Manufacture of Coloring Matters from Protocatechuic Acid and Phenols.
Year: 1891

page_text: Date of Application, 16th Nov., 1891
Complete Specification Left, 15th Aug., 1892-Accepted, 17th Sept., 1892
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE FARBWERKE VORMALS MEISTER LUCIUS
AND BRUNING, of Hoechst a Main, in the Empire of Germany, Manufacturers.]
Manufacture of Coloring Matters from Protocatechuic Acid
and Phenols.
1, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the
County of London, Chartered Patent Agent, do hereby declare the nature of
this invention to be as follows:—
When acetic acid and resorcin or pyrogallol are heated with zinc chloride
according to Nencki (Journ. f. Prakt. Chemie 23, p. 147 and 538) the following
ketones are produced:
Resacetophenon: CH, CO CH, (OH), and
Gallacetophenon CH, CO CH, (OH),
Very valuable coloring matters result when in this reaction are introduced two
bodies which up to the present time have not been industrially produced and
utilised, namely protocatechuic acid and pyrocatechin.
When, for example, 3+ parts by weight of protocatechuic acid and 32 parts by
weight of pyrocatechin and from 50 to 100 parts by weight of zinc chloride are
heated to about 150° C. for several hours, and the melt is dissolved in hot water,,
there will crystallise out tetroxydiphenyl-ketone which may be purified by
recrystallisation from water.
In this operation there may be substituted for the zinc chloride the other usual.
condensation agents such as sulphuric acid, tetrachloride of tin etc.
The tetroxydiphenylketon produced in this manner has the melting point
of 175° C.
When in the reaction described for the pyrocatechin is substituted resorcin there
results an isomeric tetroxydiphenylketon of the melting point 93° C.
A penta-oxy-diphenylketone results in analogous manner in the action of proto-
catechuic acid upon pyrogallol.
The oxyketones deriving from protocatechuic acid are prominently adapted for
printing and dyeing chromo mordanted cotton and wool.
The tints obtained excel by absolute fastness in fulling, and in purity of shade.
Dated this 16th day of November 1891.
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
Manufacture of Coloring Matters from Protocatechuic Acid
and Phenols.
I, OLIVER IMRAY, of No. 28, Southampton Buildings, Chancery Lane, in the
County of London, Chartered 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:-
When acetic acid and resorcin or pyrogallol are heated with zinc chloride
according to Nencki (Journ. f. Prakt. Chemie 23, p. 147 and 538) the following
ketones are produced :

page_text: Very valuable coloring matters result when in this reaction are introduced two
bodies which up to the present time have not been industrially produced and
utilised, namely protocatechuic acid. and pyrocatechin.
When for example, 34 parts by weight of protocatechuic acid and 32 parts by
weight of pyrocatechin and from: 50 to 100 parts by weight of zinc chloride are
heated to about 150% C. .for several hours, and.. the melt is dissolved in hot, water,
there,, will crystallise, out; tetroxydiphenylketone, which, may be purified by
recrystallisation from, water...
In this operation there may be substituted for the zinc chloride the other usual
condensation agents such as sulphuric acid, tetrachloride of tin etc.
"
The tetroxydiphenylketon produced in this manner has the melting point
of 175°C
When in the reaction described for the pyrocatechin is substituted resorcin there
results an isomeric tetroxydiphenylketon of the melting point 939 C.
A penta-oxy diphenylketone results in analogous manner in the action of proto
catechuic acid upon pyrogallol.
The oxyketones deriving from protocatechuic acid are prominently adapted for
printing and dyeing chromo mordanted cotton and wool.
The tints obtained excel by absolute fastness in fulling and purity of shade.
Having now particularly described, and ascertained the nature of, this invention
and in what manner the same.. is. to, be performed, I declare that what! I
claim, is
"
1. The production of coloring matters which dye on mordants by condensing
protocatechuic acid with pyrocatechin; resorcine or pyrogallol, substantially vas
described:
2. As a new manufacture, the coloring matters produced as set forth in the
preceding claim, and their application to industrial purposes.
Dated this 15th day of August 1892.
ABEL & IMRAY,
Agents for the Applicant