WO2011071890A1 - Methods for purifying monosaccharide mixtures containing ionic impurities - Google Patents
Methods for purifying monosaccharide mixtures containing ionic impurities Download PDFInfo
- Publication number
- WO2011071890A1 WO2011071890A1 PCT/US2010/059244 US2010059244W WO2011071890A1 WO 2011071890 A1 WO2011071890 A1 WO 2011071890A1 US 2010059244 W US2010059244 W US 2010059244W WO 2011071890 A1 WO2011071890 A1 WO 2011071890A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- glucose
- monosaccharide
- stream
- process stream
- exclusion resin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 99
- 239000012535 impurity Substances 0.000 title claims abstract description 35
- 150000002772 monosaccharides Chemical class 0.000 title claims abstract description 31
- 239000000203 mixture Substances 0.000 title description 36
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 27
- 229920005989 resin Polymers 0.000 claims description 51
- 239000011347 resin Substances 0.000 claims description 51
- WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 0.000 claims description 36
- 150000002500 ions Chemical class 0.000 claims description 35
- 230000007717 exclusion Effects 0.000 claims description 28
- 150000001720 carbohydrates Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 claims description 10
- WQZGKKKJIJFFOK-JFNONXLTSA-N L-mannopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-JFNONXLTSA-N 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 7
- SDOFMBGMRVAJNF-KUZWUUJSSA-N (2s,3s,4s)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NCC(O)[C@H](O)[C@@H](O)[C@@H](O)CO SDOFMBGMRVAJNF-KUZWUUJSSA-N 0.000 claims description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- -1 ammonium aldonates Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- 230000000112 colonic effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 159000000000 sodium salts Chemical group 0.000 claims 2
- 238000011437 continuous method Methods 0.000 claims 1
- 229940085991 phosphate ion Drugs 0.000 claims 1
- 239000012492 regenerant Substances 0.000 claims 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 13
- 229920001429 chelating resin Polymers 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001767 cationic compounds Chemical class 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002892 organic cations Chemical class 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-SOOFDHNKSA-N D-ribopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-SOOFDHNKSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 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
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 229960002737 fructose Drugs 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- WCWOEQFAYSXBRK-RWOPYEJCSA-N (2r,3s,4s,5s,6r)-2-amino-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O WCWOEQFAYSXBRK-RWOPYEJCSA-N 0.000 description 1
- WCWOEQFAYSXBRK-GASJEMHNSA-N (3r,4s,5s,6r)-2-amino-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound NC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WCWOEQFAYSXBRK-GASJEMHNSA-N 0.000 description 1
- APCLRHPWFCQIMG-UHFFFAOYSA-N 4-(5,6-dimethoxy-1-benzothiophen-2-yl)-4-oxobutanoic acid Chemical compound C1=C(OC)C(OC)=CC2=C1SC(C(=O)CCC(O)=O)=C2 APCLRHPWFCQIMG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 229920002271 DEAE-Sepharose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-KLVWXMOXSA-N L-gluconic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-KLVWXMOXSA-N 0.000 description 1
- 229940125791 MSA-2 Drugs 0.000 description 1
- 108010057081 Merozoite Surface Protein 1 Proteins 0.000 description 1
- 101710162106 Merozoite surface antigen 2 Proteins 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- GZCGUPFRVQAUEE-VANKVMQKSA-N aldehydo-L-glucose Chemical group OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-VANKVMQKSA-N 0.000 description 1
- GZCGUPFRVQAUEE-BXKVDMCESA-N aldehydo-L-mannose Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-BXKVDMCESA-N 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- QGAVSDVURUSLQK-UHFFFAOYSA-N ammonium heptamolybdate Chemical compound N.N.N.N.N.N.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Mo].[Mo].[Mo].[Mo].[Mo].[Mo].[Mo] QGAVSDVURUSLQK-UHFFFAOYSA-N 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000012539 chromatography resin Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 238000001032 ion-exclusion chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
- B01D15/1814—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns recycling of the fraction to be distributed
- B01D15/1821—Simulated moving beds
- B01D15/185—Simulated moving beds characterized by the components to be separated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
- B01D15/365—Ion-exclusion
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
- C13B20/00—Purification of sugar juices
- C13B20/14—Purification of sugar juices using ion-exchange materials
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K1/00—Glucose; Glucose-containing syrups
Definitions
- compositions include plural referents unless the context clearly dictates otherwise.
