JP2001511812A - 塩化スクロースのクロマトグラフィー精製 - Google Patents
塩化スクロースのクロマトグラフィー精製Info
- Publication number
- JP2001511812A JP2001511812A JP53598198A JP53598198A JP2001511812A JP 2001511812 A JP2001511812 A JP 2001511812A JP 53598198 A JP53598198 A JP 53598198A JP 53598198 A JP53598198 A JP 53598198A JP 2001511812 A JP2001511812 A JP 2001511812A
- Authority
- JP
- Japan
- Prior art keywords
- sucrose
- adsorbent
- fixed bed
- chloride
- reaction mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229930006000 Sucrose Natural products 0.000 title claims abstract description 43
- 239000005720 sucrose Substances 0.000 title claims abstract description 43
- 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 title claims abstract description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title claims abstract description 27
- 238000011097 chromatography purification Methods 0.000 title description 2
- 239000003463 adsorbent Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000011541 reaction mixture Substances 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 9
- 239000007791 liquid phase Substances 0.000 claims abstract description 3
- 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 claims description 20
- 239000004376 Sucralose Substances 0.000 claims description 19
- 235000019408 sucralose Nutrition 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- -1 sucrose chlorides Chemical class 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000003511 tertiary amides Chemical class 0.000 claims description 4
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- 239000003729 cation exchange resin Substances 0.000 claims 1
- 238000013375 chromatographic separation Methods 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 125000003142 tertiary amide group Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000010828 elution Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 238000013459 approach Methods 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000001212 derivatisation Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000622 liquid--liquid extraction Methods 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- BAQAVOSOZGMPRM-UGDNZRGBSA-N (2R,3R,4R,5S,6R)-2-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-5-chloro-6-(hydroxymethyl)oxane-3,4-diol 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-UGDNZRGBSA-N 0.000 description 1
- FVVCFHXLWDDRHG-UPLOTWCNSA-N (2s,3r,4s,5r,6r)-2-[(2r,3s,4r,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 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]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O1 FVVCFHXLWDDRHG-UPLOTWCNSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ONSYTLVODJIYDC-UHFFFAOYSA-N chloroamine;hydrochloride Chemical class Cl.ClN ONSYTLVODJIYDC-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WRWJHZAQLXGJQX-UHFFFAOYSA-N ethyl acetate;formic acid Chemical compound OC=O.CCOC(C)=O WRWJHZAQLXGJQX-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 235000019534 high fructose corn syrup Nutrition 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
-
- 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
