The Manufacture or Production of Phenylglycine-o-carboxylic Acid.
Year: 1899

page_text: Date of Application, 29th June, 1899
1
Complete Specification Left, 9th Mar., 1900-Accented 14th Ann
1000
PROVISIONAL SPECIFICATION.
The Manufacture or Production of Phenylglycine-o-carboxylic Acid.
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 by the Badische Anilin & Soda Fabrik of Ludwigshafen.
on-Rhine, in the German Empire) to be as follows:-
In the Specification of the Application for Letters Patent No. 25966 A.D. 1898 is
described a process for the manufacture of indigo leuco bodies and indigo, by heat-
ing anthranilic acid, its salts and esters, with polyhydroxy compounds of the fatty
series in the presence of caustic alkalies.
In working according to this invention my foreign correspondents have, by
suitably altering the process, succeeded in isolating an intermediate body formed
during the reaction, namely phenylglycine-o-carboxylic acid, which hitherto has
not been obtained in this way. For this purpose the temperature is regulated,
and, if necessary, the quantities of alkali mentioned in the herein before-men-
tioned Specification are modified in such a manner that a chemical reaction,
wherein gas
evolved, takes place, but the conditions are avoided under which
indigo leuco bodies are formed.
When using mannite, three molecular proportions of alkali to one molecular
proportion each of potassium anthranilate and mannite appear to be sufficient
but it is necessary in the case of many of the polyhydric compounds mentioned
in the aforesaid Specification to employ a larger amount of alkali in order to
obtain a good yield.
The amido acid formed can, in general, be isolated by carefully neutralising
the aqueous solution of the melt, which has previously been concentrated, if
necessary, with mineral acid.
The following examples of the manner in which this invention can be carried
out will further serve to illustrate its nature, but the invention is not confined to
these examples. The parts are by weight:-
EXAMPLE 1.
Intimately mix 137 parts of anthranilic acid with 342 parts of powdered caustic
potash, and heat the mixture to about 150° centigrade in a vessel provided with
a stirring apparatus. Slowly add 270 parts of glycerine to the mixture. Raise
the temperature to 220° centigrade, and heat for about one hour, or until the
energetic evolution of hydrogen has ceased. Dissolve the melt, when cold in
water, filter, and neutralise exactly, with mineral acid. The precipitated phenyl-
glycine-o-carboxylic acid is sufficiently pure for further use. By concentrating
the mother-liquor a further quantity of the said acid can be obtained. Re-
crystallised from methylalcohol the phenylglycine-o-carboxylic acid is obtained
in white needles, having a fusion-point of from 218°-220° centigrade.
EXAMPLE 2.
Heat an intimate mixture of 137 parts of anthranilic acid, 180 parts of manuite.