- reference to “a composition” includes mixtures of two or more of the disclosed compounds, the disclosed compounds in combination with other pharmaceutically active compounds, or the disclosed compounds, solvates or diluents of the compounds as defined herein with other pharmaceutically acceptable ingredients.
- Ion exclusion systems may employ similar resins used in ion exchange systems, but differ in that the ionic functionality of the resin is the same as that of the electrolyte and, therefore, there is little to no net exchange of ions.
- the ion exclusion resin does not contain a mixture of strongly acidic resin (e.g., a resin bearing sulfonic acid residues) and weakly basic resin (e.g., a resin bearing tertiary amine groups); for instance, in one aspect, the ion exclusion resin does not include a "mixed bed.”
- the ion exclusion resin can comprise a sulfonated polymer, for example, a sulfonated polystyrene with divinylbenzene (DVB) cross-linking which imparts physical stability to the resin polymer.
- VVB divinylbenzene
- a mixture comprising L- mannose and L-glucose can be subjected to simulated moving bed chromatography as disclosed herein. Initially, the mixture comprises L-mannose and L-glucose and the following ionic impurities: a.
- L-mannose is removed or substantially removed from the mixture after SMB chromatography is performed. While the ion exclusion resin within the SMB unit is continuously contacted with the mixture and eluted with water, a continuous stream containing the deionized monosaccharides is produced along with a second stream containing the ionic by-products.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Sustainable Development (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Saccharide Compounds (AREA)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112012013679A BR112012013679A8 (pt) | 2009-12-07 | 2010-12-07 | Método de separação de uma impureza iônica de uma corrente de processo contendo monossacarídeos, método de separação de uma impureza iônica de uma corrente de processo contendo sacarídeos, método contínuo de separação de impurezas catiônicas e aniônicas de uma corrente de processo contendo l-monossacarídeos, l-glicose possuindo uma pureza de pelo menos 98%, composição farmacêutica e método para preparo do cólon |
JP2012542243A JP2013512931A (ja) | 2009-12-07 | 2010-12-07 | イオン性不純物を含有する単糖混合物を精製する方法 |
MX2012006453A MX2012006453A (es) | 2009-12-07 | 2010-12-07 | Metodos para purificar mezclas de monosacaridos que contienen impurezas ionicas. |
EP10795131A EP2509695A1 (en) | 2009-12-07 | 2010-12-07 | Methods for purifying monosaccharide mixtures containing ionic impurities |
RU2012125189/04A RU2012125189A (ru) | 2009-12-07 | 2010-12-07 | Способ очистки смесей моносахаридов, содержащих ионные примеси |
SG2012039988A SG181150A1 (en) | 2009-12-07 | 2010-12-07 | Methods for purifying monosaccharide mixtures containing ionic impurities |
CN2010800609503A CN102725042A (zh) | 2009-12-07 | 2010-12-07 | 包含离子杂质的单糖混合物的纯化方法 |
CA2783198A CA2783198A1 (en) | 2009-12-07 | 2010-12-07 | Methods for purifying monosaccharide mixtures containing ionic impurities |
AU2010328366A AU2010328366A1 (en) | 2009-12-07 | 2010-12-07 | Methods for purifying monosaccharide mixtures containing ionic impurities |
IL220226A IL220226A0 (en) | 2009-12-07 | 2012-06-07 | Methods for purifying monosaccharide mixtures containing ionic impurities |
US13/735,805 US20130338086A1 (en) | 2009-12-07 | 2013-01-07 | Methods for purifying monosaccharide mixtures containing ionic impurities |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3082756A1 (fr) * | 2018-06-26 | 2019-12-27 | Seprosys | Procede de separation de molecules ionisees dans une solution en contenant |
