The Manufacture or Production of a New Sulphone or Diethyl Sulphone Methyl Ethyl Methan.
Year: 1888

page_text: Date of Application, 10th Nov., 1888
Complete Specification Left, 10th Aug., 1889-Accepted, 19th Oct., 1889
PROVISIONAL SPECIFICATION.
The Manufacture or Production of a New Sulphone or Diethyl
Sulphone Methyl Ethyl Methan.
1, 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, to be as follows:-
According to this invention ethyl mercaptol of methyl ethyl ketone is converted
into diethyl sulphone methyl ethyl methan by means of oxidation with oxidising agents
or the sulphone (diethyl sulphone methyl methan or diethyl sulphone ethyl methan),
obtained by means
of condensing acetic or propionic aldehyde with ethyl
mercaptane and oxidising the mercaptol thus formed, is reduced or converted into
diethyl sulphone methyl ethyl methan by treating it with methyl or ethyl haloids
in alkaline, alcoholic or aqueous solution at the temperature of a water bath with
or without pressure.
Either the methyl ethyl ketone is condensed with ethyl sulphydrate and the
new mercaptol thus obtained is oxidised into the new sulphone or the said diethyl
sulphon methyl methan or the di-ethyl sulphon ethyl methan is produced in the
first place by condensing ethyl sulph hydrate with propionic aldehyde or ethyl
sulph hydrate with acetic aidehyde and oxidising the mercaptol thus obtained.
By ethylising or methylising the sulphone resulting from this treatment the new
sulphone or diethyl sulphone methyl ethyl methan is finally obtained.
The following examples are given to illustrate the method of conducting the
processes according to this invention.
1. PROCESS FOR THE PRODUCTION OF DIETHYL SULPHONE METHYL ETHYL METHAN
FROM METHYL ETHYL KETONE.
Methyl ethyl ketone is added to the calculated quantity of ethyl mercaptane and
dry hydrochloric acid gas is introduced into the mixture.
The mixture subjected to the reaction is mixed with water after standing for
several hours the oil separating therefrom is removed, dried upon calcium chloride
and purified by rectification.
to 203 degrees Centigrade.
It boils without decomposition at from about 198
In order to convert it into the sulphone the mercaptol of methyl ethyl ketone thus
obtained is mixed with a weak slightly acidulated aqueous solution of permanganate
until the decolourising action on the permanganate ceases. The product is then
boiled and filtered.
This
After concentration the diethyl sulphone methyl ethyl methan crystallises out of the
filtrate in shining silvery scales or laminae melting at 76 degrees Centigrade.
product is soluble with difficulty in cold water but more readily soluble in hot water or
in alcohol ether or benzene. It is odourless but is slightly bitter to the taste.
2. PROCESS FOR THE PRODUCTION OF DIETHYL SULPHON METHYL ETHYL METHAN
FROM ACETIC ALDEHYDE.
Molecular quantities of acetic aldehyde and ethyl sulph hydrate are brought togethe
and dry hydrochloric acid gas is introduced into the mixture.
The product of the reaction being separated in the known manner boils without
decomposition at from 186 to 188 degrees Centigrade.

page_text: It can be readily converted into the corresponding sulphone or diethyl sulphone
methyl methan.
The oxidation takes place as hereinbefore described in connection with the first
example.
The sulphone thus obtained crystallises in shining prisms whose melting point is
75-5 degrees. It is readily soluble in water and other solvents.
To effect the conversion of the diethyl sulphon methyl methane into the diethyl
sulphon methyl ethyl methan seven parts of the sulphone are dissolved in twenty parts
of water; two and a half (2·5) parts of solid caustic soda are added and five parts of
ethyl iodide are mixed in drops with the clear solution. The reaction is completed by
boiling for one hour in a reflux cooler.
On cooling the sulphone separates in shining scales or laminae. The alkalising
proceeds very regularly and any traces of substances not acted upon can be easily
separated from the product of the reaction which is much more difficult of solution in
water than the first.
To obtain a pure product it is now simply necessary to crystallise it once out of
water.
3. PROCESS FOR THE PRODUCTION OF DIETHYL SULPHON METHYL ETHYL METHAN
FROM PROPIONIC ALDEHYDE.
When the equivalent quantity of propionic aldehyde is employed in place of the
acetic aldehyde mentioned in the preceding example the mercaptol of the propionic
aldehyde is obtained in the first instance with condensation by preserving the same
conditions.
The product, an unpleasantly smelling oil boiling at from about 190 to 200 degrees
can be very easily converted by permanganate according to the methods of treatment
already described into the diethyl sulphone ethyl methan melting at 77 degrees.
This sulphone crystallises into white milky prisms and is readily soluble in water
and other solvents.
To convert it into the diethyl-sulphone ethyl methyl methan it is treated as herein-
before described with reference to the corresponding sulphone obtained from acetic
aldehyde (Example 2), methyl iodide being employed in place of the ethyl iodide
mentioned in that example.
The alkalising proceeds regularly in this case also and owing to the relative
solubility of the product it can be readily freed from any substances that may have
escaped the action.
Dated this 10th day of November 1888
J. H. JOHNSON & Co.,
Agents.
COMPLETE SPECIFICATION.
The Manufacture or Production of a New Sulphone or Diethyl
Sulphone Methyl Ethyl Methan.
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 :--
This Invention relates to the manufacture or production of a new sulphone or
diethylsulphone methyl ethyl methan. With this object methyl ethyl ketone is con-
densed with ethyl sulphhydrate and the new mercaptol thus obtained is oxidised into
the new sulphone or according to another method of proceeding diethyl sulphone
methyl methan or di-ethyl sulphone ethyl methan is produced in the first place by

