Improvements in the Manufacture of Periodides of Isobutyl Phenols and of Isobutyl Cresols.
Year: 1890

page_text: Date of Application, 8th Nov., 1890
Complete Specification Left, 27th July, 1891-Accepted, 5th Sept., 1891
PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Periodides of Isobutyl Phenols
and of Isobutyl Cresols.
I, BENJAMIN WILLCOX of 47 Lincolns Inn Fields in the County of Middlesex
Patent Agent do hereby declare the nature of this invention (which has been com-
municated to me from abroad by Farbenfabriken vormals Friedrich Bayer & Co.
of Elberfeld in the Empire of Germany) to be as follows:-
According to the process described in the Specification accompanying my
application for Letters Patent No. 5079 of 1889 there is obtained by the action of
iodine and alkalies upon phenols and analogous substances peculiar iodine
substitution derivatives of these substances which are valuable as substitutes for
iodoform.
In the phenol series my foreign correspondents have obtained from phenol and
methyl propyl phenols (thymol and carvacrol) in particular iodine derivatives of
this description out of which the thymol derivative has already become an important
article of manufacture known as "aristol."
My foreign correspondents have now discovered that the isobutyl substitution
phenols are also capable of being subjected to the process described in the aforesaid
Specification No. 5079 of 1889 and that there can be obtained therefrom analogous
iodine derivatives which similarly to aristol can be employed with advantage for
pharmaceutical purposes.
The following is given as an example of the method of conducting the operations
in the manufacture of para-isobutyl-meta-cresol-iodide according to the present
invention.
About 164 parts by weight of para-isobutyl-meta-cresol (obtained by the action
of isobutyl alcohol upon metal cresol in the presence of chloride of zinc) are dissolved
in about 16 parts by weight of soda and 500 parts by weight of water. The
temperature of this solution being lowered with the aid of ice to about 5 degrees
Centigrade it is allowed to flow into a solution of 1016 parts of iodine in 100 parts
of calcium iodide whilst being stirred. A reddish brown flaky precipitate immediately
separates which is filtered off and purified by washing with water.
In place of previously manufactured iodine, iodine in the nascent state may be
employed it being set free by means of chloride of calcium or other substances
capable of producing the required effect.
The product having been purified by washing is dried at ordinary temperature
and then forms a reddish-brown powder which dissolves very readily with a reddish-
brown colour in ether, chloroform and olive oil being also relatively easily dissolved
in alcohol benzene and ligroin. It is not soluble in water or alkalies.
When heated in capillary tubes the reddish brown colour of the powder gradually
changes to a clear yellow; at about 98 degrees Centigrade it begins to soften
assumes a darker colour and when further heated gradually melts into a deep brown
liquid. At about 140 degrees Centigrade iodine is given off in abundance.
When a corresponding quantity of para-isobutyl-phenol or para-isobutyl-ortho-
cresol is substituted for the para-isobutyl-meta-cresol employed in the foregoing
example, analogous bodies are obtained possessing similar properties to the para-
sobutyl-meta-cresol-iodide hereinbefore described.
The para-isobutyl-ortho-cresol-iodide forms a yellow powder which dissolves
readily with a yellowish-brown colour in ether, chloroform or olive oil and, less
readily in benzene, ligroin, and alcohol. When heated to from about 60 to 70 degrees
Centigrade it commences to be decomposed acquiring a darker colour and at the
ID 7

