The Manufacture or Production of Anthraquinone Derivatives.
Year: 1895

page_text: Date of Application, 2nd Aug., 1895
Complete Specification Left, 4th May, 1896-Accepted, 6th June, 1896.
TRUVIDIONAL SEMIFICATION.
[Communicated from abroad by THE FARBENFABRIKEN, vormals FRIEDRICH
BAYER & Co., of Elberfeld, Germany.]
The Manufacture or Production of Anthraquinone Derivatives.
1, 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:-
My foreign correspondents discovered some time since a series of processes for
introducing hydroxy groups into anthraquinone and its derivatives. These
processes consist in treating the anthraquinone, or its derivatives, with oxydising
agents, for example, such as sulphuric anhydride or fuming sulphuric acid,
manganese dioxide in the presence of sulphuric acid, sulphuric acid in or without
the presence of boric acid or the like, nitrous acid, or nitric acid. The same or
similar results have been obtained on allowing the electric current .to flow through
solutions of anthraquinone or its derivatives, in concentrated sulphuric acid, or in
fuming sulphuric acid. These methods have been described, for example, in the
following Specifications of Letters Patent, viz. :-8725, 1271590, 1771290, 1872990,
4871", 13677º¹, 21717º¹, 1657, 1257992, 143453, 9739, 12742º.
My foreign correspondents have now found that in the process of introducing
hydroxy groups into anthraquinone or its derivatives, perchloric acid or salts
thereof, or materials acting in the same or a similar manner, can be used in the.
place of the above named oxidising agents.
In carrying out the new process, my foreign correspondents treat anthraquinone
its derivatives with perchloric acid, or salts thereof, in sulphuric acid or fuining
sulphuric acid solution, at elevated, or at ordinary temperature.
The process is illustrated by the following example, the parts being by weight.

page_text: care being taken that the temperature does not rise above 30 degrees Centigrade.
The mixture is then further stirred during several hours at the said temperature,
until the reaction which takes place is finished. The melt is then poured into
2000 litres (in case the parts are kilos. by weight) of icy water, mixed with 10 parts
of sodium bisulphite. The mass thus obtained is boiled and filtered off. The
resulting residue is hexaoxyanthraquinone, which may be purified in any suitable
manner.
The process takes place in any analogous manner, if other hydroxy derivatives of
anthraquinone, or of substituted anthraquinone, be employed instead of anthra-
chrysone, anthraquinone, and alizarine, used in the foregoing Examples 1, 2, and 3.
My foreign correspondents have ascertained that perchloric acid and its salts, or
the like, can be used for introducing hydroxylic groups into anthraquinone or its
derivatives, that is to say, into all bodies which are used as original materials
in the processes described in the Specifications of the aforementioned Letters
Patent.
Dated this 2nd day of August 1895.
NEWTON & SON,
Agents for the Applicant.
The Manufacture or Production of Anthraquinone Derivatives.
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 :-
These
My foreign correspondents some time ago discovered a series of processes for
introducing hydroxy groups into anthraquinone and its derivatives.
processes consist in treating anthraquinone or its derivatives with oxydising agents,
such, for example, as sulphuric anhydride or fuming sulphuric acid, manganese
dioxyde in the presence of sulphuric acid, sulphuric acid either alone or together
with boric acid or the like, nitrous acid, or nitric acid. The same or similar results
have been obtained on allowing an electric current to flow through solutions of
anthraquinone or its derivatives in concentrated sulphuric acid or in fuming
sulphuric acid. These methods have been described, for example, in the following
Specifications of Letters Patent, viz. :—

page_text: Centigrade. When the violent action which takes place is at an end, and anthra-
chrysone it no longer distinguishable in the mixture, the heating is stopped, and
the melt is allowed to cool. It contains, as chief product, hexahydroxyanthra-
quinone, which is isolated in any suitable manner.
EXAMPLE II.
10 parts of potassium perchlorate are carefully stirred into a heated solution of
10 parts of anthraquinone in 200 parts of fuming sulphuric acid (containing 20 per
cent. SO3), care being taken that the temperature of the mixture does not rise
above 150 degrees Centigrade. Oxydation takes place, quinizarine and the like
being first produced, but soon further oxydised, hexahydroxyanthraquinone
sulphonic acid being formed, and the product is isolated from the melt in any
suitable manner.
EXAMPLE III.
6 parts of potassium perchlorate are slowly stirred into a solution of 10 parts of
alizarin in 200 parts of fuming sulphuric acid, (containing 20 per cent. of anhydride),
care being taken that the temperature does not rise above 30 degrees Centigrade.
The mixture is then kept stirred during several hours at the said temperature,
until the action is at an end. The melt is then poured into 2000 litres (in case the
parts are kilos. by weight) of ice water containing 10 parts of sodium bisulphite.
The mass thus obtained is boiled and filtered. The residue is hexahydroxyanthra-
quinone, which may be purified in a suitable manner.
The process takes place in an analogous manner, if other hydroxy derivatives of
anthraquinone, or of a substituted anthraquinone, be used instead of anthrachrysone,
anthraquinone, and alizarin, prescribed in the foregoing Examples 1, 2, and 3.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed (as communicated to me from
abroad), I declare that what I claim is :-
1. The production of hydroxy derivatives of anthraquinone from anthraquinone
or its derivatives, by means of perchloric acid or salts thereof.
2. The process of introducing hydroxy groups into anthraquinone or its
derivatives, which process consists in treating solutions of the said compounds in
concentrated or fuming sulphuric acid with perchloric acid, or salts thereof, in the
manner herein before defined.
3. In the process described in the foregoing claiming clause 2, on the one hand,
the use of anthraquinone, or of the anthraquinone derivatives selected as original
materials, in the processes of introducing hydroxy groups into anthraquinone
derivatives described in the following Specifications of Letters Patent:-872590,
127150, 177120, 1872990, 4871, 13677, 217179, 16579, 125799, 12580%, 1434593,
973, 974, 97504, 2325, 3113; on the other hand, the use of perchloric acid or
of salts thereof.
DL:
1000
NEWTON & SON,
Agents for the Applicant.