Methods for chlorinating sucrose-6-ester

Abstract

Methods for chlorinating sucrose-6-esters to produce 1',4,6'-trichlorosucrose-6-esters include providing a reaction mixture in a temperature-controlled vessel at a temperature less than about 65 DEG C, the reaction mixture comprising sucrose-6-ester, a tertiary amide, and a chloroformiminium chloride salt, which forms an O-alkylformiminium chloride adduct with the hydroxyl groups of the sucrose-6-ester. The methods for chlorinating the sucrose-6-ester further include subjecting the chloroformiminium chloride salt, tertiary amide, and sucrose-6-ester reaction mixture to an elevated temperature between about 75 DEG C and 100 DEG C for a period of time sufficient to produce a chlorinated product mixture of chlorinated sucrose-6-ester products consisting essentially of 1',4,6'-trichlorogalacto-sucrose-6-ester.

Description

technical field [0001] The present invention relates to an improved process for the chlorination of sucrose-6-esters for the production of selectively chlorinated products. Background technique [0002] Selective chlorination rather than chlorination of all sucrose hydroxyl groups may be an important synthetic issue due to the varying reactivity of the hydroxyl groups. High-potency sweetener sucrose, the mixture of which is formally known as 4-chloro-4-deoxy-α-D-galactopyranose-1,6-dichloro-1,6-dideoxy-β-D-furan Glycosides, are partially chlorinated derivatives of sucrose in which chlorine is substituted for the hydroxyl groups at the 6', 4, and 1' positions. However, selective chlorination, which occurs only at the desired 6', 4 and 1' positions for the production of sucrose, begins to be a very complex and challenging synthetic problem and many successful methods have been developed over the past few years , by different synthetic routes or different procedural steps, th...

AI Technical Summary

Problems solved by technology

However, selective chlorination, which occurs only at the desired 6', 4 and 1' positions for the production of sucrose, begins to be a very complex and challenging synthetic problem and many successful methods have been developed over the past few years , obtained in different yields and / or purities by different synthetic routes or different procedural steps