IE52222B1 - Sweet chlorine-substituted disaccharides - Google Patents
Sweet chlorine-substituted disaccharidesInfo
- Publication number
- IE52222B1 IE52222B1 IE2532/81A IE253281A IE52222B1 IE 52222 B1 IE52222 B1 IE 52222B1 IE 2532/81 A IE2532/81 A IE 2532/81A IE 253281 A IE253281 A IE 253281A IE 52222 B1 IE52222 B1 IE 52222B1
- Authority
- IE
- Ireland
- Prior art keywords
- chloro
- sucrose
- compound
- deoxy
- chlorination
- Prior art date
Links
- 235000009508 confectionery Nutrition 0.000 title description 10
- 150000002016 disaccharides Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 235000003599 food sweetener Nutrition 0.000 claims abstract description 15
- 239000003765 sweetening agent Substances 0.000 claims abstract description 15
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 13
- 150000003445 sucroses Chemical class 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 238000002360 preparation method Methods 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 2
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000008501 α-D-glucopyranosides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 16
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 10
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 5
- -1 4-chloro-4-deoxy- β-D-fructofuranosyl Chemical group 0.000 abstract description 4
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 abstract 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 229930006000 Sucrose Natural products 0.000 description 33
- 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 33
- 239000005720 sucrose Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000006188 syrup Substances 0.000 description 10
- 235000020357 syrup Nutrition 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 235000000346 sugar Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004606 Fillers/Extenders Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000021736 acetylation Effects 0.000 description 4
- 238000006640 acetylation reaction Methods 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 206010013911 Dysgeusia Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 229940112822 chewing gum Drugs 0.000 description 3
- 235000015218 chewing gum Nutrition 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 235000019204 saccharin Nutrition 0.000 description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 229940034610 toothpaste Drugs 0.000 description 3
- 239000000606 toothpaste Substances 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- NEHKMVAYGOUGMP-UHFFFAOYSA-N CC(=O)OCl.CC(=O)OCl.CC(=O)OCl.CC(=O)OCl Chemical compound CC(=O)OCl.CC(=O)OCl.CC(=O)OCl.CC(=O)OCl NEHKMVAYGOUGMP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- FBPFZTCFMRRESA-NQAPHZHOSA-N Sorbitol Chemical class OCC(O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-NQAPHZHOSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
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- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940109275 cyclamate Drugs 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- 230000006196 deacetylation Effects 0.000 description 2
- 238000003381 deacetylation reaction Methods 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 235000010755 mineral Nutrition 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
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- 238000010791 quenching Methods 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 235000014214 soft drink Nutrition 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/37—Halogenated sugars
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Saccharide Compounds (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8034666 | 1980-10-28 | ||
| GB8125621 | 1981-08-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE812532L IE812532L (en) | 1982-04-28 |
| IE52222B1 true IE52222B1 (en) | 1987-08-19 |
Family
ID=26277346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2532/81A IE52222B1 (en) | 1980-10-28 | 1981-10-28 | Sweet chlorine-substituted disaccharides |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4405654A (en:Method) |
