Process for the Production of Oxymethoxybenzoic Acids.
Year: 1889

page_text: Date of Application, 4th Apr., 1889
Complete Specification Left. 2nd Jan.. 1890-Accepted, 8th Feb., 1890
PROVISIONAL. SPECIFICATION.
A Process for the Production of Oxymethoxybenzoic Acids.
I JAMES YATE JOHNSON of 47 Lincolns Inn Fields in the County of Middlesex
Gentleman do hereby declare the nature of this Invention which has been communi-
cated to me from abroad by Dr. F. von Heyden Nachfolger of Radebeul near Dresden
in the Empire of Germany, to be as follows:-
It is known that carbon acids are obtained from phenol and its homologues by
heating their alkaline salts with carbonic acid.
My foreign correspondents have discovered that in like manner it is possible to
obtain from guaiacol creosol and eugenol the following methylised dioxybenzoic acids
namely:-
Guaiacol carbon acids C, H,
COOH 1
он
O C H
2
3
COOH 1
он 2
Creosol carbon acid C, H, OUH, 3
CH, 5
COOH 1
Eugetinic acid
C. F,
O H 2
OCH 3
C₂ H
In carrying out this Invention in practice taking the manufacture of the guaiacol
carbon acid for example the process is conducted as follows:-
(1) Sodium, guaiacol or any other alkaline or earthy alkaline salt of guaiacol is
saturated with carbonic acid without heating and under pressure and afterwards heated
in a closed vessel to over one hundred degrees centigrade.
The product of the reaction is dissolved in water and mixed with a mineral acid
whereupon the guaiacol carbon acid crystallises out. This product crystallises with
aq. and melts if dehydrated at from about 148° to 150° centigrade. It gives when
in aqueous solution a blue colour with chloride of iron and is decomposed by heat into
carbonic acid and guaiacol.
(2) In place of first saturating the guaiacol salt with carbonic acid without heat in
the first instance and afterwards applying heat it may be treated with carbonic acid
and heated at the same time.
When carbonic acid is caused to pass over a guaiacol salt which is heated to upwards
of 100 degrees centigrade the following process takes place.
2 C, H. OH,
O Na
+
CO₂ = C H₂
O Na + CHO CH3
Un
OCH
Na
2 C. H. OH
+ CO,= C H ONa + C Ho°C H
OH
OCH
2 C₁ H
6
O Na
00 H₂
+ CO₂ = ( H₂ O Na
+ C% H, O C Hạ
OCH
On the other hand when carbonic acid under pressure is brought in contact with th
aiacol salt in a closed vessel heated to a temperature over 100 degrees centigrad
aiacol carbon acid is formed according to the following equation.

page_text: The product of the reaction thus obtained is dissolved in water as before and mixed
with a inineral acid.
By the same processes the known substances creosol carbon acid and eugetinic acid
are obtained.
When in place of pure creosol common beech tar creosote or a mixture of creosol
with guaiacol is employed acid mixtures are obtained whose melting points vary
greatly according to the composition of the materials but are generally lower than that
of the guaiacol carbon acid.
These acids serve for the manufacture of azo colouring matter.
COMPLETE SPECIFICATION
A Process for the Production of Oxymethoxybenzoic Acids.
I, JAMES YATE JOHNSON of 47 Lincolns Inn Fields in the County of Middlesex,
Gentleman do hereby declare the nature of this Invention (which has been communi-
cated 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 :-
It is known that carbon acids are obtained from phenol and its homologues by heating
their alkaline salts with carbonic acid.
My foreign Correspondents have discovered that in like manner it is possible to
obtain from guaiacol creosol and eugenol the following methylised dioxybenzoic acids
namely:
Guaiacol carbon acid C H₂
COOH 1
он 2
O CH
3
СООН 1
Creosol carbon acid C H₂
Ο Η 2.
0 C H 3
CH3
COOH 1
он
2
Eugetinic acid
C H₂
0 C H 3
CH
5
In carrying out this Invention in practice taking the manufacture of the guaiacol
carbon acid for example, the process is conducted as follows:
Sodium guaiacol or any other alkaline or earthy alkaline salt of guaiacol is saturated
with carbonic acid without heating and under pressure and afterwards heated in a
closed vessel to over one hundred degrees Centigrade. The product of the reaction is
dissolved in water and mixed with a mineral acid whereupon the guaiacol carbon acid
crystallises out. This product crystallises with 2 aq. and melts if dehydrated at from
about 148° to 150° Centigrade. It gives when in aqueous solution a blue colour with
chloride of iron and is decomposed by heat into carbonic acid and guaiacol.
In place of first saturating the guaiacol salt with carbonic acid without heat in the
first instance and afterwards applying heat it may be treated with carbonic acid and
.heated at the same time.
When carbonic acid is caused to pass over a guaiacol salt which is heated to upwards
of 100 degrees Centigrade the following process takes place.
он
O Na
2 C. H. OCH
+ CO₂ = 0, H₂ O Na
осн
+ CH
0 C H

page_text: On the other hand when carbonic acid under pressure is brought in contact with the
guaiacol salt in a closed vessel heated to a temperature over 100 degrees Centigrade
guaiacol carbon acid is formed according to the following equation.
By the same processes the known substances creosol carbon acid and eugetinic acid
are obtained, by the treatment of creosol or eugenol sodium or other alkaline or earthy
alkaline salt thereof as described with regard to the guaiacol salt.
When in place of pure creosol common beech tar creosote or a mixture of creosol
with guaiacol is employed, acid mixtures are obtained whose melting points vary greatly
according to the composition of the materials but are generally lower than that of the
guaiacol carbon acid.
These acids serve for the manufacture of azo colouring matters.
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 production of guaiacol-carbon acid and creosol-carbon acid and eugetinic
acid from the alkaline or earthy alkaline salts of the corresponding phenols by saturation
at a low temperature with carbonic acid under pressure and subsequently heating to
not less than 100 degrees Centigrade in a closed vessel or by causing the carbonic
acid to operate at a temperature of not less than 100 degrees Centigrade either under
pressure or otherwise substantially as herein before described.
2. Obtaining carbon acid mixtures from beech tar creosote or from the mixtures of
guaiacol and creosol resulting from the purification of the said creosote by causing
carbonic acid to act upon these products as set forth in the first claiming clause.
3. As new articles of manufacture the acids which are the product of the processes
hereinbefore described and claimed.
Dated this 2nd day of January 1890.
J. H. JOHNSON & Co.,
Agents.