Improvements in the Manufacture of Artificial, Musk.
Year: 1894

page_text: Date of Application, 4th, July, 1894
Complete Specification Left, 4th Apr., 1895-Accepted, 4th May,
1895
TRUVIDIUNAL DI MUITUATION.
[Communicated from abroad by FABRIQUES DE PRODUITS CHIMIQUES DE
THANN ET MULHOUSE, of Thann, Alsace.]
Improvements in the Manufacture of Artificial, Musk.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, Chancery
Lane, in the County of London, Consulting Engineer and Chartered Patent
Agent, do hereby declare the nature of this invention to be as follows:-
In the Specifications to previous Patents No. 18521 of 1888, No. 4963 of 1889,
No. 15687 of 1890 the preparation of artificial musk has been. described by
nitration of aromatic hydrocarbons containing two or three lateral chains one of
which must be a butylic, amylic or propylic, whilst the others are methyle, or
ethyle. Hydrocarbons of this family are butyl-toluene, butyl-xylene and. many
others.
My correspondents have found that not only the hydrocarbons of the said. series
are able to yield musk by nitration, but that, aromatic, hydrocarbons with closed
lateral chains, for instance hydrindene
shew the same behaviour i.e. that by butylation (propylation or amylation) and
nitration they are transformed into nitro derivatives possessing a strong odour
of musk.
•
To carry out this invention the butylic (or propylic or amylic) radicle is
introduced into the hydrindene by..one of the well known methods, for instance by
the method of Friedel and Crafte
are heated until no more evolution of hydrochloric acid takes place.
The mass is
poured into water, the hydrocarbon is distilled with steam and the butyle hydrindene
is purified by fractionated distillation.
The boiling point of the pure hydrocarbon is:237° to 240° C.
In order to transform the butyl hydrindene into its musk-scented trinitro
derivative, it is more convenient to prepare first the dinitro compound in a state of
purity and to submit it afterwards to a further nitration.
For this purpose 10 parts of butyl hydrindene are introduced into a well cooled
mixture of 40 parts of fuming nitric acid (specific gravity about 1.48) and
80 parts of fuming sulphuric acid containing about 15 per cent. of SO,, and is
allowed, to stand a few hours. I then pour in water, filter the nitro compound,
wash it with soda and afterwords with water, and then crystallize it out of alcohol.
I thus obtain white crystals melting at 121° and possessing no musky odour.

page_text: In order to transform the di into tri nitro derivative I introduce 10 parts of the
dinitro compound into a strong nitration mixture containing 40 parts of fuming
nitric acid and 80 parts of fuming sulphuric acid containing 30 to 40 per cent.
of SO,, and I heat at a temperature not exceeding 50 or 55° C.
After a few hours I pour in water, filter and crystallize the new compound from
alcohol.
ABEL & IMRAY,
Agents for the Applicant.
Improvements in the Manufacture of Artificial Musk.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, Chancery
Lane, in the County of London, Consulting Engineer and Chartered Patent
Agent, 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 :--
In the Specifications to previous Patents No. 18521 of 1888, No. 4963 of 1889,
No. 15687 of 1890, the preparation of artificial musk has been described by
nitration of aromatic hydrocarbons containing two or three lateral chains one of
which must be a butylic, amylic or propylic, whilst the others are methyle or
ethyle. Hydrocarbons of this family are butyl-toluene, butyl-xyline and many
others.
My correspondents have found that not only the hydrocarbons of the said series
are able to yield musk by nitration, but that aromatic hydrocarbons with closed
lateral chains, for instance hydrindene

page_text: To carry out this invention the butylic (or propylic or amylic) radicle is.
introduced into the hydrindene by one of the well known methods, for instance by
the method of Friedel and Crafts.
T
30 parts of hydrindene
7
chloride of aluminium
"
"
10
وو
"
chloride of tertiary butyle
are heated until no more evolution of hydrochloric acid takes place. The mass is
poured into water, the hydrocarbon is distilled with steam and the butyle hydrindene
is purified by fractionated distillation.
The boiling point of the pure hydrocarbon is 237° to 240° C.
In order to transform the butyl hydrindene into its musk-scented trinitro
derivative, it is more convenient to prepare first the dinitro compound in a state of
purity and to submit it afterwards to a further nitration.
For this purpose 10 parts of butyl-hydrindene are introduced into a well cooled
mixture of 40 parts of fuming nitric acid (specific gravity about 1.48) and 80 parts
of fuming sulphuric acid containing about 15 per cent. of SO,, and is allowed to
stand a few hours.
I then pour in water, filter the nitro compound, wash it with soda and afterwards
with water, and then crystallize it out of alcohol. I thus obtain white crystals
melting at 121° C. and possessing no musky odour.
In order to transform the di- into tri-nitro derivative I introduce 10 parts of the
dinitro compound into a strong nitration mixture containing 40 parts of fuming
nitric acid and 80 parts of fuming sulphuric acid containing 30 to 40 per cent.
of SO, and I heat at a temperature not exceeding 50° or 55° C.
After a few hours I pour in water, filter and crystallize the new compound from
alcohol
musk odour.
I may also effect the butylation of hydrindene by introducing the same mixed
with butylic alcohol in concentrated sulphuric acid. I obtain by this method a
mixture of the hydrocarbon and of its sulphonic acid.
The latter by nitration also yields a musk, but the previously described process
is much better.
By using chloride of propyle or amyle instead of chloride of butyle, I obtain
derivatives analogous to the butylic but presenting no advantage.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what I
claim is :-
1. The herein described process for preparing butyl hydrindene by the action of
chloride of butyle on hydrindene in presence of chloride of aluminium.
2. The modified process for preparing butyle hydrindene by the action on
hydrindene of butylic alcohol in presence of concentrated sulphuric acid.
3. The preparation by either of the above processes of the corresponding
propylic and amylic derivatives.

page_text: 4. The herein described process for transformation of the above products into
trinitro derivatives having musk like.odour.
5. The butyle, propyle and amyle hydrindene. and their trinitro derivatives
manufactured as set forth in the preceding claims.
Dated this 4th day of April 1895.
ABEL & IMRAY,
Agents for the Applicant.