CN112774448A - Method for separating acid from ester - Google Patents
Method for separating acid from ester Download PDFInfo
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- CN112774448A CN112774448A CN201911189743.7A CN201911189743A CN112774448A CN 112774448 A CN112774448 A CN 112774448A CN 201911189743 A CN201911189743 A CN 201911189743A CN 112774448 A CN112774448 A CN 112774448A
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- acid
- ester
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- organic acid
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- 239000002253 acid Substances 0.000 title claims abstract description 44
- 150000002148 esters Chemical class 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000012528 membrane Substances 0.000 claims abstract description 35
- 238000000926 separation method Methods 0.000 claims abstract description 24
- 239000011259 mixed solution Substances 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000003011 anion exchange membrane Substances 0.000 claims abstract description 9
- 238000005341 cation exchange Methods 0.000 claims abstract description 9
- 230000005684 electric field Effects 0.000 claims abstract description 6
- 239000003014 ion exchange membrane Substances 0.000 claims abstract description 6
- 230000005012 migration Effects 0.000 claims abstract description 4
- 238000013508 migration Methods 0.000 claims abstract description 4
- -1 organic acid salt Chemical class 0.000 claims description 20
- 150000007524 organic acids Chemical class 0.000 claims description 9
- OTOIIPJYVQJATP-BYPYZUCNSA-N (R)-pantoic acid Chemical compound OCC(C)(C)[C@@H](O)C(O)=O OTOIIPJYVQJATP-BYPYZUCNSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 6
- 239000012466 permeate Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 5
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical group CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003792 electrolyte Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000001728 nano-filtration Methods 0.000 claims description 3
- OTOIIPJYVQJATP-SCSAIBSYSA-N (2s)-2,4-dihydroxy-3,3-dimethylbutanoic acid Chemical compound OCC(C)(C)[C@H](O)C(O)=O OTOIIPJYVQJATP-SCSAIBSYSA-N 0.000 claims description 2
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 2
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical compound CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 238000001471 micro-filtration Methods 0.000 claims description 2
- 238000000108 ultra-filtration Methods 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 230000035699 permeability Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000011033 desalting Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SERHXTVXHNVDKA-BYPYZUCNSA-N (R)-pantolactone Chemical compound CC1(C)COC(=O)[C@@H]1O SERHXTVXHNVDKA-BYPYZUCNSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001052560 Thallis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009323 psychological health Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011426 transformation method Methods 0.000 description 1
Classifications
-
- 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
- B01D61/58—Multistep processes
-
- 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
-
- 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
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/027—Nanofiltration
-
- 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
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
-
- 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
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/147—Microfiltration
-
- 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
- B01D61/422—Electrodialysis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nanotechnology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
The invention relates to the technical field of biological industry, in particular to a method for separating acid from ester, which specifically comprises the following steps: providing N pairs of cation exchange membranes and anion exchange membranes which are sequentially arranged, leading mixed solution at least comprising acid and/or acid salt and ester to the space between the cation exchange membranes and the anion exchange membranes, carrying out migration separation on the mixed solution in an electric field environment, and then respectively collecting concentrated phase solution and dilute phase solution; n is more than or equal to 1; the invention has the beneficial effects that: according to the selective permeability of the ion exchange membrane to acid and/or acid salt and ester, under the action of an electric field, ions ionized from the acid and/or acid salt are subjected to migration motion between membranes, so that the stable and effective separation of the acid and/or acid salt and ester is realized.
Description
Technical Field
The invention relates to the technical field of separation, in particular to a method for separating acid from ester.
Background
In fine chemical production or industrial biosynthesis, an intermediate mixture containing acid and ester is often generated, and the acid and the ester in the mixture need to be separated in order to obtain a target product. In the prior art, two separation methods of acid and ester are adopted, wherein one method is an extraction method, and the other method is a distillation method. The extraction method requires extraction of the mixture with an organic reagent such as ethyl acetate, and separation of the two is achieved by virtue of the difference in solubility between the acid and the ester in immiscible solvents. The method has the following disadvantages: when conventional extraction methods are used to separate acids or esters, organic reagents are required. Commonly used extractants, such as ethyl acetate, are flammable and highly irritating and volatile. In the processes of extraction separation, solvent recovery and other industrial production activities, the use of a large amount of ethyl acetate not only brings potential safety hazards to daily production of factories, but also forms a severe operating environment and brings influences to physical and psychological health of production workers. The distillation method is adopted to realize the separation of the acid and the ester according to the difference of the boiling points of the acid and the ester, and as the distillation equipment has large energy consumption, high cost, higher temperature and larger danger coefficient, under the condition of high temperature, the problems of more reaction side products and lower yield of target products exist.
