A Process for Obtaining Carbon Acids of Meta Amido Phenol and of its Alkyl Derivatives.
Year: 1889

page_text: Date of Application, 1st Aug., 1889
Complete Specification Left, 28th Apr.. 1890-Accepted. 31st May. 1890
PROVISIONAL SPECIFICATION.
A Process for Obtaining Carbon Acids of Meta Amido Phenol and
of its Alkyl Derivatives.
I, CARL KOLBE of Radebeul near Dresden in the Empire of Germany, Chemist
do hereby declare the nature of this Invention to be as follows:-
The now carbon acids obtained as hereinafter described from meta amido phenol
and its alkyl derivatives or substitution products are produced when the meta
amido phenol or its dimethyl and diethyl derivatives for example are treated with
carbonic acid under pressure in the presence of alkalies or earthy alkalies at a high
temperature. The carbonic acid reacts more advantageously upon the meta amido
phenol in a watery alkaline solution but with the employment of dimethyl or diethyl
meta amido phenol it is necessary to employ dry alkaline amido phenate and dry
carbonic acid.
The following are given as examples illustrating the practical application of my
invention.
1. Production of meta amido phenol carbon acid.
About ten parts by weight (10 kilos) of meta amido phenol are heated under
pressure in a closed vessel to about 110 degrees Centigrade with about forty parts
by weight (40 kilos) of ammonium carbonate and about fifty parts by weight
(50 kilos) of water for about twelve hours. In place of the ammonium carbonate
the corresponding quantity of potassium or sodium carbonate can be employed. The
contents of the vessel are then to be evaporated or concentrated to about thirty
parts (30 litres) the greater part of the excess of ammonium carbonato being removed
by this operation. In the next place the impurities are precipitated in the form of
brown flakes by carefully introducing hydrochloric acid. The materials are then
filtered and the filtrate is mixed with about seven parts (7 kilos) of hydrochloric acid
thereby separating the hydrochlorate of the meta amido phenol carbon acid in short
flat needles. This product is now purified by dissolving it in soda, filtering the
solution and repeatedly precipitating with hydrochloric acid. On precipitating the
alkaline solution with diluted sulphuric acid, the sulphate is separated which dissolves
with more difficulty than the hydrochlorate.
The free amido phenol carbon acid is obtained from the hydrochlorate by adding
the calculated quantity of an alkali or acetate of soda and shaking it out with ether.
When the other has evaporated the amido phenol carbon acid remains as white
needles which after being repeatedly crystallized out of ether melt at about
148 degrees Centigrade separating into carbonic acid and meta amido phenol. The
free acid is readily soluble in water, alcohol or ether but dissolves with difficulty in
benzene, toluene or chloroform. The alkali salts are readily soluble in water the
hydrochlorate and sulphate on the other hand are soluble with difficulty and are
precipitated in the form of colourless needles, on the addition of hydrochloric or
sulphuric acid to the alkaline solution of the acid. On long continued heating of the
acid or of its salt in a watery solution a gradual decomposition takes place with
separation of carbonic acid.
2. Production of dimethyl meta amido phenol carbon acid.
About five parts by weight (5 kilos) of dimethyl meta amido phenol are mixed with
he theoretical quantity of soda lye and the solution is evaporated to dusty dryness.
The sodium dimethyl meta amido phenate thus obtained is placed in a vessel capable
f withstanding pressure and being maintained at a temperature of from about 120
o 140 degrees Centigrade is exposed for several hours to the action of dry compressed
arbonic acid. The soda salt thus obtained of the new carbon acid is extracted with
vater and the filtered solution is acidulated with acetic acid the dimethyl meta amido.
henol carbon acid. being thereby crystallized out.
D

