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. |
Citations|
| US4380476 | Jun 19, 1981 | Apr 19, 1983 | Talres Development (N.A.) N.V. | Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS) | | US4918182 | Jul 15, 1987 | Apr 17, 1990 | Tate & Lyle Public Limited Company | Sweetener | | US4950746 | Jul 18, 1988 | Aug 21, 1990 | Noramco, Inc. | Process for synthesizing sucrose derivatives by regioselective reaction | | US4980463 | Jul 18, 1989 | Dec 25, 1990 | Noramco, Inc. | Sucrose-6-ester chlorination | | US5023329 | Apr 23, 1990 | Jun 11, 1991 | Noramco, Inc. | Sucrose-6-ester production process | | US5034551 | Apr 23, 1990 | Jul 23, 1991 | Noramco, Inc. | Process for recovery of organotin esters from reaction mixtures containing the same and re-use of the recovered organotin compounds | | US5089608 | Mar 23, 1990 | Feb 18, 1992 | McNeil-PPC, Inc. | Selective 6-acylation of sucrose mediated by cyclic adducts of dialkyltin oxides and diols | | US5128248 | Sep 26, 1989 | Jul 7, 1992 | Tate & Lyle Public Limited Company | Selective acrylation of sugars | | US5136031 | Jul 9, 1990 | Aug 4, 1992 | Tate & Lyle Public Limited Company | Chlorination of sugars | | US5298611 | Mar 12, 1993 | Mar 29, 1994 | McNeil-PPC, Inc. | Sucralose pentaester production |
Referenced by|
| US5882420 | May 5, 1998 | Mar 16, 1999 | Iowa State University Research Foundation, Inc. | Linear and cyclic sucrose reaction products, their preparation and their use | | US5900478 | Jun 20, 1997 | May 4, 1999 | Iowa State University Research Foundation, Inc. | Activated mono-, di-, and polysaccharides reaction products thereof, their preparation and uses | | US5932720 | Feb 18, 1998 | Aug 3, 1999 | Tate & Lyle Public Limited Company | Solid sucralose | | US5977349 | Feb 11, 1998 | Nov 2, 1999 | McNeil-PPC, Inc. | Chromatographic purification of chlorinated sucrose | | US6007862 | May 5, 1998 | Dec 28, 1999 | Iowa State University Research Foundation, Inc. | Food and beverage compositions containing linear and cyclic sucrose reaction products | | US6031085 | Apr 13, 1998 | Feb 29, 2000 | Iowa State University Research Foundation, Inc. | Activated mono,di,oligo- and polysaccharides, reaction products thereof, their preparation and uses | | US6075139 | Jul 24, 1996 | Jun 13, 2000 | Iowa State University Research Foundation, Inc. | Linear and cyclic sucrose reaction products, their preparation and their use | | US6096882 | Apr 13, 1998 | Aug 1, 2000 | Iowa State University Research Foundation, Inc. | Activated mono-, di-, oligo- and polysaccharides, reaction products thereof, their preparation and uses | | US6281351 | May 5, 1998 | Aug 28, 2001 | Iowa State University Research Foundation, Inc. | Linear and cyclic sucrose reaction products, their preparation and their use | | US6646121 | Nov 16, 2001 | Nov 11, 2003 | McNeil-PPC, Inc. | Sucralose composition and process for its preparation | | US6703005 | Apr 5, 2001 | Mar 9, 2004 | Unilever Home & Personal Care USA, division of Conopco, Inc. | Process for the production of a deodorant or antiperspirant product | | US6809198 | Aug 1, 2003 | Oct 26, 2004 | Tate & Lyle Public Limited Company | Sucralose composition and process for its preparation | | US6890581 | Apr 5, 2002 | May 10, 2005 | Tate & Lyle Public Limited Company | Methods for buffer stabilized aqueous deacylation | | US6943248 | Apr 30, 2003 | Sep 13, 2005 | Tate & Lyle Public Limited Company | Crystalline form of sucralose, and method for producing it | | US6984732 | Mar 31, 2003 | Jan 10, 2006 | McNeil-PPC, Inc. | High-intensity sweetener composition and delivery of same | | US6998480 | Mar 8, 2002 | Feb 14, 2006 | Tate & Lyle Public Limited Company | Process for improving sucralose purity and yield | | US7018667 | Nov 13, 2001 | Mar 28, 2006 | Tate & Lyle Public Limited Company | Meltable form of sucralose | | US7049435 | Mar 8, 2002 | May 23, 2006 | Tate & Lyle Public Limited Company | Extractive methods for purifying sucralose | | US7741477 | Jan 10, 2007 | Jun 22, 2010 | Alembic Limited | Process for purification of sucralose | | US7750146 | Mar 18, 2005 | Jul 6, 2010 | Tate & Lyle PLC | Granular sucralose | | US7785650 | Jun 27, 2007 | Aug 31, 2010 | McNeil-PPC, Inc. | Method for dip coating dosage forms | | US7838668 | Apr 27, 2007 | Nov 23, 2010 | JK Sucralose Inc. | Method for crystallizing sucralose | | US7884203 | Jun 28, 2006 | Feb 8, 2011 | JK Sucralose Inc. | Method of sucralose synthesis yield | | US7951937 | Aug 29, 2006 | May 31, 2011 | V.B. Medicare Private Limited | Process for purification of trichlorogalactosucrose based on direct extraction in organic solvent from reaction mixture followed by evaporative removal of solvent | | US8017767 | Sep 18, 2006 | Sep 13, 2011 | Tate & Lyle Public Limited Company | Sucralose composition | | US8101746 | Mar 20, 2006 | Jan 24, 2012 | Tate & Lyle Technology Limited | Granular sucralose, and method of making it | | US8212022 | Apr 1, 2009 | Jul 3, 2012 | Tate & Lyle Technology Limited | Effect of carbohydrate concentration on sucralose extraction efficiency |
Claims1. 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. |