Year: 1898

page_text: A communication from the Firm of L. DURAND HUGUENIN & CIE., of Bâle, Switzer-
land, and PHILIPPE BARBIER, of Lyons, France.
I, JOHN CLAYTON MEWBURN, of the Firm of J. C. Mewburn & Ellis, of 55 and 56,
Chancery Lane, in the County of London, Chartered Patent Agents, 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:
My correspondents have found that the aldehydes of the formula C10H160, such as
lippial contained in great quantities in the essence of lippia citriodora, lemonal or
citral contained in the essence of lemon-grass, condense with non-saturated ketones
in particular mesityl oxide (methyl 2 penten 2 one 4) under the influence of alkaline
reagents such as aqueous solutions of soda, potash, baryta, alkaline alcoholic salts, and
in general all the salts of the alkalies or the alkaline earths having an alkaline
reaction condense in the conditions stated and furnish a new body :—
which is an aliphatic ketone possessing 4 ethylene bonds.
185° C. at 10 m/m pressure, its density is 0-9156 at 20° C.
of a yellowish oil not giving any distinctive odour.
Its boiling point is about.
It is obtained in the form
In order to obtain it my correspondents proceed by way of example as follows:-
A flask or other convenient receptacle is charged with 1 kilo. of lippial or citral and
1 kilo. of mesityl oxide. It is well agitated, diluted with an equal weight of alcohol
or other suitable solvent, then there is added to this cold medium about 80 c.m.c. of
an aqueous solution of caustic soda (10 per cent. solution). On being agitated the
solution becomes heated, condensation takes place rapidly and is complete at the end
of a few hours. Then the alkali is saturated preferably with acetic acid in the
desired quantity, distilled with steam to remove the volatile products, aldehyde and
ketone, which have not entered into reaction, and allowed to cool; the condensation
products are extracted with ether, the ethereal solution is distilled, rectified in
vacuum under 10 m/m pressure and the new product collected at the temperature
above stated.
In order to transform the aliphatic derivative into its odorous isomer forming the
new perfume it is submitted to the action of acid condensing agents. The perfume
thus obtained forms a new body, is a tetra-hydro-benzene derivative, with lateral
ketone chain having two ethylene bonds. It distils under 10 m/m pressure at about
162° C. Its specific gravity at 20° C. is 0.9452 and it possesses a characteristic

page_text: odour, delicate and penetrating, of the iris and violet. It is a yellow golden oil
soluble in all proportions in alcohol and fatty bodies.
For this purpose there is introduced cold one part of the acyclic ketone into
6 parts of sulphuric acid of from 60 to 70 per cent. It is well agitated cold, then the
reaction is terminated by gently heating according to the concentration of the acid.
The transformation takes place rapidly; when this is completed the liquid is run into
water or on to ice. The new body separates out in a thick oily form, which it is
sufficient. to extract with ether and to submit to rectification in a vacuum as
indicated.
These reactions can be effected in glass, enamel or in other appropriate vessel.
The proportions and also the durations and temperatures indicated above may be
varied.
Having now particularly described and ascertained the nature of the said inven-
tiou as communicated to me, and in what manner the same is to be performed,
I declare that what I claim is :-
1. The manufacture of a product applicable to the manufacture of perfumes by
condensing lippial or lemonal with methyl 2 penten 2 one 4 (oxide of mesityle) under
the influence of an alkaline reagent, substantially as described.
2. The transformation of the product of condensation obtained according to the
Claim 1 into an isomeric ketone by treating it with acid condensing agents, substan-
tially as described.
3. The new products such as are obtained in the manner set forth.
11th day of July 1898.
J. C. MEWBURN & ELLIS,
55 and 56, Chancery Lane, London, Chartered Patent Agents.