The Manufacture of Acid Salts of Piperazine and Poly Basic Acids, and the Production therefrom of Double Salts of Lithia and Piperazine.
Year: 1896

page_text: PROVISIONAL SPECIFICATION.
The Manufacture of Acid Salts of Piperazine and Poly Basic Acids,
and the Production therefrom of Double Salts of Lithia and
Piperazine.
I, ALFRED KOELLIKER Ph. D., of Benel-on-Rhine, in the Empire of Germany, do
hereby declare the nature of this invention to be as follows:-
Piperazine as Majest and Schmidt have found (Berichte der Deutschen Chem.
Gesellschaft 1890, 3723) always forms with the bi-basic uric acid, the neutral salt of
the formule
CH, CH,
COOH. NH
NH. COOH
CH,-CH,
COOH
COOH
or
CH,CH,
CH (OH-COOH. NH<
NH. COOH-CH (OH)-
CH,- CH,
CH (OH)-COOH
COOH-CH (OH)
I form these salts by the addition of an aqueous solution of one molecule of
Piperazine to a solution of a little more than two molecules of the acid. The oxalic
and tartaric salts are difficultly soluble in cold water and crystallise out of the hot
solution rapidly in long colorless needles of which the latter melt at 228° C. and the
former decompose above 250° whereas the citric salt is easily soluble in water and
crystallises out of the concentrated solution in glassy prisms melting at 95º.
These acid salts form double salts with lithia the hydrogen of the free carboxylic
groups being replaced by this metal.
To obtain these double salts I add to the aqueous solution of the aforesaid salts half
as many molecules of lithium-carbonate as they contain free carboxylic groups, that is
one molecule to one molecule of the oxalic or tartaric salt and two molecules to the
citrio salt.
The oxalic and the tartaric lithia-piperazine double salts are difficultly soluble in
cold water and are obtained in the form of white crystalline powders the citric double

page_text: salt forms a thick oil, which stiffens after some days and turns into a white crystalline
crust, which is readily soluble in water.
The Manufacture of Acid Salts of Piperazine and Poly Basic Acids,
and the Production therefrom of Double Salts of Lithia and
Piperazine.
I, ALFRED KOELLIKER, Ph. D. of Benel-on-Rhine, in the Empire of Germany, 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 :-
Piperazine, as Majert and Schmidt have found, (Berichte der Deutschen Chem.
Gesellschaft 1890, 3723,) always forms with the bi-basic uric acid the neutral salt of
CH (OH)-COOH
CH-CH,
COOH-CH (OH)
I form these salts by the addition of an aqueous solution of one molecule of
piperazine to a solution of a little more than two molecules of the acid. The oxalic
and tartaric salts are difficultly soluble in cold water and crystallise out of the hot
solution rapidly in long colorless needles of which the latter melt at 228° C. and the
former decompose above 250° whereas the citric salt is easily soluble in water and
crystallises out of the concentrated solution in glassy prisms melting at 95º.
These acid salts form double salts with lithia, the hydrogen of the free carboxylic
groups being replaced by this metal.
To obtain these double salts I add to the aqueous solution of the aforesaid salts
half as many inolecules of lithium-carbonate as they contain free carboxylic groups,
that is one molecule to one molecule of the oxalic or tartaric salt and two molecules
to the citric salt.
The oxalic and the tartaric lithia-piperazine double salts are difficultly soluble
in cold water and are obtained in the form of white crystalline powders, the citric
double salt forms a thick oil, which stiffens after some days, and turns into a
white crystalline crust, which is readily soluble in water..

page_text: Having now particularly described and ascertained the nature of my said
invention and in what manner the same is to be performed I declare that what I
claim is-
As new and useful products :-
(a) The acid salts of piperazine and oxalic, tartaric and citric acids.
(b) The double salts which lithia and piperazine form with oxalic, tartaric and
citric acids.