Manufacture of a Derivative of Phenyl 1.2. Methanoylsulphonimide.
Year: 1899

page_text: Date of Application, 6th Oct., 1899
Complete Specification Left, 22nd Nov., 1899-Accepted, 6th Jan.,
1900
Manufacture of a Derivative of Phenyl 1.2. Methanoylsulphonimide.
I, CLAUDE KENNEDY MILLS;, of 23, Southampton Buildings, in the County of
London, Patent Agent, do hereby declare the nature of this invention (a com-
munication to, me: from Léon, Cerf, of 58,, Rue de la République, Lyons; in the
Republic of France,, Merchant,) to be as follows:-
When phenyl 12. methanovlsulphonimide having the formula
This body crystalizes out from an aqueous solution in large prismatic crystals
(beautiful oblique quadratic and hexagonal crystals) which decompose at 220° C. and
give off ammonia. It is very soluble in water.;, boiling water dissolves twice its own
weight. It is slightly soluble in cold alcohol and more so in hot alcohol.
insoluble in acetone, ether, acetic ether, and benzine.
It is
By fusion with resorcin or diethylamidophenol in presence of a small quantity of
chloride of zinc, the coloured' reaction of the phtaleins is obtained.
The sweetening property of this body is much greater than that of ordinary sugar..
Its great solubility in water permits it to be used' commercially for the purpose of
sweetening. It possesses antiseptic and organoleptic properties: capable of being used
for various purposes..
PROCESS OF PREPARATION.
Through one part of phenyl 1.2. methanoylsulphonimide, to which two parts of
water have been, added., is caused to pass a current of ammonia gas, chemically pure
and perfectly free from. the empyreumatic products which it generally contains. If
the mixture is carefully shaken it will be seen that the solution of phenyl 1. 2.
methanoylsulphonimide. is obtained very readily. When the solution is completed,,the
excess, of, ammonia is driven off by heat, or better by evaporation in vacuo, and a
concentrated solution is obtained which should be colorless and odorless. The
evaporation is carried out at a low temperature preferably in vacuo.

page_text: A concentrated solution of ammonia may also be saturated by the largest possible
quantity of phenyl 1.2. methanoylsulphonimide, and the solution evaporated in the
manner above stated.
Dated this 6th day of October 1899.
HARRIS & MILLS,
23, Southampton Buildings, London, W.C., Agents.
its analysis, its properties and reactions appears to have the formula
ONH4
C*H*
PROCESSES OF PREPARATION.
Through one part of phenyl-1: 2-methanoyl-sulphonimide in suspension in two
parts of water, caused to pass a current of ammonia gas, which may be obtained
either by heating a solution of ammonia or by heating a salt of ammonia in
presence of lime.
To obtain a perfectly pure product the ammonia gas should be well purified and
deprived of the empyreumatic products which it often contains; for this purpose it
is washed by causing it to pass through a saturated solution of ammonia. It is then,
caused to pass through another receiver containing fragments of potash.
In order to obtain the maximum yield and to obtain a product as white and pure as
possible, it is preferable to effect this purification, which nevertheless is not indis-
pensable, and to conduct it at the ordinary temperature.
When using impure anhydride of benzoic orthosulphamide containing a para
derivative in rather large quantity, a very pure orthoammoniated derivative can be
obtained.
When the solution by ammonia of the substance in suspension in water is complete,
this solution is filtered and then evaporated slowly, as far as possible at a temperature
below 100° C.

page_text: By evaporating at about the temperature of 50° Centigrade and in vacuo, a very
pure product is rapidly obtained. These precautions are not however absolutely
indispensable.
When the volume of the liquor is reduced about or by evaporation, it is allowed
to cool slowly and the ammoniated derivative crystallizes into beautiful dimorphous
crystals.
The orvtale om bliana nim
described process is a neutral
body, entirely organic, which being very pure, can be burnt without leaving any
residue.
When it is heated it disengages ammonia at about 220° C., it then burns com-
pletely in the air.
It crystallizes in oblique prisms, sometimes hexagonal, sometimes quadratic.
It is extremely soluble in water, boiling water dissolves about twice its weight of
the derivative.
It is only slightly soluble in cold alcohol, but more so in hot alcohol.
It is insoluble in acetone, ether, acetic ether, and benzene.
By fusion with resorcin or diethylamido-phenol, the coloured reactions of the
phthaleins are obtained.
From the organoleptic point of view this ammoniated derivative is very interesting;
its diluted solutions, compared with those of saccharine in equal proportions, are very
considerably sweeter.
Physiological examination of the product compared with saccharine has demon-
strated very considerable advantages over the latter.
Thus in intravenous injections, saccharine is toxical when a dose of 50 centigrammes
is administered to each kilogramme of the animal, whilst the product forming the
subject of the present invention is only toxical at 85 centigrammes per kilogramme.
Being perfectly neutral it does not injure the stomach like saccharine and does not
arrest the action of the peptonizing and saccharifying ferments of digestion.
Animals have been made to absorb considerable doses of the product exceeding
1 grm, per day for each kilogramme of the animal, without ever causing the least
unfavorable action upon the organism.
The properties of this ammoniated derivative therefore show that it possesses
considerable advantages of solubility, of innocuousness, and of sweetening property,
over saccharine.
I am aware that it has been proposed to treat saccharine with a solution of ammonia,
and therefore I make no claim to such treatment, but, 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 herein described manufacture of a derivative of phenyl-1: 2-methanoylsul-
phonimide by causing ammonia gas to pass through a mixture of phenyl-1 : 2-metha-
noylsulphonimide with water and concentrating the product by evaporating under
100° C.
Dated this 22nd day of November 1899.
HARRIS & MILLS,
23, Southampton Buildings, London, W.C., Agents.