Improvements in the Manufacture of Tri-oxy-benzo-phenone, a Colouring Matter of the Oxy-ketone Group.
Year: 1890

page_text: Date of Application, 30th June, 1890
Complete Specification Left, 25th Mar., 1891-Accepted, 2nd May, 181
PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Tri-oxy-benzo-phenone, a
Colouring Matter of the Oxy-ketone Group.
I, JAMES YATE JOHNSON of 47 Lincolns Inn Fields in the County of
Middlesex, Gentleman, do hereby declare the nature of this invention which has
been communicated to me from abroad by The Badische Anilin and Soda Fabrik of
Ludwigshafen on Rhine in the Empire of Germany to be as follows:-
In the Specification of Letters Patent No. 8373 granted to me and dated
20th May 1889 the manufacture of trioxybenzophenone and the process of preparing
it from pyrogallol and benzoic acid are described. The Specification of Letters
Patent No. 9428 granted to me and dated 6th June 1889 describes improvements in
the process of preparing trioxybenzophenone consisting in the substitution of
benzoylchloride or benzoic anhydride for the benzoic acid of the process according
to the first Patent.
The present invention is based upon the discovery of another new process for the
production of trioxybenzophenone.
As is well known the condensation of benzotrichloride with pyrogallol in the
absence of water (or of substances yielding it) results in the formation of an
adjective violet dyestuff, which was known under the name of "anthracene-violet'
(sec Julius-Farbstoffe p. 124).
"
My foreign correspondents have discovered that, if these two bodies be made to
act upon one another in the presence of water or of bodies which yield up water to
them, the reaction that occurs is quite different from the preceding and results in
the production of trioxybenzophenone or as it is commercially termed “alizarine
yellow."
To further make clear the nature of this invention I give by way of illustration
and without limiting myself thereto the following directions by which it may be
carried into effect. The parts are by weight.
Take about twenty parts of pyrogallol and dissolve them in about forty parts of
spirits of wine containing about ninety per cent. of real alcohol and ten per cent. of
water. Boil the solution and then add slowly and carefully about forty parts
of benzotrichloride an energetic reaction takes place, the solution turning red.
The reaction being complete, pour the product into about three thousand parts of
boiling water and filter the solution. On cooling the trioxybenzophenone
crystallizes out. Filter, wash, press, and either dry or preserve in the form of a
paste.
Dated this 30th day of June 1890.
J. H. JOHNSON & Co.,
47, Lincoln's Inn Fields.
COMPLETE SPECIFICATION.
Improvements in the Manufacture of Tri-oxy-benzo-phenone, a
Colouring Matter of the Oxy-ketone Group.
I JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of
Middlesex Gentleman do hereby declare the nature of this invention which
invention has been communicated to me from abroad by The Badische Anilin and
Soda-Fabrik of Ludwigshafen on Rhine in the Empire of Germany and in what
manner the same is to be performed to be particularly described and ascertained
in and by the following statement :-
In the Specification of Letters Patent No. 8373 granted to me and dated

page_text: 20th May 1889 the manufacture of trioxybenzophenone and the process of preparing
it from a pyrogallol and benzoic acid are described.
The Specification of Letters Patent No. 9428 granted to me and dated 6th June
1889 describes improvements in the process of preparing trioxybenzo-phenone
consisting in the substitution of benzoylchloride or benzoic anhydride for the
benzoic-acid of the process according to the first Patent.
The present invention is based upon the discovery of another new process for the
production of trioxybenzophenone.
As is well known the condensation of benzotrichloride with pyrogallol in the
absence of water (or of substances yielding it) results in the formation of an
adjective violet dyestuff, which was known under the name of "anthracene violet"
(see Julius's "Farbstoffe" p. 124).
My foreign correspondents have discovered that if these two bodies be made to
act upon one another in the presence of water or of bodies which yield up water to
them the reaction that occurs is quite different from the preceding and results in
the production of trioxybenzophenone, or, as it is commercially termed "alizarine-
yellow.'
The following examples illustrate the manner in which this invention can be
carried into practical effect. The parts are by weight.
Example 1. Take about twenty parts of pyrogallol and dissolve them in about
forty parts of spirits of wine containing about ninety per cent. of real alcohol and
ten per cent. of water. Boil the solution and then add slowly and carefully about
forty parts of benzotrichloride. An energetic reaction takes place, the solution
turning of a reddish colour. The reaction being complete, pour the product into
about three thousand parts of boiling water and filter the solution. On cooling the
trioxybenzophenone crystallizes out. Filter wash press and either dry or preferably
preserve for use in the form of paste.
The details of the example may be varied considerably without altering the
nature of the process or of its result. To illustrate this I give a second example
Example 2. Mix about twenty parts of pyrogallol, fourteen parts of
spirits of wine (containing about ninety five per cent. of real alcohol
and five per cent. of water) sixty parts of benzotrichloride and one
hundred parts of benzene, which takes no part in the reaction, but acts as a
diluent. Stir the mixture for about ten hours. An energetic reaction takes place
causing the temperature to rise spontaneously to about forty degrees, Centigrade.
Should the temperature rise higher it may with advantage be moderated by external
cooling. The product of the operation is a thick paste which is well pressed to get
rid of the benzene and any unused benzotrichloride. The press cakes of crude
trioxybenzophenone are dissolved in about three thousand parts of boiling water
and the solution is filtered.
On cooling, the trioxy-benzophenone crystallizes out. Filter, wash, press and
either dry or preferably preserve for use in the form of paste.
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 I
claim is.
First. The manufacture of trioxybenzophenone by the action of benzotrichloride
on pyrogallol in the presence of water or of a body which yields up water.
Second. The manufacture of trioxybenzophenone as hereinbefore described
under example 1 and 2.
Dated the 25th day of March 1891.
J. H. JOHNSON & Co.,
Agents.