Improvements in the Manufacture of Benzoic Sulphinide.
Year: 1896

page_text: PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Benzoic Sulphinide.
A Communication from abroad by LA SOCIÉTÉ CHIMIQUE DES
RHÔNE. anciennement GILLIARD P. MONNET ET CARTIER, of Lyons, France,
Manufacturers.
I, GEORGE BELOE ELLIS of the Firm of J. C. Mewburn and Ellis, of 55 and 56
Chancery Lane in the County of London, Chartered Patent Agents, do hereby
declare the nature of this invention to be as follows:-
This invention relates to the manufacture of benzoic sulphinide, commonly
known as saccharin.
According to this invention, benzoic-aldehyde-ortho-sulphonic acid or its salts
is converted by treatment with phosphorus pentachloride into a chlorinated product
which is insoluble in water, soluble in benzene melts at 114° C., and dissolves in
concentrated sulphuric acid with evolution of hydrochloric acid gas.
This chlorinated product is then heated with ammoniacal solutions under high
pressure, and the ammonium salt of benzoic sulphinide (saccharin) is thereby
formed. If the chlorinated product were heated, even to boiling, with aqueous
ammonia or ammonium carbonate under ordinary pressure, it would be scarcely
altered.
The following is an example of the manner in which the invention may be
carried into effect:-20 parts of benzoic-aldehyde-ortho-sulphonate of sodium,
40 parts of phosphorus pentachloride, and 100 parts of phosphorus oxychloride
are heated together for one hour at 120° C. The oxychloride is then distilled off
and the residue poured into ice-cold water.
The desired chloride thereupon separates and may be re-crystallized from
benzene; the purified product melts at 114° C.
This product may then be heated in an autoclave with 10 times its weight
of 20 per cent. ainmonia solution for several hours between 100° and 150° C.
After the reaction has taken place, the contents of the autoclave are acidified
with a dilute mineral acid and extracted with ether. On evaporation of the
ethereal extract a product is obtained which after recrystallization from alcohol
or acetone melts at 224° C. and presents all the characteristic properties of benzoic
sulphinide (saccharin).
1000

page_text: .
A
Improvements in the Manufacture of Benzoic-Sulphinide.
Communication from abroad: by LA SOCIÉTÉ CHIMIQUE DES USINES DU
RHÔNE, anciennement GILLIARD P. MONNET, ET CARTIER, of Lyons, France,
Manufacturers.
I, GEORGE BELOE ELLIS of the Firm of J. C. Mewburn and Ellis, of 55 and 56
Chancery Lane in the County of London Chartered Patent Agents, do hereby
declare the nature of this invention and in what manner the same is to be per-
formed, to be particularly described and ascertained in and by the following
statement:
This invention relates to the manufacture of benzoic sulphinide, commonly
known as saccharin.
According to this invention, benzoic-aldehyde-ortho-sulphonic acid or its salts
are converted by treatment with phosphorus pentachloride into a chiorinated product
which is insoluble in water, soluble in benzene melts at 114° C., and dissolves in
concentrated sulphuric acid with evolution of hydrochloric acid gas.
This chlorinated product is then heated with a solution of ammonium hydrate
under high pressure, and the ammonium salt of benzoic sulphinide (saccharin) is
thereby formed. If the chlorinated product were heated, even to boiling, with
aqueous ammonia under ordinary pressure, it would be scarcely altered.
The following is an example of the manner in which the invention may be
carried into effect:-20 parts of benzoic aldehyde-ortho-sulphonate of sodium,
40 parts of phosphorus pentachloride, and 100 parts of phosphorus oxychloride
are heated together for one hour at 120° C. The oxychloride is then distilled off
and the residue poured into ice-cold water.
The desired chloride thereupon separates and may be re-crystallized from
benzene: the purified product melts at 114° C. (uncorrected).
This product may then be heated in an autoclave with 10 times its weight
of 20 per cent. solution of ammonium hydrate for several hours between 100°
and 150° C.
After the reaction has taken place, the contents of the autoclave are acidified
with a dilute mineral acid and extracted with ether. On evaporation of the
ethereal extract a product is obtained which after recrystallization from alcohol
or acetone melts at 224° C. and presents all the characteristic properties of benzoic
sulphinide (saccharin).
Having now particularly described and ascertained the nature of the said
invention as communicated to me by my said foreign correspondents and in
what manner the same is to be performed, I declare that what I claim is :-
1. In and for the manufacture of benzoic sulphinide the preparation of a
chlorinated product from benzoic-aldehyde-ortho-sulphonic-acid or a salt thereof,
substantially as described.
2. In and for the manufacture of benzoic sulphinide the preparation of
ammonium salt of benzoic sulphinide by heating the chlorinated product such as
derived from benzoic aldehyde ortho-sulphonic acid or a salt'thereof as set forth,
with a solution of ammonium hydrate under high pressure substantially as
described.
3. In the manufacture of benzoic sulphinide, converting benzoic-aldehyde-ortho-
sulphonic acid or a salt of same into a chlorinated product, and then heating this
product with a solution of ammonium hydrate under high pressure, whereby the
ammonium salt of benzoic sulphinide is obtained, substantially as set forth.

page_text: 4. The manufacture of benzoic sulphinide by heating together benzoic-aldehyde-
ortho-sulphonate of sodium, phosphorus pentachloride and phosphorus oxy-
chloride, distilling off the oxychloride, then separating the remaining chloride
from the residue and recrystallizing it, then heating this chloride with a solution
of ammonium hydrate in an, autoclave, then acidifying the contents of the
autoclave and recovering the benzoic sulphinide liberated, substantially as set
forth.
5. The manufacture of benzoic sulphinide substantially in the manner herein-
before described.
J. C. MEWBURN & ELLIS,
55 and 56 Chancery Lane, London, W.C., Chartered Patent Agents.