Process for the Production of Thio-oxydiphenyl-amine
Year: 1889

page_text: Date of Application, 7th Oct., 1889
Complete Specification Left, 27th May, 1890-Accepted, 28th June, 1890
PROVISIONAL SPECIFICATION.
A Process for the Production of Thio-oxydiphenyl-amine."'
I, MARTIN LANGE, doctor of philosophy, manufacturing chemist, residing at
Amersfoort, kingdom of Holland, do hereby declare the nature of the said invention to
be as follows:-
My invention relates to the production of thio-oxydiphenyl-amine. The method
which I employ for obtaining this substance consists in dissolving a salt of meta-
oxydiphenyl-amine in water, in adding sulphur thereto and in heating the mixture.
The sulphur will then dissolve in the solution of the said salt, and thio-oxydiphenyl-
amine will be formed.
This reaction may, with advantage, be promoted by adding an alkali or alkalic
carbonate in excess, the alkali in this case operating to dissolve the sulphur and to
form therewith sulphide of alkali, which then gives off the sulphur to the meta-oxy-
diphenyl-amine. Or, the sulphur is first dissolved with application of beat in a solution
of an alkali or alkalic carbonate, so that, according to the variable proportions of the
substances employed, a sulphide or a polysulphide is obtained, the meta-oxydiphenyl-
amine-salt is introduced into the solution of the sulphide or polysulphide, and the
mixture is heated again. Instead, however, of preparing the said alkalic sulphide or
polysulphide as described, the same may also be employed in the state in which they
form articles of commerce.
From its solution the thio-oxydiphenyl-amine can be precipitated by the addition of
an acid or an acid salt. In purified condition it consists in a light yellow, tasteless
powder, which dissolves easily in alkalies, and more difficultly in alkalic carbonates.
Alcohol and acetic acids are also solvents of the same. The solutions are of
yellow color. When heated the substance becomes brown, and it melts at about
155° Centigrade.
111 a
1000
1. COMPLETE SPECIFICATION.
A Process for the Production of Thio-oxydiphenyl-amine.
.
I, MARTIN LANGE, doctor of philosophy, manufacturing chemist, residing at
Amersfoort, kingdom of Holland, do hereby declare the nature of this invention and
in what manner the same is to be performed, to be particularly described and ascer
tained in and by the following stateinent:
My invention relates to the production of thio-oxydiphenyl-amine. The method
which I employ for 'obtaining this substance consists in dissolving a salt of meta-
oxydiphenyl-amine in water, in adding sulphur thereto and in heating the mixture.
The sulphur will then dissolve in the solution of the said salt, and thio-oxydiphenyl-
amine will be formed, containing two atoms of sulphur in its molecular formula and
forming salts with alkalies.
This reaction may, with advantage, be promoted by adding an alkali or alkalic
carbonate in excess, the alkali in this case operating to dissolve the sulphur and to
form therewith sulphide of alkali, which then gives off the sulphur to the meta-
oxydiphenyl-amine. Or, the sulphur is first dissolved with application of heat in a
solution of an alkali or alkalic carbonate, so that, according to the variable proportions
of the substances employed, a sulphide or a polysulphide is obtained, the meta-
oxydiphenyl-amine-salt is introduced into the solution of the sulphide or polysulphide,

page_text: and the mixture is heated again. Instead, however, of preparing the said alkalic
sulphide or polysulphide as described, the same may also be employed in the state in
which they form articles of commerce.
From its solution the thio-oxydiphenyl-amine can be precipitated by the addition of
an acid or an acid salt. In purified condition it consists in a light-yellow, tasteless
powder, which dissolves easily, in alkalies and likewise, though more difficultly, in
alkalic carbonates. Alcohol and acetic acids are also solvents of the same.
In pure
Water and in benzine it is insoluble. The solutions are of yellow color. When heated
the substance becomes brown; and it melts at about 155° Centigrade.
The following are prescriptions according to which the process may advantageously
be carried out in practice.
First. 240 parts by weight of sodium hydroxide are dissolved in water and 185
parts of meta-oxydiphenyl-amine-salt are added. The solution thus obtained is heated!
and 200 parts of sulphur are gradually introduced into the same, the heating being
continued until the sulphur is completely dissolved. By the addition of sodium bicar-
bonate to the hot liquor the thio-product is precipitated in the form of a light-yellow
powder. By dissolving the said powder in cold alkalic lye and reprecipitating by
means of acetic acid the product is rendered pure.
Second. 250 parts by weight of sodium hydroxide are dissolved in water, and the
solution is heated with 200 parts of sulphur until no more sulphur dissolves. The
liquor, after having been decanted from any sulphur which may have remained un-
dissolved, is then mixed with 145 parts of meta-oxydiphenyl-amine-salt, and the
mixture is heated in a closed digester up to 150° or 200° Centigrade. The further
treatment of the product is the same as stated in the first prescription.
The described thio-oxydiphenyl-amine is to be used as medicament in the treatment
of wounds. The mode of its application is the same as that of iodoform. It especially
diminishes the secretion of suppurating wounds and it possesses the advantage of having
no smell and of being absolutely innocuous.
41
1 Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what I
claim is:
1. The process of producing thio-oxydiphenyl-amine, which consists in heating
together a salt of meta-oxydiphenyl-amine, water and sulphur, substantially as and for
the purpose described.
2. The process of producing thio-oxydiphenyl-amine, which consists in heating a
salt of meta-oxydiphenyl-amine with water, sulphur and an alkali or alkalic carbonate,
or with a sulphide or polysulphide of alkali as the equivalent of sulphur and alkali or
alkalic carbonate, substantially as specified.
3. An article of manufacture consisting in a compound of meta-oxydiphenyl-amine
with two atoms of sulphur and called thio-oxydiphenyl-amine, the said compound
being a light-yellow powder easily soluble in alkalies soluble in alcohol and acetic acid,
and also, though more difficultly, soluble in alkalic carbonates, whereas it is insoluble
in pure water and benzine; the solutions being of yellow color; and the substance,
when heated, becoming brown and melting at about 155° Centigrade; substantially as
described.
Datad this 27th day of May 1800
ERNEST DE PASS,
78, Fleet Street, London, Agent for the Applicant: