Improvements relating to the Manufacture of Nitrosamines.
Year: 1894

page_text: Date of Application, 13th July, 1894
Complete Specification Left, 4th Apr., 1895-Accepted, 4th May, 1875
PROVISIONAL SPECIFICATION.
Improvements relating to the Manufacture of Nitrosamines.
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
Ludwigshafen on Rhine in the Empire of Germany) to be as follows:-
This invention consists in a new process for the production of the new class of
of nitrosoamines of the primary aromatic amido-compounds described in the
Specifications of my applications for Letters Patent No. 20605 of 1893 and
No. 3397 of 1894 on communications from my present foreign correspondents.
The said new process consists in treating, with alkalies, the nitroso-compounds
of the acid anilides or corresponding acid derivatives of the primary aromatic
amido-compounds. As instances of such compounds, I mention, the nitroso-
compounds of acet-anilide and of the acid derivatives of ortho- and para-toluidine,
para-anisidine and alpha- and beta-naphthylamine but the said process can be
applied to large numbers of analogous bodies.
The following example of a way in which this invention can be carried out in
one instance will also serve to further illustrate the nature of the invention
generally but I do not limit myself to the details of this example. The parts are
by weight:
Moisten about one part of nitroso acet-anilide with water and then mix it with
about sixty parts of caustic potash lye (containing about seventy per cent. KHO)
and heat the mixture to or about forty to fifty degrees Centigrade, till no further
decrease in the quantity of solid in suspension is noticeable. The solution obtained
has all the properties of an alkaline solution of the potassium salt of diazo-benzene.
Raise the temperature to one hundred and twenty degrees Centigrade till on testing
with sodium beta-naphtholate no dye is obtained. Work up in the usual way.
Instead of the nitroso-compound of acet-anilide that of formanilide oxalic anilide,
benzanilide, carbanilide, and the like, can be used; and in an analogous manner
also as aforesaid the nitroso-compounds of the acid derivatives of other primary
aromatic amido-compounds can be used.
Dated the 13th day of July 1894.
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, W.C., Agents.
Improvements relating to the Manufacture of Nitrosamines.
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 Ludwigshafen-on-Rhine, 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 :-
This invention consists in a new process for the production of the new class of

page_text: nitrosamines of the primary aromatic amido-compounds described in the
Specification of Letters Patent Nos. 20605 of 1893 and 3397 of 1894, both
granted to me on communications from my present foreign correspondents.
The said new process consists in treating with caustic alkali the nitroso-
compounds of the acid anilides or corresponding acid derivatives of the primary
aromatic amido-compounds. As instances of such compounds, I mention, the
nitroso-compounds of acet-anilide and of the acid derivatives of ortho and para-
toluidine, para-anisidine and alpha- and beta-naphthylamine but the said process
can be applied to large numbers of analogous bodies.
The following example of a way in which this invention can be carried out in
one instance will also serve to further illustrate the nature of the invention
generally and the manner in which it can be carried into practical effect but I do
not limit myself to the details of this example as they can in all cases be varied
in many respects without departing from the nature of this invention. The parts
are by weight.
EXAMPLE.
Moisten about one part of nitroso-acet-anilide with water and then mix it with about
sixty parts of caustic potash lye (containing about seventy per cent. KHO) and
heat the mixture to or about from forty to fifty degrees Centigrade, till no further
decrease in the quantity of solid in suspension is noticeable. The solution
obtained has all the properties of an alkaline solution of the potassium salt of
diazo-benzene. Raise the temperature to one hundred and twenty degrees
Centigrade till on testing with sodium beta-naphtholate no dye is obtained. Work
up in the usual way.
If the moistened nitroso-acetanilide of the above example be added to the caustic
potash lye already heated to a temperature of about one hundred and twenty to
one hundred and thirty degrees the intermediate production of diazo-compound is
not observable.
Instead of the nitroso-compound of acetanilide that of formanilide, oxalic
anilide, benzanilide, carbanilide, and the like, can be used; and in an analogous
manner also as aforesaid the nitroso-compounds of the acid derivatives of other
primary aromatic amido-compounds can be used.
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
1. The manufacture of nitrosamine compounds by treating the nitroso-compounds
of the acid anilides or corresponding acid derivatives of primary aromatic amido-
compounds with caustic alkali, all substantially as hereinbefore described.
2. The manufacture of nitrosamine compounds in the manner hereinbefore
described in the example.
Dated this 4th day of April 1895.
JOHNSONS & WILLCOX,
47, Lincoln's Inn Fields, London, W.C., Agents.