US10543460B2 (en) | 2013-03-08 | 2020-01-28 | Xyleco, Inc. | Upgrading process streams |
Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US556707A (en) | 1896-03-17 | steahan | ||
US4522726A (en) | 1984-07-30 | 1985-06-11 | Progress Equities Incorporated | Advanced separation device and method |
US4581447A (en) | 1984-08-13 | 1986-04-08 | Uop Inc. | Process for making a mixture of L-glucose and L-mannose |
US4764276A (en) | 1984-07-30 | 1988-08-16 | Advanced Separation Technologies Incorporated | Device for continuous contacting of fluids and solids |
US4970302A (en) | 1989-04-27 | 1990-11-13 | Allied-Signal Inc. | Selective catalytic conversion of cyanohydrins to their corresponding aldehydes without concurrent amine formation |
US5538637A (en) | 1993-09-29 | 1996-07-23 | Tennessee Valley Authority | Process for separating acid-sugar mixtures using ion exclusion chromatography |
US5547817A (en) | 1994-10-20 | 1996-08-20 | Fuji Photo Film Co., Ltd. | Photographic processing using a novel chelating complex |
US5667693A (en) * | 1995-02-02 | 1997-09-16 | Tennessee Valley Authority | Exclusion chromatographic separation of ionic from nonionic solutes |
US5928429A (en) * | 1997-10-31 | 1999-07-27 | Imperial Holly Corporation | Process for the enhancement of recovery of sugar |
US5968362A (en) | 1997-08-04 | 1999-10-19 | Controlled Enviromental Systems Corporation | Method for the separation of acid from sugars |
JP2004236623A (ja) * | 2003-02-07 | 2004-08-26 | Kagawa Univ | L−グルコースの製造方法 |
US20050244934A1 (en) * | 2004-04-13 | 2005-11-03 | Brian Foody | Recovery of inorganic salt during processing of lignocellulosic feedstocks |
WO2006007691A1 (en) * | 2004-07-16 | 2006-01-26 | Iogen Energy Corporation | Method of obtaining a product sugar stream from cellulosic biomass |
US20080041366A1 (en) | 2006-08-18 | 2008-02-21 | Iogen Energy Corporation | Method of obtaining an organic salt or acid from an aqueous sugar stream |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0409104D0 (en) * | 2004-04-23 | 2004-05-26 | Norgine Europe Bv | Compressed pharmaceutical compositions |
-
2010
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- 2010-12-07 CA CA2783198A patent/CA2783198A1/en not_active Abandoned
- 2010-12-07 SG SG2012039988A patent/SG181150A1/en unknown
- 2010-12-07 BR BR112012013679A patent/BR112012013679A8/pt not_active IP Right Cessation
- 2010-12-07 EP EP10795131A patent/EP2509695A1/en not_active Withdrawn
- 2010-12-07 JP JP2012542243A patent/JP2013512931A/ja active Pending
- 2010-12-07 AU AU2010328366A patent/AU2010328366A1/en not_active Abandoned
- 2010-12-07 KR KR1020127017570A patent/KR20120112518A/ko not_active Application Discontinuation
- 2010-12-07 WO PCT/US2010/059244 patent/WO2011071890A1/en active Application Filing
- 2010-12-07 MX MX2012006453A patent/MX2012006453A/es not_active Application Discontinuation
- 2010-12-07 RU RU2012125189/04A patent/RU2012125189A/ru not_active Application Discontinuation
-
2012
- 2012-06-06 CL CL2012001488A patent/CL2012001488A1/es unknown
- 2012-06-07 IL IL220226A patent/IL220226A0/en unknown
-
2013
- 2013-01-07 US US13/735,805 patent/US20130338086A1/en not_active Abandoned
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US556707A (en) | 1896-03-17 | steahan | ||
US4522726A (en) | 1984-07-30 | 1985-06-11 | Progress Equities Incorporated | Advanced separation device and method |
US4764276A (en) | 1984-07-30 | 1988-08-16 | Advanced Separation Technologies Incorporated | Device for continuous contacting of fluids and solids |