| EP (1) | EP0050952B1 (en:Method) |
| AR (1) | AR231452A1 (en:Method) |
| AU (1) | AU539141B2 (en:Method) |
| CA (1) | CA1183133A (en:Method) |
| DE (1) | DE3160971D1 (en:Method) |
| DK (1) | DK160052C (en:Method) |
| ES (1) | ES8301600A1 (en:Method) |
| FI (1) | FI68842C (en:Method) |
| GR (1) | GR74682B (en:Method) |
| IE (1) | IE52222B1 (en:Method) |
| IL (1) | IL64140A (en:Method) |
| NO (1) | NO148958C (en:Method) |
| PT (1) | PT73888B (en:Method) |
| TR (1) | TR21455A (en:Method) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435440A (en) * | 1976-01-08 | 1984-03-06 | Tate & Lyle Limited | Sweeteners |
| EP0067535B1 (en) * | 1981-05-22 | 1985-01-30 | TATE & LYLE PUBLIC LIMITED COMPANY | Brominated sucrose derivatives |
| ATE10003T1 (de) * | 1981-08-21 | 1984-11-15 | Tate & Lyle Public Limited Company | 4'-halogen-substituierte sucrosederivate. |
| IE55619B1 (en) * | 1982-09-13 | 1990-11-21 | Tate & Lyle Plc | 6-derivatives of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose |
| GB8525871D0 (en) * | 1985-10-21 | 1985-11-27 | Tate & Lyle Plc | Chemical compound |
| GB8622345D0 (en) * | 1986-09-17 | 1986-10-22 | Tate & Lyle Plc | Sucrose derivatives |
| GB8627139D0 (en) * | 1986-11-13 | 1986-12-10 | Tate & Lyle Plc | Sweetening composition |
| US4820528A (en) * | 1987-03-27 | 1989-04-11 | Nabisco Brands, Inc. | Sweetener composition |
| ATE83612T1 (de) * | 1987-05-15 | 1993-01-15 | Wrigley W M Jun Co | Kaugummi mit geregelter suesse. |
| US4986991A (en) * | 1987-05-15 | 1991-01-22 | Wm Wrigley, Jr., Company | Chewing gum having an extended sweetness |
| US5270460A (en) * | 1988-09-27 | 1993-12-14 | Tate & Lyle Public Limited Company | Sucrose 6,4'-dicarboxylic esters |
| US5169658A (en) * | 1989-04-19 | 1992-12-08 | Wm. Wrigley Jr. Company | Polyvinyl acetate encapsulation of crystalline sucralose for use in chewing gum |
| US5059429A (en) * | 1989-10-27 | 1991-10-22 | Warner-Lambert Company | Sucralose sweetened chewing gum |
| WO1990007859A2 (en) * | 1989-11-22 | 1990-07-26 | Wm. Wrigley Jr. Company | Method of controlling release of sucralose in chewing gum and gum produced thereby |
| MX9100585A (es) * | 1990-08-21 | 1992-04-01 | Warner Lambert Co | Agentes edulcorantes de clorodeoxiazucar,estabilizados,en forma solida y metodos para preparar los mismos |
| US5061496A (en) * | 1990-08-21 | 1991-10-29 | Warner-Lambert Company | Stabilized chlorodeoxysugar sweetening agents in liquid medium and methods for preparing same |
| US5139798A (en) * | 1990-11-21 | 1992-08-18 | Wm. Wrigley Jr. Company | Polyvinyl acetate encapsulation of codried sucralose for use in chewing gum |
| US5169657A (en) * | 1991-07-17 | 1992-12-08 | Wm. Wrigley Jr. Company | Polyvinyl acetate encapsulation of sucralose from solutions for use in chewing gum |
| NZ509220A (en) * | 1998-07-07 | 2003-07-25 | Mcneil Ppc Inc | Method of improving sweetness delivery of sucralose by the addition of 2,4-dihydroxybenzoic acid |
| US6471948B1 (en) * | 2000-03-22 | 2002-10-29 | Church & Dwight Co. Inc. | Toothpaste compositions containing cetylpyridinium chloride |
| US6355229B1 (en) | 2001-06-27 | 2002-03-12 | Church & Dwight Co., Inc. | Oral composition containing cetylpyridinium chloride and guar hydroxypropyltrimonium chloride and method of using the same |
| US7049435B2 (en) | 2002-03-08 | 2006-05-23 | Tate & Lyle Public Limited Company | Extractive methods for purifying sucralose |
| US6998480B2 (en) | 2002-03-08 | 2006-02-14 | Tate & Lyle Public Limited Company | Process for improving sucralose purity and yield |
| US20040170735A2 (en) * | 2002-04-05 | 2004-09-02 | Mcneil-Ppc, Inc. | Methods and compositions for altering the sweetness delivery profile of sucralose |
| US6890581B2 (en) * | 2002-04-05 | 2005-05-10 | Tate & Lyle Public Limited Company | Methods for buffer stabilized aqueous deacylation |
| US20060088638A1 (en) * | 2002-07-29 | 2006-04-27 | Merkel Carolyn M | Method of improving sweetness delivery of sucralose |
| WO2005087020A1 (en) * | 2004-03-05 | 2005-09-22 | Richmond Chemical Corporation | High-intensity sweetener-polyol compositions |