Disclosure of Invention
The invention aims to provide a method for separating acid from ester, which has the advantages of simple operation, environment-friendly process and high product purity.
In order to achieve the purpose, the invention adopts the technical scheme that: a acid and separation method of ester, provide N pairs of cation exchange membrane and anion exchange membrane that arrange sequentially, include the mixed solution of acid and/or acid salt and ester at least leads to between cation exchange membrane and anion exchange membrane, the mixed solution migrates and separates under the environment of electric field, then collect dense phase solution and dilute phase solution separately; n is more than or equal to 1.
The invention has the beneficial effects that: according to the selective permeability of the ion exchange membrane to acid and/or acid salt and ester, under the action of an electric field, ions ionized from the acid and/or acid salt are subjected to migration motion between membranes, so that the stable and effective separation of the acid and/or acid salt and ester is realized.
Detailed Description
A acid and separation method of ester, provide N pairs of cation exchange membrane and anion exchange membrane that arrange sequentially, include the mixed solution of acid and/or acid salt and ester at least leads to between cation exchange membrane and anion exchange membrane, the mixed solution migrates and separates under the environment of electric field, then collect dense phase solution and dilute phase solution separately; n is more than or equal to 1.
Specifically, the apparatus used in the ion exchange membrane separation treatment step may be an electrodialyzer. The separation principle using ion exchange membranes is based on the selective permeation of substances through ion membranes. The electrodialyzer adopts a commercial product, and comprises a cathode and an anode which are arranged in a polar chamber, and a plurality of membrane groups which are alternately arranged between the cathode and the anode, wherein the membrane groups comprise a cathode membrane which selectively permeates anions and an anode membrane which selectively permeates cations, and cavities between the cathode membrane and the anode membrane are alternately arranged to form a desalting chamber and a concentrating chamber. In order to realize the separation, in the present application, the clear liquid after the adsorption filtration treatment or the permeate after the membrane filtration treatment is led to the desalting chamber of the electrodialyzer, the pure water is led to the concentrating chamber of the electrodialyzer, and the polar chamber of the electrodialyzer contains 3% anhydrous sodium sulfate as electrolyte.
Further, as for the selection of the cation exchange membrane and the anion exchange membrane, a heterogeneous membrane, a semi-homogeneous membrane or a homogeneous membrane can be selected.
Further, the concentration of the acid and/or the acid salt is 0.5-300g/L, and the concentration of the ester is 0.5-300 g/L.
Further, the mixed solution at least comprises organic acid and/or organic acid salt and organic acid ester.
Further, the organic acid is connected with-COOH and-SO on the molecule3H. -RSOOH, -RCOSH.
Further, the organic acid ester is lactide or lactone formed by organic acid, the molecule of the organic acid at least contains 1 carboxylate radical, and the organic acid ester is non-electrolyte.
Further, the organic acid is at least one of lactic acid, glycolic acid, L pantoic acid, D pantoic acid, alpha hydroxybutyric acid and beta hydroxybutyric acid.
Further, the organic acid ester is at least one of glycolide, lactide, butyrolactone, valerolactone, D pantoic acid lactone and L pantoic acid lactone.
Further, the mixed solution further comprises a step of removing impurity components in the mixed solution before the ion exchange membrane separation.
Further, the method for removing impurity components in the mixed solution comprises the following steps:
1) carrying out adsorption filtration on the mixed solution, and collecting filtrate; and/or
2) Filtering the mixed solution by adopting a membrane element with the aperture of 0.001-1000 um, and collecting the permeate; and/or
3) Treating the mixed solution by using a plate separation method, and collecting plate separation clear liquid.
Further, the adsorption filter medium comprises activated carbon and/or diatomite; the membrane element is at least one of a microfiltration membrane, a nanofiltration membrane and an ultrafiltration membrane.
Example 1:
the object to be processed: DL pantoic acid lactone is subjected to enzymolysis and conversion of D pantoic acid lactone hydrolase to obtain a mixed solution containing target separation products such as D pantoic acid ammonia, L pantoic acid lactone and the like and impurities such as thalli, protein and the like.
The enzymolysis and transformation method can refer to the microbial enzyme method for preparing D-pantolactone in New Tang of south China university. Specifically, the following steps can be also included: mixing water and DL pantoic acid lactone to prepare DL pantoic acid lactone solution with the concentration of 200g/L, then adding a proper amount of D pantoic acid lactone hydrolase, adjusting the pH of the solution to 6.0-8.0 by ammonia water, converting for 10h at 30 ℃, finishing the reaction, and detecting the content of D pantoic acid ammonia in the obtained enzymolysis product to be 82 g/L.
