CN112774251A - Method for separating acid and ester mixed solution - Google Patents
Method for separating acid and ester mixed solution Download PDFInfo
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- CN112774251A CN112774251A CN201911177821.1A CN201911177821A CN112774251A CN 112774251 A CN112774251 A CN 112774251A CN 201911177821 A CN201911177821 A CN 201911177821A CN 112774251 A CN112774251 A CN 112774251A
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- Prior art keywords
- acid
- mixed solution
- ester
- separating
- resin
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- 239000011259 mixed solution Substances 0.000 title claims abstract description 43
- 239000002253 acid Substances 0.000 title claims abstract description 41
- 150000002148 esters Chemical class 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 25
- 229920005989 resin Polymers 0.000 claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 32
- 238000000926 separation method Methods 0.000 claims abstract description 31
- 238000001179 sorption measurement Methods 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- -1 organic acid salt Chemical class 0.000 claims description 22
- 239000012528 membrane Substances 0.000 claims description 17
- 238000001914 filtration Methods 0.000 claims description 15
- OTOIIPJYVQJATP-BYPYZUCNSA-N (R)-pantoic acid Chemical compound OCC(C)(C)[C@@H](O)C(O)=O OTOIIPJYVQJATP-BYPYZUCNSA-N 0.000 claims description 13
- 239000012535 impurity Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 229920001429 chelating resin Polymers 0.000 claims description 6
- 238000001471 micro-filtration Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 239000012466 permeate Substances 0.000 claims description 5
- 238000000108 ultra-filtration 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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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 compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 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
- 238000001728 nano-filtration Methods 0.000 claims description 2
- 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 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 238000010828 elution Methods 0.000 abstract description 7
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 14
- 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000003756 stirring Methods 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
- 241001052560 Thallis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000049 pigment Substances 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
- 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
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/20—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the conditioning of the sorbent material
- B01D15/203—Equilibration or regeneration
-
- 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
- B01D15/42—Selective adsorption, e.g. chromatography characterised by the development mode, e.g. by displacement or by elution
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of resin separation, in particular to a separation method of an acid and ester mixed solution; the method comprises the following steps of separating a mixed solution through resin, and respectively collecting a first effluent and a second effluent; the mixed solution at least comprises acid and/or acid salt and ester; the invention has the beneficial effects that: according to the difference of the elution speeds of the ester and the acid and/or the salt in the adsorption separation resin, the stable and effective separation of the ester and the acid and/or the salt can be realized.
Description
Technical Field
The invention relates to the technical field of resin separation, in particular to a separation method of an acid and ester mixed solution.
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 separation method of acid and ester mixed solution, 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 separation method of acid and ester mixed solution is provided, the mixed solution is separated by resin, and a first effluent and a second effluent are respectively collected; the mixed solution includes at least an acid and/or an acid salt and an ester.
The invention has the beneficial effects that: according to the difference of the elution speed of the ester and the acid and/or the salt in the resin, the stable and effective separation of the ester and the acid and/or the salt can be realized.
Detailed Description
A method for separating acid and ester mixed solution comprises separating the mixed solution with lipid, and collecting first effluent and second effluent respectively; the mixed solution includes at least an acid and/or an acid salt and an ester.
Preferably, when the resin is used for elution, the eluent is water. And water is used as an eluent, so that the separation process is clean and environment-friendly, no solvent residue exists in a separation product, and the resin is convenient to recycle.
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, the organic acid ester being a lactide or lactone formed from an organic acid, the organic acid ester being a 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; the organic acid ester is at least one of glycolide, lactide, valerolactone, D pantoic acid lactone and L pantoic acid lactone.
In order to remove impurity components in the mixed solution and avoid the influence of the blockage of the resin by macromolecular substances on the separation effect of the resin, the mixed solution further comprises a step of removing the impurity components in the mixed solution before the ion exchange membrane separation is carried out, and the method for removing the 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.
