Improvements in the Manufacture of Artificial Perfumes.
Year: 1891

page_text: Date of Application, 1st Jan., 1891-Accepted, 2nd May, 1891
COMPLETE
SPECIFICATION.
Improvements in the Manufacture of Artificial Perfumes.
We, GUSTAV LINK, of Wiesbaden, Doctor of Philosophy, and RICHARD
AVENARIUS, of Gaualgesheim, in the German Empire, Manufacturer, 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:-
Some of the methods known and used hitherto for producing artificial musk and
other substances with similar scent depended on the use of iso-amyl-alcohol as base,
by means of which were produced mixtures of trinitro compounds with bodies of
lower nitration.
The object of the process hereinafter described is to produce at once a pure
trinitro-compound, by using as base halogen combinations of tertiary amyl-alcohol.
This process which forms the object of our invention is as follows:
We add three quarters of a part of chloride of iron or bromide of iron to a
mixture consisting of one part of tertiary amylchloride, -bromide or -iodide (pro-
duced from dimethylethyl-carbinole, methylisopropyl-carbinole or from amylenes,
according to known methods) and we boil the whole until the evolution of acid has
completely ceased. The undecomposed toluole and the hydrocarbon generated are
distilled from the re-action products by means of aqueous vapour, the distillate
being dried by means of calcic chloride or potash and subjected afterwards to
fractional distillation. That part of the distillate which flows over at a temperature
of from 200° to 208° is separately collected, because tertiary amyltoluole,
the formula of which is C₁₂H₁, is contained therein. Homologues of toluole, as
for instance xylole and ethylbenzole, may be used in exactly the same manner;
they produce hydrocarbons of the formula C₁₂H-
18
20°
Said tertiary amyltoluole as well as the hydrocarbons of the formula C₁₂H20
mentioned above may now be used for manufacturing artificial musk in the
following manner :
We add one portion of tertiary amyltoluole to a mixture consisting of 6 portions
of nitric acid having a specific gravity of 1.5 and of 20 portions of fuming sulphuric
acid, and we heat the whole by means of a water-bath for a period of from
20-30 hours. The product of the reaction is then poured on ice and washed with
a diluted solution of soda and with water until it becomes neutral.
The resulting compound represents a viscid oil of a light brownish-yellow colour
which solidifies after some time into crystals. After being recrystalised several
times by means of alcohol said crystals have the appearance of prisms of light-
yellowish colour having an agreeable musk-like scent.
Having now particularly described and ascertained the nature of our said inven-
tion, and in what manner the same is to be performed, we declare that we make no
claim to the production of artificial musk by the process set forth in the Specifica-
tion No. 18521 of 1888, but what we claim is :-
1. In the manufacture of artificial perfumes: The nitrification of tertiary
amyltoluol or of its homologues, as xylole, ethylbenzole, and the like, substantially
as described.
2. In the manufacture of artificial perfumes: The nitrification of tertiary

page_text: amyltoluole or of its homologues, as xylole, ethylbenzole and the like, said tertiary
amyltoluole and its homologues being produced from the halogen-combinations of
tertiary amylalcohol, substantially as described.
Dated this 31st day of December 1890.
GUSTAV LINK.
RICHARD AVENARIUS.
By Rayner & Cassell,
Agents for the Applicants.