An Improved Process for Producing Tartaric Diphenylester as a Preparation for Medicinal Purposes.
Year: 1898

page_text: Date of Application, 10th Aug., 1898
Complete Specification Left, 24th May, 1899-Accepted, 29th July, 1899
An Improved Process for Producing Tartaric Diphenylester as a
Preparation for Medicinal Purposes.
A communication by JOACHIM ULRICH KREIS, of 27/1 Thierschstrasse, Munich, in
the Empire of Germany, Gentleman.
I, WILLIAM PHILLIPS THOMPSON, F.C.S., M.I.M.E., of The Agency for
Foreign Patent Solicitors, 6, Lord Street, Liverpool, and 6, Bank Street,
Manchester, both in the County of Lancaster, 118, New Street, Birmingham, in
the County of Warwick, and 322, High Holborn, in the County of Middlesex,
Civil Engineer, do hereby declare the nature of this invention to be as follows:-
This invention relates to the production of a preparation for medical purposes more
particularly for use in interruptions in the change of tissue, for instance in the case
of gout and the like. This preparation is a condensation product of pyrotartaric acid
and phenol.
Numerous experiments made by introducing organic acids into
carnivorous animals and the bodies of men have shown a very decided action of such
acids on the formation of uric acid. It was in fact found that these acids act
the better the greater the carbon contents. As a rule it was found that less uric
acid was found in the dejections according as the amount of oxalic acid or oxalates
contained was greater, and that the uric acid was reduced in proportion as the
carbon contents of the acids introduced were higher. The use of the said acids has
however a limit in consequence of their toxic properties. Among the acids employed
which influence the change of tissue in the direction desired, that is, which lessen
the production of uric acid, pyrotartaric acid, citric acid and phenol were found most
suitable. When the latter was used, the highest amount of oxalic acid contents was
yielded but symptoms of intoxication became soonest apparent. In order to avoid
these a preparation is employed made according to the following formula:

page_text: and the latter closed with a Bunsen valve. The flask is then placed in the boiling
water bath and kept there for 15 hours. During this time the remaining phosphorus
oxy-chloride is added at intervals of about 1 hour in such a way that after the last
dose has been added the flask is still heated for 5 hours. The contents of the
flask when cooled present a homogeneous paste and are conveyed into plenty
A thin
of cold water, thoroughly. agitated or stirred and then allowed to settle.
oil is then deposited on the bottom of the vessel and as soon as the acid liquid
standing above it has clarified it is drawn off. Fresh water is then sprinkled on
the oil and it is carefully neutralised with ammonia and the oil is then repeatedly
washed with water. During these operations the oil becomes gradually thicker. It
is then placed in a dish, alcohol is repeatedly poured thereon and poured off again
without stirring it much in order that the oil may be freed from water. Absolute
alcohol is then poured thereon in large quantity and the mass is agitated with a
glass rod for a considerable time until it has become quite crystalline, or to better
express it, the pure tartaricdiphenylester has crystallised out and all oily bye-products
have been absorbed by the alcohol. The crystalline mass is then filtered, washed
with alcohol, dried on porous earthenware dishes, and then recrystallised twice through
alcohol. The substance thus obtained shows fine sheeny needle crystals and is, as an
elementary analysis shows, pure tartariediphenylester with the formula:
On being heated the substance is partially volatile without decomposition. It
has a slight aromatic odour and no appreciable taste. It is insoluble in water but
when the water is heated melts into an oil and imparts a plainly recognizable
aromatic scent to the steam from the water. It is only with difficulty soluble in
cold alcohol but is more easily soluble in hot, this solution is not altered by
perchloride of iron. This product is easily soluble in ether and glycerine. The
solutions of these last named substances have a neutral re-action.
Attempts to obtain the substance by the action of tartrate of soda on phenol in the
presence of phosphorus oxychloride, yielded no results, as the oil obtained could not
be caused to crystallise.

page_text: An Improved Process for Producing Tartaric Diphenylester as a
Preparation for Medicinal Purposes.
A communication by JOACHIM ULRICH KREIS, of 27/1 Thierschstrasse, Munich,
in the Empire of Germany, Gentleman.
I, WILLIAM PHILLIPS THOMPSON, F.C.S., M.I.M.E., of The Agency for Foreign
Patent Solicitors, 6, Lord Street, Liverpool, and 6, Bank Street, Manchester, both in
the County of Lancaster, 118, New Street, Birmingham, in the County of Warwick;
and 323, High Holborn, in the County of Middlesex, Civil Engineer, do hereby
declare the nature of this invention and in what manner the same is to be pér-
formed, to be particularly described and ascertained in and by the following
statement:-
This invention relates to the production of a preparation for medical purposes
more particularly for use in interruptions in the change of tissue, for instance in the
case of gout and the like. This preparation is a condensation product of pyro-
tartaric acid and phenol. Numerous experiments made by introducing organic acids
into carnivorous animals and the bodies of men have shown a very decided action of
such acids on the formation of uric acid. It was in fact found that these acids act
As a rule it was found that less uric acid
the better the greater the carbon contents.
was found in the dejections according as the amount of oxalic acid or oxalates con-
tained was greater, and that the uric acid was reduced in proportion as the carbon
contents of the acids introduced were higher. The use of the said acids has however
a limit in consequence of their toxic properties. Among the acids employed which
influence the change of tissue in the direction desired, that is, which lessen the pro-
duction of uric acid, pyrotartaric acid, citric acid and phenol were found most suitable.
When the latter was used, the highest amount of oxalic acid contents was yielded
but symptoms of intoxication became soonest apparent. In order to avoid these a
preparation is employed made according to the following formula:

page_text: is then deposited on the bottom of the vessel and as soon as the acid liquid standing
above it has clarified it is drawn off. Fresh water is then sprinkled on the oil and it
is carefully neutralised with ammonia and the oil is then repeatedly washed with
water. During these operations the oil becomes gradually thicker. It is then placed
in a dish, alcohol is repeatedly poured thereon and poured off again without stirring
it much in order that the oil may be freed from water. Absolute alcohol is then
poured thereon in large quantity and the mass is agitated with a glass rod for a con-
siderable time until it has become quite crystalline, or to better express it, the pure
tartaricdiphenylester has crystallised out and all oily bye-products have been
absorbed by the alcohol. The crystalline mass is then filtered, washed with alcohol,
dried on porous earthenware dishes, and then recrystallised twice through alcohol.
The substance thus obtained shows fine sheeny needle crystals and is, as an elementary
analysis shows, pure tartaricdiphenylester with the formula:
On being heated, the substance is partially volatile without decomposition. It
has a slight aromatic odour and no appreciable taste. It is insoluble in water but
when the water is heated melts into an oil and imparts a plainly recogniazble aromatic
scent to the steam from the water. It is only with difficulty soluble in cold alcohol
but is more easily soluble in hot, this solution is not altered by perchloride of iron.
This product is easily soluble in ether and glycerine. The solutions of these last
named substances have a neutral re-action.
Attempts to obtain the substance by the action of tartrate of soda on phenol in the
presence of phosphorus oxychloride, yielded no results, as the oil obtained could not
be caused to crystallise.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed, as communicated to
me by my foreign correspondent, I declare that what I claim is :-
The process for producing tartaricdiphenylester consisting in the condensation of
tartaric acid and phenol by means of phosphorus oxychloride substantially as herein-
before set forth.