Nitranilines

Naphthalene, 216 Naphthalene picrate, 217 Naphthalene sulphonaie ofsodiiim, 218-/ J-Naphthol, 219 Naphthol yellow, 224 /i Naphthyl acetate, 222 /j-Naphthyl methyl ether, 220 /-Nitracetanilide, 153 w-Nitraniline, 154 /-Nitraniline, 153 Nitric acid (fuming), 22 NitroVienzene, 142 w-Nitrobenzoic acid, 200 Nitrogen, qualitative e rimation, 2 quantitative estimation, 13 Nitrophenol, 183 Nitrosohenzene, 146 /-Nitrosodimethylaniline, 157 Niirosoplienol, 159... 

The synthesis of cyclopropenone imines 3 has been accomplished by several methods. Thus aromatic amines, e.g. p-nitraniline, can be reacted either with diphenyl cyclopropenone in HCl/ethanol or with the ethoxy cation 75 forming the immonium cation 150, which is deprotonated by tertiary bases to the N-(p-nitro-phenyl)-imine /5/llsl ... 

The chemical character of a compound is not fundamentally altered by the introduction of a nitro-group. Thus the ring-substituted nitro-derivatives of the hydrocarbons are neutral compounds like the hydrocarbons themselves. If, however, a nitro-group enters a substance having, for instance, an acid character, then this character is thereby intensified the nitrophenols, for example, are more acidic than phenol. Correspondingly, the strength of bases is decreased by nitration the nitranilines are less basic than aniline. 

The yield of m-nitraniline when prepared as described above is only about four-fifths of the theoretically possible amount. This indicates, quite clearly, that the intermediate reduction products are reduced further much more rapidly than is an intact nitro-group. 

Of the three nitranilines the o-compound is the most feebly basic, then comes the p- and finally the w-compound. 

The unequal basicities of the three nitranilines can be illustrated by the following experiment. It is a general property of the salts of weak bases—as well as of weak acids—that in aqueous solution they are stable only if an excess of acid (or alkali) is present. When such solutions are diluted with water hydrolysis occurs as a result of the operation of the law of mass action. In the present case this phenomenon shows itself in the appearance of the yellow colour characteristic of the bases and finally, since the nitranilines are sparingly soluble in water, in their precipitation in crystalline form. The weaker the base the smaller is the amount of water which must be added in order to make the hydrolysis perceptible. 

Experiment.—Of each of the three nitranilines—they can be procured in any laboratory-—0-5 g. is separately dissolved by stirring with glass rods in three test tubes, each containing 3 c.c. of concentrated sulphuric acid. The colourless solutions thus prepared... 

If the sodium hydroxide is replaced by ammonia, p-nitraniline is formed.)... 

The intensely red azobenzene, however, is no more a dye than is nitrosobenzene. In order to make it into a dye, another group is necessary which, in virtue of its chemical nature, confers affinity towards the fibre and at the same time deepens the colour. The most important of these groups, which are called auxochromes, are OH and NH2. We have encountered their auxochromic influence in the simple cases of o-nitrophenol and the nitranilines. 

Porous carbon electrodes were used in the field of electrolyte-soluble (p-nitraniline) [34] and electrolyte -insoluble (nitrobenzene) [35] organic cathodic depolarizers. 

The use of porous carbon electrodes allows accurate control of the ratio of oxidized and reduced forms of p-nitriline by adjusting the electrolyte flow through the electrode. As a result, the reduction of p-nitraniline to p-phenylenediamine was carried out continuously at current densities three-fold greater than the current densities obtained from batch processes [34] and -45 % of the total yield was obtained, depending on the p-nitriline used [34]. 

Synonyms AI3-08926 AIDS-19458 l-Amino-4-nitrobenzene 4 Aminonitrobenzene jO-Amino nitrobenzene Azoamine red ZH Azofix Red GG salt Azoic diazo component 37 BRN 0508690 C-02126 CCRIS 1184 C.I. 37035 C.I. azoic diazo component 37 C.I. developer 17 Developer P Devol red GG Diazo fast red GG EINECS 202-810-1 Fast red base GG Fast red base 2J Fast red 2G base Fast red 2G salt Fast red GG base Fast red GG salt Fast red MP base Fast red P base Fast red P salt Fast red salt GG Fast red salt 2J IG base Naphtolean red GG base NCI-C60786 4-Nitraniline jo-Nitraniline Nitrazol 2F extra jo-Nitroaniline para-Nitroaniline 4-Nitrobenzenamine p-Nitrobenzenamine 4-Nitrophenylamine p-Nitrophenylamine PNA RCRA waste number P077 Red 2G base Shinnippon fast red GG base UN 1661. 

Walton, J.H. and Finzel, T.G. The solubility of meta-nitraniline in water, J. Am. Chem. Soc, 50(5) 1508-1510,1928. Walton, W.C. Practical Aspects of Ground ITaferMocfe/mg (Worthington, OH National Water Well Association. 1985), 587 p. Warns, T.J. Diethylhexylphthalate as an environmental contaminant - A review, Sci Total Environ., 66 1-16, 1987. 

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