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 1番目の塩化スクロースを含有しかつ上記1番目の塩化スクロースとは 異なる他の少なくとも1種の塩化スクロース、塩および溶媒から成る群から選択 される少なくとも1種の追加的成分を含有する反応混合物を液相中で分離する方 法であって、上記反応混合物を固体状吸着材の固定床の上に注入し、そしてそれ を、 (a)該1番目の塩化スクロースが該吸着材の中をある速度で通ることで、上記 1番目の塩化スクロースを豊富に含有する1番目の回収可能生成物流れが生じ、 該速度とは異なる速度で、 (b)上記追加的成分の少なくとも1つが該吸着材の中を通ることで、上記追加 的成分を豊富に含有する2番目の回収可能流れが少なくとも1つ生じるように、 脱離剤で処理することによる方法。 2. 該反応混合物が式: [式中、いろいろな塩化スクロース類に関して:] で表される二塩化スクロース類、三塩化スクロース類および四塩化スクロース類 から成る群から選択される少なくとも2種類の塩化スクロース類を含有する請求 の範囲第1項記載の方法。 3. 該反応混合物がスクラロースの製造で用いられる実際の工程流れである 請求の範囲第1項記載の方法。 4. 該塩がアルカリ、アルカリ土類金属、アンモニウムおよびアルキルアン モニウムの塩化物から成る群から選択される塩を包含する請求の範囲第1、2ま たは3項記載の方法。 5. 該溶媒が第三級アミドである請求の範囲第1、2または3項記載の方法 。 6. 該第三級アミドがN,N−ジメチルホルムアミドである請求の範囲第5 項記載の方法。 7. 該固定床の固体状吸着材がシリカゲルでありそして該脱離剤が有機溶媒 である請求の範囲第1、2および3項記載の方法。 8. 該固定床の固体状吸着材が多孔質ゲルのカチオン交換樹脂であ りそして該脱離剤が水である請求の範囲第1、2または3項記載の方法。 9. 該クロマトグラフィー分離を断続、連続−断続または連続様式で実施す る請求の範囲第1、2または3項記載の方法。 10. 該固定床の吸着材がカラム内に入っており、供給材料および脱離剤を 1つの末端部の所で注入して軸方向に移動させた後、分離を受けたか或は豊富に なった画分をもう一方の末端部の所で集める請求の範囲第1、2または3項記載 の方法。 11. 該固定床の吸着材がカラム内に入っており、供給材料および脱離剤を 周囲の所で注入して半径方向に移動させた後、分離を受けたか或は豊富になった 画分を中心部に位置する内部路に通して集める請求の範囲第1、2または3項記 載の方法。 12. 該固定床の吸着材がカラム内に入っており、供給材料および脱離剤を 中心部に位置する内部路に通して注入して半径方向に移動させた後、分離を受け たか或は豊富になった画分を周囲の所で集める請求の範囲第1、2または3項記 載の方法。 13. 該固体状吸着材の固定床が垂直に取り付けられた回転する環内に入っ ており、供給材料および脱離剤を上部の所で注入し、そして分離を受けたか或は 豊富になった画分を下部の所で集める請求の範囲第1、2または3項記載の方法 。 14. 該固体状吸着材の固定床が密封ループ内に位置する数個の連続セクシ ョンまたはカラム内に入っていて、該セクションまたはカラムの各々が個別に流 体を受け取りかつ解放する能力を有しかつそれに供給材料用口と脱離剤用口と取 り出し用口の固定配列が備わっていて、該固定配列が、該固定床の吸着材の向流 移動を模擬するように、液体の流れ の方向と並流の方向に向かって決まった間隔で作動するラチェット式になってい る請求の範囲第1、2または3項記載の方法。 15. 上記1番目の塩化スクロースが式:[式中、 R2、R4およびR7=Cl;R1=アシルオキシ基、R6=OH;そしてR3および R5=H] で表される請求の範囲第1または3項記載の方法 16. 該アシルオキシ基がアセトキシ基である請求の範囲第15項記載の方 法。 17. 該アシルオキシ基がベンゾイルオキシ基である請求の範囲第15項記 載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4698097P | 1997-02-13 | 1997-02-13 | |
US60/046,980 | 1997-02-13 | ||
PCT/US1998/002927 WO1998035974A1 (en) | 1997-02-13 | 1998-02-11 | Chromatographic purification of chlorinated sucrose |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009281022A Division JP5132665B2 (ja) | 1997-02-13 | 2009-12-10 | 塩素化スクロースのクロマトグラフィー精製 |
Publications (2)
Publication Number | Publication Date |
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JP2001511812A true JP2001511812A (ja) | 2001-08-14 |
JP4623763B2 JP4623763B2 (ja) | 2011-02-02 |
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JP53598198A Expired - Fee Related JP4623763B2 (ja) | 1997-02-13 | 1998-02-11 | 塩素化スクロースのクロマトグラフィー精製 |
JP2009281022A Expired - Fee Related JP5132665B2 (ja) | 1997-02-13 | 2009-12-10 | 塩素化スクロースのクロマトグラフィー精製 |
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US (1) | US5977349A (ja) |
EP (1) | EP0970096B1 (ja) |
JP (2) | JP4623763B2 (ja) |
KR (2) | KR100531261B1 (ja) |
AT (1) | ATE282044T1 (ja) |
AU (1) | AU6167598A (ja) |
BR (1) | BR9807377B1 (ja) |
CA (1) | CA2280784A1 (ja) |
DE (1) | DE69827482T2 (ja) |
DK (1) | DK0970096T3 (ja) |
ES (1) | ES2231964T3 (ja) |
IL (1) | IL131394A0 (ja) |
NO (1) | NO313553B1 (ja) |
NZ (1) | NZ337573A (ja) |
PT (1) | PT970096E (ja) |
TR (1) | TR199902413T2 (ja) |
WO (1) | WO1998035974A1 (ja) |
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JP2005526075A (ja) * | 2002-03-08 | 2005-09-02 | テート アンド ライル パブリック リミテッド カンパニー | スクラロース精製のための抽出法 |
