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
Arylsulphaminoarylsulphonic acids and arylsulphoxyarylsulphonic acids
precipitate gelatine but are devoid of tannoid character. The latter is
acquired by compounds belonging to this class containing two or more
sulphamino groups, or when they, in addition to one sulphamino group,
contain a sulphoxy group and another sulphonic group. According to
Ger. Pat., 297,187 (Society oc Chemical Industry, Basle), such compounds
are obtained when, for instance, sodium sulphanilide in alkaline
solution acts upon nitrotoluenesulphochloride, and the resulting
nitrotoluenesulphamino compound is subsequently reduced with acetic acid
and iron. The resulting aminotoluenesulphaminobenzenesulphonic acid is
finally treated with p-toluenesulphonic chloride till the latter
disappears. A compound of the composition
-----NH-----SO_2-----
^ ^ ^
| | | | | |
| | | |---NH---| |
V V V
SO_2Na CH_2
is thereby obtained, which, when acidified, is readily capable
of being used for tanning purposes.
The intermediary product of the aminotoluenesulphaminobenzenesulphonic
acid obtained by this process may again be employed for the purpose of
reacting with one-half molecule soda and 1 molecule
nitrotoluenesulphonic chloride. The following compound is obtained--
---NH---SO_2--- ---NH---SO_2---
^ ^ ^ CH_3 ^
| | | | | | | |
| | | | | | | |
v v ---NH---SO_2--- v v
SO_3Na CH_3 CH_3
If _p_-toluenesulphaminobenzenesulphonic chloride is condensed
with sodium sulphanilide, a compound,
---SO_2---NH--- NaSO_3
^ ^ ^
| | | | | |
| | | | | |
v v ---SO_2---NH--- v
SO_3Na
is obtained which, when acidified, exhibits tannoid properties.
On condensing sodium phenolsulphonate with nitrotoluenesulphonic
chloride, reducing the condensation product and condensing the latter
with _p_-toluenesulphonic chloride, a compound similar to the above is
obtained--
---O---SO_2---
^ ^ ^ CH_3
| | | | | |
| | | | | |
v v ---NH---SO_2--- v
NaSO_3 CH_3
Again, a similar product is obtained when
_p_-toluenesulphaminobenzenesulphonic chloride or its homologues or
isomers are condensed with sodium-_o_-cresylsulphonate--
---SO_2---NH--- SO_3Na
^ ^ ^
| | | | | |
| | | | CH_3| |
v v ---SO_2---O--- v
CH_3
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