Year: 1899

page_text: I, ISIDOR KLIMONT, of 8 Fischerstiege, Vienna, Austria, Chemist, do hereby
declare the nature of this invention to be as follows:-
This invention relates to improvements in the production of violet perfume..
Citral may be condensed with acetylacetone to a new hitherto unknown ketone,
which has for its formula-
C₁ H₂ O₂
This ketone which represents acetylpseudoionone pertains to the citral series
and converts under certain conditions into an isomerous product, the acetylionone
which has the same formula but different qualities.
The condensation of citral with acetylacetone is obtained most advantageously
by heating the said two products at a temperature of 100 degrees for several hours
in an acid solution (for instance in acetic acid, butyric acid or the like) by adding
agents withdrawing water such as anhydrous acetic acid alkali acetate, sulphate
of copper and the like.
A satisfactory result is obtained by heating on a water bath for about 12 hours
equal parts of citral, acetylacetone, acetic acid, sodium acetate and anhydrous
acetic acid.
The mixture thus obtained, repeatedly rinsed with water can be readily freed
from the exceeding reactifs by blowing through a jet of steam until no citral and
acetylacetone whatever passes over with the steam, which can be asertained from
the smell.
For further use it is not necessary to produce the acetylpseudoionone pure;
however it may be obtained in purified state by blowing again through the mass a
strong jet of steam.
As already mentioned the last described product can be converted in an
isomerous one.
This is effected by subjecting the acetylpseudoionone without increase of
temperature, to an organic acid of high percentage which, for instance may be
done by cooling sulphuric acid (80 per cent. strong) in a refrigerating mixture to
5 degrees Centrigrade and mixing therewith the acetylpseudoionone by pouring
same in, in drops and constantly stiring it.
The temperature must however not rise about 10 degrees Centrigrade and the
action of the acid must be very short, about 10 to 20 minutes, otherwise decom-
position products with bad smell will form in large quantities.
Having been subject to the action of the concentrated sulphuric acid, a product
has been obtained which in substance forms acetylionone, which has an agreeable
aromatic odour.
In this case it is also not specially necessary to thoroughly purify the product;
however this may be done by washing the product with water and soda and by
separating the same by distillation with water steam into a resin like substance
which remains in the boiler and an oily matter which passes with the steam.

page_text: By subjecting the oily product, which in substance is acetylionone, to the action
of alkalies the acetylionone will be converted into ionone.
Tlated this Treanthil 1800
F. BOSSHARDT & Co.,
Agents to Applicant.
I, ISIDOR KLIMONT, of 8 Fischerstiege, Vienna, Austria, Chemist, 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:
This invention relates to improvements in the production of violet perfume.
Citral may be condensed with acetylacetone to a new hitherto unknown ketone,
which has for its formula-
C15 H₂ U₂
This ketone which represents acetylpseudoionone pertains to the citral series
and converts under certain conditions into an isomerous product, the acetylionone,
which has the same formula but different qualities.
The condensation of citral with acetylacetone is obtained most advantageously
by heating the said two products at a temperature of 100 degrees Centrigade for
several hours in an acid solution (for instance in acetic acid, butyric acid or the
like) by adding agents withdrawing water, such as acetic anhydride, sodium or
potassium acetate, sulphate of copper all free from water and the like.
A satisfactory result is obtained by heating on a water bath for about 12 hours
equal parts of citral, acetylacetone, acetic acid, sodium acetate and anhydrous
acetic acid.
The mixture thus obtained, repeatedly rinsed with water can be readily freed
from the excess of reagents by blowing through a jet of steam until no citral and
acetylacetone whatever passes over with the steam, which can be ascertained
from the smell.
For further use it is not necessary to produce the acetylpseudoionone pure;
however it may be obtained in purified state by blowing again through the mass
a strong jet of steam.
As already mentioned the last described product can be converted in an
isomerous one.
This is effected by subjecting the acetylpseudoionone without increase of
temperature, to an inorganic acid of high percentage, which for instance may be
done by cooling a suitable excess of sulphuric acid (80 per cent. strong) in a
refrigerating mixture to 5 degrees Centrigade and mixing therewith the acetyl-
pseudoionone by pouring same in, in drops and constantly stirring it.
The temperature must however not rise above 10 degrees Centrigade and the
action of the acid must be very short, about 10 to 20 minutes, otherwise decom-
position products with bad smell will form in large quantities.
Having been subjected to the action of the concentrated sulphuric acid a product
has been obtained which in substance forms acetylionone, which has an agreeable
aromatic odour.
In this case it is also not specially necessary to thoroughly purify the product;
however this may be done by washing the product with water and soda and by

page_text: separating the same by distillation with water steam, into a resin like substance
which remains in the boiler and an oily matter which passes with the steam.
By subjecting the oily product, which in substance is acetylionone, to the action
of alkalies the acetylionone will be converted into ionone.
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:-
1st. A method of producing acetylpseudoionone by the condensation of citral
with acetylacetone under the action of acid condensation agents, for instance,
glacial acetic acid, acetic anhydride and by adding water extracting agents such
as sodium acetate, acetic anhydride, vitrol free from water and the like.
2nd. A method of converting acetylpseudionone into acetylionone, consisting
in subjecting acetylionone cold to the action of mineral acids of high percentage.
3rd. A method of converting acetylionone in ionone, consisting in subjecting
acetylionone cold or warm to the action of alkalies.
Dated this 24th day of February 1900.
F. BOSSHARDT & Co.,
4, Corporation Street, Manchester. Agents to Applicant.
F. BOSSHARDT & Co.,
4, Corporation Street, Manchester. Agents to Applicant.