DE2145084C3 - Verfahren zur Abtrennung von Citronensäure aus wäßrigen Lösungen, die Citronensäure und L(+)-Isocitronensäure enthalten - Google Patents
Verfahren zur Abtrennung von Citronensäure aus wäßrigen Lösungen, die Citronensäure und L(+)-Isocitronensäure enthaltenInfo
- Publication number
- DE2145084C3 DE2145084C3 DE2145084A DE2145084A DE2145084C3 DE 2145084 C3 DE2145084 C3 DE 2145084C3 DE 2145084 A DE2145084 A DE 2145084A DE 2145084 A DE2145084 A DE 2145084A DE 2145084 C3 DE2145084 C3 DE 2145084C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- citric acid
- isocitric
- sulfuric acid
- weight
- 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
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title claims description 257
- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 title claims description 91
- 239000007864 aqueous solution Substances 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 6
- 238000000926 separation method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 91
- 239000000243 solution Substances 0.000 claims description 17
- ODBLHEXUDAPZAU-FONMRSAGSA-N Isocitric acid Natural products OC(=O)[C@@H](O)[C@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-FONMRSAGSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 230000002906 microbiologic effect Effects 0.000 claims 1
- 229960004106 citric acid Drugs 0.000 description 81
- 239000013078 crystal Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 238000002425 crystallisation Methods 0.000 description 19
- 230000008025 crystallization Effects 0.000 description 19
- 239000012452 mother liquor Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- ODBLHEXUDAPZAU-ZAFYKAAXSA-N D-threo-isocitric acid Chemical compound OC(=O)[C@H](O)[C@@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-ZAFYKAAXSA-N 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000203 mixture Substances 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
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000011031 large-scale manufacturing process Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000004682 monohydrates Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000205490 Bdelloura candida Species 0.000 description 1
- 241000222173 Candida parapsilosis Species 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241000235035 Debaryomyces Species 0.000 description 1
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- 241000191335 [Candida] intermedia Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229940055022 candida parapsilosis Drugs 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960002303 citric acid monohydrate Drugs 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- YWORCEHQVMOKDM-UHFFFAOYSA-H tricalcium;1-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)C(O)C(C([O-])=O)CC([O-])=O.[O-]C(=O)C(O)C(C([O-])=O)CC([O-])=O YWORCEHQVMOKDM-UHFFFAOYSA-H 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 210000005253 yeast cell Anatomy 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
- C12P7/44—Polycarboxylic acids
- C12P7/48—Tricarboxylic acids, e.g. citric 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8024670 | 1970-09-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2145084A1 DE2145084A1 (de) | 1972-03-16 |
| DE2145084B2 DE2145084B2 (de) | 1980-11-20 |
| DE2145084C3 true DE2145084C3 (de) | 1981-07-02 |
Family
ID=13712949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2145084A Expired DE2145084C3 (de) | 1970-09-11 | 1971-09-09 | Verfahren zur Abtrennung von Citronensäure aus wäßrigen Lösungen, die Citronensäure und L(+)-Isocitronensäure enthalten |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3799980A (enExample) |
| AU (1) | AU458747B2 (enExample) |
| BE (1) | BE772474A (enExample) |
| CA (1) | CA960691A (enExample) |
| DE (1) | DE2145084C3 (enExample) |
| FR (1) | FR2107571A5 (enExample) |
| GB (1) | GB1365362A (enExample) |
| IE (1) | IE35629B1 (enExample) |
| IL (1) | IL37638A (enExample) |
| IT (1) | IT945760B (enExample) |
| NL (1) | NL173284C (enExample) |
| ZA (1) | ZA716088B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4139556A (en) * | 1976-04-29 | 1979-02-13 | Chevron Research Company | Mono-ol from diol and improved citric acid process |
| KR101274369B1 (ko) * | 2008-06-20 | 2013-06-13 | 아사히 가세이 케미칼즈 가부시키가이샤 | α-히드록시산의 제조 방법 |
-
1971
- 1971-09-02 IL IL37638A patent/IL37638A/en unknown
- 1971-09-08 IE IE1145/71A patent/IE35629B1/xx unknown
- 1971-09-09 DE DE2145084A patent/DE2145084C3/de not_active Expired
- 1971-09-09 GB GB4204671A patent/GB1365362A/en not_active Expired
- 1971-09-09 AU AU33306/71A patent/AU458747B2/en not_active Expired
- 1971-09-10 IT IT70005/71A patent/IT945760B/it active
- 1971-09-10 NL NLAANVRAGE7112484,A patent/NL173284C/xx not_active IP Right Cessation
- 1971-09-10 CA CA122,531A patent/CA960691A/en not_active Expired
- 1971-09-10 US US00179412A patent/US3799980A/en not_active Expired - Lifetime
- 1971-09-10 FR FR7132831A patent/FR2107571A5/fr not_active Expired
- 1971-09-10 BE BE772474A patent/BE772474A/xx not_active IP Right Cessation
- 1971-09-10 ZA ZA716088A patent/ZA716088B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU3330671A (en) | 1973-03-15 |
| IE35629B1 (en) | 1976-04-14 |
| NL173284B (nl) | 1983-08-01 |
| IT945760B (it) | 1973-05-10 |
| CA960691A (en) | 1975-01-07 |
| FR2107571A5 (enExample) | 1972-05-05 |
| US3799980A (en) | 1974-03-26 |
| NL173284C (nl) | 1984-01-02 |
| IE35629L (en) | 1972-03-11 |
| GB1365362A (en) | 1974-09-04 |
| NL7112484A (enExample) | 1972-03-14 |
| DE2145084B2 (de) | 1980-11-20 |
| DE2145084A1 (de) | 1972-03-16 |
| ZA716088B (en) | 1972-05-31 |
| IL37638A (en) | 1974-07-31 |
| IL37638A0 (en) | 1971-11-29 |
| AU458747B2 (en) | 1975-03-06 |
| BE772474A (fr) | 1972-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |