Improvements in the Manufacture of Ortho-oxyquinoline and Oxyquinoline Derivatives.
Year: 1891

page_text: Date of Application, 6th May, 1891-Accepted, 11th July, 1891
Improvements in the Manufacture of Ortho-oxyquinoline and
Oxyquinoline Derivatives.
We, ADOLF LEMBACH and ULRICH SCHLEICHER D.Ph. Technical Chemists,
both of Biebrich in the German Empire, and CARL JOSEF WOLFF D.Ph.
Technical Chemist of Wiesbaden in the German Empire, do hereby declare the
nature of this invention, and in what manner the same is to be performed, to be
particularly described and ascertained in and by the following statement :-
This invention relates to the manufacture of ortho-oxyquinoline, neutral oxy-
quinoline sulphate, oxyquinoline phenolsulphonate, oxyquinoline cresolsulphonate
and oxyquinoline sulphosalicylicate.
re boiled together for about six hours in a suitable vessel provided with an
nverted condenser, and the molten mass thus produced is diluted with 200 litres of
water.
The acid in the solution is then neutralised with soda lye and the oxyquinoline
is entirely precipitated with soda and separated by filtration. The oxyquinoline
thus obtained is subsequently purified by distillation with steam heat.
By this process, water and sulphuric acid are separated as is shewn in the
re-action :-
2 (CH,.OH. NH,. SO,H) + C,H,. OH. NO,. SO,H. + 3 (CHO)
=
= (C,H. N. OH) + 3 (SOH₂) + 8 H₂O.
29 kilos. of ortho-oxyquinoline (2 mol.)
10 kilos. sulphuric acid (1 mol.) of about 66 deg. Bé.
30 kilos. of water,
are boiled together for about six hours in a suitable vessel provided with an inverted.
condenser.
After the chemical combination has been completed, the product of the re-action
is separated by evaporating the water in a vacuum pan. Neutral oxyquinoline
sulphate remains in the pan in the form of sulphur-yellow crystals.
Instead of separating the water in a vacuum pan, the solution may be con-
centrated in a water bath or by steam heat, in which case a honey-like yellow
syrup is obtained, which upon being digested with a mixture of alcohol and ether
yields the quinoline sulphate in a fine yellow powder.
The melting point of the neutral oxyquinoline sulphate lies between 170
and 180 degrees Cent.

page_text: are boiled continuously for about a whole day in a suitable vessel provided with an
inverted condenser.
By this means a fifty per cent. solution of p-phenolsulphonic oxyquinoline is
obtained. If this solution is evaporated in a vacuum pan, at temperatures I
below 100 degrees Cent. the oxyquinoline phenolsulphonate (which is soluble in
water) remains in a yellow syrup which does not easily crystallise.
In a similar manner,
by boiling the oxyquinoline with cresolsulphonic acid and with sulphosalycilic aciċ
respectively in about molecular proportions.
In the manufacture of ortho-oxyquinoline instead of employing the ortho-nitro-
phenol-para-sulphonic acid; nitro-benzole, picric acid, or other suitable oxidising
agent may be employed. In the preparation of the oxyquinoline phenolsulphonate
instead of para-phenolsulphonic acid, the ortho-acid may be used; also, either
ortho or para- cresolsulphonic acid may be employed in the production of the
cresolsulphonate.
Further, in the preparation of the derivatives of the ortho-oxyquinoline where
phenols are used, the phenols hereinbefore described are by preference employed,
but their homologues and derivatives may be used with sulphuric acid, and the
oxyquinoline be treated therewith until the desired combinations have been
effected.
Having now particularly described and ascertained the nature of our said inven-
tion and in what manner the same is to be performed, we declare that what we
claim is :-
1. The manufacture of ortho-oxyquinoline, substantially in the manner and by
the means bereinbefore described.
2. The manufacture of neutral oxyquinoline sulphate, substantially in the manner
and by the means hereinbefore described.
3. The manufacture of oxyquinoline phenolsulphonate substantially in the
manner and by the means hereinbefore described.
4. The manufacture of oxyquinoline cresolsulphonate substantially in the manner
and by the means hereinbefore described.
5. The manufacture of oxyquinoline sulphosalicylicate substantially in the
manner and by the means hereinbefore described.
Dated this 4th day of May A.D. 1891.
WILLIAM E. HEIS,
Agent for the Applicants.