The impurity removal treatment aims to remove impurity components in the mixed solution and improve the resin elution effect, and the impurity removal modes include but are not limited to the above modes. In fact, through the mixing and stirring of the activated carbon or the diatomite and the filtration treatment or the filtration treatment of the microfiltration membrane, part of impurity components in the mixed solution can be removed, and the influence on the resin separation effect caused by the blockage of the resin by macromolecular substances is avoided. The ultrafiltration membrane can intercept and remove substances such as micromolecular protein, amino acid, pigment and the like in the mixed solution, further facilitates subsequent resin separation treatment, and prolongs the cycle service life of the resin.
In the actual separation, the mixing, stirring and filtering treatment of activated carbon or diatomite, or the filtering treatment of a microfiltration membrane, or the filtering treatment of an ultrafiltration membrane can be selected at will to remove impurities, and any two ways can be selected to be combined in any order, or the combination of three filtering ways, or the combination of four filtering ways to improve the impurity removal effect.
Further, the adsorption filter medium comprises activated carbon and/or diatomite; the membrane element is at least one of a microfiltration membrane with the aperture of 20-200 nm, a nanofiltration membrane and an ultrafiltration membrane with the molecular weight cutoff of 1000-10000D.
Further, the resin is weak polar or nonpolar adsorption separation resin. The weak polar or non-polar adsorption separation resin has the characteristic of less or no adsorption to acid and ester, and acid and/or salt and ester can flow out in the adsorption separation resin in a sectional way to realize the separation purpose.
Further, the resin is selected from at least one of Tulsion ADS-600, Tulsion ADS-800, Amberlite XAD7-HP, Amberlite XAD16-HP, Amberlite XAD-1180N, DIAION HP2MGL, DIAION SP2MGS, under-the-road XDA-8G, under-the-road LX-158, under-the-road LSA-12. The above products are all commercially available.
The technical scheme of the present invention is further described in detail with reference to examples 1 to 4.
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 pantoate, 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:
taking 1L of the above enzymolysis product, loading onto adsorption resin column (resin: XDA-8G; resin column: glass chromatographic column with inner diameter of 2.6cm and length of 90cm, 4 pieces), adding water for elution after the feed liquid is fed, collecting D-pantoic acid ammonia solution, and collecting pantoic acid lactone solution. The D-pantoic acid ammonia solution is concentrated to obtain D-pantoic acid ammonia, the purity of the product is 98.3 percent, and the yield is 98.6 percent.
Example 2:
DL pantoic acid lactone is treated according to the enzymolysis conversion method of the embodiment 1, 1L of enzymolysis product is taken, added with a proper amount of activated carbon, stirred and stood for 20 minutes, repeatedly stirred and stood for filtration, then the filtration is carried out again by adopting a microfiltration membrane with the aperture of 100nm, permeate is collected and loaded on an adsorption resin column (model: LX-158; resin column: glass chromatographic column with the inner diameter of 2.6cm and the length of 90cm and 4), after feed liquid is fed, water is added for elution, D-pantoic acid ammonia solution is collected firstly, and then pantoic acid lactone solution is collected. And concentrating the D-pantoic acid ammonia solution to obtain D-pantoic acid ammonia with the product purity of 99.1 percent and the yield of 99.5 percent.
Example 3:
DL pantoic acid lactone is treated according to the enzymolysis conversion method of the embodiment 1, 1L of enzymolysis products are taken, firstly, microfiltration membranes with the aperture of 100nm are used for filtering the enzymolysis products, then, ultrafiltration membranes with the molecular weight cutoff of 2500D are used for filtering the obtained permeate again, adsorption resin columns (model: LX-12; resin columns: glass chromatographic columns with the inner diameter of 2.6cm and the length of 90cm and 4) on the permeate are collected, after the feed liquid is fed, water is added for elution, D-pantoic acid ammonia solution is collected firstly, and then, pantoic acid lactone solution is collected. And concentrating the D-pantoic acid ammonia solution to obtain D-pantoic acid ammonia with the product purity of 99.2 percent and the yield of 99.5 percent.
Claims (9)
1. A method for separating acid and ester mixed solution is characterized in that: separating the mixed solution by resin, and respectively collecting a first effluent and a second effluent; the mixed solution includes at least an acid and/or an acid salt and an ester.
