The Manufacture or Production of a New Chemical Compound, suitable for Medicinal Purposes.
Year: 1897

page_text: [Communicated from abroad by THE FARBENFABRIKEN, VORMALS FRIEDRICH
BAYER & Co., of Elberfeld, Germany.]
The Manufacture or Production of a New Chemical Compound,
suitable for Medicinal Purposes.
I, HENRY EDWARD NEWTON, of the Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, Patent Agent, do hereby declare the nature
of this invention to be as follows:-
It is known that by acting with phosphorous oxychloride on salicylic acid, salicylid
is formed, and that, on treating gallic acid with phosphorous oxychloride, tannin is
produced.
My foreign correspondents have now found, that this process proceeds in a totally
different manner, if phosphorous oxychloride is allowed to act on a mixture of equi--
molecular proportions of salicylic acid and gallic acid. According to the researches
of my foreign correspondents, a new condensation product is thus obtained, which
process may be illustrated by the following equation:-
:-
It distinctly differs from salicylid and tannin, forming a white amorphous powder
insoluble in water, ether, and chloroform, scarcely soluble in cold alcohol and in cold
alkaline carbonates, but readily soluble in caustic alkalies. When dissolved in
caustic alkalies, it is precipitated by the addition of acids. It melts at about
O 210 degrees Centigrade, undergoing decomposition, and begins to liquefy at a some-
075

page_text: what lower temperature. By caustic alkalies and alkaline carbonates, at elevated
temperatures, it is gradually split into its components, viz., salicylic acid and gallic
acid.
In order to illustrate the production of this new compound, the following example
is given, which however is merely typical. The parts are by weight.
EXAMPLE.
40 parts of salicylic acid are mixed very intimately with 56 parts of gallic acid.
From about 30 to 40 parts of phosphorous oxychloride, and, if desired, any indifferent
solvent or diluent (such as toluene or the like) are added to the above mixture. The
mass is then gradually heated, say, by means of an oil bath, to about 130 degrees
Centigrade. Hydrochloric gas soon begins to be set free, and the mixture at first
assumes a slightly reddish tinge, & subsequently a light yellow colour. After some
hours, the reaction is complete, the mixture forming a solid mass. Ice water is then
added, in order to remove the metaphosphoric acid formed during the reaction and
the phosphorous oxychloride used in excess. After this treatment, the solid mass is
cut up, repeatedly washed with hot water, and finally dried. The yield is almost
theoretical.
Of course, my foreign correspondents do not limit themselves to the particulars
above given, as these can be varied within wide limits. Thus, for instance, other
chlorides of phosphorous or phosphoric anhydride, or other dehydrating agents acting
in the same or a similar manner, may be substituted for phosphorous oxychloride used
in the above example. Gallic acid may be replaced, though less advantageously, by a
corresponding quantity of tannin.
It is to be noted that, on using a considerable excess of phosphorous oxychloride,
and allowing the same to act on the mixture of equimolecular parts of salicylic acid
and gallic acid, another condensation product, containing phosphoric acid is formed,
in case the reaction is not interrupted in due time, that is to say, as soon as the
calculated quantity of hyrochloric gas has been set free.
According to the researches of my foreign correspondents, the new condensation
product, having the formula above given, unites in itself the properties of salicylic
acid and those of tannin or gallic acid, & it may be used with advantage for
medicinal purposes.
Dated this 90th day of April 1807
The Manufacture or Production of a New Chemical Compound,
suitable for Medicinal Purposes.
I, HENRY EDWARD NEWTON, of the Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, Patent Agent, 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 :--
It is known that, by acting with phosphorus oxychloride on salicylic acid, salicylid
is formed, and that, on treating gallic acid with phosphorus oxychloride, tannin is
produced.
My foreign correspondents have now found that if phosphorus oxychloride is allowed
to act on a mixture of equimolecular proportions of salicylic acid and gallic acid, a

page_text: new and valuable condensation product is obtained, the production of which may be
illustrated by the following equation ÷-
It differs distinctly from salicylid and tannin, forming a white amorphous powder,
insoluble in water, ether, chloroform; is only slightly soluble in cold alcohol, and in
When dissolved in
cold alkaline carbonates, but is readily soluble in caustic alkalies.
It melts at about 210
caustic alkalies, it is precipitated by the addition of acids.
degrees Centigrade, undergoing decomposition, and begins to liquefy at a somewhat
lower temperature. By caustic alkalies and alkaline carbonates, at elevated
temperatures, it is gradually split into its components, viz., salicylic acid and gallic
acid.
In order to illustrate the production of this new compound, the following example
is given, which, however, is merely typical. The parts are by weight :-
EXAMPLE.
-
40 parts of salicylic acid are mixed very intimately with 50 parts of gallic acid.
From about 30 to 40 parts of phosphorus oxychloride, and, if desired, any indifferent
solvent or diluent (such as toluene or the like), are added to the above mixture. The
mass is then gradually heated, say by means of an oil bath, to about 130 degrees
Centigrade. Hydrochloric gas soon begins to be set free, and the mixture at first
After some
assumes a slightly reddish tinge, and subsequently a light yellow colour.
hours, the reaction is complete the mixture forming a solid mass. Ice water is then
added, in order to remove the meta-phosphoric acid formed during the reaction, and
the phosphorus oxychloride used in excess. After this treatment, the solid mass is
cut up, repeatedly washed with hot water, and finally dried. The yield is almost
theoretical.
It may be here remarked that my foreign correspondents do not intend to limit
themselves to the particulars above given, as these may be varied considerably. Thus,
for instance, other chlorides of phosphorus or phosphoric anhydride, or other dehy-
drating agents acting in the same or a similar manner, may be substituted for
phosphorus oxychloride used in the above example. The free gallic acid and salicylic
acid may be replaced by corresponding quantities of their alkaline salts.
According to the researches of my foreign correspondents, the new condensation
product, having the formula above given, unites in itself the properties of salicylic
acid and those of tannin or gallic acid, and it may therefore be used with advantage
for medicinal purposes.
Having now particularly described and ascertained the nature of the said

page_text: invention and in what manner the same is to be performed, I declare that what I
claim is:
1. The process for producing a new condensation product from salicylic acid and
gallic acid, or salts thereof, substantially as herein before described.
2. The production of a new condensation product from salicylic acid and gallic acid,
by allowing phosphorus oxychloride, or other chlorides of phosphorus, or phosphoric
anhydride, or other dehydrating agents acting in the same or a similar manner, to act
on a mixture of equi-molecular proportions of salicylic acid and gallic acid, or of salts
thereof, substantially as herein before described.
3. The new condensation product above described.
.4. The use of the new condensation product hereinbefore described for medicinal
purposes.
Dated