CN114656355A - Method for extracting pyruvic acid from fermentation liquor - Google Patents
Method for extracting pyruvic acid from fermentation liquor Download PDFInfo
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- CN114656355A CN114656355A CN202011526508.7A CN202011526508A CN114656355A CN 114656355 A CN114656355 A CN 114656355A CN 202011526508 A CN202011526508 A CN 202011526508A CN 114656355 A CN114656355 A CN 114656355A
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- pyruvic acid
- organic solvent
- pretreatment
- carbon dioxide
- phase
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- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 title claims abstract description 95
- 229940107700 pyruvic acid Drugs 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000000855 fermentation Methods 0.000 title claims abstract description 16
- 230000004151 fermentation Effects 0.000 title claims abstract description 16
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003960 organic solvent Substances 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 17
- 239000012074 organic phase Substances 0.000 claims abstract description 16
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 15
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims abstract description 13
- 229940076788 pyruvate Drugs 0.000 claims abstract description 13
- 239000012071 phase Substances 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 6
- 241001052560 Thallis Species 0.000 claims abstract description 5
- 238000000605 extraction Methods 0.000 claims abstract description 5
- 229920002521 macromolecule Polymers 0.000 claims abstract description 5
- 244000005700 microbiome Species 0.000 claims abstract description 5
- 238000007599 discharging Methods 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 6
- 238000000108 ultra-filtration Methods 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005191 phase separation Methods 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 238000001471 micro-filtration Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 6
- 239000002351 wastewater Substances 0.000 abstract description 4
- 230000007797 corrosion Effects 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 3
- 238000004065 wastewater treatment Methods 0.000 abstract description 3
- 239000002535 acidifier Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- -1 pyruvic acid series compounds Chemical class 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940018333 calcium pyruvate Drugs 0.000 description 1
- UZWMCCLZMHPPKW-UHFFFAOYSA-L calcium;2-oxopropanoate Chemical compound [Ca+2].CC(=O)C([O-])=O.CC(=O)C([O-])=O UZWMCCLZMHPPKW-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019990 fruit wine Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000004021 metal welding Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000004728 pyruvic acid derivatives Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- PZAZKCRGLOGBPZ-UHFFFAOYSA-M sodium dihydrogen phosphate 2-oxopropanoic acid Chemical compound P(=O)([O-])(O)O.C(C(=O)C)(=O)O.[Na+] PZAZKCRGLOGBPZ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- 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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for extracting pyruvic acid from fermentation liquor comprises the following steps: (1) pretreatment: separating and removing thalli, other visible solid substances and macromolecular substances from microorganism fermentation liquor containing pyruvic acid to obtain pretreatment liquor containing pyruvate; (2) extraction: adding an organic solvent capable of dissolving pyruvic acid into the pretreatment solution obtained in the step (1), fully stirring and introducing carbon dioxide to obtain an organic phase rich in pyruvic acid and a water phase with lower pyruvic acid content; (3) phase splitting: discharging the water phase, releasing the pressure of the organic phase, distilling the organic phase under reduced pressure, and removing the organic solvent and water dissolved in the organic solvent to obtain a crude pyruvic acid product; (4) and distilling the obtained crude pyruvic acid product by using a molecular distiller to obtain a pure pyruvic acid product. The invention utilizes high pressure CO2Dissolving in water as acidifier instead of sulfuric acid or hydrochloric acidThe conversion from pyruvate to pyruvic acid is combined with the organic phase transfer process by using the strong acid, so that the process flow is shortened; strong acid is not used, so that the corrosion to equipment is reduced; the treated wastewater has no acid residue, so that the cost of wastewater treatment is greatly reduced.
Description
Technical Field
The invention relates to a method for extracting pyruvic acid from fermentation broth, belonging to the technical field of microorganism fermentation broth separation.
Background
Pyruvic acid is an important organic synthesis intermediate with the molecular formula of CH3COCOOH is widely applied to the fields of pharmacy, daily chemicals, agricultural chemicals, food and the like. The application in the aspect of drug synthesis is very wide, and the method can be generally used for synthesizing drugs for treating hypertension, protease inhibitors, antiviral agents, sedatives and the like. Besides, the pyruvic acid series compounds can also be used for synthesizing medicaments for treating diseases such as tumors, ulcers, osteoporosis and the like. It is particularly noteworthy that calcium pyruvate is one of the major components of the currently marketed weight-loss drugs for fire-explosion. The pyruvic acid derivative is also widely applied to the fields of cosmetics, metal welding, air fresheners, fruit wine preservatives and the like.
