Saccharinate

C (decomp.) It is made by the oxidation of toluene-o-sulphonamide with alkaline permanganate. Saccharin has about 550 times the sweetening power of sucrose, and is used extensively as a sweetening agent, usually in the form of the sodium salt. The use of saccharin is restricted in the U.S. 

Although benzenesulphonyl chloride has for simplicity been used in the above discussion, tolucne-/>- sulphonyl chloride, CHaCeH SO Cl, is more frequently used in the laboratory, owing to its much lower cost, the latter being due in turn to the fact that toluene-p-sulphonyl chloride is a by-product in the commercial preparation of saccharin. Toluene-p sulphonyl chloride is a crystalline substance, of m.p. 68° the finely powdered chloride will, however, usually react readily with amines in the Schotten-Baumann reaction it does not react so readily with alcohols, but the reaction may be promoted considerably by first dissolving the chloride in some inert water-soluble solvent such as acetone. 

Students arc strongly advised not to attempt identification of the soluble carbohydrates by taste—quite apart from the fact that other compounds (c.g., saccharin] also have a sweet taste, the tasting of an imperfectly identified organic compound u too dangerous an operation. 

Pseudo-saccharin ethers. Pseudo-saccharin chloride (Section VII,26) reacts with alcohols to give ethers (0 alkyl derivatives of saccharin) ... 

Heat a little pseudo-saccharin chloride with excess of the anhydrous alcohol in a test-tube until hydrogen chloride is no longer evolved. Recrystallise from alcohol or other organic solvent. 

Pseudo-saccharin ethers. When pseudo-saccharin chloride is heated with an excess of a phenol, 0-aryl derivatives of saccharin are produced (compare Section 111,27, 7). 

Heat 0 5 g. of pseudo-saccharin chloride with an excess of the phenol to 125-140° for 15-20 minutes hydrogen chloride is evolved. Wash the product with dilute sodium hydroxide solution and then with water. Recrystallise the derivative from ethanol. 

The melting points of some 0-aryl saccharin derivatives are phenol, 182° o-cresol, 163° m-cresol, 146° p-cresol, 172° o-nitrophenol, 236° p-nitrophenol, 192°. 

Saccharin (imide of o-sulphobenzoic acid). Upon oxidising o toluene-sulphonamide with potassium permanganate in alkaline solution, the sodium salt of o-sulphonamidobenzoic acid is formed, which upon acidifying with concentrated hydrochloric acid or warming passes spontaneously into the cyclic imide of o-sulphobenzoic acid or saccharin ... 

Saccharin Itself is sparingly soluble in cold water, but the imino hydrogen is acidic and the compound forms a water-soluble sodium salt. The latter is about 600 times as sweet as cane sugar. 

Pseudo saccharin chloride (II) is prepared by the action of phosphorus penta-chloride upon saccharin (I) ... 

Hydrolysis of saccharin (o-sulphobenzoic imide) (Section IV, 209) with dilute hydrochloric acid yields acid ammonium 0 sulphobenzoate, w hich upon... 

Zemplen helped his students in many ways. I remember an occasion in the difficult postwar period. The production of the famous Hungarian salami, interrupted by the war, was just in the process of being restarted for export. The manufacturer wanted a supportive analysis from the well-known professor. Zemplen asked for a suitable sample of some hundreds of kilograms, on which the whole institute lived for weeks. When it was gone he rightly could offer an opinion that the product was quite satisfactory. After the war, grain alcohol was for a long time the only available and widely used laboratory solvent, and, not unexpectedly, it also found other uses. Later, when it was denatured to prevent human consumption, we devised clever ways for its purification. The lab also manufactured saccharine, which was... 

Saccharin was discovered at Johns Hopkins Uni versity in 1879 in the course of research on coal tar derivatives and is the oldest artificial sweetener In spite of Its name which comes from the Latin word for sugar saccharin bears no structural relationship to any sugar Nor is saccharin itself very soluble in wa ter The proton bonded to nitrogen however is fairly acidic and saccharin is normally marketed as its water soluble sodium or calcium salt Its earliest applications were not in weight control but as a... 

Saccharin sucralose and aspartame illustrate the diversity of structural types that taste sweet and the vitality and continuing development of the in dustry of which they are a part ... 

The concentrations of benzoic acid, aspartame, caffeine, and saccharin in a variety of beverages are determined in this experiment. A Gig column and a mobile phase of 80% v/v acetic acid (pH = 4.2) and 20% v/v methanol are used to effect the separation. A UV detector set to 254 nm is used to measure the eluent s absorbance. The ability to adjust retention times by changing the mobile phase s pH is also explored. 

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