page_text: same time gradually running together. Iodine vapour is generated on further
heating.
The para-isobutyl-phenol-iodide forms a green powder which is readily soluble
in ether and chloroform and less readily soluble in alcohol, benzene, ligroin, or olive
oil and which when heated in capillary tubes to about 150 degrees Centigrade
gradually fuses or melts together with decomposition and separation of iodine. It
is insoluble in water.
Dated this 8th day of November 1890
J. H. JOHNSON & Co.,
Agents.
COMPLETE SPECIFICATION.
Improvements in the Manufacture of Periodides of Isobutyl Phenols
and of Isobutyl Cresols.
I BENJAMIN WILLCOX of 47 Lincolns Inn Fields in the County of Middlesex
Patent Agent do hereby declare the nature of this invention which has been
communicated to me from abroad by the Farbenfabriken vormals Friedrich
Bayer & Co. of Elberfeld in the Empire of Germany and in what manner the
same is to be performed, to be particularly described and ascertained in and by the
following statement:-
According to the process described in the Specification of Letters Patent No. 5079
of 1889 granted to me there are obtained by the action of iodine and alkalies upon
phenols and analogous substances, peculiar iodine substitution derivatives of these
substances which are valuable as substitutes for iodoform.
In the phenol series my foreign correspondents have already obtained from phenol
and from the methyl-propyl-phenols (thymol and carvacrol) several such iodine
derivatives of which the thymol derivative has already become an important
article of manufacture known as " aristol."
My foreign correspondents have now discovered that the isobutyl phenols and
isobutyl cresols may be subjected to the process described in the aforesaid Specifi-
cation No. 507989 and that in this manner analogous iodine derivatives of high
value result which can advantageously be employed for pharmaceutical purposes.
The following is given as an example of the process for the manufacture of para-
isobutyl-meta-cresol-iodide according to the present invention.
FIRST EXAMPLE.
MANUFACTURE OF THE IODIDE OF PARA-ISOBUTYL-META-CRESOL.
About 164 parts by weight of para-isobutyl-meta-cresol (which is obtained by
the action of isobutyl alcohol upon meta cresol in the presence of chloride of zinc)
are dissolved in about 16 parts by weight of soda and 500 parts by weight of water.
After the temperature of this solution has been lowered with the aid of ice to about
5 degrees Centigrade it is allowed to flow into a solution such as may be prepared
by dissolving 101-6 parts by weight of iodine in water with the aid of 100 parts by
weight of potassium-iodide admixture being secured by stirring. The reddish-brown
flaky precipitate which immediately separates is filtered off and purified by washing
with water and constitutes the para-isobutyl-meta-cresol-iodide produced according
to this process.
In place of iodine as such, it may be employed with the same result in the nascent
state; that is liberated by means of chloride of lime or other substances capable of
producing the same effect.
The para-isobutyl-meta-cresol-iodide obtained in the one or the other manner
forms, when dried at ordinary temperature, a reddish-brown powder that dissolves,
very readily, and with a reddish-brown colour, in ether, chloroform and olive oil, is
also easily soluble in alcohol, benzene and ligroin but is not dissolved by water or
alkalies.

page_text: When heated in capillary tubes the reddish-brown colour of the powder gradually
changes to a clear yellow. At about 98 degrees Centigrade it begins to soften
assuming a darker colour. When further heated it gradually melts into a deep
brown liquid. At about 140 degrees Centigrade iodine is given off in abundance.
When a corresponding quantity of para-isobutyl-ortho-cresol or para-isobutyl-
phenol is substituted for the para-isobutyl-meta-cresol employed in the aforesaid
example, analogous iodine products are obtained possessing properties similar to
those of the para-isobutyl-meta-cresol-iodide herein before described.
The para-isobutyl-ortho-cresol-iodide forms a yellowish powder which dissolves
readily, with a yellowish-brown colour, in ether, chloroform or olive oil but less
readily in benzene, ligroin and alcohol. When heated to from about 60 to 70 degrees
Centigrade it commences to decompose acquiring a darker colour and at the same
time gradually running together. Iodine vapours are liberated on further heating.
The para-isobutyl-phenol-iodide forms a green powder, easily soluble in ether
and chloroform but less readily soluble in alcohol, benzene, ligroin or olive oil.
When it is heated in capillary tubes to about 150 degrees Centigrade it gradually
melts together decomposition and separation of iodine resulting. It is insoluble in
water and alkalies.
Having now particularly described and ascertained the nature of the said inven-
tion and in what manner the same is to be performed I declare that what I
claim is :-
1) The production of iodine derivatives of para-isobutyl-phenol, para-isobutyl-
ortho-cresol and para-isobutyl-meta-cresol by acting with iodine and alkalies upon
para-isobutyl-phenol-para-isobutyl-ortho-cresol or para-isobutyl-meta-cresol sub-
stantially as herein before described.
2) As new pharmaceutical products of manufacture the following iodine derivatives
para-isobutyl-phenol-iodide ; para-isobutyl-ortho-cresol-iodide and para-isobutyl-
meta-cresol-iodide.
Dated this 27th day of July 1891
J. H. JOHNSON & Co.,
47, Lincoln's Inn Fields, Agents.