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Патент USA US2137279

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Patented Nov. 22, 1938
‘
4
2,131,279
PATENT OFFICE _
2,137,279 ‘
‘
PROGE
ss FOR THE MANUFACTURE ‘ or‘
PH'rnALIo DI-DIETHYLAMIDE
'
Felix ,Haffner, Tubingen, and‘Ftitz Sommer, Ber
lin, Germany, assignors to the ?rm Chemische
.Fabrik Griinau, Landshoff. & Meyer, A. G.,
Berlin-Grunau, Germany, a‘ company‘ of Ger
‘many
No Drawing. Original application February '7,
1935,‘ Serial No.‘ 5,494, now Patent No. 2,057,145,
dated October 13, 1936. Divided and this ap
plication September 9, 1936, Serial No. 99,956
‘In Germany February 9,1934
‘
(CL. 260-558)
"58 Claims.
phthalyl ‘dichloride is slowly introduced into this
7 ‘ This is a ,divisional‘ application of;_our appli
cation Ser. No. 5,494 ?led on February 7th 1935, ,so'lutionwwh‘ile stirring, the temperature being
issued as Patent No. 2,057,145, on Oct. 13, 1936, ‘maintained at about 15° C. The o-phthalic di
for improvements ‘in and relating to a pharma .diethylamide thus formed is salted out by sa
ceutical preparation for stimulating the respira— ‘urating the aqueous solution with common salt.
The oil separating on the surface is removed.
tory centre and increasing the circulation.
The present invention relates to the process
for the manufacture of phthalic di-diethylamide,
which is especially adapted to the use as a phar
10 maceutical preparation for stimulating the re
spiratory centre and increasing the circulation.
According to “Annales de Chimie” 1928, vol.
9, pages 59-60 and 64-65, it has been known to
produce o-phthalic di-dimethylamide by react-v
15 ing phthalyldichloride with diethylamine in an
hydrous benzene' Such a process, however, is
not adapted to produce larger quantities of o
phthalic di-diethylamide and has the disadvanl
tage of employing the very in?ammable and ex
20 pensive solvent benzene.
”
_
The main object of our invention is to provide
a process by means-of which o-phthalic di-di
ethylamide may be manufactured in a simple
manner and in large quantities.
25
'
In order to carry out our invention into prac
tice the reaction of a halide ‘of phthalic acid with
diethylamine is caused in an aqueous solution, and
the phthalic di-diethylamide thus formed is salt
ed out by saturating the solution with common
The crude product thus obtained may be
30 salt.
puri?ed by re-dissolving it in water, ?ltering the
aqueous solution through active charcoal and
salting out the o-phthalic di-diethylamide again
by saturation with common salt. A complete
puri?cation may then be eliected by a subsequent
35
40
the solution with the addition of 200 grams of
active charcoal and salting out the reaction prod 10
uct again from the ?ltrate. Then a complete
puri?cation of the oily reaction product thus puri
?ed is carried out by a subsequent distillation in
vacuo, to which it is subjected. In the vacuum
distillation under a pressure of 5 mm. of mer 15
cury, a distillate passing over between 175° and
180° C. is obtainediwhich at ?rst forms an al
most colorless liquid and which later on solidi
?es to large crystals of a melting point of about
39° C. The crystals are readily soluble in water.
If desired, half of the speci?ed quantity of
diethylamine may be taken, if instead thereof
the equivalent quantity of alkali or alkali car
bonate is added’ for binding the hydrochloric acid
of the aqueous solution. If, for example, .525
kilogram of calcined soda is added to the aque 25
ous solution, .8 kilogram of diethylamine may be
used instead of 1.6 kilograms as stated above.
We have shown a preferred embodiment of our
invention, but it is clear, that numerous changes 30
may be made without departing from the spirit
of our invention.
