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There is disclosed a process for producing sucralose from sucralose-6-ester whereby the sucralose-6-ester is deacylated directly either prior to or after removal of the tertiary amide reaction vehicle from the neutralized chlorination reaction mixture, to produce an aqueous solution of sucralose plus salts and impurities, from which sucralose is recovered by extraction and is then preferably purified by crystallization.

InventorsJuan L. Navia, Robert E. Walkup, Nicholas M. Vernon, David S. Neiditch
Original AssigneeMcNeil-PPC, Inc.
Current U.S. Classification536/124; 127/46.3; 536/4.1; 536/119; 536/127
International Classification: C07G 1700; C07H 100; C07H 300

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Citations

Cited PatentFiling dateIssue dateOriginal AssigneeTitle
US4380476Jun 19, 1981Apr 19, 1983Talres Development (N.A.) N.V.Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS)
US4918182Jul 15, 1987Apr 17, 1990Tate & Lyle Public Limited CompanySweetener
US4950746Jul 18, 1988Aug 21, 1990Noramco, Inc.Process for synthesizing sucrose derivatives by regioselective reaction
US4980463Jul 18, 1989Dec 25, 1990Noramco, Inc.Sucrose-6-ester chlorination
US5023329Apr 23, 1990Jun 11, 1991Noramco, Inc.Sucrose-6-ester production process
US5034551Apr 23, 1990Jul 23, 1991Noramco, Inc.Process for recovery of organotin esters from reaction mixtures containing the same and re-use of the recovered organotin compounds
US5089608Mar 23, 1990Feb 18, 1992McNeil-PPC, Inc.Selective 6-acylation of sucrose mediated by cyclic adducts of dialkyltin oxides and diols
US5128248Sep 26, 1989Jul 7, 1992Tate & Lyle Public Limited CompanySelective acrylation of sugars
US5136031Jul 9, 1990Aug 4, 1992Tate & Lyle Public Limited CompanyChlorination of sugars
US5298611Mar 12, 1993Mar 29, 1994McNeil-PPC, Inc.Sucralose pentaester production

Referenced by

Citing PatentFiling dateIssue dateOriginal AssigneeTitle
US5882420May 5, 1998Mar 16, 1999Iowa State University Research Foundation, Inc.Linear and cyclic sucrose reaction products, their preparation and their use
US5900478Jun 20, 1997May 4, 1999Iowa State University Research Foundation, Inc.Activated mono-, di-, and polysaccharides reaction products thereof, their preparation and uses
US5932720Feb 18, 1998Aug 3, 1999Tate & Lyle Public Limited CompanySolid sucralose
US5977349Feb 11, 1998Nov 2, 1999McNeil-PPC, Inc.Chromatographic purification of chlorinated sucrose
US6007862May 5, 1998Dec 28, 1999Iowa State University Research Foundation, Inc.Food and beverage compositions containing linear and cyclic sucrose reaction products
US6031085Apr 13, 1998Feb 29, 2000Iowa State University Research Foundation, Inc.Activated mono,di,oligo- and polysaccharides, reaction products thereof, their preparation and uses
US6075139Jul 24, 1996Jun 13, 2000Iowa State University Research Foundation, Inc.Linear and cyclic sucrose reaction products, their preparation and their use
US6096882Apr 13, 1998Aug 1, 2000Iowa State University Research Foundation, Inc.Activated mono-, di-, oligo- and polysaccharides, reaction products thereof, their preparation and uses
US6281351May 5, 1998Aug 28, 2001Iowa State University Research Foundation, Inc.Linear and cyclic sucrose reaction products, their preparation and their use
US6646121Nov 16, 2001Nov 11, 2003McNeil-PPC, Inc.Sucralose composition and process for its preparation
US6703005Apr 5, 2001Mar 9, 2004Unilever Home & Personal Care USA, division of Conopco, Inc.Process for the production of a deodorant or antiperspirant product
US6809198Aug 1, 2003Oct 26, 2004Tate & Lyle Public Limited CompanySucralose composition and process for its preparation
US6890581Apr 5, 2002May 10, 2005Tate & Lyle Public Limited CompanyMethods for buffer stabilized aqueous deacylation
US6943248Apr 30, 2003Sep 13, 2005Tate & Lyle Public Limited CompanyCrystalline form of sucralose, and method for producing it
US6984732Mar 31, 2003Jan 10, 2006McNeil-PPC, Inc.High-intensity sweetener composition and delivery of same
US6998480Mar 8, 2002Feb 14, 2006Tate & Lyle Public Limited CompanyProcess for improving sucralose purity and yield
US7018667Nov 13, 2001Mar 28, 2006Tate & Lyle Public Limited CompanyMeltable form of sucralose
US7049435Mar 8, 2002May 23, 2006Tate & Lyle Public Limited CompanyExtractive methods for purifying sucralose
US7741477Jan 10, 2007Jun 22, 2010Alembic LimitedProcess for purification of sucralose
US7750146Mar 18, 2005Jul 6, 2010Tate & Lyle PLCGranular sucralose
US7785650Jun 27, 2007Aug 31, 2010McNeil-PPC, Inc.Method for dip coating dosage forms
US7838668Apr 27, 2007Nov 23, 2010JK Sucralose Inc.Method for crystallizing sucralose
US7884203Jun 28, 2006Feb 8, 2011JK Sucralose Inc.Method of sucralose synthesis yield
US7951937Aug 29, 2006May 31, 2011V.B. Medicare Private LimitedProcess for purification of trichlorogalactosucrose based on direct extraction in organic solvent from reaction mixture followed by evaporative removal of solvent
US8017767Sep 18, 2006Sep 13, 2011Tate & Lyle Public Limited CompanySucralose composition
US8101746Mar 20, 2006Jan 24, 2012Tate & Lyle Technology LimitedGranular sucralose, and method of making it
US8212022Apr 1, 2009Jul 3, 2012Tate & Lyle Technology LimitedEffect of carbohydrate concentration on sucralose extraction efficiency

