CA1331017C - Procede de separation de l'acide ceto-2 l gulonique a partir d'un mout de fermentation - Google Patents
Procede de separation de l'acide ceto-2 l gulonique a partir d'un mout de fermentationInfo
- Publication number
- CA1331017C CA1331017C CA000610976A CA610976A CA1331017C CA 1331017 C CA1331017 C CA 1331017C CA 000610976 A CA000610976 A CA 000610976A CA 610976 A CA610976 A CA 610976A CA 1331017 C CA1331017 C CA 1331017C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- gulonic
- keto
- filtration
- gulonic acid
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000000855 fermentation Methods 0.000 title claims abstract description 9
- 230000004151 fermentation Effects 0.000 title claims abstract description 9
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 159000000007 calcium salts Chemical class 0.000 claims abstract 2
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 claims description 19
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 239000011575 calcium Substances 0.000 claims description 9
- 229910052791 calcium Inorganic materials 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 238000005189 flocculation Methods 0.000 claims description 4
- 230000016615 flocculation Effects 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000008394 flocculating agent Substances 0.000 claims description 3
- 238000000108 ultra-filtration Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000005341 cation exchange Methods 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000005349 anion exchange Methods 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 238000005115 demineralization Methods 0.000 abstract description 2
- 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 abstract 3
- 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 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 239000002028 Biomass Substances 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
- 150000004682 monohydrates Chemical class 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 239000012465 retentate Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 235000011132 calcium sulphate Nutrition 0.000 description 2
- 239000001175 calcium sulphate Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 101100166829 Mus musculus Cenpk gene Proteins 0.000 description 1
- 101100046790 Mus musculus Trappc2 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002328 demineralizing effect Effects 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- UPMFZISCCZSDND-JSCKKFHOSA-M sodium;(2s,3s,4r,5s)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Na+].OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C([O-])=O UPMFZISCCZSDND-JSCKKFHOSA-M 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/803—Physical recovery methods, e.g. chromatography, grinding
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8811902 | 1988-09-13 | ||
| FR8811902A FR2636343B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-09-13 | 1988-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1331017C true CA1331017C (fr) | 1994-07-26 |
Family
ID=9369930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000610976A Expired - Lifetime CA1331017C (fr) | 1988-09-13 | 1989-09-11 | Procede de separation de l'acide ceto-2 l gulonique a partir d'un mout de fermentation |
Country Status (15)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3976832B2 (ja) * | 1996-04-30 | 2007-09-19 | ディーエスエム アイピー アセッツ ビー．ブイ． | ２−ケト−ｌ−グロン酸の単離方法 |
| US6187570B1 (en) * | 1998-05-26 | 2001-02-13 | The Electrosynthesis Company, Inc. | Electrodialysis methods for purification and recovery of gluconic acid derivatives |
| US6153791A (en) * | 1999-08-02 | 2000-11-28 | Archer-Daniels-Midland Company | Process for purifying 2-keto-L-gulonic acid |
| US6902917B1 (en) * | 1999-08-03 | 2005-06-07 | Archer-Daniels-Midland Company | Process for recovery of organic acids from fermentration broths |
| US6670505B1 (en) * | 2000-03-07 | 2003-12-30 | Eastman Chemical Company | Process for the recovery of organic acids from aqueous solutions |