At present, two industrial methods for synthesizing pyruvic acid are chemical methods and biological synthesis methods, and the biological synthesis methods mainly convert cheap carbon source substances or other substances into pyruvic acid by using microbial fermentation or enzyme methods. Biological methods (including fermentation method and enzyme conversion method) for preparing pyruvic acid, the product contains other metabolites and some impurities, such as sugar, protein, colloidal substances and the like, the components are very complex, and pyruvic acid must be extracted by physical and chemical methods. Furthermore, in order to bring the bacteria or enzymes to the appropriate pH range, lactate is usually used as substrate and the resulting product is usually pyruvate.
Patent CN106496022A relates to a method for extracting pyruvic acid from microorganism fermentation liquor or enzyme conversion liquor, which adopts the technical routes of concentration, acidification, extraction and distillation. Wherein concentrated sulfuric acid is added in the acidification step. In other disclosed technical routes, common inorganic acids such as sulfuric acid, hydrochloric acid, phosphoric acid and the like are also commonly used for the acidification of pyruvate. The traditional inorganic acid is used for acidification, the reaction liquid and the reaction wastewater are acidic, the requirements on the corrosion resistance of the reaction vessel and a wastewater discharge pipeline are high, and the wastewater treatment cost is high.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the method for extracting pyruvic acid from the fermentation liquor, which has mild treatment conditions, simple and safe operation process and no pollution to operators and environment, and does not add any traditional inorganic acid.
In order to achieve the technical purpose, the technical scheme of the invention is as follows:
a method for extracting pyruvic acid from fermentation liquor comprises the following steps:
(1) pretreatment: separating and removing thalli, other visible solid substances and macromolecular substances from microorganism fermentation liquor containing pyruvic acid to obtain pretreatment liquor containing pyruvate;
(2) extraction: adding an organic solvent capable of dissolving pyruvic acid into the pretreatment solution obtained in the step (1), fully stirring and introducing carbon dioxide to obtain an organic phase rich in pyruvic acid and a water phase with lower pyruvic acid content;
(3) phase separation: discharging the water phase, releasing the pressure of the organic phase, distilling the organic phase under reduced pressure, and removing the organic solvent and water dissolved in the organic solvent to obtain a crude pyruvic acid product;
(4) refining: and distilling the obtained crude pyruvic acid product by using a molecular distiller to obtain a pure pyruvic acid product.
Further, the method for separating and removing the thalli, other visible solid substances and macromolecular substances in the step (1) comprises one or a combination of more of centrifugation, filtration, microfiltration and ultrafiltration in the prior art.
Further, the ratio of the adding amount of the organic solvent in the step (2) to the volume of the pretreatment liquid is more than 1: 1, preferably 3: 1-6: 1.
further, the organic solvent in step (2) is a solvent which can dissolve pyruvic acid and is not completely miscible with water, and is selected from at least one of dichloroethane, diethyl ether, ethyl acetate and butyl acetate.
Further, the carbon dioxide introduced in the step (2) is carbon dioxide with a certain pressure, and the pressure is more than or equal to 2MPa, preferably more than or equal to 4MPa, and more preferably 5 MPa-10 MPa.
Further, in the step (2), the temperature of the solution is kept between 0 and 50 ℃, preferably between 10 and 40 ℃.
Further, after the carbon dioxide is introduced in the step (2), keeping the temperature for more than or equal to 1 hour, preferably 1 to 3 hours.
Further, before the organic solvent is added in the step (2), the step of evaporating and concentrating the pretreatment solution is also included, so that the concentration of pyruvate in the pretreatment solution is more than or equal to 80g/L, preferably more than or equal to 100 g/L.
Further, the operating conditions of the reduced pressure distillation in the step (3) are as follows: 10-30 kPa, 40-60 ℃.
Further, the operating conditions of the molecular still in step (4) are as follows: 0.5 to 2kPa, 50 to 70 ℃.
