IMPROVEMENTS IN THE PRODUCTION OF CERTAIN DERIVATIVES OF META- OXYBENZALDEHYDE
Year: 1882

page_text: LETTERS PATENT to Joseph Anthony Dixon of 151 St. Vincent Street
Glasgow in the County of Lanark North Britain Solicitor for an Invention
of IMPROVEMENTS IN THE PRODUCTION OF CERTAIN DERIVATIVES OF META-
OXYBENZALDEHYDE A communication from abroad by Dr. Carl Koenig, of
Höchst-am-Main, in the Empire of Germany a Director of the Farbwerke
vorm Meister Lucius and Bruning, a Company carrying on business as
Chemical Manufacturers
PROVISIONAL SPECIFICATION left by the said Joseph Anthony Dixon at
the Office of the Commissioners of Patents on the 28th February 1882.
JOSEPH ANTHONY DIXON, of 151 St. Vincent Street, Glasgow, in the County of
Lanark, North Britain, Solicitor. "IMPROVEMENTS IN THE PRODUCTION OF CERTAIN
DERIVATIVES OF METAOXYBENZALDEHYDE." [A communication from abroad by
Dr. Carl Koenig, of Höchst-am-Main, in the Empire of Germany a Director of the
Farbwerke vorm: Meister Lucius and Bruning, a Company carrying on business
as Chemical Manufacturers.]
In the Specification filed in pursuance of Letters Patent granted to me the said
Joseph Anthony Dixon dated 18th May A.D. 1881. No. 2179, I have described the
processes of nitroylizing metaoxybenzaldehyde and metamethoxylbenzaldehyde.
In working these processes it has been found that besides the mono-nitro-
compound leading to vanillin there are also formed derivatives of orthonitrobenzal-
dehyde, namely, metaoxyorthonitrobenzaldehyde, and metamethoxylorthonithoben-
zaldehyde, which can be used for the production of colouring matters and otherwise.
The separation of the isomeric-nitro-compounds is easily effected through
crystallization from alcohol, chloroform, and similar solvents.
The nature of the present Invention consists in the production of the said
orthonitrometaoxybenzaldehyde and of orthonitrometamethoxylbenzaldehyde from
the metaoxybenzaldehyde in the way hereinbefore mentioned

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed by
the said Joseph Anthony Dixon in the Great Seal Patent Office on the 18th
August 1882.
JOSEPH ANTHONY DIXON of 151 St. Vincent Street, Glasgow, in the County of
Lanark, North Britain, Solicitor "IMPROVEMENTS IN THE PRODUCTION OF
CERTAIN DERIVATIVES OF METAOXYBENZALDEHYDE. A communication from
abroad by Dr. Carl Köenig of Hochst-am-Main in the Empire of Germany, a
Director of the Farbwerke, vorm: Meister, Lucius, and Brüning, a Company carrying
business as Chemical Manufacturers.
The nature of and mode of performing the present Invention consists in the
production of orthonitrometaoxybenzaldehydes and of orthonitrometamethoxyl-
benzaldehydes from metaoxybenzaldehyde in the way hereinafter mentioned or
referred to.
In the Specification filed in pursuance of Letters Patent granted to me the said
Joseph Anthony Dixon dated 18th May A. D. 1881 No. 2179, I bave described the
processes of nitroylizing metaoxybenzaldehyde and also of nitroylizing the meta-
methoxylbenzaldehyde, which is, as therein described derived therefrom.
It has been found by the person from whom I have received the communication
of this Invention that in working the said processes besides the mono nitro
compounds leading to vanillin there are also formed isomeric derivatives of ortho-
nitrobenzaldehyde namely, metaoxyorthonitrobenzaldehyde and metamethoxyl-
onitrobenzaldehyde, which can be used for the production of colouring matters
and otherwise, for example for the production of metaoxy- and meta-meth-
oxyl-indigo. It will be readily understood that on nitroylizing the metaoxy-
benzaldehyde or the metamethoxylbenzaldehyde the ortho-nitro substitution
product exists or may exist under two isomeric forms or modifications in the case
of each of the said meta mother substances respectively-in other words two
orthonitrometaoxybenzaldehydes and two orthonitrometamethoxylbenzaldehydes
are produced, either or both of which may be used for the purposes aforesaid.
The separation of the isomeric ortho- and para-nitro compounds is easily effected
through crystallization from alcohol, chloroform, and similar solvents.
As convenient methods of effecting the separation of the said isomeric ortho-
and para-nitro compounds I give the following processes but it would be both
impossible and unnecessary to attempt to include all the variations in the modes of
separation which chemists might have recourse to.-This Invention consists in the
discovery of the fact that by nitroylizing the aforesaid metaoxy and metamethoxyl
bodies isomeric ortho-nitro derivatives are produced and may be separated from
the isomeric para-nitro bodies all in manner described, or in manner substantially
similar thereto.-The separation of the nitrometaoxybenzaldehydes resulting from
the nitroylizing of metaoxybenzaldehyde may be conveniently effected as follows:-
The product resulting from the nitroylizing of metaoxybenzaldehyde-which
besides the paranitrometaoxybenzaldehyde contains two isomeric orthonitrome-
taoxybenzaldehydes-is dissolved in boiling water. By the time that the solution
has cooled down to 122°-140° Fahrenhelt (50°-60° centigrade) the alpha-
orthonitrometaoxybenzaldehyde, crystallizing in the form of yellow scales of the
melting point 230-4° Fahrenheit (128° centigrade) has mostly separated; when the
temperature of the mother lye descends further, a crystallization is formed con-
sisting of a mixture of betaorthonitrometaoxybenzaldehyde crystallizing in long
needles of the melting point 298-8° Fahrenheit (160° centigrade) with paranitro-
metaoxybenzaldehyde of the melting point 248-4° Fahrenheit (138° centigrade).