2. The method for separating an acid and ester mixed solution 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 method for separating an acid and ester mixed solution 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 for separating an acid and ester mixed solution according to claim 3, wherein: the organic acid is connected with-COOH and-SO on the molecule3H. -RSOOH, -RCOSH, said organic acid ester being a lactide or lactone formed from an organic acid.
5. The method for separating an acid and ester mixed solution according to claim 3, wherein: 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; the organic acid ester is at least one of glycolide, lactide, valerolactone, D pantoic acid lactone and L pantoic acid lactone.
6. The method for separating an acid and ester mixed solution according to claim 1, wherein: the mixed solution further comprises a step of removing impurity components in the mixed solution before the resin separation, and the method for removing the 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.
7. The method for separating an acid and ester mixed solution according to claim 6, wherein: the adsorption filter medium comprises activated carbon and/or diatomite; the membrane element is at least one of a microfiltration membrane with the aperture of 20-200 nm, a nanofiltration membrane and an ultrafiltration membrane with the molecular weight cutoff of 1000-10000D.
8. The method for separating an acid and ester mixed solution according to claim 1, wherein: the resin is ion exchange resin or macroporous adsorption resin.
9. The method for separating an acid and ester mixed solution according to claim 1, wherein: the resin is selected from at least one of Tulsion ADS-600, Tulsion ADS-800, Amberlite XAD7-HP, Amberlite XAD16-HP, Amberlite XAD-1180N, DIAION HP2MGL, DIAION SP2MGS, under-the-road XDA-8G, under-the-road LX-158, under-the-road LSA-12.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911177821.1A CN112774251A (en) | 2019-11-27 | 2019-11-27 | Method for separating acid and ester mixed solution |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911177821.1A CN112774251A (en) | 2019-11-27 | 2019-11-27 | Method for separating acid and ester mixed solution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112774251A true CN112774251A (en) | 2021-05-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911177821.1A Pending CN112774251A (en) | 2019-11-27 | 2019-11-27 | Method for separating acid and ester mixed solution |
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| Country | Link |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1761742A (en) * | 2003-03-03 | 2006-04-19 | 第一精密化学株式会社 | Process for producing lactonase and utilization thereof |
| CN101016242A (en) * | 2007-01-19 | 2007-08-15 | 中国科学院山西煤炭化学研究所 | Method of preparing linolenic acid and linolenic acid lower member ester by urea column chromatography |
| CN107628963A (en) * | 2017-10-16 | 2018-01-26 | 宁夏金维制药股份有限公司 | A kind of vitamin B5The preparation method of crude product |
| CN108675979A (en) * | 2018-06-14 | 2018-10-19 | 东北农业大学 | A kind of method of black rice procyanidine extraction and its basic structural unit detection |
| CN110201420A (en) * | 2019-06-27 | 2019-09-06 | 上海渔霁生物技术有限公司 | A kind of chromatographic system and method separating organic acid and organic acid esters |
-
2019
- 2019-11-27 CN CN201911177821.1A patent/CN112774251A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1761742A (en) * | 2003-03-03 | 2006-04-19 | 第一精密化学株式会社 | Process for producing lactonase and utilization thereof |
| CN101016242A (en) * | 2007-01-19 | 2007-08-15 | 中国科学院山西煤炭化学研究所 | Method of preparing linolenic acid and linolenic acid lower member ester by urea column chromatography |
| CN107628963A (en) * | 2017-10-16 | 2018-01-26 | 宁夏金维制药股份有限公司 | A kind of vitamin B5The preparation method of crude product |
| CN108675979A (en) * | 2018-06-14 | 2018-10-19 | 东北农业大学 | A kind of method of black rice procyanidine extraction and its basic structural unit detection |
| CN110201420A (en) * | 2019-06-27 | 2019-09-06 | 上海渔霁生物技术有限公司 | A kind of chromatographic system and method separating organic acid and organic acid esters |
Non-Patent Citations (1)
| Title |
|---|
| 德里克: "化学之书", 重庆大学出版社, pages: 214 * |
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Application publication date: 20210511 |