page_text: and 230 parts of powdered caustic potash, in a vessel provided with a stirring
arrangement for about two hours until the evolution of hydrogen has ceased.
Work up the melt as in the preceding example.
EXAMPLE 3.
Intimately mix 137 parts of anthranilic acid, 180 parts of well dried starch,
and 224 parts of powdered caustic potash, and, whilst stirring, heat, to begin
with, for one hour at 210° centigrade, then for a quarter of an hour at 250°
centigrade. Work up the melt as in Example 1.
In a similar way the other polyhydric bodies mentioned in the aforesaid
Specification can, by heating with anthranilic acid and caustic alkali, be employed
for producing phenylglycine-o-carboxylic acid.
Dated this 29th day of June 1899
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C., Agents.
UUMI LEIN
DIMUIFICATION.
The Manufacture or Production of Phenylglycine-o-carboxylic Acid.
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 the Badische Anilin & Soda Fabrik of Lud-
wigshafen-on-Rhine, in the German Empire) and in what manner the same is to
be performed to be particularly described and ascertained in and by the following
statement:—
:
In the Specification of Letters Patent No. 25966 A.D. 1898 is described
a process for the manufacture of indigo leuco bodies and indigo, by heat-
ing anthranilic acid, its salts and esters, with polyhydroxy compounds of the fatty
series in the presence of caustic alkalies.
In working according to this invention my foreign correspondents have, by
suitably altering the process, succeeded in isolating an intermediate body formed
during the reaction, namely, phenyl-glycine-o-carboxylic acid, which hitherto has
not been obtained in this way. For this purpose the temperature is regulated,
and if necessary the quantities of alkali mentioned in the Specification of the
aforesaid Letters Patent are modified in such a manner that a chemical reaction,
wherein gas is evolved, takes place, but the conditions are avoided under which
indigo leuco bodies are formed.
When using mannite, three molecular proportions of alkali to one molecular
proportion each of potassium anthranilate and mannite appear to be sufficient
but it is necessary in the case of many of the polyhydric compounds mentioned
in the Specification of the aforesaid Letters Patent, to employ a larger amount of
alkali in order to obtain a good yield.
The amido acid formed can, in general, be isolated by carefully neutralising
the aqueous solution of the melt, which has previously been concentrated, if
necessary, with mineral acid.
The following examples of the manner in which this invention can be carried
out will further serve to illustrate its nature, but the invention is not confined to
these examples. The parts are by weight:
EXAMPLE 1.
Intimately mix one hundred and thirty seven parts of anthranilic acid
with three hundred and forty two parts of powdered caustic potash, and heat the
mixture to about one hundred and fifty degrees centigrade in a vessel provided

page_text: with a stirring apparatus. Slowly add two hundred and seventy parts of
glycerine to the mixture. Raise the temperature to two hundred and twenty
degrees centigrade, and heat for about one hour, or until the energetic evolution
of hydrogen has ceased. Dissolve the melt, when cold, in water, filter, and
neutralise exactly, with mineral acid. The precipitated phenyl-glycine-o-carboxylic
acid is sufficiently pure for further use. By concentrating the mother-liquor a
further quantity of the said acid can be obtained. Re-crystallised from methyl-
alcohol the phenyl-glycine-o-carboxylic acid is obtained in white needles, having
a fusion-point of from two hundred and eighteen to two hundred and twenty
degrees centigrade.
EXAMPLE 2.
Heat an intimate mixture of one hundred and thirty seven parts of anthranilic
acid, one hundred and eighty parts of mannite, and two hundred and thirty
parts of powdered caustic potash, in a vessel provided with a stirring arrangement
for about two hours until the evolution of hydrogen has ceased. Work up the
melt as in the preceding example.
EXAMPLE 3.
Intimately mix one hundred and thirty seven parts of anthranilic acid,
one hundred and eighty parts of well dried starch, and two hundred and twenty
four parts of powdered caustic potash, and, whilst stirring, heat, to begin with,
for one hour at two hundred and ten degrees centigrade, then for a quarter of
an hour at two hundred and fifty degrees centigrade. Work up the melt as
in Example 1.
In a similar manner the other polyhydric bodies mentioned in the Specification
of the aforesaid Letters Patent can, by heating with anthranilic acid and caustic
alkali be employed for producing phenylglycine-o-carboxylic acid.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what
I claim is:
1. The manufacture of phenylglycine-o-carboxylic acid by heating anthranilic
acid, its salts, or esters, with the polyhydroxy compounds of the fatty series in
the presence of caustic alkalies and so regulating the temperature that a
chemical reaction, in which gas is evolved, takes place, but the conditions are
avoided under which indigo leuco bodies are formed; all substantially as herein.
before described.
2. The manufacture of phenylglycine-o-carboxylic acid by heating anthranilic
acid, its salts, or esters, with the polyhydroxy compounds of the fatty series in
the presence of caustic alkalies and so regulating the temperature and quantity
of alkali employed that a chemical reaction, in which gas is evolved, takes place,
but the conditions are avoided under which indigo leuco bodies are formed; all
substantially as hereinbefore described.
3. The manufacture of phenylglycine-o-carboxylic acid substantially as herein-
before described in the several examples hereinbefore given.
Dated this 9th day of March 1900.
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C., Agents.