Process for the Production of Ortho-toluolsulphochloride by the action of Chlorine on Ortho-toluolsulphonic Acid Salts in Presence of Phosphorus and a Suitable Dissolvent for the Last- named, for Example Bisulphide of Carbon.
Year: 1898

page_text: Date of Application, 14th May, 1898
Complete Specification Left, 11th Nov., 1898-Accepted, 23rd Dec.,
1898
MUY MIŪNAL DEPUIFICATION.
Process for the Production of Ortho-toluolsulphochloride by the
action of Chlorine on Ortho-toluolsulphonic Acid Salts in
Presence of Phosphorus and a Suitable Dissolvent for the Last-
named, for Example Bisulphide of Carbon.
1, Dr. FRITZ HAUFF, of Feuerbachi, near Stuttgart, Germany, Manufacturer,
do hereby declare the nature of this invention to be as follows:--
It is well known that the production of phosphoruspentachloride and its manipula-
tion is associated with manifold difficulties and inconveniences. The idea of allowing
the phosphoruspentachloride to act at once in a nascent state for the purpose of the
production of orthotoluolsulphochloride so that it need not appear at all as such, has
induced me to make suitable experiments to that end. These experiments have
shown that orthotoluolsulphochloride in considerable quantity can be obtained from
phosphorus and orthotoluol sulphonic acid salts in the following extremely easy
manner.
In a leaden apparatus with a cooling contrivance a certain quantity of phosphorus
is dissolved in bisulphide of carbon and the quantity of finely ground orthotoluol-
sulphonic acid salts (as settled by experiments and as indicated below). suspended.
Into this, chlorine is introduced until no further absorption occurs which can easily
be determined with the potassium iodide re-action.
Hereupon the bisulphide of carbon is distilled off and directly applied for a
further operation. The residuary contains the chloride in considerable quantity.
The phosphorus acts inerely as a vehicle for the transmission of the chlorine in the
sense of the following equation

page_text: It is obvious that in this process the cost of expensive phosphoruspentachloride is
reduced more than one half and that no mechanical difficulties arise owing to the
simple application of fluid chlorine and the circumstance that a crystallising of the
inlet opening for the chlorine is not observable because solid phosphorus pentachloride
does not appear at all.
Process for the Production of Ortho-toluolsulphochloride by the
Action of Chlorine on Ortho-toluolsulphonic Acid Salts in
Presence of Phosphorus and a Suitable Dissolvent for the Last-
named, for Example Bisulphide of Carbon.
I, Dr. FRITZ HAUFF, of Feuerbach, near Stuttgart, Germany, Manufacturer, 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:-
It is well known that the production of phosphoruspentachloride and its manipu-
lation is associated with manifold difficulties and inconveniences.
The idea of allowing the phosphoruspentachloride to act at once in a nascent state
for the purpose of the production of ortho-toluolsulphochloride, so that it need not
appear at all as such, has induced me to make suitable experiments to that end.
These experiments have shown that ortho-toluolsulphochloride in
any desired
quantity can be obtained from phosphorus and ortho-toluolsulphonic acid salts in the
following extremely easy manner.
In a leaden apparatus with a cooling contrivance, a certain quantity of phosphorus
is dissolved in bi-sulphide of carbon, and the quantity of finely ground ortho-toluol-
sulphonic acid salts (as settled by experiments and as indicated below) suspended.
Into this, chlorine is introduced until no further absorption occurs, which can easily be
determined with the potassium iodide re-action. Hereupon the bi-sulphide of carbon
is distilled off and directly applied for a further operation.
The residuary contains the chloride in quantitative yield. The phosphorus acts
merely as a vehicle for the transmission of the chlorine in the sense of the following
equation

page_text: There results a residuary, which when treated with watery ammonia yields 32 kg.
ortho-toluolsulphonamid, that is nearly the theoretical quantity.
It is obvious, that in this process the cost of the expensive phosphorus-penta-
chloride is reduced more than one half, and that no mechanical difficulties arise,
owing to the simple application of fluid chlorine and the circumstance that a
crystallizing of the inlet opening for the chlorine is not observable because solid
phosphorus-pentachloride does not appear at all.
Having now particularly described and ascertained the nature of this invention
and in what manner the same is to be performed I declare that what I
claim is :-
The process for the production of ortho-toluolsulphochloride by the action of
chlorine on ortho-toluolsulphonic acid salts in presence of phosphorus and a suitable
dissolvent for the last-named, for example bi-sulphide of carbon, substantially as
described.
The 11th day of November 1898.
H. GARDNER,
Patent Agent, 166, Fleet Street, London,
Agent for the said Dr. Fritz Hauff.