CN112174845A - Preparation method of D-panthenol - Google Patents
Preparation method of D-panthenol Download PDFInfo
- Publication number
- CN112174845A CN112174845A CN202011033252.6A CN202011033252A CN112174845A CN 112174845 A CN112174845 A CN 112174845A CN 202011033252 A CN202011033252 A CN 202011033252A CN 112174845 A CN112174845 A CN 112174845A
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- Prior art keywords
- panthenol
- solvent
- reaction
- aminopropanol
- mixed solution
- Prior art date
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- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 title claims abstract description 47
- 239000011703 D-panthenol Substances 0.000 title claims abstract description 46
- 235000004866 D-panthenol Nutrition 0.000 title claims abstract description 45
- 229960003949 dexpanthenol Drugs 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 23
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000005917 acylation reaction Methods 0.000 claims abstract description 16
- 239000011259 mixed solution Substances 0.000 claims abstract description 15
- SERHXTVXHNVDKA-BYPYZUCNSA-N (R)-pantolactone Chemical compound CC1(C)COC(=O)[C@@H]1O SERHXTVXHNVDKA-BYPYZUCNSA-N 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 20
- 229920005989 resin Polymers 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 13
- 239000002994 raw material Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000003463 adsorbent Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 9
- -1 D-pantoic acid lactone Chemical class 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- GHOKWGTUZJEAQD-UHFFFAOYSA-N pantothenic acid Chemical compound OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004909 Moisturizer Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of D-panthenol, which comprises the following steps: carrying out acylation reaction on D-pantolactone and 3-aminopropanol in a solvent to obtain a mixed solution containing D-panthenol; wherein the reaction temperature of the acylation reaction is 10-35 ℃. The D-panthenol prepared by the preparation method provided by the invention has higher yield and higher purity; meanwhile, the recovered solvent can be reused continuously, and the method is safe and environment-friendly.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and relates to a preparation method of D-panthenol.
Background
Panthenol is also known as provitamin B5Can be divided into 3 forms of DL-form, D-form and L-form, wherein only D-form has bioactivity, and L-form has no bioactivity; d-panthenol is an optically active stereoisomer of panthenolAnd (3) a body.
D-panthenol is an equivalent of D-pantothenic acid and is widely applied to the industries of medicines, foods, feeds and cosmetics. In the food industry, the product is used as a nutritional supplement and a fortifier, promotes the metabolism of protein, fat and carbohydrate of human bodies, maintains the skin and mucous membranes, improves the luster of hair, enhances the immunity and prevents diseases; in the cosmetic industry, the care effect on the skin is manifested by deeply penetrating moisturizers, stimulating the growth of epithelial cells, promoting wound healing, and playing an anti-inflammatory role; the hair care effect is characterized by a lasting moisturizing function, hair is prevented from being split and damaged, the density of the hair is increased, and the luster of the hair is improved; nail care appears to improve nail hydration, imparting flexibility to the nail.
At present, in a synthesis method of D-panthenol, D-pantolactone and 3-aminopropanol are heated and reacted in a reaction kettle under the condition that ethanol is used as a solvent, and the reaction kettle is subjected to vacuum concentration to obtain the D-panthenol; in addition, CN101851171A discloses a method for preparing D-panthenol, which comprises reacting D-pantoic acid lactone with 3-aminopropanol under the solvent-free condition to obtain D-panthenol, wherein the solvent is omitted, the step of vacuum concentration for removing the solvent is omitted, but the reaction requirement is high, and the quality requirement for the raw materials of D-pantoic acid lactone and 3-aminopropanol is too high; and because the D-panthenol is thick, the reaction is carried out under the condition of no addition of a solvent, the generated material of the D-panthenol is thick, so that part of 3-aminopropanol and D-pantolactone cannot contact with each other and cannot react sufficiently, the obtained D-panthenol is poor in quality, the raw material residue is high, and the obtained products cannot meet the application requirement on the purity of the D-panthenol.
Therefore, it is desired to develop a process for producing D-panthenol with high yield and high purity.
Disclosure of Invention
The invention aims to provide a preparation method of D-panthenol, which has the advantages of high yield and high purity of the D-panthenol obtained by the preparation method; meanwhile, the recovered solvent can be reused continuously, and the method is safe and environment-friendly.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a process for the preparation of D-panthenol, comprising the steps of:
carrying out acylation reaction on D-pantolactone and 3-aminopropanol in a solvent to obtain a mixed solution containing D-panthenol;
wherein the reaction temperature of the acylation reaction is 10-35 ℃, such as 15 ℃, 20 ℃, 25 ℃, 30 ℃ and the like.