Claims

1. A process for producing sucralose from a feed mixture of (a) 6-O-acyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose, (b) salt including alkali metal or alkaline earth metal chloride, (c) water, and (d) other chlorinated sucrose by-products, in a reaction medium comprising a tertiary amide, wherein said process comprises:

(i) deacylating the 6-O-acyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose by raising the pH of the aqueous solution of (a), (b), (c) and (d) to about 11 (.+-.1) at a temperature and for a period of time sufficient to effect said deacylation, to produce an aqueous solution comprising sucralose, salt including alkali metal or alkaline earth metal chloride, and other chlorinated sucrose by-products, in a reaction medium comprising a tertiary amide;
(ii) removing said tertiary amide; and
(iii) recovering sucralose from the product of step (ii).

2. The process of claim 1 wherein step (ii) is carried out by steam stripping.

3. The process of claim 2 wherein the tertiary amide is N,N-dimethylformamide.

4. The process of claim 3 wherein the 6-O-acyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose is 6-O-acetyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose or 6-O-benzoyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose.

5. The process of claim 4 wherein the step of extracting sucralose from the product of step (iii) is carried out by a batch, continuous, or continuous counter-current extraction.

6. The process of claim 5 wherein the sucralose is further purified by crystallization.

7. The process if claim 6 wherein the crystallization is carried out from water or ethyl acetate.

8. A process for producing sucralose from a feed mixture of (a) 6-O-acyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose, (b) salt including alkali metal or alkaline earth metal chloride, (c) water, and (d) other chlorinated sucrose by-products, in a reaction medium comprising a tertiary amide, wherein said process comprises:

(i) removing said tertiary amide to produce an aqueous solution of (a), (b) and (d) from which a major proportion of the tertiary amide in said feed mixture has been removed;
(ii) deacylating the 6-O-acyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose by raising the pH of the aqueous solution product of step (i) to a pH of at least about 11 (.+-.) at a temperature and for a period of time sufficient to effect said deacylation, to produce an aqueous solution comprising sucralose, salt including alkali metal or alkaline earth metal chloride, and other chlorinated sucrose by-products; and
(iii) recovering sucralose from the product of step (ii).

9. The process of claim 8 wherein the 6-O-acyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose is 6-O-acetyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose or 6-O-benzoyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose.

10. The process of claim 9 wherein step (iii) is carried out by extracting sucralose from the product of step (ii) by an organic solvent, followed by crystallization of sucralose from said organic solvent.

11. The process of claim 10 wherein said organic solvent is ethyl acetate.

12. The process of claim 9 wherein step (iii) is carried out by extracting sucralose from the product of step (ii) by an organic solvent, followed by crystallization of sucralose from water.

13. The process of claim 9 wherein the tertiary amide is N,N-dimethylformamide.

14. The process of claim 13 wherein the removal of the tertiary amide in Step (i) is effected by steam distillation.

15. The process of claim 11 wherein the step of extracting sucralose from the product of step (ii) is carried out by a batch, continuous, or continuous counter-current extraction.