CA2332323A1 - Electrodialysis methods for purification and recovery of gluconic acid derivatives - Google Patents
Electrodialysis methods for purification and recovery of gluconic acid derivatives Download PDFInfo
- Publication number
- CA2332323A1 CA2332323A1 CA002332323A CA2332323A CA2332323A1 CA 2332323 A1 CA2332323 A1 CA 2332323A1 CA 002332323 A CA002332323 A CA 002332323A CA 2332323 A CA2332323 A CA 2332323A CA 2332323 A1 CA2332323 A1 CA 2332323A1
- Authority
- CA
- Canada
- Prior art keywords
- gluconic acid
- acid derivative
- klg
- compartment
- process according
- 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.)
- Abandoned
Links
- 238000000909 electrodialysis Methods 0.000 title claims abstract description 147
- 238000000034 method Methods 0.000 title claims abstract description 72
- 238000011084 recovery Methods 0.000 title description 34
- 238000000746 purification Methods 0.000 title description 18
- VBUYCZFBVCCYFD-UHFFFAOYSA-N D-arabino-2-Hexulosonic acid Natural products OCC(O)C(O)C(O)C(=O)C(O)=O VBUYCZFBVCCYFD-UHFFFAOYSA-N 0.000 claims abstract description 145
- VBUYCZFBVCCYFD-NUNKFHFFSA-N 2-dehydro-L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-NUNKFHFFSA-N 0.000 claims abstract description 140
- 238000000855 fermentation Methods 0.000 claims abstract description 77
- 230000004151 fermentation Effects 0.000 claims abstract description 77
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 230000008569 process Effects 0.000 claims abstract description 47
- 238000000338 in vitro Methods 0.000 claims abstract description 29
- 239000012528 membrane Substances 0.000 claims description 131
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 95
- 239000012141 concentrate Substances 0.000 claims description 83
- 239000000243 solution Substances 0.000 claims description 53
- -1 gluconic acid derivative anion Chemical class 0.000 claims description 51
- 239000003011 anion exchange membrane Substances 0.000 claims description 47
- 230000007935 neutral effect Effects 0.000 claims description 43
- 239000012535 impurity Substances 0.000 claims description 40
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 38
- 239000007864 aqueous solution Substances 0.000 claims description 24
- 150000001450 anions Chemical class 0.000 claims description 22
- 150000007522 mineralic acids Chemical class 0.000 claims description 22
- 239000005515 coenzyme Substances 0.000 claims description 20
- 229960005070 ascorbic acid Drugs 0.000 claims description 19
- 235000010323 ascorbic acid Nutrition 0.000 claims description 19
- 239000011668 ascorbic acid Substances 0.000 claims description 19
- 150000001449 anionic compounds Chemical class 0.000 claims description 18
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 18
- 238000005349 anion exchange Methods 0.000 claims description 13
- 238000005341 cation exchange Methods 0.000 claims description 13
- 238000001599 direct drying Methods 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 5
- 150000004692 metal hydroxides Chemical class 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229950006191 gluconic acid Drugs 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- RGHNJXZEOKUKBD-SKNVOMKLSA-N L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SKNVOMKLSA-N 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims description 3
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 claims description 3
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002699 waste material Substances 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 239000012264 purified product Substances 0.000 claims 2