page_text: condensing ethyl sulph hydrate with propionic aldehyde or with acetic aldehyde and
oxidising the mercaptol thus obtained and is then treated with methyl or ethyl haloids
in an alkaline, alcoholic or aqueous solution at the temperature of a water bath with or
without pressure so that by thus ethylising or methylising the sulphone resulting from
the preceding operation the new sulphone or di-ethyl sulphone methyl ethyl methan
may be finally obtained.
The following examples are given to illustrate the way in which the processes
according to this Invention may be con lucted.
1. PROCESS FOR THE PRODUCTION
OF DIETHYL
SULPHONE METHYL ETHYL METHAN
FROM METHYL ETHYL KETONE.
Methyl ethyl ketone is added to the calculated quantity of ethyl mercaptane and dry
hydrochloric acid gas is introduced into the mixture. After standing for several hours
the materials are mixed with water the oil separating therefrom is removed, dried upon
calcium chloride and purified by rectification. It boils without becoming decomposed
at from about 198 to 203 degrees centigrade. In order to convert it into the sulphone,
the mercaptol of methyl ethyl ketone thus obtained is mixed with a weak aqucons
solution of permanganate with the addition of a small quantity of acid until the
decolourising action on the permanganate ceases. The product is then boiled down
and filtered. After concentration the diethyl sulphone methyl ethyl methan crystallises
out of the filtrate in shining silvery scales or laminæ melting at 76 degrees centigrado.
This product is soluble with difficulty in cold water but more readily soluble in hot
water or in alcohol, ether or benzene. It is odourless and slightly bitter to the
taste.
2. PROCESS FOR THE PRODUCTION OF DIETHYL SULPHONE METHYL ETHYL METHAN
FROM ACETIC ALDEHYDE.
Molecular quantities or proportions of acetic aldehyde and ethyl sulph hydrate are
brought together and dry hydrochloric acid gas is introduced into the mixture. The
product of the reaction being separated in the known manner boils without decomposi-
tion at from 186 to 188 degrees centigrade. It can be readily converted into the
corresponding sulphone or diethyl sulphone methyl methan.
The oxidation takes
The
place as hereinbefore described in connection with the first example.
sulphone thus obtained crystallises in shining prisms whose melting point is 75.5
degrees centigrade. It is readily soluble in water and other solvents.
To effect the conversion of the diethyl sulphone methyl methan into the diethyl
sulphone methyl ethyl methan about seven parts of the sulphone are dissolved in
twenty parts of water; two and a half parts of austic soda are added and five
parts of ethyl iodide are mixed in drops with the cr tion. The reaction is coun-
pleted by boiling for about an hour in a reflux cool. cooling the sulphone
separates in shining scales or laminae. The alkylising pro. very regularly or
smoothly and any traces of substances not acted upon can be easily rated from the
product of the reaction which is much more difficult of solution in wa
than is the
product of the first process. To obtain a pure product it is now simply necessary to
crystallise it once out of water.
3. PROCESS FOR THE PRODUCTION
OF DIETHYL SULPHONE METHYL ETHYL METHAN
FROM PROPIONIC ALDEHYDE.
When the equivalent quantity of propionic aldehyde is employed in place of the
acetic aldehyde mentioned in the preceding example the mercaptol of the propionic
aldehyde is obtained in the first instance in the condensation process by preserving the
same conditions. The product (which is an unpleasantly smelling oil boiling at from
about 190 to 200 degrees centigrade) can be very easily converted by permanganate
according to the methods of treatment already described into the diethyl sulphone

page_text: ethyl methan melting at 77 degrees centigrade. This sulphone crystallises into white
milky prisms and is readily soluble in water and other solvents. To convert it into the
diethyl sulphone ethyl methyl methan it is treated as hereinbefore described with
reference to the corresponding sulphone obtained from acetic aldehyde (Example 2)
methyl iodide being employed in place of the ethyl iodide mentioned in that example.
The alkylising proceeds regularly in this case also and owing to the relative solubility
of the product it can be readily freed from any substances that may have escaped the
action.
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. Converting ethyl mercaptol of methyl ethyl ketone into diethyl sulphone
methyl ethyl niethan by means of oxidation with oxidising agents as hereinbefore
described.
2. Reducing or converting the sulphone (diethyl sulphone methyl methan or diethyl
sulphone ethyl methan), obtained by condensing acetic or propionic aldehyde with
ethyl mercaptan and oxidising the mercaptol thus formed, into diethyl sulphone
methyl ethyl methan by treating it with methyl or ethyl haloids in alkaline, alcoholic
or aqueous solution at the temperature of a water bath with or without pressure sub-
stantially as hereinbefore described.
3. The products manufactured or produced as hereinbefore described and claimed.
Dated this 10th day of Angust 1889
J. H. JOHNSON & Co.,
Agents.