The separation treatment steps are as follows:
5L of the above-mentioned enzymatic hydrolysate was introduced into a desalting chamber of an electrodialyzer (manufactured by Zhejiang Saite Membrane technology Co., Ltd., type: GCM-E-10, membrane number: 10 pairs), electrodialysis was performed at 50V, and then a solution in a concentration chamber was collected to obtain D-pantoic acid ammonia solution, which was concentrated to obtain D-pantoic acid ammonia with a purity of 98.7%. And collecting the solution in the desalting chamber to obtain a pantoic acid lactone solution.
Example 2:
the difference from example 1 is that the separation process steps are as follows:
5L of the enzymolysis product was filtered through a ceramic membrane and a nanofiltration membrane to remove impurities, and the obtained permeate was introduced into a desalting chamber of an electrodialyzer (manufactured by GCM-E-10, model number: 10 pairs) and subjected to electrodialysis at 50V. And collecting the solution in the concentration chamber to obtain D-pantoic acid ammonia solution, and concentrating to obtain D-pantoic acid ammonia with the purity of 99.2%. And collecting the solution in the desalting chamber to obtain a pantoic acid lactone solution.
Claims (10)
1. A method for separating an acid from an ester, comprising: providing N pairs of cation exchange membranes and anion exchange membranes which are sequentially arranged, leading mixed solution at least comprising acid and/or acid salt and ester to the space between the cation exchange membranes and the anion exchange membranes, carrying out migration separation on the mixed solution in an electric field environment, and then respectively collecting concentrated phase solution and dilute phase solution; n is more than or equal to 1.
2. The process according to claim 1, wherein: the concentration of the acid and/or the acid salt is 0.5-300g/L, and the concentration of the ester is 0.5-300 g/L.
3. The process according to claim 1, wherein: the mixed solution at least comprises organic acid and/or organic acid salt and organic acid ester.
4. The method of claim 2, wherein the acid is selected from the group consisting of: the organic acid is connected with-COOH and-SO on the molecule3H. -RSOOH, -RCOSH.
5. A process according to claim 3 for the separation of an acid from an ester, characterized in that: the organic acid ester is lactide or lactone formed by organic acid, and the organic acid ester is non-electrolyte.
6. The method of claim 2, wherein the acid is selected from the group consisting of: the organic acid is at least one of lactic acid, glycolic acid, L pantoic acid, D pantoic acid, alpha hydroxybutyric acid and beta hydroxybutyric acid.
7. The method of claim 2, wherein the acid is selected from the group consisting of: the organic acid ester is at least one of glycolide, lactide, valerolactone, D pantoic acid lactone and L pantoic acid lactone.
8. The process according to claim 1, wherein: the mixed solution further comprises a step of removing impurity components in the mixed solution before the ion exchange membrane separation is carried out.
9. The method of claim 8, wherein: the method for removing impurity components in the mixed solution comprises the following steps:
1) carrying out adsorption filtration on the mixed solution, and collecting filtrate; and/or
2) Filtering the mixed solution by adopting a membrane element with the aperture of 0.001-1000 um, and collecting the permeate; and/or
3) Treating the mixed solution by using a plate separation method, and collecting plate separation clear liquid.
10. The process of claim 9 for separating an acid from an ester, wherein: the adsorption filter medium comprises activated carbon and/or diatomite; the membrane element is at least one of a microfiltration membrane, a nanofiltration membrane and an ultrafiltration membrane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911189743.7A CN112774448A (en) | 2019-11-27 | 2019-11-27 | Method for separating acid from ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911189743.7A CN112774448A (en) | 2019-11-27 | 2019-11-27 | Method for separating acid from ester |
Publications (1)
| Publication Number | Publication Date |
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| CN112774448A true CN112774448A (en) | 2021-05-11 |
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| CN201911189743.7A Withdrawn CN112774448A (en) | 2019-11-27 | 2019-11-27 | Method for separating acid from ester |
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| Country | Link |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN209243063U (en) * | 2018-10-30 | 2019-08-13 | 北京建筑大学 | A kind of resource utilization system of brewed spirit by-product yellow water |
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2019
- 2019-11-27 CN CN201911189743.7A patent/CN112774448A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN209243063U (en) * | 2018-10-30 | 2019-08-13 | 北京建筑大学 | A kind of resource utilization system of brewed spirit by-product yellow water |
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Application publication date: 20210511 |