Manufacture or Production of Salols.
Year: 1893

page_text: Date of Application, 30th Mar., 1893
Complete Specification Left, 28th Dec., 1893-Accepted, 3rd Feb., 1894
PROVISIONAL SPECIFICATION.
Manufacture or Production of Salols.
I, Dr. CARL KOLBE of Radebeul, near Dresden, in the Kingdom of Saxony, do
hereby declare the nature of this invention to be as follows:-
In the Specification of Letters. Patent granted to Marcel von Nencki and
myself dated the 16th June 1886, and in the Specifications of Letters Patent
granted to me dated respectively 22nd July 1887 No. 10260; 12th September 1888
No. 13169; and 28th October 1890 No. 17221 various processes are described for
the manufacture of the so-called salols with the employment of dehydrating
agents.
Now if in these processes, with the employment of salicylic acid, the phenols
referred to therein be replaced by the substituted phenols, o- and p- chlor-, brom-,
iodo-phenol; v- and as- dichlorine-, di-bromine-, di-iodine-phenol, and by tri-
chlorine-, tri-bromine-, tri-iodine-phenol, then according to the present
"
invention substituted salols will be obtained as new bodies.
In the manufacture of these new salols, dehydrating agents are employed, as
before. Of such dehydrating agents, several are mentioned in the said prior
Specifications No. 801888 and 1026087, such as chlorides or oxychlorides of
phosphorus or of sulphur, or acid sulphates of the alkalies. It may be mentioned
that phosgene or thionylchloride may also be used as a dehydrating agent. The
substituted salols thus obtained have a greater therapeutic action than salol
(salicylic acid phenol) heretofore obtained.
The mode of carrying out the present invention may be explained by aid of the
following example:
To a mixture of 128 kilos. of p-chlorine-phenol and 138 kilos. of salicylic acid,
there is added at a temperature of about 140° C., 52 kilos. of phosphorus penta-
chloride, which can however be replaced by other suitable dehydrating agent.
After the generation of hydrochloric acid has caused, the product of the reaction
is washed with water and with solution of soda, and is then recrystallized
from alcohol. In this manner there is obtained salicylate of p-chlorine-phenol
C.H
OH
0 in colorless crystals, and having a melting point of 73° C.
In like manner, there can be obtained from salicylic acid and the above
mentioned substituted phenols, by the action of dehydrating agents, amongst
others, the following substituted salols :-

page_text: ONa
When boiled with alkalies, saponification sets in. The new substances mentioned
form very effective medicines that are distinguished from the corresponding
chlorine-, bromine-, or iodine phenols, more particularly by their want of smell,
and by their want of or weak taste.
Dated this 30th day of March 1893.
W. LLOYD WISE,
Per F. J. Brougham,
46, Lincoln's Inn Fields, London, W.C., Agent for the Applicant.
COMPLETE SPECIFICATION.
Manufacture or Production of Salols.
I, Dr. CARL KOLBE, of Radebeul, near Dresden, in the Kingdom of Saxony
do hereby declare the nature, of this invention and in what manner the same is to 2
be performed to be particularly described and ascertained in and by the following
statement:-
In the Specification of Letters Patent granted to Mercel von Nencki and myself
dated the 16th June 1886, and in the Specifications of Letters Patent granted to me
dated respectively 22nd July 1887 No. 10260; 12th September 1888 No. 13169; 3
and 28th October 1890 No. 17221 various processes are described for the manu-
facture of the so-called salols with the employment of dehydrating agents.
Now if in these processes, with the employment of salicylic acid, the phenols
referred to therein be replaced by the substituted phenols, or substitution phenols,
o-m- and p-chlor-, brom-, and iodo-phenol; v- and as-dichlor-, di-brom-, di-iodo- 3
phenol, and by tri-chlor-, tri-brom-, tri-iodo-phenol.... then according to the present
invention, substituted salols or substitution salols or salicylic-acid-ethers will be
obtained as new bodies.

page_text: In the manufacture of these new salols, dehydrating agents are employed, as
before. Of such dehydrating agents, several are mentioned in the said prior
Specifications Nos. 801888 and 102607, such as chlorides or oxychlorides of
phosphorus or of sulphur or acid sulphates of the alkalies. It may be mentioned
that phosgene, or thionylchloride may also be used as a dehydrating agent. The
substituted or substitution salols thus obtained have a greater therapeutic action
than salol (salicylic acid phenol or salicylate of phenol) heretofore obtained.
The mode of carrying out the present invention may be explained by aid of the
following example :-
To a mixture of 128 kilos. of p-chlor-phenol and 138 kilos. of salicylic acid,
heated to a temperature of about 140° C. there is added 52 kilos. of phosphorus
pentachloride, which can however be replaced by other suitable dehydrating agent
the heating of the mixture being continued until the generation of hydrochloric
acid has ceased. The product of the re-action is washed with water and with
solution of soda, and is then recrystallized from alcohol. In this manner there is
obtained salicylate of p-chlor-phenol

page_text: The new compounds are colorless, soluble in alcohol, and insoluble in water.
With solution of soda they form salts according to the formula
1000
When boiled with alkalies, saponification sets in. The new substances mentioned
form very effective medicines that are distinguished from the corresponding chlorine-,
bromine, or iodine phenols, more particularly by their want of smell, and by their
want of or weak taste.
Having now particularly described and ascertained the nature of the said inven-
tion and in what manner the same is to be performed I declare that what 1
claim is:
:
1. The manufacture or production of substituted or substitution salols or salicylic
acid ethers by the action of dehydrating agents upon a mixture of one or other of
the substituted or substitution phenols o- m- and p- chlor-, brom- and iodo-phenol,
v- and as-di-chlor-, di-brom-, and di-iodo-phenol, and tri-chlor-, tri-brom-, and tri-
iodo-phenol, and salicylic acid, substantially as herein described.
2. The several new substituted or substitution salols or salicylic-acid-ethers
consisting of salicylates of o-, m- and p- chlor-, brom-, and iodo-phenol; of v- and
as-di-chlor-, di-brom-, and di-icdo-phenol; and of tri-chlor-, tri-brom-, and tri-iodo-
phenol, these products having the properties herein before described.
Dated this 28th day of December 1893.
For the Applicant,
W. LLOYD WISE,
46, Lincoln's Inn Fields, London, W.C., Chartered Patent Agent.