Improvements in the Manufacture of Aniline and Naphthylamine Derivatives and Colouring Matters therefrom.
Year: 1898

page_text: Date of Application, 24th May, 1898
Complete Specification Left, 24th Feb., 1899-Accepted, 25th Mar., 1899
Improvements in the Manufacture of Aniline and Naphthylamine
Derivatives and Colouring Matters therefrom.
We, READ HOLLIDAY & SONS; LIMITED, of Huddersfield, JOSEPH TURNER, of
Spink Field Road, Birkby, Huddersfield, and HARRY DEAN, of Greenhead Road,
Huddersfield, do hereby declare the nature of this invention to be as follows:-
This invention relates to the manufacture of certain chlorine derivatives of the
sulphonic acids of aniline and naphthylamine and colouring matters therefrom.
In the Specification of our application for Letters Patent dated June 8th 1897
and Nod. 13999 we have described the preparation of two isomeric chlor naphthy-
lamine sulphonic acids from chlor naphthaline sulphonic acid 1:4.
Valuable products are also obtained by nitrating and reducing other chlor
benzene and naphthalene sulphonic acids, more especially the following yield
useful products. The chlor benzene sulphonic acids 1:4 and 1:3, the chlor
naphthalene mono sulphonic acids 1:5, 1:8 and 1:2, and the chlor naphthalene
disulphonic acids 1:3:6 and 1:2:4. The chlorine derivatives of the sulphonic
acids of aniline and naphthylamine thus obtained are to be used for the manu-
facture of intermediate products.
Colouring matters are also formed by combining the diazo compounds of the
said chlor amido sulpho acids with the known dye stuff components or by com-
bining the acids themselves with diazo or tetrazo compounds.
Dated the 24th day of Ma.. 1000
WM. BROOKES & SON,
55 & 56, Chancery Lane, London, Agents for the Applicants.
Improvements in the Manufacture of Aniline and Naphthylamine
Derivatives and Colouring Matters therefrom.
•
We, READ HOLLIDAY & SONS LIMITED, of 11, Cambridge Buildings, Upperhead
Row, Huddersfield, in the County of York, Manufacturing Chemists, JOSEPH
TURNER, of Spink Field Road, Birkby, Huddersfield, and HARRY DEAN, of Green-
head Road, Huddersfield, both as aforesaid, Chemists, do hereby declare the nature
of this invention and in what manner the same is to be performed, to be par-
ticularly described and ascertained in and by the following statement :-
―
This invention relates to the manufacture of certain chlorine derivatives of the
sulphonic acids of aniline and naphthylamine and colouring matters therefrom.
[Price 8d.1

