Improvements in the Manufacture of Artificial Musk.
Year: 1895

page_text: Date of Application, 1st June, 1895
Complete Specification Left, 18th Feb., 1896-Accepted, 21st Mar., 1896
[Communicated from abroad by the Firm of FABRIQUES DE PRODUITS
CHIMIQUES DE THANN ET DE MULHOUSE, of Thann, Alsace, in the Empire
of Germany.]
Improvements in the Manufacture of Artificial Musk.
I, HENRY HARRIS LAKE, of the Firm of Haseltine, Lake & Co. Patent
Agents, 45 Southampton Buildings, in the County of Middlesex, do hereby...
declare the nature of this invention to be as follows:-
It has been shown by previous Specifications Nos. 18521/1888 and 4963/1889,
that butylated (or amylated, or propylated) hydrocarbons on nitration yield nitro-
derivatives, smelling strongly of musk. It has further been shown (compare
Specification 13613/1891) that one atom of hydrogen, being in meta-position to
both the others may be substituted in some of these hydrocarbons, as butyltoluene
for instance, by an alkylated hydroxyle group. Thus the trinitrobutylcresol-'
other

page_text: We have now discovered that this last, atom of hydrogen in butyltoluene may
also be substituted by an atom of halogen without altering the smelling properties
of the compound.
In order to obtain the above mentioned substance we treat metahalogenated
butyltoluene with a mixture of fuming nitric and sulphuric acid.
The meta-balogenated butyltoluenes, metabromine butyltoluene for instance, may
be obtained by treating butylmetacresol with pentabromide of phosphorus:
-
CH, CH, PBr. = C.H, - CH3 + POBr, + HBr
- CH
- C.H,
but it is more advantageous to prepare them by the action of chloride of butylene
on metabalogenated toluenes.
As an example I will describe the way of preparing metabrominebutyltoluene
and its trinitroderivative as follows:
I gradually add one part of chloride of aluminium to the mixture of four parts
of metabrominetoluene and. four parts of chloride of butyl without heating and
allow the mixture to stand for several hours. When hydrochloric acid has ceased
to evolve we pour the whole into water and subject the crude oil, which separates
out, to fractional distillation. The liquid distilling between 230 and 250° C. chiefly
contains the metabrominebutyltoluene, which in a purified state boils at from 243
to 246° C.
The pure body, or the product boiling from 230 to 250° is slowly introduced
in a mixture of fuming nitric and sulphuric acid, well cooled. All the oil run in,
the liquid is heated on the water bath until a sample on pouring into cold water
solidifies at once. The mixture is then poured into water, the solid nitroderivative
filtered off and crystallized from alcohol or any other suitable solvent. Trinitro-
butyl bromotoluene crystallises in yellowish white needles melting point 129° C.
and possesses a strong smell of musk.
Dated this 1st day of June 1895.
HASELTINE, LAKE & Co.,
45 Southampton Buildings, London, W.C., Agents for the Applicant.
improvements in the manufacture of Artificial Musk.
I, HENRY HARRIS LAKE, of the Firm of Haseltine, Lake & Co., Patent Agents,
45 Southampton Buildings, in the County of Middlesex, 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 :-
It has been shown by previous Specifications No. 18521/1888 and 4963/1889,
that butylated (or amylated, or propylated) hydrocarbons on nitration yield nitro-
derivatives, smelling strongly of musk. It has further been shown (compare
Specification 13613/1891) that one atom of hydrogen, being in meta-position to
both the others may be substituted in some of these hydrocarbons, as butyltoluene

page_text: We have now discovered that this last atom of hydrogen in butyltoluene may
also be substituted by an atom of halogen without altering the smelling properties
of the compound.
In order to obtain the above mentioned substance we treat metahalogenated
butyltoluene with a mixture of fuming nitric and sulphuric acid.
The meta-halogenated butyltoluenes, metabrom inebutyltoluene for instance, may
be obtained by treating butylmetacresol with pentabromide of phosphorus:
We have now discovered that this last atom of hydrogen in butyltoluene may
also be substituted by an atom of halogen without altering the smelling properties
of the compound.
In order to obtain the above mentioned substance we treat metahalogenated
butyltoluene with a mixture of fuming nitric and sulphuric acid.
The meta-halogenated butyltoluenes, metabrom inebutyltoluene for instance, may
be obtained by treating butylmetacresol with pentabromide of phosphorus:
-
OH
-
– Br
-
CH, – CH, + PBг. = CH₁ - CH₂ + POBг, + HBr
-
- CH,
- CH,
but it is more advantageous to prepare them by the action of butylchloride on
metahalogenated toluenes.
As an example we describe the way of preparing metabrominebutyltoluene and
its trinitroderivative as follows:
We gradually add one part of chloride of aluminium to the mixture of four parts
of metabrominetoluene and four parts of chloride of butyl, without heating and
allow the mixture to stand for several hours. When hydrochloric acid has ceased
to evolve we pour the whole into water and subject the crude oil, which separates
out, to fractional distillation. The liquid distilling between 230° and 250° C. chiefly
contains the metabromine butyltoluene, which in a purified state boils at from 243
to 246° C.
The pure body, or the product boiling from 230 to 25° is slowly introduced into
a mixture of fuming nitric and sulphuric acid, well cooled. All the oil run in, the
liquid is heated on the water bath until a sample on pouring into cold water
solidifies at once. The mixture is then poured into water, the solid nitroderivative

page_text: filtered off and crystallized from alcohol or any other suitable solvent. Trinitro-
butyl bromotoluene crystallizes in yellowish white needles, melting point 129°, and
possesses a strong smell of musk.
The chlorotrinitrobutyltoluene is prepared in an absolutely analogous manner
and its properties are almost the same as those of the bromoderivative.
Having now particularly described and ascertained the nature of the said inven-
tion and in what manner the same is to be performed, as communicated to me
by my foreign correspondents, I declare that what I claim is :—
1. The manufacture of artificial musk by nitrating metahalogenated butyl-
toluenes, as metabromo- or metachlorobutyltoluene for instance, substantially as
.specified.
1
2. The musky smelling metahalogenonitroderivatives, as bromo- and chloronitro-
Dated this 18th day of February 1896.
HASELTINE, LAKE & Co.,
45 Southampton Buildings, London, W.C., Agents for the Applicant.