Synthetic Tannins, Their Synthesis, Industrial Production and ApplicationGrasser, Georg
Science
Synthetic Tannins, Their Synthesis, Industrial Production and Application
Grasser, Georg
Tannins
This supposition was adopted by Stiasny [Footnote: _Gerber_, 1905, 233.]
and Kauschke [Footnote: _Collegium_, 1906, 362.] and the latter points
out that these easily soluable substances exhibit tanning
properties. Nierenstein [Footnote: _Ibid_., 1906 424.] was further able
to show that by all processes of condensation between phenols (or
hydroxybenzoic acids) and formaldehyde, compounds of the character of
hydroxyaurine (or hydroxyaurinecarboxylic acid) were formed in addition
to the insoluble hydroxydiphenylmethanes (or
hydroxydiphenylmethanecarboxylic acids), the former possessing the
characteristic tannophor group and hence precipitating gelatine, _i.e._,
exerting tanning action. If the formation of leather is viewed in the
light of Schiff's base, [Footnote: _Ibid_., 1905, 159.] one may
consider the constitution of a hexahydroxyaurinecarboxylic acid leather
as follows:--
_C_6H_2(OH)_3.COOH
C{-C_6H_2(OH)_3.COOH
|_}C_6H_2(OH)_2.COOH
R-N
In the preparation of these and similar condensation products,
Nierenstein and Webster [Footnote: _Ber_., 1908, 41, 80.] observed a
peculiar steric effect of the carboxyl group. Each 2.5 gm. of the phenol
or the acid in question were dissolved in 30 c.c. of water, the solution
brought to boil and 5 c.c. formaldehyde (20 per cent.) and 2.5
c.c. hydrochloric acid added drop by drop; the precipitate formed was
filtered off after twenty-four hours, dried at 110° C. to constant
weight, extracted (in a Gooch crucible) freely with water, and the
residue again dried at 110° C. till constant. The following values were
obtained:--
Total Insol. Aq. Sol. Aq. Oxy-
Precipitate Diphenylmethane aurinecarboxylic
in Grammes. Derivatives Acid.
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