US4581447A (en) | 1984-08-13 | 1986-04-08 | Uop Inc. | Process for making a mixture of L-glucose and L-mannose |
US4970302A (en) | 1989-04-27 | 1990-11-13 | Allied-Signal Inc. | Selective catalytic conversion of cyanohydrins to their corresponding aldehydes without concurrent amine formation |
US5538637A (en) | 1993-09-29 | 1996-07-23 | Tennessee Valley Authority | Process for separating acid-sugar mixtures using ion exclusion chromatography |
US5628907A (en) * | 1993-09-29 | 1997-05-13 | Tennessee Valley Authority | Process for separating acid-sugar mixtures using ion exclusion chromatography |
US5547817A (en) | 1994-10-20 | 1996-08-20 | Fuji Photo Film Co., Ltd. | Photographic processing using a novel chelating complex |
US5667693A (en) * | 1995-02-02 | 1997-09-16 | Tennessee Valley Authority | Exclusion chromatographic separation of ionic from nonionic solutes |
US5968362A (en) | 1997-08-04 | 1999-10-19 | Controlled Enviromental Systems Corporation | Method for the separation of acid from sugars |
US6391204B1 (en) | 1997-08-04 | 2002-05-21 | Controlled Environmental Systems Corporation | Method for the separation of acid from sugars |
US6419828B1 (en) * | 1997-08-04 | 2002-07-16 | Controlled Environmental Systems Corporation | Method for the separation of acid from sugars |
US5928429A (en) * | 1997-10-31 | 1999-07-27 | Imperial Holly Corporation | Process for the enhancement of recovery of sugar |
JP2004236623A (ja) * | 2003-02-07 | 2004-08-26 | Kagawa Univ | L−グルコースの製造方法 |
US20050244934A1 (en) * | 2004-04-13 | 2005-11-03 | Brian Foody | Recovery of inorganic salt during processing of lignocellulosic feedstocks |
WO2006007691A1 (en) * | 2004-07-16 | 2006-01-26 | Iogen Energy Corporation | Method of obtaining a product sugar stream from cellulosic biomass |
US20080041366A1 (en) | 2006-08-18 | 2008-02-21 | Iogen Energy Corporation | Method of obtaining an organic salt or acid from an aqueous sugar stream |
Non-Patent Citations (3)
Title |
---|
NEUMAN R P ET AL: "Sulfuric acid-sugar separation by ion exclusion", REACTIVE POLYMERS, ION EXCHANGERS, SORBENTS, ELSEVIER, vol. 5, no. 1, 1 January 1987 (1987-01-01), pages 55 - 61, XP024146177, ISSN: 0167-6989, [retrieved on 19870101], DOI: DOI:10.1016/0167-6989(87)90165-6 * |
R. A. MEYERS: "Handbook of Petroleum Refining Processes", 1986, MCGRAW-HILL BOOK COMPANY, pages: 8.85 - 8.87 |
RAYMER G S ET AL: "An open-label trial of L-glucose as a colon-cleansing agent before colonoscopy", GASTROINTESTINAL ENDOSCOPY, ELSEVIER, NL, vol. 58, no. 1, 1 July 2003 (2003-07-01), pages 30 - 35, XP004855636, ISSN: 0016-5107, DOI: DOI:10.1067/MGE.2003.293 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10543460B2 (en) | 2013-03-08 | 2020-01-28 | Xyleco, Inc. | Upgrading process streams |
FR3082756A1 (fr) * | 2018-06-26 | 2019-12-27 | Seprosys | Procede de separation de molecules ionisees dans une solution en contenant |
Also Published As
Publication number | Publication date |
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KR20120112518A (ko) | 2012-10-11 |
US20130338086A1 (en) | 2013-12-19 |
JP2013512931A (ja) | 2013-04-18 |
CN102725042A (zh) | 2012-10-10 |
CL2012001488A1 (es) | 2012-10-12 |
CA2783198A1 (en) | 2011-06-16 |
IL220226A0 (en) | 2012-09-24 |
AU2010328366A1 (en) | 2012-06-21 |
BR112012013679A2 (pt) | 2016-08-16 |
BR112012013679A8 (pt) | 2016-09-06 |
EP2509695A1 (en) | 2012-10-17 |
SG181150A1 (en) | 2012-07-30 |
RU2012125189A (ru) | 2014-01-20 |
MX2012006453A (es) | 2012-11-23 |
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