IMPROVE- MENTS IN THE PRODUCTION OF COLORING MATTERS SUITABLE FOR DYEING AND PRINTING
Year: 1883

page_text: LETTERS PATENT to Charles Denton Abel of N° 28 Southampton Buildings
Chancery Lane in the County of Middlesex for an Invention of IMPROVE-
MENTS IN THE PRODUCTION OF COLORING MATTERS SUITABLE FOR DYEING
AND PRINTING Communicated to him from abroad by the Farbwerke vormals
Meister Lucius and Brüning of Hoechst-am-Main in the Empire of Germany,
a Company carrying on business as Chemical Manufacturers
PROVISIONAL SPECIFICATION left by the said Charles Denton Abel at
the Office of the Commissioners of Patents on the 5th January 1883.
"
CHARLES DENTON ABEL of N° 28 Southampton Buildings Chancery Lane in
the County of Middlesex "IMPROVEMENTS IN THE PRODUCTION OF COLORING
MATTERS SUITABLE FOR DYEING AND PRINTING Communicated to bim from
abroad by the Farbwerke vormals Meister Lucius and Brüning of Hoechst-am-
Main in the Empire of Germany, a Company carrying on business as Chemical
Manufacturers
The object of this invention is the production of coloring matters from
paranitrobenzylidene chloride, or bromide, their other derivatives and from
paranitrobenzylidene anilide, toluidide or xylidide. It is well known that it is
possible to obtain the nitroleucobases of triphenylmethane, its homologues or
similar bydrocarbons by the action of paranitrobenzaldehyde upon aromatic
monamines.
Considering the difficulties with which the technical preparation of paranitro-
benzaldehyde is fraught, it appeared desirable to find out another method for the
preparation of the said leucobases.
The chlorine, bromine &c, &c. derivatives of paranitrotoluol as well as paranitro-
benzylidene anilide, toluidide and xylidide, corresponding with paranitrobenzalde-
bydo seemed well adapted for taking the place of paranitrobenzaldehyde in the
synthesis of nitroleucobases, as is shewn in the following equations:

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed by
the said Charles Denton Abel in the Great Seal Patent Office on. the
30th June 1883.
-
CHARLES DENTON ABEL of N° 28 Southampton Buildings Chancery Lane in
the County of Middlesex "IMPROVEMENTS IN THE PRODUCTION OF COLORING
MATTERS SUITABLE FOR DYEING AND PRINTING A communication to me from
abroad by the Farbwerke vormals Meister Lucius and Brüning of Hoechst-ain-
Main in the Empire of Germany a Company carrying on business as Chemical
Manufacturers
The object of this invention is the production of coloring matters from
paranitrobenzylidene chloride, or bromide, their ether derivatives and from
paranitrobenzylidene anilide, toluidide or xylidide. It is well known that it is
possible to obtain the nitroleucobases of triphenylmethane, its homologues or
similar hydrocarbons by the action of paranitrobenzaldehyde upon aromatic
monamines.
Considering the difficulties with which the technical preparation of paranitro-
benzaldehyde is fraught, it appeared desirable to find out another method for the
preparation of the said leucobases.
The chlorine, bromine &c, &c, derivatives of paranitrotoluol as well as para-
nitrobenzylideneanilide, toluidide and xylidide, corresponding with paranitro-
benzaldehyde seemed well adapted for taking the place of paranitrobenzaldehyde
in the synthesis of nitroleucobases, as is shewn in the following equations:
NO. C, H. CH: Cl. + 2 C H, NH, = NO, C, H. CH (C, H, NH₂), 2 HCI.
NO, C, H, CH: NC, H, + C, H³ NH, = NO,C, H, CH (C, H, NH₂)..
The experiments of my correspondents have confirmed this view and thereby put
me into possession of a new method for the preparation of nitroleucobases which
forms the subject of this application for a patent.
I will first give a description of the way in which the hitherto unknown parani. -
trobenzylidene chloride is obtained.
Pure and well-crystallizing nitrotoluol is heated in an oil bath to a temperaturo
of 260° F. (130° C) and while gradually raising the temperature to 320° F.
(160° C.) a current. of chlorine gas is passed in until the calculated amount has
been absorbed. The mass resulting from the reaction is washed with water, dilute
carbonate of soda solution, and again with water and finally it is crystallized from
alcohol.
The conditions under which the nitroleucobases are. formed from paranitroben-
zylidene chloride or bromide or their ether-derivatives differ from those which have
to be observed when paranitrobenzylidene anilide, toluidide or xylidide are used as
may be seen from the following description.'
PREPARATION OF NITRODIAMIDOTRIPHENYLMETHANE,
A. 1. 20 parts of paranitrobenzylidene chloride dissolved in 30 to 40 parts of a
medium such as ligroine, benzine or alcohol are allowed to act upon 19 parts of
aniline for several hours at the temperature of a water bath. The solvent is then
distilled off, the residue is extracted with water and the solution obtained is filtered
off from resinous products. The nitroleucobase is precipitated from the filtrate by
the addition of an alkali.
A. 2. 23 parts of paranitrobenzylidene anilide along with 13 parts of chlorby-

page_text: apparatus supplied with a reverted cooler. The alcohol is then distilled off and
the residue treated in the same manner as that obtained in the way described
under A. 1.
PRODUCTION OF NITRODIAMIDODIPHENYLTOLYLMETHANE.
B. 1. 23 parts of paranitrobenzylidene anilide along with 14.5 parts of orthoto-
luidine hydrochloride are dissolved in alcohol and heated for several hours in an
apparatus supplied with a reverted cooler. The alcohol is next distilled off and
the residue treated in the same manner as described for the production of nitro-
diamidotriphenylmethane.
B. 2. 24 parts of paranitrobenzylidene toluidide are heated upon the water-bath
with 13 parts of aniline hydrochlorate and 30 to 40 parts of alcohol. When
the reaction is completed the nitroleucobase formed is soparated as described
under A. 1.
It may here be observed that the nitroleucobases obtained from aniline, toluidine,
xylidene, cumidine, naphthylamine, mono- and dimethylaniline, mono- and diethyl-
aniline, methylxylidine, diphenylamine and phenylnaphthylamine by the above
described methods are distinguished by the following properties: they are solid
bodies varying in color from yellow to brownish-red, they melt under boiling
water to form a wax-like reddish-yellow mass, their sulphates dissolve but
sparingly in water, and their hydrochlorides but sparingly in concentrated hydro-1
chloric acid.
Having thus described the nature of this invention and in what manner the
same is to be performed as communicated to me by my foreign correspondents, I
claim:-
First. The method substantially as herein described of producing paranitroben-
zyledene chloride from paranitrotoluol.
Second. The method substantially as herein described of producing nitroleuco-
bases from the primary, secondary and tertiary aromatic monamines by the aid of
paranitrobenzyledene chloride or bromide or their respective ether derivatives.
Third. The method substantially as herein described of producing nitroleucobases
from the salts of the bases enumerated in the preceding claim by the aid of
paranitrobenzaledene anilide, toluidide and xylidide.
In Witness whereof I the said Charles Denton Abel have hereunto set my
hand and seal this thirtieth day of June in the year of our Lord One
thousand eight hundred and eighty three.
AUTR A