- 235000010633 broth Nutrition 0.000 description 32
- 239000012527 feed solution Substances 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 27
- 239000002585 base Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 229910001868 water Inorganic materials 0.000 description 18
- 238000002425 crystallisation Methods 0.000 description 16
- 230000008025 crystallization Effects 0.000 description 16
- 238000011033 desalting Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 244000005700 microbiome Species 0.000 description 12
- 150000001768 cations Chemical class 0.000 description 10
- 238000013508 migration Methods 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 239000003957 anion exchange resin Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 239000003729 cation exchange resin Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000008151 electrolyte solution Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229910001410 inorganic ion Inorganic materials 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Chemical group 0.000 description 2
- 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 2
- 229920000557 Nafion® Polymers 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- MNIQECRMTVGZBM-UHFFFAOYSA-N 3-(1-methylpyrrolidin-2-yl)pyridine;7h-purin-6-amine Chemical compound NC1=NC=NC2=C1NC=N2.CN1CCCC1C1=CC=CN=C1 MNIQECRMTVGZBM-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 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 1
- 239000005715 Fructose Substances 0.000 description 1
- 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 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 235000021310 complex sugar Nutrition 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000009285 membrane fouling Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000021309 simple sugar Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/58—Aldonic, ketoaldonic or saccharic acids
- C12P7/60—2-Ketogulonic acid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/42—Electrodialysis; Electro-osmosis ; Electro-ultrafiltration; Membrane capacitive deionization
- B01D61/44—Ion-selective electrodialysis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/42—Electrodialysis; Electro-osmosis ; Electro-ultrafiltration; Membrane capacitive deionization
- B01D61/44—Ion-selective electrodialysis
- B01D61/445—Ion-selective electrodialysis with bipolar membranes; Water splitting
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/141—Feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Zoology (AREA)
- Urology & Nephrology (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Water Treatment By Electricity Or Magnetism (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8679298P | 1998-05-26 | 1998-05-26 | |
| US60/086,792 | 1998-05-26 | ||
| US09/318,348 US6187570B1 (en) | 1998-05-26 | 1999-05-25 | Electrodialysis methods for purification and recovery of gluconic acid derivatives |
| US09/318,348 | 1999-05-25 | ||
| PCT/US1999/011671 WO1999061647A1 (en) | 1998-05-26 | 1999-05-26 | Electrodialysis methods for purification and recovery of gluconic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2332323A1 true CA2332323A1 (en) | 1999-12-02 |
Family
ID=26775159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002332323A Abandoned CA2332323A1 (en) | 1998-05-26 | 1999-05-26 | Electrodialysis methods for purification and recovery of gluconic acid derivatives |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6187570B1 (enExample) |
| EP (1) | EP1084264A4 (enExample) |
| JP (1) | JP2003523164A (enExample) |
| CN (1) | CN1258598C (enExample) |