| US6320061B1 (en) | 2000-06-05 | 2001-11-20 | Eastman Chemical Company | Solvent exchange process |
| GB0119864D0 (en) | 2001-08-15 | 2001-10-10 | Cerestar Holding Bv | Process for the manufacture of 2-keto-L-gulonic acid |
| 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 |
| KR100491687B1 (ko) * | 2002-02-05 | 2005-05-27 | 한국배연탈황탈질(주) | 유해가스 제거제 및 그의 제조방법 |
| DE10231890B4 (de) | 2002-07-12 | 2004-07-01 | Basf Ag | Verfahren zur Abtrennung von Ascorbinsäure aus einem polaren, Ascorbinsäure und 2-Keto-L-gulonsäure enthaltenden Lösungsmittel |
| CA2510026A1 (en) * | 2002-12-19 | 2004-07-08 | Basf Aktiengesellschaft | Method for extracting 2-ketone-l-gulonic acid from a polar, preferably aqueous solvent |
| CN103073601B (zh) * | 2013-02-01 | 2015-08-19 | 东北制药集团股份有限公司 | 一种2-酮基-l-古龙酸溶液加晶种的可控浓缩结晶方法 |
| DE102015216815A1 (de) | 2015-09-02 | 2017-03-02 | Thyssenkrupp Ag | Verfahren und Anlage zur Gewinnung einer in einem Fermentationsprozess hergestellten Carbonsäure |
| CN111943993A (zh) * | 2019-05-16 | 2020-11-17 | 帝斯曼知识产权资产管理有限公司 | 回收2-酮-l-古洛糖酸的改进方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2539472A (en) * | 1949-07-15 | 1951-01-30 | William P Ratchford | Process for the purification of certain water-soluble hydroxycarboxylic acids |
| JPS5135486A (en) * | 1974-09-20 | 1976-03-25 | Shionogi Seiyaku Kk | 22 keto ll guronsan no seizohoho |
| US4421924A (en) * | 1980-05-05 | 1983-12-20 | Pfizer Inc. | Ascorbic acid intermediates and their preparation |
| EP0213591B1 (en) * | 1985-08-28 | 1992-03-25 | F. Hoffmann-La Roche Ag | Process for the manufacture of keto gulonic acid |
| DK171869B1 (da) * | 1985-10-22 | 1997-07-21 | Takeda Chemical Industries Ltd | Fremgangsmåde til fremstilling af 2-keto-L-gulonsyre samt biologisk ren mikroorganismekultur til anvendelse ved fremgangsmåden |
-
1988
- 1988-09-13 FR FR8811902A patent/FR2636343B1/fr not_active Expired - Lifetime
-
1989
- 1989-09-11 AT AT89402467T patent/ATE117024T1/de not_active IP Right Cessation
- 1989-09-11 EP EP89402467A patent/EP0359645B1/fr not_active Expired - Lifetime
- 1989-09-11 ES ES89402467T patent/ES2066010T3/es not_active Expired - Lifetime
- 1989-09-11 CA CA000610976A patent/CA1331017C/fr not_active Expired - Lifetime
- 1989-09-11 US US07/405,126 patent/US4990441A/en not_active Expired - Lifetime
- 1989-09-11 DE DE68920520T patent/DE68920520T2/de not_active Expired - Lifetime
- 1989-09-12 DK DK198904498A patent/DK173272B1/da not_active IP Right Cessation
- 1989-09-12 JP JP1234813A patent/JP3013995B2/ja not_active Expired - Lifetime
- 1989-09-12 KR KR1019890013268A patent/KR0142084B1/ko not_active Expired - Lifetime
- 1989-09-12 IE IE291289A patent/IE66570B1/en not_active IP Right Cessation
- 1989-09-12 RU SU894614906A patent/RU1774951C/ru active
- 1989-09-12 HU HU894820A patent/HU202282B/hu unknown
- 1989-09-13 PT PT91711A patent/PT91711B/pt not_active IP Right Cessation
- 1989-09-13 YU YU176489A patent/YU46969B/sh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02150286A (ja) | 1990-06-08 |
| EP0359645B1 (fr) | 1995-01-11 |
| KR0142084B1 (ko) | 1998-06-15 |
| ATE117024T1 (de) | 1995-01-15 |
| DK449889D0 (da) | 1989-09-12 |
| YU176489A (en) | 1990-12-31 |
| FR2636343A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-03-16 |
| US4990441A (en) | 1991-02-05 |
| EP0359645A1 (fr) | 1990-03-21 |
| IE66570B1 (en) | 1996-01-24 |
| DK173272B1 (da) | 2000-06-05 |
| HU202282B (en) | 1991-02-28 |
| DK449889A (da) | 1990-03-14 |
| DE68920520T2 (de) | 1995-05-24 |
| FR2636343B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-11-25 |
| HUT51337A (en) | 1990-04-28 |
| PT91711A (pt) | 1990-03-30 |
| RU1774951C (ru) | 1992-11-07 |
| PT91711B (pt) | 1995-05-31 |
| IE892912L (en) | 1990-03-13 |
| JP3013995B2 (ja) | 2000-02-28 |
| DE68920520D1 (de) | 1995-02-23 |
| YU46969B (sh) | 1994-09-09 |
| KR900004940A (ko) | 1990-04-13 |
| ES2066010T3 (es) | 1995-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |