WO2007052305A2 - Novel method of extraction of 6-o-protected trichlorogalac tose from the chlorinated mass - Google Patents
Novel method of extraction of 6-o-protected trichlorogalac tose from the chlorinated mass Download PDFInfo
- Publication number
- WO2007052305A2 WO2007052305A2 PCT/IN2006/000329 IN2006000329W WO2007052305A2 WO 2007052305 A2 WO2007052305 A2 WO 2007052305A2 IN 2006000329 W IN2006000329 W IN 2006000329W WO 2007052305 A2 WO2007052305 A2 WO 2007052305A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tgs
- dmf
- acetate
- ester
- extraction
- Prior art date
Links
- 238000000605 extraction Methods 0.000 title claims abstract description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 32
- 235000019408 sucralose Nutrition 0.000 claims abstract description 18
- 239000000284 extract Substances 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- FACOTAQCKSDLDE-YKEUTPDRSA-N [(2R,3R,4R,5R,6R)-6-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-3-chloro-4,5-dihydroxyoxan-2-yl]methyl acetate Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](COC(=O)C)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 FACOTAQCKSDLDE-YKEUTPDRSA-N 0.000 claims abstract description 7
- 238000002955 isolation Methods 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 4
- 239000012266 salt solution Substances 0.000 claims abstract description 3
- 230000002378 acidificating effect Effects 0.000 claims abstract 2
- 230000020176 deacylation Effects 0.000 claims abstract 2
- 238000005947 deacylation reaction Methods 0.000 claims abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 238000000746 purification Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000005660 chlorination reaction Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 150000003511 tertiary amides Chemical class 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- AFHCRQREQZIDSI-OVUASUNJSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(=O)C=2C=CC=CC=2)O1 AFHCRQREQZIDSI-OVUASUNJSA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- AFHCRQREQZIDSI-UHFFFAOYSA-N sucrose-6-benzoate Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC(=O)C=2C=CC=CC=2)O1 AFHCRQREQZIDSI-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 5
- 239000004376 Sucralose Substances 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000006196 deacetylation Effects 0.000 description 3
- 238000003381 deacetylation reaction Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003445 sucroses Chemical class 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000244489 Navia Species 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005257 alkyl acyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- -1 sucrose Chemical class 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Definitions
- sucrose-6-acetate or any other equivalent sucrose-6-ester, could be carried out using any of the conventional Vilsmeier reagents prepared from phosphorus oxychloride, phosphorus pentachloride, phosgene or [Bis(trichloromethyl) carbonate] and solvents like DMF or dimethylacetamide.
- the present invention relates to a novel process and a novel strategy for isolation of the 6-protected trichlorogalactosucrose derivatives from the reaction mixtures obtained from the chlorination of the 6-acyl sucrose.
- the acyl group could be an aromatic acyl group like benzoyl, substituted aromatic acyl group such as paramethoxy benzoyl group or alkyl acyl group namely acetyl group.
- the 6-protected-trichlorogalactosucrose derivative could be deprotected by conventional alkaline hydrolysis to produce the desired trichlorogalactosucrose.
- One embodiment of this invention relates to protecting DMF as well as TGS-6-ester from destruction by adjusting the pH of the neutralized chlorinated reaction mixture to pH 5 to 7, then extracting the same by immiscible or partially immiscible organic solvents, washing the organic solvent extract with saturated aqueous salt solution to achieve removal of DMF and recovery of the extracted organic ingredients from the organic solvent extract by applying appropriate method of purification including but not limited to solvent extraction, column chromatography and the like.
- TGS-6-ester isolated either in crude or pure form is de-esterified at alkaline pH and TGS formed is isolated by applying one or more of a purification process.
- a solvent covers use of all known solvents, of one or more of them, either singly, or in combination as a mixture or as used successively and "a process of purification” encompasses one or more or all the known processes applicable in the context.
