Improvements in the Manufacture of Toluene Sulpho Chlorides.
Year: 1894

page_text: PROVISIONAL SPECIFICATION.
[Communicated from abroad by PROSPER MONNET, of 8 Quai de Retz Lyons,
Fiance, Chemist ]
Improvements in the Manufacture of Toluene Sulpho Chlorides.
ג'ן
1, HAROLD 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 manufacture of toluenesulphochlorides from toluene, especially of the liquid
toluenesulphochloride commonly known as orthotoluenesulphochloride and used in
the manufacture of sacchain, as usually carried out, is a tedious operation involving
a number of processes and producing a small yield.
According to the present invention chlorsulphonic acid is made to react with
toluene under certain specific conditions, whereby the whole of the toluene is
converted into toluenesulphochloride, which can be separated into the liquid
and solid forms in the usual way, no bye-products of an organic character being
formed.
The action of chlorsulphonic acid upon toluene has previously been studied by
Claesson and Wallin under other conditions (Berichte der Deutschen Chemischen
Gesellschaft, XII, 1848), and with different results, only about half the toluene
being converted into toluenesulphochlorides, and half into toluene-sulphonic acids.
The present inventor finds that by keeping the temperature of the reacting mass
between the limits of 0° and 5° C., and by employing a large excess of chlor-
sulphonic acid the reaction takes place according to the equation.
ABEL & IMRAY,
Agents for the Applicant.

page_text: Improvements in the Manufacture of Toluene Sulpho Chlorides
I, HAROLD 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 manufacture of toluene sulpho chlorides from toluene, especially of the liquid
toluene sulpho chloride commonly know as ortho toluene-sulpho chloride and used
in the manufacture of saccharin, as usually carried out, is a tedious operation
involving a number of processes and producing a small yield.
According to the present invention, chloi sulphonic acid is made to react with
tolueno under certain specific conditions, whereby the whole of the toluene is
converted into toluene sulpho chloride, which can be separated into the liquid and
solid forms in the usual way, no byc-products of an orgame character being
formed.
The action of chloisulphonic acid upon toluene has previously been studied by
Claesson and Wallin under other conditions (Berichte der Deutschen Chemischen
Gesellschaft, XII 1848) and with different results, only about half the toluene
being converted into toluene sulpho chlorides and half into toluene sulphonic
aerds.
My foreign correspondent has found that, by keeping the temperature of the
reacting mass between the limits of 0° and 5º C., and by employing a large excess
of chlorsulphonie-neid the reaction takes-place according-to-the equation:
OIL
The operation may be conveniently-performed as follows.
Into 400 kilos. chlorsulphonie acid cooled at 0° C there are run-slowly in with
constant stirring 100 kilos. toluene, the temperature of, the mass being never
allowed to rise above 5° C. When all the toluene has boen added, the mixture 19
constantly stirred for twelve hours in order to complete the reaction, pluring which
time the temperature is kept.botween 0° and 5°C. The resulting mass is, then
poured over ice, whereupon the toluene sulpho chlorides separase in the form of a
Liquid oily layer containing some solidified para toluone sulpho chloride, and can be
removed from the ice when melted by decantation. The yield of sulpho chlorides
obtained in this manner corresponds to that theoretically required according to the
above equation..
-
To separate the solid para-chloride from the liquid, the mass is cooled to 20° C.
for,twelve hours, the liquid chloride is run off and treated again in the same way
until no more para-chloride is deposited. Even when the temperature is only so
low as
12° C. satisfactory separation may be effected.
-
The amount of liquid chloride, remaining constitutes 60 per cent of the total
theoretical yield of chlorides, and 'when washed with cold water is sufficiently pure
for use as ortho-toluene-sulpho-chloride for techincal purposes.
.
Having now partacularly described and ascertained 'the nature of this-inven-
tion and in what mauner-the same is to bo performed, I declare that what I
olaim 18:―
1. The manufacture of toluene-sulpho-chlorides by acting with chlorsulphonic
acid in large excess on toluene at a temperature not exceeding 5° C., substantially
no dosunbed

page_text: 2. The direct conversion of toluene by means of chlorsulphonic acid into toluene
sulpho chlorides mostly in the liquid form, substantially as described.
Dated this 27th day of September 1895.
ABEL & IMRAY,
Agents for the Applicant.