Manufacture of Meta-nitranilin-sulpho Acid and its Analogues.
Year: 1895

page_text: Date of Application, 29th July, 1895
Complete Specification Left, 29th Apr., 1896-Accepted, 30th May, 1896
[Communicated from abroad by THE FARBWERKE, vormals MEISTER LUCIUS
AND BRUNING, of Hoechst a/Main, in the Empire of Germany, Chemical
Manufacturers.]
Manufacture of Meta-nitranilin-sulpho Acid and its Analogues.
I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane; in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention to be as follows:-
The mono nitrated hydrocarbons of the benzol series are not acted upon,
or only with difficulty acted on by acid or neutral sulphites, but these salts
react with m-dinitro benzol, and produce products which are readily soluble in
water.
In this manner there may be produced the alkaline salts of the nitro-amido-
sulpho acids, the reaction taking place in the simplest case according to the
following equation
CH.(NO), + (H₂SO₁), = HSO₂С₂H,
+ (H₂SO₁),
NO
A solution of 5 kilos. of neutral sodium sulphite is heated in 20 to 25 litres of
water to boiling point, and then 1.68 kilos. of m-dinitro benzol are added in small
quantities with energetic stirring. When the dinitro benzol melts, an energetic
reaction begins which generally renders farther heating superfluous.
After a short time, the whole mixture has dissolved to form a clear yellow brown
liquid from which, on adding to it 2.5 to 3 kilos. of crude hydrochloric acid, the
new nitro amido sulpho acid may be separated in the form of small brownish black
needles.
1-82 kilos. of dinitrotoluol (C'H3N2O,NO₂) are added to a solution of 5 kilos.
of neutral sodium sulphite in 20 litres of water and 2 to 3 litres of alcohol, and
further treated as mentioned in Example 1. In this case, the reaction takes place
less smoothly than in the case of dinitrobenzol.
It
The m-nitranilin-sulpho acid forms, in the pure state, almost colourless needles,
which are with great difficulty soluble in cold water, and melt without becoming
decomposed. It is readily soluble in free alkaline carbonates and acetates.
becomes converted by nitrous acid into a diazo compound which is soluble only
with great difficulty.
The nitro-toluidin-sulpho acid is somewhat more readily soluble in water than
the m-nitranilin-sulpho acid.

page_text: According to the above properties, the latter does not appear to be the same as
the sulpho
acid produced by Post and Hartung (Ann. 205. 102) from.
m-nitranilin.
ليوم
3
CT 1
1007
ABEL & IMRAY,
Agents for the Applicant.
Manufacture of Meta-nitranilin-sulpho Acid and its Analogues.
I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention and in what manner the same is to be performed to be particularly
described and ascertained in and by the following statement :-
The mono nitrated hydrocarbons of the benzol series are not acted upon,
or only with difficulty acted on by acid or neutral sulphites, but these salts
react with m-dinitro benzol, and produce products which are readily soluble in
water.
In this manner there may be produced the alkaline salts of the nitro-amido-
sulpho acids, the reaction taking place in the simplest case according to the
following equation
NTIT
CH(NO2)2 + (H₂SO3)3
-
HSO,C,H,
+ (H₂SO4)2
NO.
1.82 kilos. of dinitro-toluol (C'H₂N'O₂NO₂) are added to a solution of 5 kilos.
of neutral sodium sulphite in 20 litres of water and 2 to 3 litres of alcohol, and
further treated as mentioned in Example 1. In this case, the reaction takes place
less smoothly than in the case of dinitrobenzol.
The m-nitranilin-sulpho acid forms, in the pure state, almost colourless needles,
which are with great difficulty soluble in cold water, and melt without becoming
decomposed. It is readily soluble in free alkaline carbonates and acetates. It
becomes converted by nitrous acid into a diazo compound which is soluble only
with great difficulty.
The nitro-toluidin-sulpho acid is somewhat more readily soluble in water than the
m-nitranili sulpho acid.
According to the above properties, the latter does not appear to be the same

page_text: as the sulpho acid produced by Post and Hartung (Ann. 205. 102) from
m-nitranilin.
Having now particularly described and ascertained the nature of this inven
tion and in what manner the same is to be performed, I declare that what I
claim is :-
The herein described manufacture of nitro-amido-sulpho acids by treating
m-dinitrobenzol and m-dinitrotoluol with an aqueous or dilute alcoholic solution of
sodium sulphite or of another sulphite having similar action.
Dated this 29th day of April 1896.
ABEL & IMRAY,
Agents for the Applicant.