Improvements in the Manufacture and Production of Perfumes.
Year: 1898

page_text: PROVISIONAL SPECIFICATION.
Improvements in the Manufacture and Production of Perfumes.
I, JAMES YATE JOHNSON, of 47, Lincoln's Inn Fields in the County of London
Gentleman, do hereby declare the nature of this invention, (which has been
communicated to me by Albert Verley, of 7, Quai de Seinè, Courbevoie, near
Paris, in the Republic of France, Electrician), to be as follows;-
My foreign correspondent has discovered a new class of bodies suitable for use
in perfumery which have never previously been manufactured or isolated. These
bodies are of the nature of acetals of an aromatic glycol. The principal members
of this class have an odour of jasmine and one of them is the odoriferous principle
of the natural extract of jasmine and can also be prepared therefrom in the
manner hereinafter set forth.
In order to explain this invention I will take the leading member of the class
which I call the methylic acetal of phenylglycol. Its composition is shewn by
the following diagram : —
50 grammes of phenylglycol,
300 grammes water.
125 grammes sulphuric acid,
100 grammes formic aldehyde.
After a short time a light oil separates out which floats on the surface. It is
extracted with ether and rectified in vacuo. It boils at 101° Centigrade under
12mm. pressure. It possesses the odour of jasmine. This body may be con-
sidered to be a type of the class. Other bodies of this class may be obtained
by substitution of monovalent radicals for the hydrogen atoms in the benzine
ring or bivalent radicals in the side ring in the position occupied by the methyl
group CH, in the diagram I have already given, i.e. between the two oxygen
atoms.
As an example of these other bodies I will describe the preparation of ethylic
acetal of phenyl-glycol which is the body obtained by replacing the methylic

page_text: group CH, by the ethylic group CH-CH, in the position referred to. Its
structure is therefore given by the following diagram:-
100 grammes sulphuric acid.
are mixed together and 40 grammes of ordinary aldehyde are then added. An
oil at once commences to separate out in the cold and the reaction is finished by
heating for a few minutes on the water bath. The oil is extracted with ether
and the product is subjected to distillation in vacuo. The body boils at 103° Centi-
grade under 12mm. pressure. It also has an odour of jasmine.
The body first above mentioned is the principal odoriferous constituent in the
natural extract of jasmine and may be obtained from it in the following way.
The extract of jasmine is freed from fatty matters and non-volatile impurities
and is then subjected to fractional distillation. The portion boiling at 101° Centi-
grade at 12mm. pressure is thus separated and will be found to contain the
principal odoriferous constituent of the extract and to be of the composition of
the methylic acetal of phenylglycol above described.
1000
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C.,
Agents.
COMPLETE SPECIFICATION.
Improvements in the Manufacture and Production of Perfumes.
I, JAMES YATE JOHNSON, of 47, Lincoln's Inn Fields in the County of London
Gentleman, do hereby declare the nature of this invention, (which has been
communicated to me from abroad by Albert Verley, of 7, Quai de Seinè, Courbevoie,
near Paris, in the Republic of. France, Electrician), and in what manner the same is
to be performed to be particularly described and ascertained in and by the
following statement:-
My foreign correspondent has discovered a new class of bodies suitable for use
in perfumery which bodies have never previously to his said discovery been
manufactured or isolated.
The said bodies are of the nature of alkyl acetals of an aromatic glycol. The
principal members of this class have an odour of jasmine and one of them is
the odoriferous principle of the natural extract of jasmine and can be prepared
therefrom in the manner hereinafter set forth.

page_text: In order to explain this invention and the manner in which it can be per-
formed. I will take the leading member of the class which I call the methylic
acetal of phenylglycol. Its composition is shewn by the diagram.
A mixture of 50 grammes of phenylglycol
300 grammes of water
125 grammes of sulphuric acid
and 100 grammes of formic alhehyde
is heated on the water bath and after a short time a light oil separates out and
floats on the surface. It is removed and extracted with ether and rectified in
vacuo. It boils at 101 degrees Centigrade under 12mm. pressure. It possesses
the odour of jasmine. This body may be considered as a type of the class. Other
bodies of this class may be obtained by substitution of monovalent radicals for
the hydrogen atoms in the benzene ring, or bi-valent radicals in the side ring;
in the position occupied by the methyl group CH, in the diagram hereinbefore
given i.e. between the two oxygen atoms.
As an example of these other bodies I will describe the preparation of ethylic
acetal of phenylglycol which is the body obtained by replacing the methylic
group CH, by the ethylic group CH-CH, in the position referred to.
ture is therefore given by the diagram
Its struc-
An
are mixed together and 40 grammes of ordinary aldehyde are then added.
oil at once, and in the cold, commences to separate out, and the reaction is finished
by heating for a few minutes on the water bath. The soil is extracted with
ether and the product is subjected to distillation in vacuo. The body boils at
103° Centigrade under 12mm. pressure. It has an odour of jasmine.
The body first hereinbefore described is the principal odoriferous constituent in
the natural extract of jasmine and can be obtained from it in the following
way: The extract of jasmine is freed from fatty matters and non-volatile
impurities and is then subjected to fractional distillation. The portion boiling at
101 degrees Centigrade at 12mm. pressure is thus separated and will be found
to contain the principal odoriferous constituent of the extract and to be of the
composition of the methylic acetal of phenyl-glycol hereinbefore described.

page_text: Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed, I declare that what
I claim is:
1. The manufacture and production of perfumes of the nature of alkyl acetals
of an aromatic glycol as hereinbefore defined.
2. The manufacture and production of methylic acetal of phenylglycol as
herein before described.
3. The manufacture and production of ethylic acetal of phenylglycol as
herein before described.
4. As new articles of manufacture the alkyl acetals of phenylgycol which can
be produced as hereinbefore explained.
Dated this 16th day of November 1898.
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C.,
Agents.