Synthetic Tannins, Their Synthesis, Industrial Production and ApplicationGrasser, Georg
Science
Synthetic Tannins, Their Synthesis, Industrial Production and Application
Grasser, Georg
Tannins
If DIPHENYLMETHANE, (C_6H_5)_2CH_2, is heated with excess sulphuric
acid, a dark blue mass, easily soluble in water, is obtained. The
product gently heated with formaldehyde yields a brown, water-soluble
condensation product; once condensation is complete, the product will
stand stronger heat. If, on the other hand, more formaldehyde is added,
brown, water-insoluble bakelites are formed. The water-soluble
condensation product precipitates gelatine, but not aniline
hydrochloride. Dissolved in water, it possesses tannoid properties: the
pelt is, however, tanned on the surface only, the intermediary layers
being merely pickled; after four days in the solution, the pelt after
drying was found to be converted into a greyish-brown, badly coloured
leather, which was empty, hard, and possessed but little tensile
strength.
CARBAZOLE (dibenzopyrrole),
^ _____ ^
| | | |
| |__ __| |
v v v
N_3
on the other hand, was found a suitable base for the commercial
production of synthetic tannins; its use is protected by Ger. Pat,
290,965.
TRIPHENYLMETHANE, (C_6H_5)_3CH, heated with excess sulphuric acid,
yields a nearly black mass which, when condensed with formaldehyde in
the cold, and subsequently heated, yields a mass which is soluble in
water. With gelatine and aniline hydrochloride it exhibits reactions
similar to those given by the diphenylmethane condensation products; its
tanning properties also are similar to those of the latter. The
resultant leather is black, but is soft and full and possesses good
tensile strength.
Baeyer's observation, [Footnote: _Ber_., 1872, 5, 280, 1096.] that
pyrogallol on condensation with formaldehyde yields an amorphous body
soluble in water, which precipitates gelatine and is very similar to
tannin, was confirmed by Caro [Footnote: _Ibid_., 1892, 25, 947.] and
Kahl. [Footnote: _Ibid_., 1898, 31, 114.] These investigators found
that by the condensation of phenols and hydroxybenzoic acids with
formaldehyde, diphenylmethane derivatives were formed; pyrogallol yields
hexahydroxydiphenylmethane--
C_6H_2(OH)_3
CH_2{
C_6H_2(OH)_3
Nierenstein [Footnote: _Collegium_, 1905, 221.] repeated these
experiments, and found that in addition to the insoluble
diphenylmethanes, water-soluble bodies were formed, which latter
precipitate gelatine. The condensation product yielded by gallic acid
was identified as hexahydroxyaurinecarboxylic acid--
_C_6H(OH)_3COOH
C{-C_6H(OH)_3COOH
| }C_6H(OH)_2COOH
O
which is formed in addition to hexahydroxydiphenylmethane-dicarboxylic
acid--
C_6H(OH)_3COOH
CH_2{
C_6H(OH)_3COOH
Baeyer's experiment with pyrogallol probaly also yields, according to
Nierenstein, another compound of the following constitution--
C_6H_2(OH)_3
C{-C_6H_2(OH)_3
|_}C_6H_2(OH)_2
O
Nierenstein considers these bodies confirmation of his hypothesis of the
existence of a "tannophor,"--CO--, in the tannins.
Public-domain text, read in full here on John Shaqi.
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