Oxathiazinone dioxides
Oxathiazinone dioxides belong to the group of oxathiazines , heterocyclic compounds which, in addition to three carbon atoms, each contain an oxygen, sulfur and nitrogen atom in the six-membered ring. The best-known representative is the potassium salt of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide, which is used as a sweetener under the name Acesulfame -K. There are a large number of derivatives which have differently substituted alkyl groups in positions 5 and 6 of the ring . Cations can be sodium, potassium, and calcium ions.
Manufacturing
The classic method is the reaction of fluorosulfone isocyanate (OCN-SO 2 F) with butynes , such as 1- or 2-butyne, or 1-hexyne and ring closure with sodium hydroxide solution. 2-butyne thus reacts to form N -fluorosulfonyl-α-methylacetacetic acid amide as an intermediate which forms 5,6-dimethyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide with ring closure.
Another method is the reaction of ketones with fluorosulfonic acid isocyanate. From acetone obtained so that 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide, and from 2-butanone, 5,6-dimethyl-3,4-dihydro -1,2,3-oxathiazin-4-one-2,2-dioxide.
properties
All oxathiazinone dioxides are thermally and chemically stable compounds. With alkali metal ions and calcium ions, they form stable salts which have a melting point of over 200 ° C and differ in solubility in water depending on the substituents. All compounds are non-toxic. All derivatives are sweeteners, with the sodium salt of 5-ethyl-6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide being the highest (250) and the unsubstituted 3, 4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide has the lowest (10) sweetness .
literature
- Karl Clauss, Harald Jensen: Oxathiazinondioxide, a new group of sweeteners. In: Angewandte Chemie. Vol. 85, No. 22, 1973, pp. 965-973, doi : 10.1002 / anie.19730852202