When nitrous acid acts upon an amido-derivative of a benzenoid hydrocarbon
in the presence of a mineral acid, there is formed a compound in which the
amido-group is replaced by a pair of nitrogen atoms joined together in a
certain way, which is different to the mode of combination in the azines.
This pair of nitrogen atoms is combined on the one hand with the
hydrocarbon residue, and on the other with the residue of the mineral
acid. The resulting compound is very unstable; its solution decomposes
very readily, and generally has to be kept cool by ice. Freezing machines
turning out large quantities of ice are kept constantly at work in
factories where these produces are made. The latter are known as
"diazo-compounds"--Griess's compounds _par excellence_--and they are
prepared on a large scale by dissolving a salt of the amido-base,
generally the hydrochloride, in water with ice, and adding sodium nitrite.
The result is a diazo-salt; aniline, for example, giving diazobenzene
chloride, and toluidine diazotoluene chloride. Similarly all
amido-derivatives of a benzenoid character can be "diazotised." The
importance of this discovery will be seen more fully in the next chapter.
At present we are more especially concerned with aniline.
The extreme instability of the diazo-salts enables them to combine with
the greatest ease with amido-derivatives and with other compounds. The
very property which in the early days rendered their investigation so
difficult, and which taxed the ingenuity of chemists to the utmost, has
now placed these compounds in the front rank as colour generators. When a
diazo-salt acts on an amido-derivative there is formed a compound which is
more or less unstable, but which readily undergoes transformation under
suitable conditions into a stable substance in which two hydrocarbon
residues are joined together by the pair of nitrogen atoms. These products
are dye-stuffs, known as "azo-colours," and aniline yellow, Bismarck
brown, and chrysoidine are the oldest known technical compounds belonging
to the group. The parent substance is "azobenzene," and these three
colouring-matters are mono-, di- and triamido-azobenzene respectively.
Public-domain text, read in full here on John Shaqi.
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