The invention specifically selects the temperature of acylation reaction to be 10-35 ℃, and the reaction can be finished in a short time at the temperature, so that the side reaction can be avoided, the impurity content in the product is reduced, and the product quality is improved. If the reaction temperature is too high, more unreacted raw materials are contained in the finally obtained product, so that the product quality is slightly poor; if the reaction temperature is low, the reaction temperature is high, and the reaction temperature needs to be controlled, which in turn leads to poor production efficiency.
In a preferred embodiment of the present invention, the reaction temperature of the acylation reaction is 20 to 30 ℃, for example, 22 ℃, 24 ℃, 25 ℃, 26 ℃, 28 ℃, etc.
The reaction temperature of 20-30 ℃ is preferably selected, namely the reaction is carried out at room temperature, so that the process of heating or cooling is avoided, the reaction time is short, and the product quality is high.
In order to further improve the yield of D-panthenol and reduce the waste of raw materials, the molar ratio of D-pantolactone to 3-aminopropanol is (1.01-1.05):1, such as 1.02:1, 1.03:1, 1.04:1, etc.
The solvent is methanol and/or ethanol.
In the invention, the preparation method further comprises the steps of filtering and concentrating the mixed solution containing the D-panthenol to obtain the D-panthenol.
The filtration according to the invention is carried out using a resin column.
In a preferred embodiment of the present invention, the resin filled in the resin column is an ester adsorbent resin, and is preferably an ester adsorbent resin FB-02.
The invention filters and uses the resin column packed with ester adsorbent resin, and limited D-pantoic acid lactone slightly excessive in the invention, D-pantoic acid lactone slightly excessive is combined with filtering and carried on, can guarantee the complete reaction of 3-amino propanol, guarantee the final D-pantoic alcohol has better yield, can remove D-pantoic acid lactone not completely reacted, so as to make the final product have higher purity; moreover, the resin column filtration also has the function of decoloring.
As a preferable technical scheme of the invention, the concentration is water bath scraper vacuum concentration.
In order to ensure the high purity of the product, the temperature of the water bath is less than or equal to 70 ℃, such as 68 ℃, 65 ℃, 60 ℃, 58 ℃, 55 ℃, 50 ℃, 45 ℃, 40 ℃, 35 ℃, 30 ℃ and the like.
The method adopts the water bath scraper to recover the solvent in vacuum, so that the solvent residue of the product can be ensured to be low, the recovered solvent can be repeatedly used after simple rectification, the production cost is reduced, and the environmental pollution is reduced.
As one of the preferable technical proposal of the invention, the preparation method comprises the following steps:
(1) carrying out acylation reaction on D-pantolactone and 3-aminopropanol in a solvent at the reaction temperature of 10-35 ℃ to obtain a mixed solution containing D-panthenol;
(2) and filtering the mixed solution containing the D-panthenol through a resin column to remove unreacted raw materials, and then removing the solvent by vacuum concentration by using a water bath scraper to obtain the D-panthenol.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention limits the reaction temperature of 10-35 ℃, so that the reaction can be completed in a short time, and the product has less impurities and higher purity;
(2) the invention limits the D-pantoic acid lactone to be slightly excessive, and introduces the resin column for filtration, so that the unreacted D-pantoic acid lactone can be removed by the resin column while the 3-aminopropanol is ensured to be completely reacted, and the filtration also has the function of decolorization;
(3) the invention adopts a water bath scraper vacuum solvent removal mode, the temperature of the water bath is required to be below 70 ℃, and the solvent can be removed while the product has higher purity.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
A method for preparing D-panthenol comprises the following steps:
(1) dissolving 1310kg of D-pantolactone in 1500L of methanol, adding 750kg of 3-aminopropanol into a reaction kettle, heating to 28 ℃ for acylation reaction for 6 hours to obtain a mixed solution containing D-panthenol;
(2) filtering the mixed solution with resin column (filled with adsorption ester resin FB-02), introducing the filtrate into water bath type scraper concentrator, and recovering methanol under reduced pressure at water bath temperature of 65 deg.C to obtain D-panthenol.
Examples 2 to 3
The difference from example 1 is that in this example, the molar ratio of D-pantolactone to 3-aminopropanol is 1.01:1 (example 2), 1.05:1 (example 3).
Example 4
A method for preparing D-panthenol comprises the following steps:
(1) dissolving 1306kg of D-pantolactone in 1500L of methanol, adding 750kg of 3-aminopropanol into a reaction kettle, heating to 25 ℃ to perform acylation reaction for 8 hours to obtain a mixed solution containing D-panthenol;
(2) filtering the mixed solution by a resin column, and recycling methanol from the filtrate in a water bath type scraper concentrator at 68 ℃ under reduced pressure to obtain the D-panthenol.
