Process of Producing Esters from Fatty Acids with Oreosote, Guajacol, or Creosol.
Year: 1893

page_text: Date of Application, 18th Mar., 1893
Complete Specification Left, 16th Dec., 1893-Accepted, 27th Jan., 1894
PROVISIONAL SPECIFICATION
[Communicated from abroad by the Firm of Dr. F. VON HEYDEN NACHFOLGER,
Chemical Works, in Rodebeul, near Dresden, Germany.]
Process of Producing Esters from Fatty Acids with Oreosote,
Guajacol, or Creosol.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, in the County
of London, Consulting Engineer and Chartered Patent Agent, do hereby declare
the nature of this invention to be as follows :-
This invention relates to the manufacture of esters of creosote, guajacol, and
creosol. In particular the esters of oleic acid and stearic acid are contemplated,
but other acids obtainable from fatty matters can be employed, as for example
caprylic, capric, lauric, myristic, palmitic, arachidic, cerotic; ricinic, acids, linoleic
acid, eruca acid, caproic acid and sebacic acid.
The production of the ester is effected by the reaction underheating of dehydrat-
ing agents, such as phosphorus trichloride, phosphorus oxychloride, phosphorus
pentachloride, sulphuric oxychloride, chloric carbonoxide acid alkali sulphates, and
the like, upon a mixture of, for example, oleic acid or stearic acid or their salts on
the one hand, with creosote, guajacol, or creosol or their salts on the other hand.
This process can also be carried out in two distinct phases, by first causing the
said chlorine compounds to act upon the said acids or salts, and then causing the
acid chloride so produced to react upon the said phenols or their salts.
The commercial stearic acid, which consists of a mixture of stearic acid and
palmitic acid, may be used.
The process will be rendered clear by the following example.
85 parts of creosote (Pharm. Germ. III) are mixed with 70 parts of oleic
acid, and to the mixture are added 40 parts of phosphorus trichloride, whereupon
the mixture is gradually heated to 135° C. in an oil bath.
The mixture is maintained at this temperature until the production of hydro-
chloric acid vapours ceases. The reaction product is freed from acids and
by-products by washing with water, and is then in the form of a yellow oil of
a mild pleasant flavour, reminding somewhat of creosote.
It is insoluble in water, soluble with difficulty in 90 per cent. alcohol, soluble in
absolute alcohol, ether, benzine, chloroform, fats, oils &c. With the white or yolk
of eggs or gum arabic and water it readily forms an emulsion, and is in its behaviour
very similar to oils. By means of alkalies it is readily saponified, more slowly by
means of water or acids.
From the alkaline soap solution acids separate an oil, smelling strongly of creosote,
which has an extraordinarily caustic action upon mucous membranes, as it again
contains free creosol together with the oleic acid.
In an analogous manner the esters of oleic and stearic acids, on the one hand, and
of guajacol and creosol, on the other hand, are obtained.
In the following the new esters of these two acids will be more particularly
characterised.
I.
The oleic acid-creosote-ester of beechwood-tar creosote (Ph. Germ. III) pro-
duces an oil which is insoluble in water, soluble with difficulty in 90 per cent.
alcohol and readily soluble in absolute alcohol, ether, benzine, chloroform, sulphide
of carbon, fatty oils &c. By the reaction of nitric acid in the presence of mercury

page_text: 11.
The stearic acid-creosote-ester of beechwood-tar creosote (Ph. Germ. III) is a
pale yellow oil, insoluble in water, soluble with difficulty in 90 per cent. alcohol,
easily soluble in absolute alcohol, ether, benzine, sulphide of carbon, fatty oils &c.

page_text: In these formulæ R indicates the guajacol-, creosyl-, and creosote-rest.
All the said esters are oil-like substances of neutral reaction, insoluble in water,
soluble in alcohol and ether.
All the said esters are free from the intense smell and flavour of creosote
guajacol, and creosol.
They do not act caustically or burning upon mucous membranes like those
substances do, and they are intended to replace them for medicinal purposes.
They are saponified by means of alkalies and in the organic system.
Dated this 18th day of March 1893.
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
Process of Producing Esters from Fatty Acids with Creosote,
Guajacol, or Creosol.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, 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 :-
This invention relates to the production of esters resulting from combining
creosote, guajacol or creosol with fatty acids, especially oleic and stearic acid, but
also other acids obtainable from fatty matters, such as caprylic, capric, lauric,
myristic, palmitic, arachidic, ricinic, linoleic, erucic, caproic, sebacic &c. acid, being
available.
The esters are produced by heating dehydrating agents, such as trichloride,
pentachloride or oxychloride of phosphorus, oxychloride of sulphur, oxychloride
of carbon, acid sulphates of alkalies and the like, with a mixture prepared of the
fatty acids (or their salts) and creosote, guajacol or creosol (or their salts). This
process may also be divided into two separate stages, by firstly allowing the
aforesaid chlorine compounds to act upon the fatty acids or their salts and then
causing the chloride of oleic or stearic acid so produced to act upon the phenols
mentioned, or their salts.
For the manufacture, common commercial stearic acid which is known to be a
mixture of stearic and palmitic acid, may be used.
The process will be clearly exemplified by the following example.
85 parts of creosote are mixed with 170 parts of oleic acid, and then 40 parts
of trichloride of phosphorus are added, which mixture is heated gradually up
to 135 degrees C. in an oil bath, this temperature being kept on until there is no
more production of vapours of hydrochloric acid. The product of reaction is
washed with water to remove acids and secondary products, the result being a
yellow oil of a mild, pleasant flavour, reminding somewhat of creosote.
It is insoluble in water, soluble with difficulty in alcohol of 90%, soluble in
absolute alcohol, ether, benzine, chloroform, fatty oils &c. By means of alkalies
it is easily saponified; with more difficulty by water and acids. With the yolk or
white of eggs or gum arabic and water it can easily be emulsioned, and it shows
generally a great resemblance to fatty oils. From the alkaline soap solution acids
separate an oil which has a strong smell of creosote and has an extremely caustic
action upon mucous membranes, as it contains again free creosote besides free
oleic acid.
In the same way the esters from guajacol and creosol and oleic or stearic acid are
produced.

page_text: Having now particularly described and ascertained the nature of my said inven-
tion and in what manner the same is to be performed I declare that what I
claim is :-
1. A process of producing esters from guajacol, creosol or creosote, and from the
oleic, stearic, caprylic, capric, lauric, myristic, palmitic, arachic, cerotic, ricinic,
linoleic, erucic, caproic and sebacic acids by treating guajacol, creosol, creosote, or
their salts, with the chlorides of the acids named or with the acids or their salts in
the presence of a condensing medium.
2. As new manufactures, the esters herein set forth, irrespective of the manner in
which they are produced.
Dated this 16th day of December 1893.
ABEL & IMRAY,
Agents for the Applicant.