Synthetic Tannins, Their Synthesis, Industrial Production and Application — John Shaqi
Synthetic Tannins, Their Synthesis, Industrial Production and ApplicationGrasser, Georg
Science
Synthetic Tannins, Their Synthesis, Industrial Production and Application
Grasser, Georg
Tannins
Hydrolysis of digallic acid yields gallic acid; oxidation, on the other
hand, ellagic acid and luteic acid (Luteo Säure), which can be separated
by shaking with pyridine. The reduction of digallic acid yields, by
different methods, the same reduction compound, [Footnote: Nierenstein,
Abderhalden's "Handb. d. biochem. Arbeitsm.," vi. 154.] viz., the
racemic leucodigallic acid, which differs from digallic acid by being
devoid of any tannoid properties; the latter distinction may be ascribed
to the transformation of the tannophor group--CO.O--, to the
tannoid-inactive group CH(OH)--O--.
The successful resolving of racemic leucodigallic acid into both of its
optically active components can only be brought about through the _d_-
or _l_-hexacarbethoxyleucodigallic acid on introducing the latter into a
1 per cent. pyridine solution and heating to 45°-50° C., whereby the
_d_- or _l_-acid is formed accompanied by a strong evolution of carbon
dioxide.
Hydrolysis of leucogallic acid yields gallic acid and gallic aldehyde;
oxidation by means of hydrogen peroxide yields ellagic acid and luteic
acid, and oxidation with potassium persulphate and sulphuric acid, in
acetic acid solution, yields purpurotannin (see below) [Footnote:
Liebig's _Ann_., 1912, 386, 318.].
Another distinct difference between digallic acid and leucodigallic acid
is the fact that the formaldehyde condensation product of the former
resembles gallic acid, whereas that of the latter resembles tannin; it
is therefore probable that the leucodigallic acid part of the tannin
molecule imparts this characteristic property to tannin.
---CO.O---
^ ^
| | | |
HO V OH COOH V OH
OH OH
[Illustration: Digallic Acid becomes...]
---CO.O---
^ ^ OH
| | | |
HO V OH COOH V OH
OH OH
[Illustration: Luteic Acid becomes...]
---CO.O---
^ ^ OH
| | | |
HO V --O.CO-- V OH
OH OH
[Illustration: Ellagic Acid becomes...]
COOH COOH
^ _______ ^
| | | |
HO V ---O--- V OH
OH OH
[Illustration: Purpuro Tannin.]
3. Ellagic Acid
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