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SACCHARIN

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Originally appearing in Volume V23, Page 970 of the 1911 Encyclopedia Britannica.
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SACCHARIN , the name given to several distinct chemical sub-stances. The saccharin of See also:

commerce, so named from its excessively sweet See also:taste, is a See also:coal-See also:tar product, being the imide of orthosulphobenzoic See also:acid, CeH4< CO >NH. It may be prepared by the oxidation of ortho-toluenesulphonamide See also:CH3•See also:C6H4•SO2NH2, with See also:potassium permanganate (C. Fahlberg and I. Remsen, Ber., 1879, 12, p. 469); by the electrolytic oxidation of the above sulphonamide (See also:German patent 35211); by the See also:action of concentrated sulphuric acid on ortho-sulphamidobenzoic acid, See also:NH2•SO2•C6H4•See also:CO2H (German patent 113720); by warming the chloride of ortho-sulphobenzoic acid phenyl ester (SO2C1•C4H4• CO2C.H6) with excess of aqueous See also:ammonia (R. See also:List and M. See also:Stein, Ber., 1898, 31, p. 1662); and from See also:benzaldehyde orthosulphonic acid by See also:conversion into its acid chloride, which with ammonia yields the corresponding acid-See also:amide, which gives saccharin on oxidation with atmospheric See also:oxygen (German patent 94948). It is a crystalline See also:powder which melts at 220° C. with partial decomposition. It is soluble with difficulty in See also:cold See also:water, but is moderately soluble in hot water and readily soluble in See also:alcohol. By the action of concentrated hydrochloric acid at 15o° C. it is decomposed into ammonia and ortho-sulphobenzoic acid.

With See also:

phosphorus pentachloride above 200° C. it yields ortho= chlornitrobenzene. See also:Sodium saccharin, C6H4(CO)•(SO2)•N•Na, 2H2O, is used under the name of " soluble saccharin " or "crystallose," and is readily soluble in hot water. The ammonium See also:salt is named " sucramine." Saccharin is, largely used for sweetening purposes, pure saccharin being 500 times sweeter than See also:sugar. Until 1891 the commercial product contained about 40 % of the tasteless See also:para See also:compound and was only 300 times as sweet as sugar; the mixture, however, is now separated by dissolving out the saccharin with See also:xylene, in which solvent the para compound is insoluble. Saccharin is used as a sugar substitute for diabetic patients. It is interesting to See also:note that o-sulphobenzoic acid has an acid taste, and the sulphamide is tasteless; the sweetness of saccharin therefore appears to be connected with the formation of a cyclic anhydride. In the See also:United See also:Kingdom there is an import See also:duty of Is. 3d. per oz. on saccharin and similar products, and manufacturers have to take out a See also:licence. In the United States the import duty is $1.5o+to% ad valorem per lb. See also:Austria-See also:Hungary, See also:France, See also:Belgium and See also:Germany prohibit the importation. On the estimation of saccharin in commercial samples and for its detection in foods and beverages see J. H.

Kastle, Jour. Chem. See also:

Soc., 1905, 87, p. 5o3; E. M'K. Chace, Jour. Amer. Chem. Soc., 1904, 39, p. 1627. The See also:lactones of the saccharic acids are also known as " saccharins." By boiling dextrin or laevulose with See also:milk of See also:lime the so-called " See also:sac- See also:CH2OH•CH•CHOH•Q(OH)•See also:CH2 charin," a lactone of the See also:formula, 0 CO is obtained (E. Pefigot, Ber., 188o, 13, p.

196; H. Kiliani, Ber., 1882, 15, p. 2954). It crystallizes in large prisms, has a See also:

bitter taste, and is easily soluble in hot water. Potassium permanganate oxidizes it to carbonic and acetic acids. See also:Heating with See also:caustic potash to 200 °C. gives formic and lactic acids, and when reduced by h vdriodic acid and phosphorus it is converted into ay-dimethylbutyrolactone. Iso-saccharin " and " See also:meta-saccharin " are formed by the action of lime on milk sugar (H. Kiliani, Ber., 1885, 18, p. 631). The former melts at 95 C., and on reduction by hydriodic acid and phosphorus is converted into ay-dimethylvalerolactone. Meta-saccharin melts at 141-142° C. and is easily soluble in water.

End of Article: SACCHARIN

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