Salicylic acid is employed also for the manufacture of certain azo-dyes in
a way that it will be very instructive to consider, because the process
used may be taken as typical of the general method of preparing such
compounds. Solutions of diazo-salts act not only upon amido- and
diamido-compounds, as we have seen in the case of aniline yellow and
chrysoidine, but also upon phenols, forming acid azo-colours. This
important fact was made known in 1870 by the German chemists Kekule and
Hidegh, but more than six years elapsed before this discovery was taken
advantage of by the technologist. Large numbers of these acid azo-dyes are
now made from various diazotised amido-compounds combined with different
phenols and phenolic acids. The mode of procedure is to diazotise the
amido-compound by sodium nitrite and hydrochloric acid in the manner
already described, and then add the diazo-salt solution to the phenolic
compound dissolved in alkali. The colouring-matter is at once formed.
Salicylic acid possesses the characters both of an acid and a phenol. It
combines readily with diazo-salts under the circumstances described, and
gives rise to azo-dyes, some of which are of technical value.
The manufacture of azo-dyes from salicylic acid brings us into contact
with certain amidic compounds which figure so largely in the tinctorial
industry that they may be conveniently dealt with here. These bases are
not azo-compounds themselves, but they are prepared from azo-compounds,
viz. from the azobenzene and azotoluene which were spoken about in the
last chapter. When these are reduced by acid reducing-agents, they become
converted into diamido-bases which are known as benzidine and tolidine
respectively. These bases can be diazotised, and as they contain two
amido-groups, they form double diazo-salts, _i.e._ tetrazo-salts, which
are capable of combining with amido-compounds, or phenols, in the usual
way. Thus diazotised benzidine and tolidine combine with salicylic acid to
form valuable yellow azo-dyes known as "chrysamines." The dyes of this
class obviously contain two azo-groups.
Some other uses of carbolic acid must next be considered. Of the
colouring-matters derived from coal-tar, none is more widely known than
the oldest artificial yellow dye, picric acid. This is a phenol
derivative, and was first obtained as long ago as 1771 by Woulfe, by
acting upon indigo with nitric acid. Laurent in 1842 was the first to
obtain this dye from carbolic acid, from which compound it is still
manufactured by acting upon the sulpho-acid with nitric acid. Chemically
considered, it is trinitrophenol. It has a very wide application as a dye,
and has been used as an explosive agent. A similar colouring-matter was
made from cresol in 1869, and introduced under the name of "Victoria
yellow," which is dinitro-cresol. Other dyes derived directly or
indirectly from phenol will take us back once again to toluene.
Public-domain text, read in full here on John Shaqi.
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