A Process for the Manufacture of Aromatic Nitro-sulpho-chlorides,
Year: 1895

page_text: Date of Application, 26th July, 1895
Complete Specification Left, 13th Apr., 1896-Accepted, 25th July, 1896
PROVISIONAL SPECIFICATION.
A Process for the Manufacture of Aromatic Nitro-sulpho-chlorides,
I GEORGE WILLIAM JOHNSON of 47 Lincoln's Inn Fields, in the County of
London, Patent Agent do hereby declare the nature of this invention (which has
been communicated to me from abroad by Dr. F. von Heyden, Nachfolger, of
Radebeul, near Dresden in the German Empire) to be as follows
:-
Aromatic nitro-sulpho-chlorides have hitherto been prepared by an extremely
complicated process. For example in order to obtain nitro-benzol-sulpho-chloride,
it has been necessary, in the first place, to convert the nitro-benzol in the presence
of sulphuric acid, into nitro-benzol-sulphonic acid. By the addition of chalk, the
surplus of sulphuric acid was then transformed into gypsum; the gypsum was next
separated from the nitro-benzol sulphonate of calcium by filtration after which by
the addition of soda, the calcium was converted into sodium salt, which was then
filtered off from the carbonate of lime, whereupon it was steamed dried, and lastly,
in the presence of phosphorpenta chloride, converted into nitro-benzol-sulpho-
chloride which was separated from the phosphor-oxy-chloride by distillation or by
treatment with water.
This series of complicated operations my foreign correspondent has succeeded in
materially simplifying thereby rendering the manufacture less expensive, and this
object is attained by treating the nitro benzol or other aromatic nitro body with
chlor-hydrin-sulphuric acid
он
₂OH)
SO,
CI
so that by a single operation nitro sulpho
Incidentally a small quantity of the nitro sulphonic acid forms at the same time.
I am aware that, before this, by the action of chlor-hydrin sulphuric acid upon
non uitrified hydro carbons, sulphochlorides have been produced such as toluene-
Bulpho-chlorate from toluene but in preparing non-nitred sulpho-chloride, it is
necessary to cool the chlor-hydrin and to add the hydro-carbon but very slowly
thereto. If the same method were applied to nitro-hydrocarbon, practically no
chloride would be obtained and to obtain it, it is requisite to heat the mass of
reagents, and the entire quantity of the nitro-hydrocarbon may be mixed with the
chlor-hydrin beforehand and at one time.

page_text: The aqueous mother-lye, contains in addition to sulphuric acid, a small amount of
nitro-benzol-sulphonic acid which in the well known manner may be converted into
sodium salt, from which by treatment with chlorides of mineral acids, there may
be derived a further small quantity of nitro-benzol-sulpho-chloride. If instead of
the nitro-benzol, ortho-nitro-toluene or para-nitro-toluene, or nitro-meta-xylol or
chlor-nitro-benzol, be employed, the following chlorides will be obtained:
Nitro-toluene-sulpho-chloride (CH, NO, SO₂CI = 1 : 2 : 4)
"
"
"
وو
(
"
"
"
= 1:4:2)
Nitro-xylol-sulpho-chloride (CH, CH,: SO,C1: NO, = 1:2:4:6)
Chlor-uitro-benzol-sulpho-chloride (CI: NO, SO,C1
= 1:3:1).
These nitro-sulpho-chlorides may be utilized in a variety of ways as intermediate
products for the ulterior production of other chemical agents.
Dated this 26th day of July 1895.
JOHNSONS & WILLCOX,
47 Lincoln's Inn Fields, London, W.C., Agents.
COMPLETE SPECIFICATION.
A Process for the Manufacture of Aromatic Nitro-sulpho-chlorides.
I, GEORGE WILLIAM JOHNSON, of 47 Lincoln's Inn Fields, in the County of
London, Patent Agent, do hereby declare the nature of this invention (which has
been communicated to me from abroad by Dr. F. von Heyden, Nachfolger, of
Radebeul, near Dresden, in the German Empire) and in what manner the same
is to be performed, to be particularly described and ascertained in and by the
following statement :-
Aromatic nitro-sulpho-chlorides have hitherto been prepared by an extremely
complicated process. For example in order to obtain nitro-benzol-sulpho-chloride,
it has been necessary, in the first place, to convert the nitro-benzol, in the presence
of sulphuric acid, into nitro-benzul-sulphonic acid. By the addition of chalk, the
surplus of sulphuric acid was then transformed into gypsum; the gypsum was next
separated from the nitro-benzol-sulphonate of calcium by filtration, after which,
by the addition of soda, the calcium salt was converted into sodium salt, which was
then filtered off from the carbonate of lime, whereupon it was steamed dried, and
lastly, in the presence of phosphor-penta-chloride, converted into nitro-benzol-
sulpho-chloride, which was separated from the phosphor-oxy-chloride by distillation
or by treatment with water.
This series of complicated operations my foreign correspondent has succeeded in
materially simplifying, thereby rendering the manufacture less expensive; and this
object is attained by treating the nitro-benzol or other aromatic nitro body with
он
chlor-bydrin-sulphuric acid
acid (SO,
(So,OH)
so that by a single operation, nitro-sulpho-
chloride is directly obtained; the reaction taking place in accordance with following
formula
OH
CH.NO, + 2 SO,
CI
==
CH
NO,
SO.CL
+ HCl + H₂SO..

page_text: "
"
"
دو
(
ور
"
"
= 1:4:2)
Nitroxylol-sulpho-chloride (CH: CH, : SO,CI : NO, = 1 : 2 : 4 : 6)
Chlor-nitro-benzol-sulpho-chloride (Cl: NO, SO,CI = 1 : 3:
:
5?).
These nitro-sulpho-chlorides may be utilized in a variety of ways as intermediate
products for the ulterior production of other chemical agents.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed I declare that
what I claim is :—
The manufacture of aromatic nitro-sulpho-chlorides by treating nitro-benzol,
ortho nitro toluene or para nitro-toluene or meta nitroxylol or chlor-nitro-benzol
or other aromatic nitro body with chlor-hydrin-sulphuric acid as hereinbefore set
forth.
Dated this 13th day of Anvil 1896
JOHNSONS & WILLCOX,
47 Lincoln's Inn Fields, London, W.C., Agents.