page_text: By recrystallisation out of heated toluene this product is obtained in the form of
colourless needles which melt at from about 145 to 146 degrees Centigrade with
separation of carbonic acid. These needles dissolve with difficulty. in water but
dissolve more readily in heated alcohol benzene 'or toluene.
The hydrochlorate dissolves readily in water.
The alkaline salts are likewise readily soluble.
On prolonged heating of the dimethyl meta amido phenol carbon acid in a neutral
or slightly acid solution a separation of carbonic acid and reformation of-meta amido
phenol takes place.
•
A carbon acid can be obtained in like manner from diethyl meta amido plienol.
The carbon acids obtained as herein before described are valuable in the manufacture
of colouring matter.
1000
J. H. JOHNSON & Co.,
47, Lincoln's Inn Fields, London, W.C., Agents.
COMPLETE SPECIFICATION.
A Process for Obtaining Carbon Acids of Meta Amido Phenol and
of its Alkyl Derivatives.
I CARL KOLBE of Radebeul near Dresden in the Empire of Germany Chemist
do hereby declare the nature of this invention and in what manner the same is to be
performed to be particularly described and ascertained in and by the following
statement :
The new carbon acids obtained as hereinafter described from meta amido phenol
and its alkyl derivatives or substitution products are produced when the meta amido
phenol or its dimethyl and diethyl derivatives for example are treated with carbonic
acid under pressure in the presence of alkalies or earthy alkalios at a high temperature.
The carbonic acid reacts more advantageously upon the meta amido phenol in a watery
alkaline solution but with the employment of dimethyl or diethyl meta amido phenol
it is necessary to employ dry alkali amido phenate and dry carbonic acid.
The following are given as examples illustrating the practical application of my
Invention.
1. Production of meta amido phenol carbon acid.
About ten parts by weight (10 kilos) of meta amido phenol are heated under
pressure in a closed vessel to about 110° degrees Centigrade with about forty parts.by
weight (40 kilos) of ammonium carbonate and about fifty parts by weight (50 kilos)
of water for about twelve hours. In place of the ammonium carbonate the corre
sponding quantity of potassium or sodium carbonate can be employed. The contents
of the vessel are then to be evaporated or concentrated to about thirty parts (30 litres)
the greater part of the excess of ammonium carbonate being removed by this operation:
In the next place the impurities are precipitated in the form of brown flakes. by
carefully introducing. hydrochloric acid. The materials are then filtered and the
filtrate is mixed with about seven parts (7 kilos) of bydrochloric acid thereby separating
the hydrochlorate of the meta amido phenol carbon acid.in.short flat needles.. This
product is now purified by dissolving it in soda, filtering the solution and repeatedly
precipitating with hydrochloric acid. On precipitating the alkaline solution with
diluted sulphuric acid, the sulphate is separated which dissolves with more difficulty
than the hydrochlorate.
The free amido phenol carbon acid is obtained from the hydrochlorate by adding
the calculated quantity of an alkali or acetate of soda and shaking it out with ether.
When the ether has evaporated the amido phenol carbon acid remains as-white, needles
which after being repeatedly crystallised out of ether melt at about 148 degrees
Centigrade separating into carbonic acid and meta amido phenol. The free acid is
readily soluble in water, alcohol or ether but dissolves with difficulty in benzene;
toluene, or chloroform. The alkali salts are readily soluble in water the hydrochlorate
i

page_text: and sulphate on the other hand are soluble with difficulty and are precipitated in the
form of colourless needles on the addition of hydrochloric or sulphuric acid to the
alkaline solution of the acid. On long continued heating of the acid or of its salts in
a watery solution a gradual decomposition takes place with separation of carbonic
acid.
2. Production of dimethyl meta amido phenol carbon acid. About five parts by
weight (5 kilos) of dimethyl meta amido phenol are mixed with the theoretical
quantity of an alkaline lye prepared for example with soda or potash and the
solution is evaporated to dusty dryness. The sodium or potassium dimethyl meta
amido phenate thus obtained is placed in a vessel capable of withstanding pressure
and being maintained at a temperature of from about 120 to 140 degrees Centigrade
is exposed for several hours to the action of dry compressed carbonic acid. The soda
salt thus obtained of the new carbon acid is extracted with water and the filtered
solution is acidulated with acetic acid the dimethyl meta amido phenol carbon acid
being thereby crystallised out.
By recrystallisation out of heated toluene this product is obtained in the form of
colourless needles which melt at from about 145 to 146 degrees Centigrade with
separation of carbonic acid. It dissolves with difficulty in water but dissolves more
readily in heated alcohol, benzene or toluene. The hydrochlorate dissolves readily in
water. The alkaline salts are likewise readily soluble. On prolonged heating of the
dimethyl meta amido phenol carbon acid in a neutral or slightly acid solution a
separation of carbonic acid and reformation of meta amido phenol takes place.
A carbon acid can be obtained in like manner from diethyl meta amido phenol.
The carbon acids obtained as hereinbefore described are valuable in the manufacture
of colouring matter.
Having now particularly described and ascertained the nature of my said Inven-
tion and in what manner the same is to be performed I declare that what I
claim is:
1. The production of carbon acids of meta-amido-phenol and of its alkyl derivatives
or substitution products by treating meta-amido-phenol or its said derivatives or
substitution products with carbonic acid under pressure in the presence of alkalies.or
earthy alkalies at a high temperature substantially as hereinbefore described.
2. The production of meta-amido-phenol carbon acid as herein before described under
example 1.
3. The production of dimethyl- or diethyl-meta-amido phenol carbon acid as herein-
before described under example 2.
4. As new articles of manufacture products such as are obtained by the means
claimed by the preceding claiming clauses.
Dated this 28th day of April 1890.
J. H. JOHNSON & Co.,
Agents.