| CA (1) | CA2332323A1 (enExample) |
| WO (1) | WO1999061647A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6187570B1 (en) * | 1998-05-26 | 2001-02-13 | The Electrosynthesis Company, Inc. | Electrodialysis methods for purification and recovery of gluconic acid derivatives |
| US6495013B2 (en) | 2000-07-13 | 2002-12-17 | The Electrosynthesis Company, Inc. | Bipolar membrane electrodialysis of multivalent metal salts whose corresponding base is insoluble |
| US7238532B1 (en) * | 2001-06-01 | 2007-07-03 | David Michael Philbrook | Isothiazolone monitoring in aqueous systems |
| US6712946B2 (en) * | 2001-06-18 | 2004-03-30 | The Electrosynthesis Company, Inc. | Electrodialysis of multivalent metal salts |
| DE10149869A1 (de) * | 2001-10-10 | 2003-04-24 | Basf Ag | Verfahren zur Isolierung von Salzen von organischen Säuren aus einer Fermentationsbrühe und zur Freisetzung der organischen Säure |
| DE102004001187A1 (de) * | 2004-01-05 | 2005-08-04 | Basf Ag | Verfahren zur Herstellung von Keto-L-gulonsäuresprühgranulaten |
| CN100528304C (zh) * | 2004-03-17 | 2009-08-19 | Ge爱奥尼克斯公司 | 用于有机产物的生产线和处理 |
| US7630103B2 (en) * | 2005-03-16 | 2009-12-08 | Kabushiki Kaisha Toshiba | Image reading apparatus and image forming apparatus |
| WO2008100798A1 (en) | 2007-02-09 | 2008-08-21 | Primafuel, Inc. | Biodiesel production method and apparatus |
| US8137527B1 (en) | 2008-07-28 | 2012-03-20 | Primafuel, Inc. | Carbon dioxide isolation and generation |
| CA2735909C (en) * | 2008-09-08 | 2019-05-21 | Jurag Separation A/S | Process for controlling the ph and level of target ions of a liquid composition |
| AT513562A1 (de) | 2012-11-14 | 2014-05-15 | Annikki Gmbh | Verfahren zur Gewinnung von Zuckerderivaten |
| CN104313633B (zh) * | 2014-07-22 | 2016-09-07 | 宜宾丝丽雅集团有限公司 | 一种双极膜法制备葡萄糖酸的生产工艺 |
| CN104383813B (zh) * | 2014-11-04 | 2017-05-31 | 帝斯曼江山制药（江苏）有限公司 | 一种古龙酸发酵液的综合处理方法 |
| US11254959B2 (en) | 2016-05-23 | 2022-02-22 | Annikki Gmbh | Process for the conversion of sugars |
| CN106349055B (zh) * | 2016-08-24 | 2017-12-01 | 山东福洋生物科技有限公司 | 一种葡萄糖酸钠母液的新型分离提取方法 |
| CN113441009B (zh) * | 2021-06-22 | 2022-07-22 | 黑龙江新和成生物科技有限公司 | 一种维生素c的双极膜酸化生产工艺及装置 |
| WO2025006789A2 (en) * | 2023-06-27 | 2025-01-02 | Solugen, Inc. | Electrodialysis for processing of sugar acid solutions |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3619396A (en) * | 1969-01-29 | 1971-11-09 | Cpc International Inc | Enzymatic production of gluconic acid |
| US3964985A (en) | 1974-10-29 | 1976-06-22 | Ionics, Incorporated | Electrodialysis apparatus and process for ion modification |
| JPS5910796B2 (ja) | 1976-11-11 | 1984-03-12 | 塩野義製薬株式会社 | ２↓−ケト↓−ｌ↓−グロン酸ナトリウム高純度結晶の採取方法 |
| DE3621781A1 (de) * | 1985-07-05 | 1987-01-15 | Takeda Chemical Industries Ltd | Verfahren zur reinigung von l-ascorbinsaeure |
| DE3542861A1 (de) * | 1985-12-04 | 1987-06-11 | Huels Chemische Werke Ag | Verfahren zur gewinnung von l-aepfelsaeure |
| JPS62146595A (ja) * | 1985-12-20 | 1987-06-30 | Daicel Chem Ind Ltd | 醗酵による有機酸の連続製造方法 |
| US5143834A (en) | 1986-06-11 | 1992-09-01 | Glassner David A | Process for the production and purification of succinic acid |
| US4885247A (en) | 1988-04-19 | 1989-12-05 | Michigan Biotechnology Institute | Recovery and purification of lactate salts from whole fermentation broth by electrodialysis |
| US5202476A (en) | 1988-04-29 | 1993-04-13 | Takeda Chemical Industries, Ltd. | Purification of 2-keto-L-gulonic acid |
| NL8801516A (nl) | 1988-06-14 | 1990-01-02 | Suiker Unie | Werkwijze voor de fermentatieve bereiding van organische zuren. |
| FR2636343B1 (enExample) | 1988-09-13 | 1994-11-25 | Rhone Poulenc Sante | |
