Synthetic Tannins, Their Synthesis, Industrial Production and ApplicationGrasser, Georg
Science
Synthetic Tannins, Their Synthesis, Industrial Production and Application
Grasser, Georg
Tannins
It should be noted that in both these experiments with concentrated
formaldehyde solution a slight increase in temperature occurs
concurrently with the process of condensation. If the experiments are
carried out on the water bath, a gelatinous mass is instantly formed,
which assumes the colours of grey, dirty light violet and dark violet,
in the order named, and which, whilst left several hours--or when heated
on the water bath--is suddenly converted into the insoluble, brown,
gluey mass above referred to.
3. If, for the purpose of condensation, phenolsulphonic acid to which 10
per cent, of water has been added, is employed, the reaction proceeds
very quickly and energetically. If one-sixth of its volume of
formaldehyde (1:3 of the 30 per cent. solution) is added drop by drop to
a cold solution of phenolsulphonic acid, a reddish, milky solution
results, which assumes a slightly lighter colour on addition of more
formaldehyde and deposits an insoluble flocculent precipitate. If the
solution is kept below 45° C., by artificial cooling, the light colour
is maintained, but a gelatinous precipitate is soon formed, the
viscosity of which increases on stirring, and finally is converted into
an insoluble, tough, gummy mass. If, on the other hand, the mass is
heated at the beginning of the reaction, or if the amount of
formaldehyde is increased and the mass cooled during reaction,
effervescence occurs, and a cheesy, dirty-coloured mass results, which,
on cooling, rapidly becomes solid and yields a very firm, elastic,
rubbery mass, which is absolutely insoluble in water.
4. The condensation proceeds exceedingly violently when concentrated
phenolsulphonic acid is acted upon by one-sixth of its volume of
formaldehyde. If the latter is firstly added drop by drop to the
phenolsulphonic acid, a gel immediately results, the temperature of
which quickly increases on further addition of formaldehyde and suddenly
boils over, yielding a reaction product which, when cooled, forms a
dirty violet, firm, elastic, and rubbery mass, insoluble in alkalies and
hardly affected by organic solvents.
Finally, if the amounts of concentrated phenolsulphonic acid and
formaldehyde stated above are mixed, strong effervescence occurs and
heat is evolved, and a dirty blackish-violet mass is instantly formed
which, on cooling, yields a rather brittle, hard product insoluble in
water.
5. Totally different end-products are, however, obtained when the
addition of formaldehyde (30 per cent.) in the proportion of one-sixth
of the volume of dilute phenolsulphonic acid (1 plus 9 aq.) to the
latter is extended over several hours. In this case a slightly
opalescent liquid is obtained which, when left twelve hours, is
transformed into a brown mass soluble in water, which strongly
precipitates gelatine and possesses tanning properties. Hence direct
tannoid substances are obtained by this method of condensation.
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