Manufacture of an Aromatic Dinitro-compound and a new Diamido- compound Derived therefrom.
Year: 1899

page_text: Date of Application, 16th Mar., 1899
Complete Specification Left, 27th Nov., 1899-Accepted, 18th Jan., 1900
Manufacture of an Aromatic Dinitro-compound and a new Diamido-
compound Derived therefrom.
I, CHARLES DENTON ABEL, of Birkbeck Bank Chambers, Southampton. Build-
ings, in the County of London, Consulting Engineer and Chartered Patent Agent,
do hereby declare the nature of this invention (as communicated to me from
abroad by Actien Gesellschaft für Anilin Fabrikation, of Berlin, in the Empire
of Germany, Chemical Manufacturers), to be as follows:-
This invention relates to the production of symmetrical dinitrochlorobenzene
(NO, NO,:01 = 1:3:5) and of chlorometa-phenylenediamine (CI: NH; NH,
1:3:5) therefrom.
=
-
Symmetrical 1:3:5-dinitrochlorobenzene has hitherto only been prepared by
substituting chlorine for the amido-group in dinitroaniline (NO, NO, NH,
1:3:5) (compare Bader, Berichte der deutschen chemischen Gesellschaft, XXIV,
1665). This rather troublesome manner in which the said dinitro-chlorobenzene
had hitherto to be prepared, is no doubt the reason why this product has not
yet been used for industrial purposes.
It has been tried repeatedly to prepare chloro-derivatives of meta-dinitro-
benzene by the direct action of chlorine on this compound with or without the
aid of a carrier; the result however of these experiments was always a total or
partial substitution of chlorine for the nitro-groups (compare Korrow,. Berichte
der deutschen chemischen Gesellschaft XXIV, 2939; Lobry de Bruyn, Berichte
der deutschen chemischen Gesellschaft XXIV, 3749).
My foreign correspondents have now found that contrary to these observations
meta-dinitrobenzene, can easily be transformed into a chloro-derivative namely
the symmetrical dinitrochloro-benzene at a temperature of 100º C. and in the
presence of a chlorine carrier such as ferric chloride until the weight, of the
mixture has increased by an amount corresponding with the absorption of
1 atomic proportion of chlorine. The product of the reaction is washed with
luke-warm water and the dinitrochlorobenzene formed is then allowed to solidify.
By. recrystallisation from alcohol the compound is obtained in the form of
white needles melting at 59° C. and having all the properties mentioned by
Bader as above referred to.
As meta-dinitrobenzene is an easily obtainable and cheap raw material; this
new process considerably. simplifies the manufacture of 1:3:5-dinitrochloro-
benzene and allows the use of this compound for the production of new and
valuable intermediate products for the manufacture of colouring matters., „Thus
our, correspondents have further found that meta-dinitrochlorobenzene; prepared
as above described, may easily be converted into a new chloro-meta-pheny-
lenediamine (CI:NH: NH, 1:3:5) by treating it with reducing agents.
Chloro-meta-phenylenediamine obtained in this manner crystallises from water
in the form of colourless crystals melting at 100 to 103° C; it is little soluble
in cold water, more soluble in boiling water and dissolves easily in alcohol, ether,
=

page_text: benzene and similar solvents. It can be employed for the production of new
colouring matters and as a developer in dyeing. In this latter respect it is
distinguished by yielding with suitable compounds valuable green black shades.
Dated this 16th day of March 1899.
Manufacture of an Aromatic Dinitro-compound and a New Diamido-
compound Derived therefrom.
I, CHARLES DENTON ABEL, of Birkbeck Bank Chambers, Southampton Build-
ings, in the County of London, Consulting Engineer and Chartered Patent Agent,
do hereby declare the nature of this invention (as communicated to me from
abroad by Actien Gesellschaft für Anilin Fabrikation, of Berlin, in the Empire
of Germany, Chemical Manufacturers), and in what manner the same is to be
performed, to be particularly described and ascertained in and by the following
statement:
-
This invention relates to the production of symmetrical dinitrochlorobenzene
(NO, NO, Cl = 1:8:5) and of chlorometa-phenylenediamine (CI : NH, : NH,
1:3:5) therefrom.
=
Symmetrical 1:3:5-dinitrochlorobenzene has hitherto only been prepared by
substituting chlorine for the amido-group in dinitraniline (NO, NONH
1:3:5) (compare Bader, Berichte der deutschen chemischen Gesellschaft XXIV,
1665). This rather troublesome manner in which the said dinitro-chlorobenzene
had hitherto had to be prepared, is no doubt the reason why this product has
not yet been used for industrial purposes.
It has been tried repeatedly to prepare chloro-derivatives of meta-dinitro-
benzene by the direct action of chlorine on this compound with or without the
aid of a carrier; the result however of these experiments was always a total or
partial substitution of chlorine for the nitro-groups (compare Karrow, Berichte
der deutschen chemischen Gesellschaft XXIV, 2939; Lobry de Bruyn, Berichte
der deutschen chemischen Gesellschaft XXIV, 3749).
My foreign correspondents have now found that, contrary to these observations,
meta-dinitrobenzene can easily be transformed into a chloro-derivative namely
the symmetrical dinitrochloro-benzene at a temperature of 100° C. and in the
presence of a chlorine carrier such as ferric chloride until the weight of the
mixture has increased by an amount corresponding with the absorption of
1 atomic proportion of chlorine. The product of the reaction is washed with
luke-warm water and the dinitrochlorobenzene formed is then allowed to solidify.
By recrystallisation from alcohol the compound is obtained in the form of
white needles melting at 59° C. and having all the properties mentioned by
Bader as above referred to.
As meta-dinitrobenzene is an easily obtainable and cheap raw material, this
new process considerably simplifies the manufacture of 1:3:5-dinitrochloro-
benzene and allows the use of this compound for the production of new and
valuable intermediate products for the manufacture of colouring matters. Thus
our correspondents have further found that meta-dinitrochlorobenzene, prepared
as above described, may easily be converted into a new chloro-meta-pheny-
lenediamine (CI: NH: NH₂ 1:3:5) by treating it with reducing agents
in the manner usually adopted for reducing nitro-compounds. Thus the meta-
=

page_text: dinitrochlorobenzene may be treated with iron and mineral acid or with zinc
dust and a mineral acid or with stannous chloride and hydrochloric acid. To
isolate the chlorometaphenylenediamine from the liquid in which the reduction
has been effected with, say, stannous chloride and hydrochloric acid, excess of
caustic soda is added and the base is separated by filtration and purified by
crystallisation from water. Chlorometa-phenylenediamine obtained in this man-
ner crystallises from water in the form of colourless crystals melting at 100 to
103° C.; it is little soluble in cold water, more soluble in boiling water, and
dissolves easily in alcohol, ether, benzene and similar solvents. It can be em-
ployed for the production of new colouring matter and as a developer in dyeing.
In this latter respect it is distinguished by yielding with suitable compounds
valuable green-black shades.
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 herein described manufacture of symmetrical dinitrochlorobenzene by
treating melted meta-dinitrobenzene in the presence of a chlorine-carrier with
gaseous chlorine until absorption of one atomic proportion of chlorine is effected.
2. The herein described manufacture of chloro-meta-phenylenediamine by
treating symmetrical dinitrochloro-benzene with reducing agents.
3. Chloro-meta-phenylenediamine manufactured as above set forth.
Tinted th: orth Johan 1900
th: 74 1000
ABEL & IMRAY,
Agents for the Applicant.