DE419814C - Process for the preparation of highly chlorinated nitrogen-containing hydroaromatic products - Google Patents

Description

Process for the preparation of highly chlorinated nitrogenous hydroaromatic Products. According to . the main patent 400254 are in the representation of the highly chlorinated nitrogen-containing hydroaromatic products serving as starting material Amines dissolved in an inert solvent before chlorination with dry Hydrochloric acid gas treated to avoid deep decomposition of the molecule. It has now been found that in negatively substituted amines, which compared to the otherwise unsubstituted a weakening in the reactivity of the amino group show how this in the decrease of the basicity, in the oxidizing capacity and others Properties is expressed, this protection of the amino group by hydrochloric acid becomes unnecessary. Aniline becomes largely when chlorine is introduced into a benzene solution decomposed. The chlorinated and nitrated anilines, however, no longer. Just like that the proportions of a-naphthylamine and its derivatives. The f-naphthylamine is something more consistent; however, protection by means of hydrochloric acid gas is recommended here. In the case of the negatively substituted aminoanthraquinones, the introduction of gaseous Hydrochloric acid is also superfluous before the start of the chlorination. Because by the patent 115048 is known that, for example, a-aminoanthraquinone by chlorine directly without Salt acid protection can be converted into chlorine-substituted a-aminoanthraquinone, so can therefore in one operation, starting from aminoanthraquinone, easily the corresponding highly chlorinated nitrogenous hydroaromatic products can be obtained according to the present simplified procedure.

On the other hand, the process of patent 125o94 is likely to be highly chlorinated Products obtained from i, 5-diaminoanthraquinone; but these are not uniform, relatively less highly chlorinated and likely, since they are made in glacial acetic acid will not be free of nitrogen-free saponification products.

Example I.

In a solution of 2.0 g of 2,5-dichloroaniline in 6oo cm3 of chlorobenzene chlorine is passed in directly with ice cooling. The result is a thick paste that becomes thin with further introduction of chlorine. Now it is heated to about 100 °, whereby everything goes into solution. When everything is resolved, will ; read in chlorine interrupted, filtered off and the chlorobenzene distilled off in vacuo. It part a crystalline body emerges. After repeated crystallization from petroleum ether colorless leaflets with a melting point of 125 ° are obtained.

The analysis showed that 8 CI occurred. N CI N CI 'from left C1 \ / \ "Cl CI @@ \ @ cl \ CI; @ ('-CI Calculated for H Cl or CI! CI 76, `o percent Ch, / M @ / C1 C1 C1 Cl found 76.2 percent C12. Example II. Metachloroaniline, chlorinated just like Example I, gives the same product. Example III.

1, 3-dichloro-ß-naphthylamine, chlorinated according to Example I, gives the im Main patent Example 13 described chlorine derivative.

Example IV. 1-chloro-f-naphthylamine, chlorinated according to Example I, gives the same product as example 3.

Example V.

2, .I-dichloro-a-naphthylamine, chlorinated according to Example I, gives that Chlorine derivative described in the main patent Example 2. Example VI.

/ j - Aminoanthraquinone, chlorinated according to Example I, is given in the main patent Chlorine derivative described in Example 5.

Example VII.

a - Aminoanthraquinone, chlorinated according to Example I, is given in the main patent Example .4 described chlorine derivative.

Claims (1)

PATENT-ANsPRu cu: Modification of the procedure according to patent d.oo25q., to the effect that starting from negatively substituted amines, even with omission the introduction of dry hydrochloric acid gas prior to exposure to chlorine the chlorination is carried out so far that uniform, highly chlorinated nitrogen-containing hydroaromatic products are created.