- the neutralized mass was filtered through the filter press to remove extraneous solids in the solution. Then the solution was subjected to
- sucrose-6-acetate 80 kg was chlorinated by the Vilsmeier reagent generated by PCI 5 . (252.8 kg) and DMF (480 kg). After chlorination, the reaction mass was neutralized using 30% sodium hydroxide solution and then the pH was again brought back to 5.0 by addition of dilute HCI. The total volume of the filtered solution was found to be 3200L. Then the solution was filtered to remove extraneous solids and was subjected to Packed column Liquid-Liquid extraction using 1 :3.5 times of ethyl acetate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002620902A CA2620902A1 (en) | 2005-08-30 | 2006-08-29 | Novel method of extraction of 6-o-protected trichlorogalactose from the chlorinated mass |
GB0803649A GB2443146A (en) | 2005-08-30 | 2006-08-29 | Novel method of exraction of 6-0-protected trichlorogalac tose from the chlorinated mass |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN1048/MUM/2005 | 2005-08-30 | ||
IN1048MU2005 | 2005-08-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2007052305A2 true WO2007052305A2 (en) | 2007-05-10 |
WO2007052305A3 WO2007052305A3 (en) | 2007-07-12 |
Family
ID=38006313
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IN2006/000329 WO2007052305A2 (en) | 2005-08-30 | 2006-08-29 | Novel method of extraction of 6-o-protected trichlorogalac tose from the chlorinated mass |
Country Status (5)
Country | Link |
---|---|
CN (1) | CN101253188A (en) |
CA (1) | CA2620902A1 (en) |
GB (1) | GB2443146A (en) |
WO (1) | WO2007052305A2 (en) |
ZA (1) | ZA200801751B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012522035A (en) * | 2009-03-30 | 2012-09-20 | テート アンド ライル テクノロジー リミテッド | Process for removing dimethylamine |
US10370398B2 (en) | 2016-06-23 | 2019-08-06 | Tate & Lyle Technology Limited | Liquid-liquid extraction of DMF |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5498709A (en) * | 1994-10-17 | 1996-03-12 | Mcneil-Ppc, Inc. | Production of sucralose without intermediate isolation of crystalline sucralose-6-ester |
US5530106A (en) * | 1993-03-12 | 1996-06-25 | Mcneil-Ppc, Inc. | Recovery of sucralose intermediates |
US20060205936A1 (en) * | 2005-03-14 | 2006-09-14 | Sl Laboratories, Llc | Chlorination of Sucrose-6-esters |
-
2006
- 2006-08-29 CA CA002620902A patent/CA2620902A1/en not_active Abandoned
- 2006-08-29 CN CNA2006800313211A patent/CN101253188A/en active Pending
- 2006-08-29 GB GB0803649A patent/GB2443146A/en not_active Withdrawn
- 2006-08-29 WO PCT/IN2006/000329 patent/WO2007052305A2/en active Application Filing
-
2008
- 2008-02-22 ZA ZA200801751A patent/ZA200801751B/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5530106A (en) * | 1993-03-12 | 1996-06-25 | Mcneil-Ppc, Inc. | Recovery of sucralose intermediates |
US5498709A (en) * | 1994-10-17 | 1996-03-12 | Mcneil-Ppc, Inc. | Production of sucralose without intermediate isolation of crystalline sucralose-6-ester |
US20060205936A1 (en) * | 2005-03-14 | 2006-09-14 | Sl Laboratories, Llc | Chlorination of Sucrose-6-esters |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012522035A (en) * | 2009-03-30 | 2012-09-20 | テート アンド ライル テクノロジー リミテッド | Process for removing dimethylamine |
US10370398B2 (en) | 2016-06-23 | 2019-08-06 | Tate & Lyle Technology Limited | Liquid-liquid extraction of DMF |
US10899783B2 (en) | 2016-06-23 | 2021-01-26 | Tate & Lyle Technology Limited | Liquid-liquid extraction of DMF |
Also Published As
Publication number | Publication date |
---|---|
CN101253188A (en) | 2008-08-27 |
CA2620902A1 (en) | 2007-05-10 |
GB2443146A (en) | 2008-04-23 |
GB0803649D0 (en) | 2008-04-02 |
ZA200801751B (en) | 2009-10-28 |
WO2007052305A3 (en) | 2007-07-12 |
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