IMPROVEMENTS IN THE PRODUCTION OF ORTHO-NITRO-META-METHYL-BENZAL- DEHYDE FROM META-METHYL-BENZALDEHYDE (ToLUYL-ALDEHYDE) AND IN THE PRODUCTION OF METHYL INDIGO
Year: 1882

page_text: LETTERS PATENT to John Erskine of 151 St. Vincent Street Glasgow in
the County of Lanark North Britain Solicitor for an Invention of
IMPROVEMENTS IN THE PRODUCTION OF ORTHO-NITRO-META-METHYL-BENZAL-
DEHYDE FROM META-METHYL-BENZALDEHYDE (ToLUYL-ALDEHYDE) AND IN
THE PRODUCTION OF METHYL INDIGO A. communication to him from abroad
by the Farbwerke vorm: 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 John Erskine at the Office
of the Commissioners of Patents on the 7th July 1882.
JOHN ERSKINE, of 151 St. Vincent Street, Glasgow, in the County of Lanark,
North Britain, Solicitor. "IMPROVEMENTS IN THE PRODUCTION OF ORTHO-
NITRO META-METHYL-BENZALDEHYDE FROM META-METHYL-BENZALDEHYDE
(TOLUYL-ALDEHYDE) AND IN THE PRODUCTION OF METHYL INDIGO.” [A com-
munication to him from abroad by the Farbwerke vorm: Meister Lucius and
Brüning, of Hoechst-am-Main, in the Empire of Germany a Company carrying on
business as Chemical Manufacturers]
The nature of this Invention is the production of Ortho-Nitro-Meta-Methyl-
Benzaldehyde from Toluyl - aldehyde, otherwise known as Meta - Methyl-
Benzaldehyde, and the transformation of the said Meta-Methyl-Ortho-Nitro-
Benzaldehyde into Meta-Methyl-Indigo.
The toluylaldehyde, which can be produced from metaxylol after well known
methods, on being nitrated behaves like the metabromobenzoic acid, that is to say,
it allows the bydrogen atom standing in ortho position with respect to the CHO
group to be replaced by the nitro-group.
The metamethyl-ortho-nitro-benzaldehyde thus formed is easily transformed into
meta-methyl-indion

page_text: The special method which I follow in carrying out my Invention is as follows:-
I dissolve (keeping the materials and mixture cool all the time), 12 parts of
toluylaldehyde in six times the quantity by weight of concentrated sulphuric
acid. Into this solution I cause to flow slowly at a temperature not exceeding
59° Fahrenheit (15° Centigrade), a cold mixture of 10 parts of nitric acid with 5
20 parts of concentrated sulphuric acid. When the mass resulting from the
reaction is poured into ice-water the nitro-aldehyde produced separates in form of
an oil, which is then washed with water and a dilute carbonate of soda solution
consecutively. For the production of methyl-indigo it may either be used directly
or previously purified by distilling in a current of steam.
1

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed by
the said John Erskine in the Great Seal Patent Office on the 23rd December
1882.
JOHN ERSKINE, of 151 St. Vincent Street, Glasgow, in the County of Lanark,
North Britain, Solicitor. "IMPROVEMENTS IN THE PRODUCTION OF ORTHO-
NITRO-META-METHYL-BENZALDEHYDE FROM META-METHYL-BENZALDEHYDE (TOLUYL-
ALDEHYDE) AND IN THE PRODUCTION OF METHYL INDIGO," the said Invention
being a communication to me from Abroad by the Farbwerke vorm: Meister,
Lucius, and Brüning, of Hoechst-am-Main, in the Empire of Germany, a Company
carrying on business as Chemical Manufacturers.
The nature of this Invention is the production of Ortho-Nitro-Meta-Methyl-
benzaldehyde, from Toluyl - aldehyde, otherwise known as Meta - Methyl -
Benzaldehyde, and the transformation of the said Meta-Methyl-Ortho-Nitro-
Benzaldehyde into Meta-Methyl-Indigo.
The Toluyl-aldehyde, which can be produced from meta-xylol after well known
methods, on being nitrated, behaves like the metabromobenzoic acid, that is to say,
it allows the hydrogen atom standing in ortho position with respect to the
CHO group to be replaced by the nitro-group.
The
meta-methyl-ortho-nitro-benzaldehyde thus formed is easily transformed
into meta-methyl-indigo.
The special method which the communicators of this Invention follow in carrying
out the said Invention is the following:-Keeping the materials and mixture cool
all the time, 12 parts of toluyl-aldehyde are dissolved in six times the quantity by
weight of concentrated sulphuric acid. Into this solution there is caused to flow
slowly at a temperature not exceeding 59° Fahrenheit (15° Centigrade), a cold
mixture of ten parts of nitric acid with 20 parts of concentrated sulphuric acid.
When the mass resulting from the reaction is poured into ice-water the nitro-
aldehyde produced separates in form of an oil, which is then washed with water
and a dilute carbonate of soda solution consecutively. For the production of
methyl-indigo it may either be used directly or previously purified by distilling in
a current of steam.
Having now described and particularly ascertained the nature of the said
Invention, and the system mode or manner in or under which the same is or may
be used or practically carried into effect, it is to observed in conclusion that
what is considered to be novel and original and therefore claimed as the Invention
secured to the Inventors by the hereinbefore in part recited Letters Patent is :-
The production of ortho-nitro-meta-methyl-benzaldehyde from meta-methyl-
benzaldehyde by nitrating the meta-inethyl-benzaldehyde, all in manner herein-
before described, or in manner substantially the same.
. In witness whereof I the said John Erskine have hereunto set my hand
and seal this twenty-second day of December in the year of Our Lord
One thousand eight hundred and eighty two
PART