- and di-nitro benzene, without the addition of hydrocarbon material Refs 1) P. Winant, USP 914624 (1909) JSCI 28, 787 (1909) 2) C. Ellis, Chemistry of... 

It is obvious here to think of an interaction of the Debye type of the appreciable moment of the nitro or carbonyl group with the readily polarizable unsaturated C — C bond in the unsaturated hydrocarbons or with the likewise readily polarizable free electron pair in the amines, etc. Actually the stability increases with increasing polarizability, compare for example, the heat of formation of j-trinitrobenzene with, respectively, benzene, naphthalene and anthracene AH 0.6, 3.4 and 4.4 kcal. In the series mono-, di- and tri-nitro-benzene with acenaphthene AH also increases with increasing number of partial moments, namely AH — o, 1.35 and 2.45 kcal. Nevertheless this explanation is inadequate, nitromethane with a moment [x = 3.54 D gives very much less stable compounds than nitrobenzene with (X = 4,22 D, while nitrosobenzene with [x =3.2 D gives stronger colour effects than nitrobenzene. 

The mono-nitro toluenes, like the mono-chlor toluenes being di-substituted benzenes, are known in the three isomeric forms. 

Mono nitro — O Nitroso Phenyl hydroxyl Amino benzene... 

Homologous Amines. Toluidines.—The amino derivatives of the homologues of benzene are formed by the same kind of reactions as those for preparing aniline, viz., the reduction of the homologous mono-nitro compounds. The- amino toluenes in which the amino group is substituted in the benzene ring are known as toluidines, and there are, of course, three isomeric compounds, orthoj meta and para. In the ordinary nitration of toluene the ortho and para compounds are formed. By indirect methods (p. 532) the meta-nitro toluene may also be prepared. These nitro compounds by reduction yield the corresponding toluidines. 

The direct chlorination or bromination of aniline takes place more easily than that of benzene, the result being the symmetrical tri-chlor or tri-brom aniline, viz., i-amino 2-4-6-tri-chlor benzene, C6H2CI3-(NH2) and I-amino 2-4-6-tri-brom benzene, CeH2Br3(NH2). The mono-halogen anilines are prepared by reducing mono-chlor nitro benzenes, or by halogenating acetanilide and then hydrolyzing. 

Nitro-phenolic compounds euid nitrous acid are similarly formed during the nitration of other aromatic hydrocarbons. Of those studied, the order from highest to lowest in proportion of by-products to mono-nitro product was - o-xylene, p-xylene, toluene, ethyl benzene, mesitylene, m-xylene, benzene. 

Mr W.D. Field groups the solvents of pyroxyline into classes thus Two of the monohydric alcohols compound ethers of the fatty acids with monohydric alcohols, aldehydes simple and mixed ketones of the fatty acid series. These four classes inelude the greater number of the solvents of pyroxyline. Those not included are as follows —Amyl-nitrate and nitrite, methylene-di-methyl ether, ethidene-diethyl ether, amyl-chloracetate, nitro-benzene and di-nitro-benzene, eoumarin, eamphor, glacial acetic acid, and mono-, di-, and tri-acetin. 

The mono-, chloro-, bromo-, and iodo-benzenes are colourless liquids of peculiar odour. Di-chloro-, di-bromo-benzenes, tri- and hexa-chloro- and bromo-benzenes, are also known and mono-chloro-, C 6 H 4 C1(CH 3 ), and bromo-toluenes, together with di derivatives in the ortho, meta, and para modifications. The nitro-benzenes and toluenes are used as explosives. The following summary is taken from Dr A. Bemthsen s "Organic Chemistry" —... 

Quite lately a patent has been taken out for a mixture of nitro- naphthalene or di-nitro-benzene with ammonium nitrate, and consists in using a solvent for one or other or both of the ingredients, effected in a wet state, and then evaporating off the solvent, care being taken not to melt the hydrocarbon. In this way a more intimate mixture is ensured between the particles of the components, and the explosive thus prepared can be fired by a small detonator, viz, by 0.54 grms. of fulminate. Favier s explosive also contains mono-nitro-naphthalene (8.5 parts), together with 91.5 parts of nitrate of ammonia. This explosive is made in England by the Miners Safety Explosive Co. A variety of roburite contains chloro-nitro-naphthalene. Romit consists of 100 parts ammonium nitrate and 7 parts potassium chlorate mixed with a solution of 1 part nitro-naphthalene and 2 parts rectified paraffin oil. 

It would, however, be quite erroneous to assume that picric acid cannot explode when simply heated. On the contrary, Berthelot has proved that this is not the case. If a glass tube be heated to redness, and a minute quantity of picric acid crystals be then thrown in, it will explode with a curious characteristic noise. If the quantity be increased so that the temperature of the tube is materially reduced, no explosion will take place at once, but the substance will volatilise and then explode, though with much less violence than before, in the upper part of the tube. Finally, if the amount of picric acid be still further increased under these conditions, it will undergo partial decomposition and volatilise, but will not even deflagrate. Nitro-benzene, di-nitrobenzene, and mono-, di-, and tri-nitro-naphthalenes behave similarly. 

Benzene, mono-nitro- and di-nitro-benzene, 134. Bergmann and Junk on nitro-cellulose tests, 268. Bemthsen summary of nitro-benzenes, 133. Blasting gelatine, 119. 

The Pd(OAc)2-promoted reaction of styrene with benzene was applied to mono-substituted benzenes such as toluene, ethylbenzene, anisole, chlorobenzene and nitrobenzene. The results are given in Table 2.2. Methyl, ethyl, and metho)gr groups are ortho-para-directing, while the nitro group is metadirecting. 

A study of the nitration of 3-, 4-, and 5-phenylisothiazoles reveals a strong deactivation of the benzene nucleus by the heterocyclic ring. The calculated electron densities of the phenylisothiazoles are not in entire agreement with the observed orientation of the nitro-groups in the resulting mixtures of mono-nitro-derivatives. ... 

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