Compared with the prior art, the method has the following advantages:
the invention utilizes high pressure CO2The sodium pyruvate phosphate is dissolved in water to be used as an acidifier to replace strong acids such as sulfuric acid, hydrochloric acid and the like, and the conversion from pyruvate to pyruvic acid is combined with the organic phase transfer process, so that the process flow is shortened; strong acid is not used, so that the corrosion to equipment is reduced; the treated wastewater has no acid residue, so that the cost of wastewater treatment is greatly reduced.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Detailed Description
The following non-limiting examples are presented to enable those of ordinary skill in the art to more fully understand the present invention and are not intended to limit the invention in any way.
Example 1
(1) Pretreatment: pumping a crude product water solution containing pyruvic acid (the crude product water solution containing pyruvic acid is pyruvic acid fermentation liquor directly prepared by fermentation or pyruvic acid-containing water solution obtained by other ways) into a centrifuge, and centrifuging to remove thalli and other visible solid matters. Centrifugation conditions: at normal temperature, the rotating speed is 3000 r/min. Filtering out impurities by ultrafiltration, wherein the membrane material of the tubular membrane component of the ultrafiltration membrane component is a polyethylene membrane with the molecular weight cutoff of 500-3000 Da, and the ultrafiltration conditions are as follows: normal temperature and operation pressure of 0.4-1.0 MPa. And (3) evaporating and concentrating the ultrafiltration filtrate under reduced pressure at the temperature of 65 ℃ under the condition of 200Pa to ensure that the concentration of pyruvate is 100g/L, thus obtaining a pretreatment solution containing pyruvate.
(2) Extraction: adding 100mL of the pretreatment solution containing pyruvate into a reaction kettle, adding 300mL of dichloroethane as an organic solvent, introducing carbon dioxide into the reaction kettle, pressurizing to 5MPa, operating at 10 ℃, keeping constant temperature and constant pressure, and fully stirring for reaction for 1 h.
(3) Phase separation: standing until the water phase and the organic phase are completely separated, keeping the pressure to discharge the lower water phase, then cooling and depressurizing, recovering carbon dioxide, and dissolving pyruvic acid in the organic phase. Removing dichloroethane in the organic phase by using a reduced pressure distillation method under the conditions of 10kPa and 40 ℃ to obtain crude pyruvic acid.
(4) Refining: and (3) distilling the crude pyruvic acid product by a molecular distiller at 1kPa and 50 ℃ to obtain a refined pyruvic acid product.
Example 2
On the basis of example 1, 600mL of ethyl acetate was added as an organic solvent in step (2), and the reaction time was 3 h.
Example 3
On the basis of example 1, 500mL of organic solvent diethyl ether was added in step (2), and the pressure of carbon dioxide gas was 10 MPa.
Example 4
On the basis of example 1, 400mL of butyl acetate as an organic solvent was added in step (2), and the pressure for introducing carbon dioxide was 4 MPa. The reduced pressure distillation temperature in the step (3) was 60 ℃.
Example 5
On the basis of example 1, 400mL of butyl acetate as an organic solvent was added in step (2), and the pressure for introducing carbon dioxide was 2 MPa. The reduced pressure distillation temperature in the step (3) was 60 ℃.
Comparative example 1
The pretreatment solution containing pyruvate obtained by the method of the step (1) of the example 1 is added with concentrated sulfuric acid to adjust the pH value to be less than or equal to 2.0, 100mL of the solution is added into a reaction kettle, 300mL of organic solvent ethyl acetate is added into the reaction kettle, the operation temperature is 20 ℃, and the solution is kept at a constant temperature and a constant pressure and is fully stirred for reaction for 1 h. Standing until the water phase and the organic phase are completely separated, discharging the lower water phase, and dissolving pyruvic acid in the organic phase. Then, a pyruvic acid refined product is obtained according to the steps (3) and (4) of the example 1.
Table 1.