page_text: In the Specification of Letters Patent granted to us dated June 8th 1897 and
Nod. 13999 we have described the preparation of two isomeric chlor naphthyl-
amine sulphonic acids from chlor naphthalene sulphonic acid 1:4 valuable pro-
ducts are also obtained by nitrating and reducing other chlor benzene and
naphthalene sulphonic acids, more especially the following yield useful products.
The chlor benzene, sulphonic acids 1:4 and 1:3, the chlor naphthalene mono
sulphonic acids 1:5, 1:8 and 1:2 and the chlor naphthalene disulphonic
acids 1:3:6 and 1:2:4. The chlorine derivatives of the sulphonic acids of aniline
and naphthylamine thus obtained are to be used for. the manufacture of inter-
mediate products.
Colouring matters are also formed by combining the diazo compounds of the
said chlor amido sulpho acids with the known dye stuff components or by com-
bining the acids themselves with diazo or tetrazo compounds.
The following examples serve to illustrate the nature of our invention.
I
$
EXAMPLE 1. PRODUCTION OF CHILOR, ANILINE SULPHONIC ACID.
100 parts of chlor benzene para sulphonic acid are dissolved in about 300 parts
of sulphuric acid and nitrated by slowly running in a mixture of 40 parts sulphuric
acid with 40 parts nitric acid containing 80% real HNO3, the temperature being
kept preferably below 30° C. After standing a few hours the mixture may be
poured out into several times it weight of water and reduced by the addition of
iron borings. When completely reduced the excess of acid and iron are removed
by means of lime and the calcium salt converted into the sodium salt in the usual
manner. The solution of the sodium salt is then evaporated down to a small bulk
and hydrochloric acid added, the chlor aniline sulphonic acid separates out in a
crystalline form.
In a similar manner we may form amido sulphonic acids from chlor benzene
sulphonic acid 1:3 and the chlor naphtalene sulphonic acids 1:5, 1:8 and 1:2.
EXAMPLE 2 PRODUCTION OF CHLOR NAPHTYLAMINE DISULPHONIC ACID.
100 parts chlor naphtalene disulphonic acid 1:3:6 are dissolved in about 400
parts of sulphuric acid, and nitrated by the addition of a mixture of 25 parts
sulphuric acid and 25 parts nitric acid containing 80% real HNO3. When all
the nitro sulphuric acid has been added the mixture is heated on a water bath to
finish the reaction. The product is then reduced and the chlor naphtylamine
di-sulphonic acid isolated in the same manner as described in Example 1. For
the chlor naphtalene disulphonic acid 1:3:6 we may substitute the chlor naphtalene
disulphonic acid 1:2:4 with the production of an isomeric chlor naphtylamine
disulphonic acid.
EXAMPLE 3. BLUISH RED WOOL DYE.
20.8 kilos. of chlor aniline sulphonic acid are diazotised in the usual manner
and run into a solution containing 32 kilos. of dioxynaphtalene disulphonic acid
1:8:3:6 dissolved in carbonate of soda.
A deep red is at once produced and the colour formation is complete in a few
hours. It is then separated by means of common salt, filtered, pressed and dried.
EXAMPLE 4. BLUISH RED COTTON DYE.
21.2 parts tolidine are tetrazotised in the well known. manner and run into a
solution containing 56 kilos. of the sodium salt of chlornaphtylamine sulphonic
acid in the presence of sodium acetate. After standing a few days the mixture is
made alkaline with sodium carbonate and the dyestuff isolated in the usual manner.
EXAMPLE 5.
21.2 kilos. tolidine are converted into the tetrazo compound and run into a
solution containing 28 kilos. of the sodium salt of the chlor naphtylamine sul-
phonic acid in the pracanes of and.....
C

page_text: mediate compound is complete a solution containing 35 kilos. of sodium naphtionate
70% is added. After allowing to stand a few days the formation of the colouring
matter is complete, it is then made alkaline and salted out, filtered, pressed and
dried. The chlor naphtylamine sulphonic acid referred to in Examples 4 and 5
is prepared by the nitration and reduction of chlor naphtalene sulphonic acid 1:5,
and probably possesses the constitution 1:5:8-C1: S.0,H: NH.
Having now particularly described and ascertained the nature of our said
invention, and in what manner the same is to be performed, we declare that what
we claim is:-
1. The production of chlor amido sulpho acids by the nitration and reduction
of, the chlor benzene sulphonic acids 1:4 and 1:3, the chlor naphtalene sulphonic
acids 1:5, 1:2, and 1:8, the chlor naphtalene disulphonic acids 1:3:6 and 1:2:4.
2. The production of colouring matters by combining the diazo compounds of
the chlor amido sulpho acids referred to in the preceding claim, with amines,
phenols, amido phenols, their sulpho, or carbo acids.
3. The production of colouring matters by the action of tetrazo compounds
upon two molecules of the above mentioned chlor amido sulpho acids, or with one
molecule of any of the above chlor amido sulpho acids and one molecule of other
amines, phenols, amido phenols, or their sulpho or carbo acids.
4. The production of chlor amido sulpho acids and colouring matters therefrom
as set forth in the preceding claims.
1
WM. BROOKES & SON,
55 & 56, Chancery Lane, London, Agents for the Applicants.