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
When sulphides or mercaptans in glacial acetic acid solution are heated
with permanganate, the resulting sulphonic acid compounds exhibit great
similarity to compounds containing free carboxyl groups. The sulphonic
acid group may also be directly introduced either by concentrated, or by
fuming sulphuric acid, or by elimination of halogen by the action of
sodium or silver sulphite on the halogen derivatives of the aliphatic
compounds. Saturated hydrocarbons do not react with sulphur trioxide,
but unsaturated hydrocarbons are readily attacked by SO_3. Similarly,
halogenated compounds and alcohols react with concentrated or fuming
sulphuric acid forming sulphonic and hydrosulphonic acids respectively.
The aromatic compounds form, as a rule, sulphonic acids with much
greater facility. Benzene, for instance, is easily converted into the
_m_-disulphonic acid by gently heating with fuming sulphuric acid;
stronger heating converts the _m_- into the _p_-disulphonic acid, and at
190° C. the trisulphonic acid is formed. Toluene treated with fuming
sulphuric acid first yields _o_- and _p_-sulphonic acids, finally _o_-
and _p_-disulphonic acids, ethylbenzene at the boiling point
_p_-ethylbenzene-sulphonic acid. Of the three isomeric xylenes _o_- and
_m_-xylene dissolve in concentrated, _p_-xylene in fuming sulphuric acid
only.
The action of sulphuric acid on naphthalene is stronger even than on
benzene. Equal parts of naphthalene and sulphuric acid heated to 100°
C. yield 80 per cent. [Greek: a] and
20 per cent. [Greek: b]-monosulphonic acid. At 160°-170°C. 25 per cent
[Greek: a]- and 75 per cent. [Greek: b]-sulphonic acid is formed, and at
higher temperatures [Greek: b]-monosulphonic acid only. If, on the other
hand, 8 parts of naphthalene are heated with 3 parts of concentrated
sulphuric acid to 180° C., two different naphthyldisulphonic acids are
obtained.
Complete solution of the substance in sulphuric acid is, generally
speaking, a criterion of complete sulphonation. A completely sulphonated
compound should remain clear on dilution with water, or, in case
precipitation occurs, the precipitate should be completely soluble in
alkali or ammonia. It is necessary to submit the product to this test,
since many organic substances are soluble in concentrated sulphuric acid
without undergoing any alteration in composition.
Phosphoruspentoxide or potassium sulphate considerably increase the
sulphonating property exhibited by fuming sulphuric acid.
The separation of the sulphonic acids from sulphuric acid is effected by
salting out the former with common salt, or by removing the sulphuric
acid with calcium, barium, or lead salts, provided that the sulphonic
acid salts of these metals are soluble in water.
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