JP2005526767A (ja) * | 2002-03-08 | 2005-09-08 | テート アンド ライル パブリック リミテッド カンパニー | スクラロースの純度および収率を改善するためのプロセス |
WO2006088017A1 (ja) * | 2005-02-16 | 2006-08-24 | National University Corporation Hokkaido University | 4位ハロゲン化ガラクトース含有糖鎖及びその応用 |
JP2009509925A (ja) * | 2005-08-30 | 2009-03-12 | ファームド メディケア プライヴェート リミテッド | 疎水性親和性クロマトグラフィに基づく塩素化スクロースの生成方法 |
JP2011515454A (ja) * | 2008-03-26 | 2011-05-19 | テート アンド ライル テクノロジー リミテッド | スクラロースを製造する方法 |
JP2012522035A (ja) * | 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 | ジメチルアミンを除去するプロセス |
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DK0970096T3 (da) * | 1997-02-13 | 2005-03-21 | Tate & Lyle Plc | Kromatografisk oprensning af chloreret saccharose |
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US20060276639A1 (en) * | 2005-06-01 | 2006-12-07 | Healthy Brands, Llc | Conversion of sucralose-6-ester to sucralose |
US20100197906A1 (en) * | 2005-06-06 | 2010-08-05 | Pharmed Medicare Private Limited | Method for purification of chlorinated sucrose derivatives from reaction mixture by chromatography |
JP2009538293A (ja) * | 2006-05-23 | 2009-11-05 | ヴイ ビー メディケア プライヴェート リミテッド | トリクロロガラクトスクロース製造のプロセスストリームからのジメチルホルムアミド及び他の溶媒の回収 |
CN101029062B (zh) * | 2007-04-09 | 2011-06-15 | 淄博联技甜味剂有限公司 | 三氯蔗糖的合成工艺 |
US8436156B2 (en) * | 2008-01-04 | 2013-05-07 | Tate & Lyle Technology Limited | Method for the production of sucralose |
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GB2544217B (en) | 2014-08-08 | 2020-03-25 | Tate & Lyle Tech Ltd | Chlorination of sucrose-6-esters |
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ZA807578B (en) * | 1979-12-18 | 1981-11-25 | Tate & Lyle Patent Holdings | Crystalline 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose |
EP0043649B1 (en) * | 1980-07-08 | 1984-09-12 | TATE & LYLE PUBLIC LIMITED COMPANY | Process for the preparation of 4, 1',6'-trichloro-4,1',6'-trideoxygalactosucrose (tgs) |
ZA817425B (en) * | 1980-10-28 | 1982-10-27 | Tate & Lyle Patent Holdings | Sweet chlorine-substituted disaccharides |
DE3262120D1 (en) * | 1981-05-22 | 1985-03-14 | Tate & Lyle Plc | Brominated sucrose derivatives |
GB8316201D0 (en) * | 1982-09-13 | 1983-07-20 | Tate & Lyle Plc | Sucrose derivatives |
GB8822673D0 (en) * | 1988-09-27 | 1988-11-02 | Tate & Lyle Plc | Selective acylation of sugars |
US4980463A (en) * | 1989-07-18 | 1990-12-25 | Noramco, Inc. | Sucrose-6-ester chlorination |
JPH06253879A (ja) * | 1993-03-01 | 1994-09-13 | Snow Brand Milk Prod Co Ltd | グルクロン酸結合オリゴ糖の分離方法 |
US5530106A (en) * | 1993-03-12 | 1996-06-25 | Mcneil-Ppc, Inc. | Recovery of sucralose intermediates |
EP0687491A1 (en) * | 1994-06-16 | 1995-12-20 | Daicel Chemical Industries, Ltd. | Simulated moving bed chromatographic separation process |
US5498709A (en) * | 1994-10-17 | 1996-03-12 | Mcneil-Ppc, Inc. | Production of sucralose without intermediate isolation of crystalline sucralose-6-ester |
DK0970096T3 (da) * | 1997-02-13 | 2005-03-21 | Tate & Lyle Plc | Kromatografisk oprensning af chloreret saccharose |
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1998
- 1998-02-11 DK DK98906453T patent/DK0970096T3/da active