page_text: These two isomeric compounds can be separated by repeated recrystallization from
water.
The separation of the nitrometamethoxylbenzaldehydes resulting from the
nitroylizing of metamethoxylbenzaldehyde may be conveniently effected as
follows: When the hydrogen atom of metamethoxylbenzaldehyde is, in manner
mentioned in my said Specification, replaced by the nitro group three isomeric
mono-nitro substitution products are formed. One of these may be understood as
deriving from the paranitrobenzaldehyde and the two others as derivatives from
the orthonitrobenzaldehyde.
The agents best adapted for dissolving the product resulting from the nitroy-
lizing are benzol or chloroform. From theso solvents the alpha-orthonitrometa-
methoxylbenzaldehyde of the melting point 192-6° Fahrenheit (107° centigrade)
crystallizes in large prisins, the isomeric betaorthonitro compound in long needles
of the melting point 147-6°-149-4° Fahrenheit, (82°-83° centigrade) and the
paranitrometamnethoxylbenzaldehyde in concentrically grouped needles of the
melting point 177.4°, Fahrenheit (98° centigrade).
I wish further to explain that I claim the production of the ortho nitro
derivatives of methoxy- and metamnethoxylbenzaldehyde by nitroylizing the
metaoxy- and metaimethoxylbenzaldehyde in manner mentioned in said Specification
No. 2179 A.D. 1881 whether the said metaoxy- and metamethoxyl bodies are
themselves prepared in manner mentioned in said Specification or otherwise.
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, I would observe in conclusion that what
I consider to be novel and original and therefore claim as the Invention secured to
me by the hereinbefore in part recited Letters Patent is :-
First The production of both and each of the two orthonitro modifications
herein before mentioned of metaoxyorthonitrobenzaldehyde by nitroylizing metaoxy-
benzaldehyde in manner mentioned in said Specification No. 2179 A.D. 1881 and
separatim, the separation of the same from the isomeric metaoxyparanitrobenzal-
dehyde produced at the same time all in manner hereinbefore specified or referred
to or in manner substantially the same.
Second The production of both and each of the two orthonitro modifications
herein before mentioned of metamethoxylorthonitrobenzaldehyde by nitroylizing
metamethoxylbenzaldehydo in manner mentioned in said Specification No. 2179
A.D. 1881, and, separatim, the separation of the same from the isomeric para nitro
body produced at the same time in manner herein before described, or referred to,
or in manner substantially the same.
In witness whereof I, the said Joseph Anthony Dixon have hereunto set my
hand and seal this Eighteenth day of May in the year of our Lord One
thousand eight hundred and eighty two.