| US5282939A (en) * | 1988-09-20 | 1994-02-01 | Basf Aktiengesellschaft | Removal of salts by electrodialysis |
| US5464760A (en) | 1990-04-04 | 1995-11-07 | University Of Chicago | Fermentation and recovery process for lactic acid production |
| JP3134236B2 (ja) * | 1992-01-30 | 2001-02-13 | 株式会社林原生物化学研究所 | α−グリコシル−Ｌ−アスコルビン酸高含有物の製造方法とその製造のための分離システム |
| CN1048282C (zh) | 1993-07-09 | 2000-01-12 | 武田药品工业株式会社 | 生产2－酮－l－古洛糖酸的方法 |
| US5522995A (en) * | 1995-02-28 | 1996-06-04 | Cockrem; Michael C. M. | Process for recovering organic acids from aqueous salt solutions |
| US5681728A (en) * | 1995-06-07 | 1997-10-28 | Chronopol, Inc. | Method and apparatus for the recovery and purification of organic acids |
| EP0779286B1 (de) * | 1995-12-14 | 2002-03-27 | F. Hoffmann-La Roche Ag | Herstellung von Ascorbinsäure |
| CN1102073C (zh) * | 1997-06-30 | 2003-02-26 | 电合成公司 | 回收抗坏血酸的电化学方法 |
| US6187570B1 (en) * | 1998-05-26 | 2001-02-13 | The Electrosynthesis Company, Inc. | Electrodialysis methods for purification and recovery of gluconic acid derivatives |
-
1999
- 1999-05-25 US US09/318,348 patent/US6187570B1/en not_active Expired - Fee Related
- 1999-05-26 EP EP99953361A patent/EP1084264A4/en not_active Withdrawn
- 1999-05-26 JP JP2000551029A patent/JP2003523164A/ja active Pending
- 1999-05-26 CN CNB998064831A patent/CN1258598C/zh not_active Expired - Fee Related
- 1999-05-26 CA CA002332323A patent/CA2332323A1/en not_active Abandoned
- 1999-05-26 WO PCT/US1999/011671 patent/WO1999061647A1/en not_active Ceased
-
2000
- 2000-11-28 US US09/724,443 patent/US6541228B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1258598C (zh) | 2006-06-07 |
| WO1999061647A1 (en) | 1999-12-02 |
| US6541228B1 (en) | 2003-04-01 |
| EP1084264A1 (en) | 2001-03-21 |
| EP1084264A4 (en) | 2005-11-23 |
| CN1302336A (zh) | 2001-07-04 |
| WO1999061647A9 (en) | 2001-03-08 |
| US6187570B1 (en) | 2001-02-13 |
| WO1999061647A8 (en) | 2000-12-21 |
| JP2003523164A (ja) | 2003-08-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6712946B2 (en) | Electrodialysis of multivalent metal salts | |
| EP1320410B1 (en) | Bipolar membrane electrodialysis of multivalent metal salts | |
| US6541228B1 (en) | Electrodialysis methods for purification and recovery of gluconic acid derivatives | |
| US6224731B1 (en) | Apparatus and process for electrodialysis of salts | |
| US6627061B2 (en) | Apparatus and process for electrodialysis of salts | |
| JP2872723B2 (ja) | コハク酸の製造及び精製方法 | |
| US5268079A (en) | Process for the isolation and purification of free acids, starting from their salts, by electrodialysis | |
| EP0577207B1 (fr) | Procédé de fabrication d'une solution aqueuse d'hydroxyde de sodium | |
| EP0560422B1 (fr) | Procédé de fabrication d'hydroxyde de sodium | |
| WO1992011079A1 (en) | Method to produce sodium citrate using electrodialysis | |
| CA1272982A (en) | Method for the recovery of lithium from solutions by electrodialysis | |
| US5064538A (en) | Membrane process for acid recovery | |
| JP3959403B2 (ja) | 有機酸の精製方法 | |
| US7217349B2 (en) | Method of separating multivalent ions and lactate ions from a fermentation broth | |
| JP2820206B2 (ja) | ジペプチドエステルの精製方法 | |
| CA2028300C (en) | Membrane process for acid recovery | |
| JP2000093754A (ja) | アルドン酸塩の分離方法 | |
| CN119306587A (zh) | 一种用双极膜电渗析制备葡萄糖酸的方法 | |
| WO2024213736A1 (en) | Production of organic acid from monovalent acid salt via electrodialysis using a two-compartment electrodialysis unit | |
| AU7318991A (en) | Separation/recovery of ammonium salts via electrodialytic water splitting |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |