PRODUCTION OF A NEW SOLID BASE BY REACTION OF ALDEHYDE AND HYDROCHLORATE OF ANILINE, OR THEIR EQUIVALENTS
Year: 1883

page_text: LETTERS PATENT to John Imray of N° 28. Southampton Buildings Chancery
Lane in the County of Middlesex for an Invention of "PRODUCTION OF A
NEW SOLID BASE BY REACTION OF ALDEHYDE AND HYDROCHLORATE OF
ANILINE, OR THEIR EQUIVALENTS" communicated to him from Abroad by the
Actien Gesellschaft für Anilin-Fabrikation of Berlin in the German Empire,
an Incorporated Company
PROVISIONAL SPECIFICATION left by the said John Imray at the Office
of the Commissioners of Patents on the 31st August 1883.
"
"
JOHN IMRAY of N° 28 Southampton Buildings, Chancery Lane in the county
of Middlesex PRODUCTION OF A NEW SOLID BASE BY REACTION OF ALDEHYDE
AND BYDROCHLORATE OF ANILINE, OR THEIR EQUIVALENTS [communicated to
him from Abroad by the Actien Gesellschaft für Anilin-Fabrikation of Berlin in
the German Empire, an Incorporated Company]
It has been found that when Aldehyde acts on a hot solution of Aniline in
presence of hydrochloric acid, bydrochlorate of chinaldine is produced. But when
3 molecules of Aldehyde act at ordinary temperature on an aqueous or alcoholic
solution of 2 molecules of hydrochlorate of aniline, there is no longer produced
hydrochlorate of liquid chinaldine, C₁, H, N, but a salt of a new solid base baving
the composition C₁s H₂, N₂, differing from the Ethyliden-diphenylamine and the
Diethyliden-diphenylamine which can be derived from Aniline and Aldehyde.
This invention relates to the production of this compound by the following
process.
8 kilogrammes of hydrochlorate of Aniline are dissolved in 16 Litres of water,
cooled with ice, and introduced into a well cooled dilute solution of 5 kilogrammes
of Aldehyde. The mixture assumes a yellow color changing towards brown, and
gradually thickens, but its heating must by prevented by cooling with ice. In
three to four days, the reaction is complete, and the liquor being then evaporated,
the hydrochlorate of the new base is obtained as a brownish red mass readily

page_text: soluble in water. On treating a solution of this salt with alkali, the base separates
in white flakes. In its dry state it is a white amorphous powder, insoluble in
water, slightly soluble in boiling alcohol, but readily soluble under heat in benzol
or amylic alcohol. Chinaldine is not formed by boiling the base with hydrochloric
acid, but if the dry hydrochlorate of the base be heated to fusion, alone, or in
presence of a metallic chloride, such as Chloride of iron, the hydrochlorate of
Chinaldine is formed. This product is more readily obtained by melting the salt
with chloride of Zinc, but in this case, the double salt of chloride of zinc and
chinaldine is formed.
Instead of employing common Aldehyde in the process described, an equivalent
quantity of Paraldehyde, Aldol or Acetale may be used, and salts of Aniline other
than the hydrochlorate may likewise be employed. When Aldehyde is made to
act on salts of Toliudine, Anisidine, Xylidine, or Naphthylamine, combinations are
formed analogous to the base C₁, H₂ N, above mentioned, and these can, in a similar
manner, be converted into Chinaldines.

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed by
the said John Imray in the Patent Office on the 7th February 1884.
JOHN IMRAY of N° 28 Southampton Buildings, Chancery Lane, in the county
of Middlesex PRODUCTION OF A NEW SOLID BASE BY REACTION OF ALDEHYDE
AND HYDROCHLORATE OF ANILINE OR THEIR EQUIVALENTS A communication to
me from abroad by the Actien Gesellschaft für Anilin-Fabrikation of Berlin, in
the German Empire, an incorporated company,
It has been found that when Aldehyde acts on a hot solution of Aniline in presence
of hydrochloric acid, hydrochlorate of Chinaldine is produced. When, however,
aldehyde acts upon a diluted solution of hydrochlorate of aniline at ordinary
temperature, a mixture of solid bases is formed from which, amongst others, a body
of the formula C₁s H₂, N, can be isolated. The production of these bases can be
effected in the following manner.
8 kilogrammes of hydrochlorate of aniline are dissolved in 16 litres of water,
and, while stirring, introduced into a diluted solution of aldehydo which has to be
kept cool. The liquor at first assumes a yellow, then a brownish tint, and gradually
thickens. The reaction is complete after three to to four days. By evaporating the
solution, the hydrochlorate of the new base is obtained as a brownish red mass,
easily soluble in water. By addition of a alkali to the solution of this salt, the
free base separates in white flakes. It forms in its dry state a white amorphous
powder, insoluble in water, little soluble in alcohol, but easily soluble in hot
benzole or amylic alcohol. By boiling the base with hydrochloric acid, Chinaldine
is not formed. If, however, the dry hydrochlorate of this base is melted alone or
in presence of metallic chlorides, the hydrochlorate of chinaldine is formed. If
chloride of zinc is employed in that reaction, the double salt of Chloride of zinc
and chinaldine is formed.
For the production of these bases, the common aldehyde can be replaced by the
equivalent quantity of paraldehyde, aldol, acetal or crotonaldehyde, and the
hydrochlorate of aniline by other salts of aniline.
Aldehyde and the other above named bodies act in an analogous manner also on
toluidine anisidine, xylidine or napthylamine, and produce analogous bases, from
which chinaldines can be obtained by the same process as from the base made from
aniline.
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―
The production of bases by tho action of aldehyde, paraldehyde, aldol, acetal,
or crotonaldehyde upon the salts of aniline, toluidine anisidine or naphthylamine,
and the conversion of these bases into the corresponding Chinaldines.
In Witness whereof I the said John Imray have hereunto set my hand and
seal this seventh day of February in the year of our Lord one thousand, eight
hundred and eighty-four.