Synthetic Tannins, Their Synthesis, Industrial Production and ApplicationGrasser, Georg
Science
Synthetic Tannins, Their Synthesis, Industrial Production and Application
Grasser, Georg
Tannins
O= ^=_____ ^ OH
| | | |
| |== __| |
=v v v
C
|
C_6H_5
In alkalies, the hydroxylated triphenylmethanes dissolve without
imparting any colour to the solution; by concentrated sulphuric acid
they are taken up with intense coloration.
If the hydroxyls occupy the ortho-position to methyl, they may form
xanthenes by splitting off water--
O
^ ^ ^
| | | |
| | | |
CH_3 v v v CH_3
CH
|
C_6H_5
In the benzene series this reaction is difficult to establish, and has
to be induced by distilling the particular dihydroxy-diphenylmethane at
ordinary pressure. In the naphthalene series, on the other hand, the
ring closes up by, for instance, the condensation of [Greek: b]-naphthol
with benzaldehyde or paraldehyde, and yields the following compounds:--
C_10H_6 C_10H_6
C_6H_5-CH{ }O CH_3-CH{ }O
C_10H_6 C_10H_6
These xanthenes are white, silk-glossy needles, which are soluble in
water and in alkalies. In concentrated sulphuric acid, they are taken up
with beautiful fluorescence.
6. Summary
From the qualitative reactions of the different condensation products
described it may be seen that their tannoid properties are not dependent
on whether they precipitate gelatine or are adsorbed by hide powder or
not. Hydroxynaphthylmethanesulphonic acid, for instance, precipitates
gelatine but does convert pelt into leather; on the other hand, sodium
dicresylmethanesulphonate does not precipitate gelatine, and neither
does it tan pelt; nevertheless it is adsorbed by hide powder as "tanning
matter". The author discovered that _o_-nitrophenol does not precipitate
gelatine, but has some tanning action on both hide powder and pelt.
Relatively to the possibilities of forming condensation products
possessing tannoid properties, the following may be stated:--
All mono- and polyhydric phenols may be converted into true tanning
matters by either condensing them as such, or after their conversion
into the corresponding sulphonic acids, by substances capable of
eliminating the elements of water. It makes no difference to the final
product whether the condensation is the first step followed by
sulphonation and consequent solubilisation of the intermediary insoluble
product, or whether, vice versa, the sulphonic acid is subjected to
condensation. Alkaline solution of phenols may also be condensed, the
reaction products, when condensed, constituting tanning matters soluble
in water.
Among the substitution products of the phenols, the thio-, chloro-,
bromo-, nitro-, and aminophenols as a rule yield tanning matters similar
in character.
The quinones are as such--_i.e._, without being condensed--substances
possessing tannoid properties.
The aromatic dihydric alcohols are easily condensed with the different
sulphonic acids and yield valuable tanning matters.
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