The Manufacture and Production of New Products from Aromatic Nitro-derivatives.
Year: 1896

page_text: Date of Application, 6th July, 1896
Complete Specification Left, 3rd Apr., 1897-Accepted, 22nd May, 1897
PROVISIONAL SPECIFICATION.
The Manufacture and Production of New Products from
Aromatic Nitro-derivatives.
I, JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of London
Gentleman do hereby declare the nature of this invention (which has been
communicated to me from abroad by the Badische Anilin & Soda Fabrik of
Ludwigshafen-on-Rhine in the Empire of Germany) to be as follows:-
My foreign correspondents have discovered that a complete chemical change is
effected if certain aromatic nitro-derivatives be added to weak fuming sulphuric
acid and exposed to its action at ordinary temperature, for a short time. New
products result which by further treatment in various ways yield colouring matters.
As instances of the aromatic nitro derivatives which can be used, I mention
the 1. 1 and 1. 4' dinitronaphthalene.
The following example will serve to further illustrate the production of a new
product from a dinitro-naphthalene but the invention is not confined to the example.
The parts are by weight.
EXAMPLE. PRODUCTION OF A NEW PRODUCT FROM 1.11 DINITRO-
NAPHTHALENE.
Add gradually about ten parts of 1. 11 dinitro-naphthalene to about fifty parts of
fuming sulphuric acid (containing about 12 to 23 per cent. free anhydride SO,) and
stir the mixture whilst maintaining the temperature at about 40 to 50 degrees
Centigrade. Continue this treatment until a portion poured into water dissolves in
caustic soda, yielding a yellow solution. When this point is attained, pour the
mass into water and collect the precipitate on the filter. If it be desired to purify
the product it can be recrystallised from glacial acetic acid.
The new body so obtained is not a colouring matter but it is endowed with great
chemical activity, entering into a large number of reactions by which colouring
matters can be obtained. Thus for instance on treatment with fuming sulphuric
acid (containing about 40 per cent. free anhydride SO₂) and preferably in the
presence of sulphur, colouring-matter is obtained which is soluble in water and dyes
chrome mordanted wool brownish-yellow shades which are fast to light and milling.
But colouring-matters can also be obtained in many other ways, for example by
taking sulphuric acid of various strength, with, or without, the addition of boracic
acid, or similar reagents, brown to red colouring matters can be obtained. Dyes
can also be obtained by treating the new product with caustic soda, or by nitrating
it further on reducing, a base is obtained which can be used as a component in the
manufacture of azo dyes.
In a manner similar to that described in the above example a new product can be
obtained from the 1. 4' dinitronaphthalene and this body similarly yields colouring
matters which differ in shade from the corresponding products obtained from the
isomeric dinitronaphthalene.
Dated this 6th day of Jul, 1000.
Ju
JOHNSONS & WILLCOX,
47 Lincoln's Inn Fields, London, W.C., Agents.

page_text: The Manufacture and Production of New Products from
Aromatic Nitro-derivatives.
I, JAMES YATE JOHNSON of 47 Lincoln's Inn Fields in the County of London
Gentleman do hereby declare the nature of this invention (which has been
communicated to me from abroad by the Badische Anilin and Soda Fabrik of
Ludwigshafen-on-Rhine in the Empire of Germany) and in what manner the same
is to be performed, to be particularly described and ascertained in and by the
following statement:-
My foreign correspondents have discovered that a complete chemical change is
effected, if 1. 11 dinitro-naphthalene or 1.4¹ dinitronaphthalene be added to weak.
fuming sulphuric acid exposed to its action at ordinary temperature for a short time
new products resulting which, by further treatment in various ways, yield colouring
matters.
I
The following example will serve to further illustrate the production of a new
product from a dinitro-naphthalene but the invention is not confined to the details
of this example. The parts are by weight.
EXAMPLE. PRODUCTION OF A NEW PRODUCT FROM 1. 1' DINITRO-
NAPHTHALENE.
Add gradually about ten parts of 1. 11 dinitro-naphthalene to about fifty parts of
fuming sulphuric acid (containing about 12 to 23 per cent. free anhydride SO3) and
stir the mixture whilst maintaining the temperature at about 40 to 50 degrees
Centigrade until a portion of the mass poured into water dissolves in caustic soda
yielding a yellow solution. When this point is attained pour the mass into water,
and collect the precipitate on the filter. If it be desired to purify the product it
can be recrystallised from glacial acetic acid.
The new body so obtained is not a colouring matter but it is endowed with great
chemical activity and is capable of entering into a large number of reactions, by
which colouring matters can be obtained. Thus for instance, on treatment with
fuming sulphuric acid (containing about 40 per cent. free anhydride SO,) and
preferably in the presence of sulphur, colouring matter is obtained which is soluble
in water and dyes chrome-mordanted wool brownish-yellow shades which are fast
against the action of light and milling. Colouring matters can also be obtained in
many other ways from the said new body for example by treatment with sulphuric
acid of various strengths with, or without, the addition of boracic acid, or similar
reagents, brown to red colouring matters can be obtained. Dyes can also be
obtained by treating the new product with caustic soda, or by nitrating it; further
on reducing a base is obtained which can be used as a component in the manufacture
of azo dyes.
In a manner similar to that described in the foregoing example a new product can
be obtained from the 1. 4' dinitro-naphthalene and this body similarly yields on
treatment as aforesaid, colouring matters which differ in shade from the corre-
sponding products obtained from the isomeric dinitro-naphthalene.
Having now particularly described and ascertained the nature of this inven-
tion and in what mauner the same is to be performed 1 declare that what I
claim is
1. The manufacture of new products by submitting 1. 1' dinitro-naphthalene or

page_text: 1.41 dinitro naphthalene to the action of weak fuming sulphuric acid substantially
as hereinbefore described.
2. The manufacture of the new products in the manner set forth in the
example.
3. As new articles of manufacture the new products such as can be obtained by-
the means claimed by the preceding claiming clauses.
Dated this 3rd day of April 1897.
JOHNSONS & WILLCOX,
47 Lincoln's Inn Fields, London, W.C., Agents.