Improvements in the Manufacture of Oxyphthalic Acids (Phenol Dicarbonic Acids).
Year: 1890

page_text: Date of Application, 19th Aug., 1890
Complete Specification Left, 1st May, 1891-Accepted, 6th June, 1891
PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Oxyphthalic Acids (Phenol
Dicarbonic Acids).
I JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of Middlesex
Gentleman do hereby declare the nature of the said 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 to be as follows:-
In the compound ethers of the three oxybenzoic acids the hydrogen of the
hydroxyl may be replaced by one of the metals of the alkalies; these compounds
which present a certain analogy to salts may be obtained dry.
If the anhydrous compounds be treated (in the dry state) with carbonic acid in
an autoclave under pressure and at a temperature of 140° to 180° Centigrade the
alkaline salts of the acid compound ethers of the phenoldicarbonic acids (oxyphthalic
acids) are formed and the process goes on with ease exactly in the same way as in
the formation of salicylic acid from the phenolates of the alkalies. The nature of
the reaction can be seen from the following equation.
CH
-
+ CO. = C.H,OH
AAD
The contents of the autoclave after the operation is concluded dissolve in water
and on adding any, of the mineral acids to the filtrate the acid compound ethers of
oxyphthalic acids are precipitated.
Through splitting up of the methyl aethyl etc. by means of hydrochloric acid ·
or by any other suitable means the phenoldicarbonic acids (oxyphthalic acids) may
be formed.
In this manner are formed :-
1. The beta-oxyisophthalic acid from the so called gaultheria salt of sodium, which
acid was first prepared by Reimer and Tiemann.
2. Burkhardt and Jacobsen's oxyterephthalic acid from the sodium salt of the
compound ethyl ether of the meta-oxy-benzoic acid.
3. Ost's alpha phenolicarbonic acid from the sodium compound of the compound
ethyl ether of the para-oxy-benzoic acid.
Dated this 10th dor of Avest 1800
J. H. JOHNSON & Co.,
47, Lincoln's Inn Fields, London, W.C., Agents.
COMPLETE SPECIFICATION.
Improvements in the Manufacture of Oxyphthalic Acids (Phenol
Dicarbonic Acids).
I JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of Middlesex
Gentleman do hereby declare the nature of this invention which has been con:-
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:-
In the alkyle ethers of the oxy-meta- and para-oxybenzoic acids and their
homologues the hydrogen of the hydroxyl may be replaced by one of the alkaline

page_text: metals. These compounds (with the alkaline metals) present a certain analogy to
salts and can be obtained dry without saponification of the ethers taking place.
If the anhydrous compounds be treated (in the dry state) with carbonic acid in
a closed vessel or autoclave for some time (say for several hours) under pressure
and at a temperature of 140° to 180° Centigrade the alkaline salts of the said com-
pound ethers of the phenol-di-carbonic acids (oxyphthalic acids) and of their
homologues are formed and the process goes on with ease exactly in the same way
as in the formation of salicylic acid from the alkaline phenolates when treated
with carbonic acid. The nature of the reaction can be seen from the following
equation.
COOCnH₂n + 1
COOCnH₂n + 1
C.H₁
+ CO₂ = CH, OH
The contents of the closed vessel or autoclave after the operation is concluded are
dissolved in water and on adding any of the mineral acids to the filtrate the acid
compound ethers of oxyphthalic acids are precipitated.
Through splitting up of the alkyle by means of hydrochloric acid or by any
other suitable means the phenol-di-carbonic acids (oxyphthalic acids) are finally
gained.
In this manner are formed.
-
1. The beta-oxy-iso-phthalic acid from the so called gaultheria salt of sodium
which acid was first prepared by Reimer and Tiemann.
2. The oxy-tere-phthalic acid of Burkhardt and Jacobsen from the sodium salt
of the compound ethyl-ether of the meta-oxy-benzoic acid.
3. The alpha-phenol-di-carbonic acid of Ost from the sodium compound of the
compound ethyl-ether of the para-oxy-benzoic acid.
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.-
The conversion of the alkyle-ethers of the alkaline salts of oxy-meta- and para-
oxybenzoic carbonic acids and their homologues into the acid compound ethers of
the phenol-di-carbonic acids (oxyphthalic acids) by treating such ethers with
carbonic acid in a closed vessel or autoclave under pressure and at a temperature
of from 140° to 180° Centigrade as hereinbefore set forth.
Dated this 1st day of May 1801