Improvements in the Manufacture of Artificial Perfumes.
Year: 1891

page_text: Date of Application, 3rd Jan., 1891-Accepted, 28th Mar., 1891
COMPLETE SPECIFICATION.
Improvements in the Manufacture of Artificial Perfumes.
We, GUSTAV LINK, of Wiesbaden, German Empire, 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:-
The combinations of isodibutylene with halogenhydracids, when boiled with
aromatic hydrocarbons, as for instance with toluol, meta xylol, ethylbenzole and the
like, in the presence of chloride or bromide of iron, divide partly into tertiary
butyltolylmethane and into polymeric propylenes, and partly into isopropyltoluol
and tertiary butyltolylmethylhydride; as subsidiary products arise small quanti-
ties of hydrocarbons of the formula C₁H. The following formulæ explain the
process for toluol.
15 24"
24
The object of the process hereinafter described is to produce tertiary butyltolyl-
methane and its homologues carburetted hydrogen of the formula C₁H, and
homologues and their trinitro-compounds by nitrification with fuming nitric acid
and fuming sulphuric acid.
Unto a mixture of 1 part of isodibutylene hydro-chloride, hydro-bromide or
hydro-iodide and 7 parts toluol is added by degrees parts of chloride or bromide
of iron and then allowed to boil in a reflux-cooler until the evolution of acid has
been completed. The carburetted hydrogen generated hereby and the toluol in
excess are distilled from the product and the distillate subjected to fractional
distillation after being dried by calcic chloride or potash. That portion of this
destillate given off at a temperature between 190°-205° contains tertiary-butyl-
tolylmethane of the formula C,,H₁, and that given off at a temperature between
230°-250° contains hydrocarbon of the formula CH
Instead of toluol its homologues as xylole, ethylbenzole or others may be also
TDA71

page_text: 13
used; hydrocarbons being thereby produced of the formulæ CHCH26 etc.
which are employed in the preparation of artificial musk in the following
manner :
1 part of tertiary butyltolylmethane is added, while being properly cooled, unto
a mixture of 6 parts of nitric acid of a specific gravity of 1,525 and 20 parts of
fuming sulphuric acid. This being well mixed is heated in a water-bath as long as
20 to 30 hours. The reaction-product is hereafter poured on ice and then washed
with a diluted solution of soda and also with water until all the neutral reaction
takes place, that is to say, until all the acid is neutralized. The resulting product
is a viscid oil of a light brownish colour, which solidifies into crystals after some
time. These are recrystallised repeatedly in alcohol and result in bright leaves
and long needles of a pale yellowish colour which possess an intensive musk-
like smell.
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 what we
claim is:-
―:
1. In the manufacture of artificial perfumes: The generation of tertiary
butyltolylmethane and of its homologues, and the generation of a hydrocarbon,
having the formula C1, H2, and of its homologues, by boiling isobutylene, hydro-
chloride, hydro-bromide or hydro-iodide with toluol or with its homologues, in the 2
presence of chloride or bromide of iron, for the purpose set forth.
2. In the manufacture of artificial perfumes: The generation of the trinitro-
compounds of tertiary butyltolylmethane or its homologues, and of a hydrocarbon,
having the formula C₁H, or its homologues, by nitrifying said hydrocarbons by
fuming nitric acid and fuming sulphuric acid, for the purpose set forth.
15
Dated this 31st day of December 1890.
GUSTAV LINK.
RICHARD AVENARIUS.
By Geo. Thos. Hyde,
4, Moorfields, London, E.C., Agent for the Applicants.