Sucrose-6-ester chlorination

  • US 4,980,463 A
  • Filed: 07/18/1989
  • Issued: 12/25/1990
  • Est. Priority Date: 07/18/1989
  • Status: Expired due to Term
First Claim
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1. A process for the chlorination of sucrose-6-esters to produce 6'"'"', 4,1'"'"'-trichloro-sucrose-6-esters which comprises the steps of:

  • (a) adding at least seven molar equivalents of an acid chloride to a reaction mixture containing a sucrose-6-ester and a tertiary amide to form a chloroformiminium chloride salt in the presence of said sucrose-6-ester, whereby the chloroformiminium salt forms an O-alkylformiminium chloride adduct with the hydroxyl groups of the sucrose-6-ester;

    (b) subjecting the reaction mixture product of step (a) to an elevated temperature not higher than about 85°

    C. for a period of time sufficient to produce a mixture of chlorinated sucrose-6-ester products consisting essentially of monochlorosucrose-6-ester, 4,6'"'"'-dichlorosucrose-6-ester, and 1'"'"',6'"'"'-dichlorosucrose-6-ester; and

    (c) subjecting the reaction mixture product of step (b) to an elevated temperature of at least about 100°

    C. but not higher than about 130°

    C. for a period of time sufficient to produce a chlorinated product comprising predominanly 1'"'"',4,6'"'"'-trichlorosucrose-6-ester.

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