What we claim is:
1. A process for the manufacture of phthalic
vacuum distillation.
di-diethylamide comprising the steps of reacting
phthalyl dichloride with diethylamine in an 35
Our process has the advantage of the elimi
nation of a very easily in?ammable solvent. Fur
aqueous solution, and salting out the phthalic di
diethylamide thus formed by saturating the solu
thermore, it has been found, that the reaction of
a halide of phthalic acid with diethylamine, a
so-called Schotten-Baumann-reaction, provides a
considerable yield also in an aqueous solution,
this being a feature, which could not at allbe
tion with common salt.
2. A process for the manufacture of phthalic
(ii-diethylamide comprising the steps of reacting 40
1 mol of a halide of phthalic acid with 4 mols of
sufficient, if the reaction takes place in the pres
diethylamine in an aqueous solution, and salting
out the phthalic (ii-diethylamine thus formed
by saturating the solution with common salt.
45
3. A process for the manufacture of phthalic
ence of a quantity of alkali or alkali carbonate
di-diethylamide comprising the steps of reacting
equivalent to 2 mols of diethylamine, while the
1 mol of phthalyl dichloride with 4 mols of di
ethylamine in an aqueous solution, and salting
foreseen. Another advantage of our invention
45 consists therein, that 2 mols of diethylamine are
hitherto known process employing a benzene so
5
Preferably the oily crude product is puri?ed by
dissolving it in about 6 litres of water, ?ltering
lution requires 4 mols of diethylamine.
' -
The invention will be illustrated by the fol
lowing example:
Example
.
1.6 kilograms of diethylamine (98%) are dis
5; solved in 3.2 kilograms of water. 1 kilogram of
out the phthalic di-diethylamide thus formed by 50
saturating the solution with common salt.
4. A process for the manufacture of phthalic
di-diethylamide comprising the steps of reacting
1 mol of a halide of phthalic acid with 2 mols of
diethylamine in an aqueous solution in the pres 65
2
2,187,279
ence of 2 equivalents of a compound having an
phthalyl dichloride with diethylamine in an
aqueous solution, salting out the phthalic di
diethylamide thus formed by saturating the solu
tion with common salt.
tion with common salt, re-dissolving the thus ob
5. A process for the manufacture of phthalic " tained crude product in water, ?ltering the solu
di-diethylamide comprising the steps of reacting a tion thus obtained through active charcoal, salt
1 mol of phthalyl dichloride with 2 mols of di
ing out the reaction product again from the ?l
ethylamine in an aqueous solution in the presence trate, and distilling the thus formed reaction
alkaline effect, and salting out the phthalic di
diethylamide thus formed by saturating the solu
10
of 2 equivalents of a compound having an alkaline >
product in vacuo.
eiiect, and salting out the phthalic di-diethyl
amide thus formed by saturating the solution
di-diethylamide comprising the steps of reacting
with common salt.
6. A process for the manufacture of phthalic
di-diethylamide comprising the steps of reacting
15 a halide of phthalic acid with diethylamine in an
aqueous solution, salting out the phthalic di
diethylamide thus formed by saturating the solu
tion with common salt, re-dissolving the thus ob
tained crude product in water, ?ltering the solu
20c tion thus obtained through active charcoal, salt
ing out the reaction product again from the ?l
trate, and distilling the thus formed reaction
product in vacuo.
7. A process for the manufacture of phthalic
di-‘diethylamide comprising the steps of reacting
8. A process for the manufacture of phthalic
1 mol of phthalyl chloride with 2 mols of di
ethylamine in an aqueous solution in the pres
ence of 2 equivalents of a compound having an
alkaline effect, salting out the phthalic di-diethyl 15
amide thus formed by saturating the solution
with common salt, re-dissolving the thus ob
tained crude product in water, ?ltering the solu
tion thus obtained through active charcoal, salt
ing out the reaction product again from the ?l 20
trate, and distilling the thus formed reaction
' product in vacuo.
FRITZ SOMIVIER.
FELIX HAFFNER.
25
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