- 1998-02-11 PT PT98906453T patent/PT970096E/pt unknown
- 1998-02-11 AU AU61675/98A patent/AU6167598A/en not_active Abandoned
- 1998-02-11 IL IL13139498A patent/IL131394A0/xx not_active IP Right Cessation
- 1998-02-11 KR KR10-1999-7007368A patent/KR100531261B1/ko not_active IP Right Cessation
- 1998-02-11 NZ NZ337573A patent/NZ337573A/en unknown
- 1998-02-11 KR KR1020057014662A patent/KR100619874B1/ko not_active IP Right Cessation
- 1998-02-11 AT AT98906453T patent/ATE282044T1/de not_active IP Right Cessation
- 1998-02-11 US US09/022,071 patent/US5977349A/en not_active Expired - Lifetime
- 1998-02-11 JP JP53598198A patent/JP4623763B2/ja not_active Expired - Fee Related
- 1998-02-11 WO PCT/US1998/002927 patent/WO1998035974A1/en active IP Right Grant
- 1998-02-11 DE DE69827482T patent/DE69827482T2/de not_active Expired - Fee Related
- 1998-02-11 TR TR1999/02413T patent/TR199902413T2/xx unknown
- 1998-02-11 EP EP98906453A patent/EP0970096B1/en not_active Expired - Lifetime
- 1998-02-11 ES ES98906453T patent/ES2231964T3/es not_active Expired - Lifetime
- 1998-02-11 CA CA002280784A patent/CA2280784A1/en not_active Abandoned
- 1998-02-11 BR BRPI9807377-0A patent/BR9807377B1/pt not_active IP Right Cessation
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1999
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US5298611A (en) * | 1993-03-12 | 1994-03-29 | Mcneil-Ppc, Inc. | Sucralose pentaester production |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005526075A (ja) * | 2002-03-08 | 2005-09-02 | テート アンド ライル パブリック リミテッド カンパニー | スクラロース精製のための抽出法 |
JP2005526767A (ja) * | 2002-03-08 | 2005-09-08 | テート アンド ライル パブリック リミテッド カンパニー | スクラロースの純度および収率を改善するためのプロセス |
JP4916089B2 (ja) * | 2002-03-08 | 2012-04-11 | テート アンド ライル テクノロジー リミテッド | スクラロースの純度および収率を改善するためのプロセス |
WO2006088017A1 (ja) * | 2005-02-16 | 2006-08-24 | National University Corporation Hokkaido University | 4位ハロゲン化ガラクトース含有糖鎖及びその応用 |
JP2009509925A (ja) * | 2005-08-30 | 2009-03-12 | ファームド メディケア プライヴェート リミテッド | 疎水性親和性クロマトグラフィに基づく塩素化スクロースの生成方法 |
JP2011515454A (ja) * | 2008-03-26 | 2011-05-19 | テート アンド ライル テクノロジー リミテッド | スクラロースを製造する方法 |
JP2012522035A (ja) * | 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 | ジメチルアミンを除去するプロセス |
Also Published As
Publication number | Publication date |
---|---|
NO313553B1 (no) | 2002-10-21 |
ATE282044T1 (de) | 2004-11-15 |
NZ337573A (en) | 2000-06-23 |
CA2280784A1 (en) | 1998-08-20 |
AU6167598A (en) | 1998-09-08 |
WO1998035974A1 (en) | 1998-08-20 |
KR100619874B1 (ko) | 2006-09-06 |
DK0970096T3 (da) | 2005-03-21 |
EP0970096B1 (en) | 2004-11-10 |
EP0970096A1 (en) | 2000-01-12 |
BR9807377B1 (pt) | 2009-12-01 |
PT970096E (pt) | 2005-03-31 |
KR100531261B1 (ko) | 2005-11-28 |
TR199902413T2 (xx) | 2000-01-21 |
NO993920L (no) | 1999-10-11 |
JP2010090160A (ja) | 2010-04-22 |
US5977349A (en) | 1999-11-02 |
IL131394A0 (en) | 2001-01-28 |
ES2231964T3 (es) | 2005-05-16 |
BR9807377A (pt) | 2001-06-19 |
DE69827482T2 (de) | 2005-12-15 |
DE69827482D1 (de) | 2004-12-16 |
JP5132665B2 (ja) | 2013-01-30 |
NO993920D0 (no) | 1999-08-13 |
KR20050093860A (ko) | 2005-09-23 |
JP4623763B2 (ja) | 2011-02-02 |
KR20000071081A (ko) | 2000-11-25 |
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