| US20060188629A1 (en) * | 2005-01-21 | 2006-08-24 | Greg Liesen | Method for the purification of sucralose |
| KR20080016826A (ko) * | 2005-06-01 | 2008-02-22 | 팜드 메디케어 프리베이트 리미티드 | 용매 추출에 의한 염소화 수크로스 유도체의 정제 방법 |
| CA2623071A1 (en) * | 2005-09-22 | 2007-05-24 | Pharmed Medicare Pvt. Ltd. | Novel preparation of 6-o-acyl chlorosucrose from anhydrous chlorinated reaction mass |
| US20070100139A1 (en) * | 2005-10-31 | 2007-05-03 | Healthy Brands, Llc | Methods for chlorinating sucrose-6-ester |
| CN100420697C (zh) * | 2006-08-30 | 2008-09-24 | 河北苏科瑞科技有限公司 | 一种制备蔗糖-6-有机酸酯的方法 |
| AR070082A1 (es) * | 2008-01-04 | 2010-03-10 | Tate & Lyle Technology Ltd | Metodo para la produccion de sucralosa |
| EP2254677A1 (en) * | 2008-03-20 | 2010-12-01 | Tate & Lyle Technology Limited | Removal of acids from tertiary amide solvents |
| US8436157B2 (en) * | 2008-03-26 | 2013-05-07 | Tate & Lyle Technology Limited | Method for the production of sucralose |
| CN101981044B (zh) * | 2008-04-03 | 2014-08-06 | 塔特和莱利技术有限公司 | 碳水化合物浓度对三氯半乳蔗糖萃取效率的影响 |
| AR071134A1 (es) * | 2008-04-03 | 2010-05-26 | Tate & Lyle Technology Ltd | Cristalizacion de sucralosa a partir de chorros que contienen sucralosa |
| US20090299055A1 (en) * | 2008-04-03 | 2009-12-03 | Tate & Lyle Technology Limited | Purification of Sucralose Containing Feed Streams for Sucralose Crystallization |
| WO2009124113A1 (en) * | 2008-04-03 | 2009-10-08 | Tate & Lyle Technology Ltd. | Extraction of less polar impurities from sucralose containing aqueous feed streams |
| US8497367B2 (en) * | 2008-04-03 | 2013-07-30 | Tate & Lyle Technology Limited | Sucralose purification process |
| GB2474311B (en) * | 2009-10-12 | 2012-10-17 | Tate & Lyle Technology Ltd | Low temperature, single solvent process for the production of sucrose-6-ester |
| GB2474310B (en) | 2009-10-12 | 2012-02-29 | Tate & Lyle Technology Ltd | Process for the production of sucrose-6-ester |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1543167A (en) * | 1976-01-08 | 1979-03-28 | Tate & Lyle Ltd | Sweeteners |
| EP0030804B1 (en) * | 1979-12-18 | 1983-10-19 | TATE & LYLE PUBLIC LIMITED COMPANY | Crystalline 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose |
| GB2079749B (en) | 1980-07-08 | 1984-05-31 | Tate & Lyle Ltd | Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose |
-
1981
- 1981-10-16 CA CA000388116A patent/CA1183133A/en not_active Expired
- 1981-10-19 EP EP81304876A patent/EP0050952B1/en not_active Expired
- 1981-10-19 DE DE8181304876T patent/DE3160971D1/de not_active Expired
- 1981-10-26 NO NO813595A patent/NO148958C/no unknown
- 1981-10-26 GR GR66359A patent/GR74682B/el unknown
- 1981-10-27 DK DK474881A patent/DK160052C/da not_active IP Right Cessation
- 1981-10-27 TR TR21455A patent/TR21455A/xx unknown
- 1981-10-27 AU AU76841/81A patent/AU539141B2/en not_active Ceased
- 1981-10-27 PT PT73888A patent/PT73888B/pt unknown
- 1981-10-27 FI FI813357A patent/FI68842C/fi not_active IP Right Cessation
- 1981-10-28 AR AR287242A patent/AR231452A1/es active
- 1981-10-28 IL IL64140A patent/IL64140A/xx unknown
- 1981-10-28 ES ES506661A patent/ES8301600A1/es not_active Expired
- 1981-10-28 IE IE2532/81A patent/IE52222B1/en unknown
-
1982
- 1982-04-26 US US06/371,995 patent/US4405654A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES506661A0 (es) | 1982-12-16 |
| PT73888B (en) | 1983-01-25 |
| AU7684181A (en) | 1982-05-06 |
| NO813595L (no) | 1982-04-29 |
| FI68842C (fi) | 1985-11-11 |
| EP0050952B1 (en) | 1983-09-21 |
| IE812532L (en) | 1982-04-28 |
| FI813357L (fi) | 1982-04-29 |
| AU539141B2 (en) | 1984-09-13 |
| DK474881A (da) | 1982-04-29 |
| IL64140A (en) | 1984-10-31 |
| DK160052B (da) | 1991-01-21 |
| DE3160971D1 (en) | 1983-10-27 |
| FI68842B (fi) | 1985-07-31 |
| TR21455A (tr) | 1984-06-06 |
| EP0050952A1 (en) | 1982-05-05 |
| CA1183133A (en) | 1985-02-26 |
| NO148958B (no) | 1983-10-10 |
| US4405654A (en) | 1983-09-20 |
| DK160052C (da) | 1991-06-10 |
| PT73888A (en) | 1981-11-01 |
| AR231452A1 (es) | 1984-11-30 |
| IL64140A0 (en) | 1982-01-31 |
| GR74682B (en:Method) | 1984-07-03 |
| ES8301600A1 (es) | 1982-12-16 |
| NO148958C (no) | 1984-01-18 |
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