Improvements in the Manufacture of Antiseptic Agents.
Year: 1894

page_text: Date of Application, 11th Aug., 1894
Complete Specification Left, 8th May, 1895-Accepted, 15th June, 1895
PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Antiseptic Agents.
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 Dr. F. Von Heyden Nachfolger of Radebeul
near Dresden in the Empire of Germany) to be as follows:-
By replacing in phenol (C.H.OH) one or more atoms of hydrogen by methyl
(CH) or halogen (CIBrl) or by the nitro group (NO,) substituted phenol is
obtained and according to the point at which the substituent enters, ortho, meta or
para substituted phenol is produced. What has hitherto prevented these substituted
phenols from being adopted, more generally than they have been, as antiseptic
agents, was their poisonous nature, their caustic action, their intense odour and
acrid taste.
Now we have found that substituted phenol may be rendered far more suitable
than it has been hitherto for use as an antiseptic medium by effecting a conversion
and thereby producing a carbonic acid compound.
This conversion is most simply effected by the action of phosgen upon substituted
phenol or phenol-salt in accordance with the following equations.

page_text: p-chloro-phenol carbonate which remains behind is crystallized out of the alcohol,
producing colourless crystals melting at 154° Centigrade.
Instead of allowing the reaction to be completed in one stage, as described, the
stages represented by the above equations I and II may be gone through
separately the phen-oxy-carbonyl-chloride (1) being obtained in the first place and
then allowed to react in conjunction with a second molecule of substituted phenol
or phenol-salt (II).
In most cases it will be found more convenient to "bind" the hydrochloric acid
produced by the reaction, by causing the phosgen and substituted phenol-salt to
react upon each other. Thus for example, a solution of ochloro phenol in an
equivalent quantity of soda lye is saturated with phosgen until neutral reaction
sets in.
The o-chloro-phenol carbonate which is caused to separate by this process is
crystallized out of the alcohol and thereby purified, forming colourless crystals
melting at 55° Centigrade.
+
Antiseptic agents produced in this manner differ from the initial product i.e. the
corresponding substituted phenol by the following properties :
They are neutral, practically free from poison and exercise no caustic or
corrosive action, being in fact, indifferent when brought into contact with the skin,
in addition to which they are perfectly free, or nearly so from any odour and
taste. In appearance they are solid crystalline colourless substances insoluble in
water, but soluble in alcohol and ether. The melting points of these new substances,
as well as the chemical formulæ representing them, may be found by referring to
the following table :-
:―

page_text: 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 com-
municated to me from abroad by Dr. F. Von Heyden Nachfolger of Radebeul
near Dresden 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:-
By replacing in phenol (C,H,OH) an atom or atoms of hydrogen by methyl
(CH3) or halogen (Cl, Br,I) or by the nitro group (N.O2) substituted phenol is
obtained and according to the point at which the substituent enters, ortho, meta or
para substituted phenol is produced. What has hitherto prevented these substituted
phenols from being adopted, more generally than they have been, as antiseptic
agents, was their poisonous nature, their caustic action, their intense odour and
acrid taste.
Now my foreign correspondent has found that substituted phenol may be rendered
far more suitable than it has been hitherto for use as an antiseptic medium by
effecting a conversion and thereby producing a carbonic acid compound.
This conversion is most simply effected by the action of phosgen upon substituted
phenol or phenol-salt in accordance with the following equations:
- OH
- OCOCI

page_text: p-chloro-phenol carbonate which remains behind is crysallized out of the alcohol,
producing colourless crystals melting at 154° Centigrade.
Instead of allowing the reaction to be completed in one stage, as described the
stages represented by the above equations I and II may be conducted separately,
the phen-oxy-carbonyl-chloride (1) being obtained in the first place and then
allowed to react in conjunction with a second molecule of substituted phenol or
phenol-salt (11).
In most cases it will be found more convenient to "bind" or fix the hydrochloric
acid produced by the reaction by causing the phosgen and substituted phenol-salt
to react upon each other. Thus for example, a solution of o-chloro-phenol in an
equivalent quantity of soda lye is saturated with phosgen until neutral reaction
sets in. The o-chloro-phenol carbonate which is caused to separate by this process
is crystallized out of the alcohol and thereby purified, forming colourless-crystals
melting at 55° Centigrade.
Antiseptic agents produced in this manner differ from the initial product,
(i.e. the corresponding substituted phenol) by the following properties.
They are neutral, practically free from poison and exercise no caustic or
corrosive action, being in fact indifferent when brought into contact with the skin,
in addition to which they are perfectly free, or nearly so from any odour and
taste. In appearance, they are solid crystalline colourless substances, insoluble in
water, but soluble in alcohol and ether. The melting points of these new
substances, as well as the chemical formulæ representing them, may be found by
referring to the following table :

page_text: 2. As articles of manufacture new antiseptic agents having the characteristics
herein before described and such as can be obtained as hereinbefore set forth and
claimed.
Dated this 8th day of May 1905
JOHNSONS & WILLCOX,
Agents for the Applicant.