Claims (10)
1. A method for extracting pyruvic acid from fermentation liquor comprises the following steps:
(1) pretreatment: separating and removing thalli, other visible solid substances and macromolecular substances from microorganism fermentation liquor containing pyruvic acid to obtain pretreatment liquor containing pyruvate;
(2) extraction: adding an organic solvent capable of dissolving pyruvic acid into the pretreatment solution obtained in the step (1), fully stirring and introducing carbon dioxide to obtain an organic phase rich in pyruvic acid and a water phase with lower pyruvic acid content;
(3) phase separation: discharging the water phase, releasing the pressure of the organic phase, distilling the organic phase under reduced pressure, and removing the organic solvent and water dissolved in the organic solvent to obtain a crude pyruvic acid product;
(4) refining: and distilling the obtained crude pyruvic acid product by using a molecular distiller to obtain a pure pyruvic acid product.
2. The method according to claim 1, wherein the step (1) of separating and removing the thallus, other visible solid substances and macromolecular substances comprises one or more of centrifugation, filtration, microfiltration and ultrafiltration in the prior art.
3. The method according to claim 1, wherein the ratio of the added amount of the organic solvent in the step (2) to the volume of the pretreatment solution is more than 1: 1, preferably 3: 1-6: 1.
4. the method according to claim 1, wherein the organic solvent of step (2) is at least one selected from the group consisting of dichloroethane, diethyl ether, ethyl acetate and butyl acetate.
5. The method according to claim 1, wherein the carbon dioxide introduced in step (2) is carbon dioxide with a pressure of 2MPa or more, preferably 4MPa or more, and more preferably 5MPa to 10 MPa.
6. The method according to claim 1, wherein the solution temperature is maintained in the range of 0 to 50 ℃ in step (2).
7. The method according to claim 1, wherein the carbon dioxide is maintained for 1 hour or more after the carbon dioxide is introduced in the step (2).
8. The method as claimed in claim 1, wherein the step (2) further comprises, before adding the organic solvent, evaporating and concentrating the pretreatment solution so that the pyruvate concentration in the pretreatment solution is not less than 80 g/L.
9. The method according to claim 1, wherein the reduced pressure distillation in step (3) is carried out under the following operating conditions: 10-30 kPa, 40-60 ℃.
10. The method of claim 1, wherein the operating conditions of the molecular still of step (4) are: 0.5 to 2kPa, 50 to 70 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011526508.7A CN114656355A (en) | 2020-12-22 | 2020-12-22 | Method for extracting pyruvic acid from fermentation liquor |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011526508.7A CN114656355A (en) | 2020-12-22 | 2020-12-22 | Method for extracting pyruvic acid from fermentation liquor |
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| CN114656355A true CN114656355A (en) | 2022-06-24 |
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| CN202011526508.7A Pending CN114656355A (en) | 2020-12-22 | 2020-12-22 | Method for extracting pyruvic acid from fermentation liquor |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080242889A1 (en) * | 2007-03-30 | 2008-10-02 | Ge Healthcare Limited | Method for the production of pyruvic acid |
| CN105209420A (en) * | 2012-12-21 | 2015-12-30 | Ee-特邦生物燃料有限责任公司 | System and process for obtaining products from biomass |
| CN106496019A (en) * | 2016-10-13 | 2017-03-15 | 江南大学 | A kind of method for extracting alpha Ketoglutarate and pyruvic acid from microbial fermentation solution or enzymatic conversion liquid simultaneously |
| CN106496022A (en) * | 2016-10-13 | 2017-03-15 | 江南大学 | A kind of method for extracting pyruvic acid from microbial fermentation solution or enzymatic conversion liquid |
-
2020
- 2020-12-22 CN CN202011526508.7A patent/CN114656355A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080242889A1 (en) * | 2007-03-30 | 2008-10-02 | Ge Healthcare Limited | Method for the production of pyruvic acid |
| CN105209420A (en) * | 2012-12-21 | 2015-12-30 | Ee-特邦生物燃料有限责任公司 | System and process for obtaining products from biomass |
| CN106496019A (en) * | 2016-10-13 | 2017-03-15 | 江南大学 | A kind of method for extracting alpha Ketoglutarate and pyruvic acid from microbial fermentation solution or enzymatic conversion liquid simultaneously |
| CN106496022A (en) * | 2016-10-13 | 2017-03-15 | 江南大学 | A kind of method for extracting pyruvic acid from microbial fermentation solution or enzymatic conversion liquid |
Non-Patent Citations (1)
| Title |
|---|
| 杨锐: "工业化发酵法生产丙酮酸", 《发酵科技通讯》, vol. 38, no. 04, pages 20 - 22 * |
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