Example 5
A method for preparing D-panthenol comprises the following steps:
(1) 1300kg of D-pantolactone is dissolved in 1500L of methanol, 750kg of 3-aminopropanol is added into a reaction kettle, and the temperature is raised to 35 ℃ for acylation reaction for 6 hours to obtain a mixed solution containing D-panthenol;
(2) filtering the mixed solution by a resin column, and recycling methanol from the filtrate in a water bath type scraper concentrator at 68 ℃ under reduced pressure to obtain the D-panthenol.
Comparative examples 1 to 2
The difference from example 1 is that in this comparative example, the temperature of the acylation reaction in step (1) was 45 ℃ (comparative example 1), 5 ℃ (comparative example 2).
Comparative example 3
The difference from example 1 is that in this comparative example, the water bath temperature in step (2) was 80 ℃.
Performance testing
The samples provided in examples 1 to 5 and comparative examples 1 to 3 were subjected to performance tests in accordance with the cosmetic raw material D-panthenol test standard GB/T33306-:
TABLE 1
The embodiment and the performance test show that the preparation method provided by the invention is simple and feasible, the yield of the prepared D-panthenol is high, the purity is high, the residual amount of the solvent and the unreacted raw materials is very small, and all indexes of the solvent and the unreacted raw materials meet the specification.
As can be seen from the comparison of example 1 with examples 2 to 3, the molar ratio of D-pantolactone to 3-aminopropanol in the present invention is (1.01-1.05):1, which is more effective; as can be seen from the comparison of example 1 and comparative examples 1-2, the acylation reaction temperature in the present invention needs to be in the range of 10-35 deg.C, and the final product has high yield and less impurities; as can be seen from the comparison of example 1 and comparative example 3, the temperature of the water bath during solvent recovery needs to be below 70 ℃ to maintain a high purity of the product.
The applicant states that the present invention is illustrated by the above examples to the preparation of D-panthenol according to the present invention, but the present invention is not limited to the above detailed methods, i.e., it is not meant that the present invention must rely on the above detailed methods to be carried out. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A method for producing D-panthenol, comprising the steps of:
carrying out acylation reaction on D-pantolactone and 3-aminopropanol in a solvent to obtain a mixed solution containing D-panthenol;
wherein the reaction temperature of the acylation reaction is 10-35 ℃.
2. The method according to claim 1, wherein the reaction temperature of the acylation reaction is 20 to 30 ℃.
3. The production method according to claim 1 or 2, wherein the molar ratio of D-pantolactone to 3-aminopropanol is (1.01-1.05): 1.
4. The production method according to any one of claims 1 to 3, wherein the solvent is methanol and/or ethanol.
5. The method according to any one of claims 1 to 4, wherein the method further comprises filtering and concentrating a mixed solution containing D-panthenol to obtain the D-panthenol.
6. The production method according to claim 5, wherein the filtration is performed using a resin column.
7. The preparation method according to claim 6, wherein the resin packed in the resin column is an ester-based adsorbent resin.
8. The method of any one of claims 5-7, wherein the concentrating is a water bath blade vacuum concentrating.
9. The method of claim 8, wherein the temperature of the water bath is 70 ℃ or less.
10. The method for preparing according to any one of claims 1 to 9, comprising the steps of:
(1) carrying out acylation reaction on D-pantolactone and 3-aminopropanol in a solvent at the reaction temperature of 10-35 ℃ to obtain a mixed solution containing D-panthenol;
(2) and filtering the mixed solution containing the D-panthenol through a resin column to remove unreacted raw materials, and then removing the solvent by vacuum concentration by using a water bath scraper to obtain the D-panthenol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011033252.6A CN112174845B (en) | 2020-09-27 | 2020-09-27 | Preparation method of D-panthenol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011033252.6A CN112174845B (en) | 2020-09-27 | 2020-09-27 | Preparation method of D-panthenol |
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| Publication Number | Publication Date |
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| CN112174845A true CN112174845A (en) | 2021-01-05 |
| CN112174845B CN112174845B (en) | 2024-01-12 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113317512A (en) * | 2021-05-19 | 2021-08-31 | 安徽华恒生物科技股份有限公司 | Preparation method and application of D-panthenol aqueous solution with high stability |
| CN114292203A (en) * | 2021-12-29 | 2022-04-08 | 安徽泰格生物科技有限公司 | Preparation method of DL-panthenol |
| WO2022219173A1 (en) * | 2021-04-15 | 2022-10-20 | Dsm Ip Assets B.V. | Production of panthenol |
| EP4108654A1 (en) * | 2021-06-23 | 2022-12-28 | DSM IP Assets B.V. | Production of panthenol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB646758A (en) * | 1948-07-23 | 1950-11-29 | Hoffmann La Roche | Process for the manufacture of panthenol derivatives |
| CN1367253A (en) * | 2002-01-29 | 2002-09-04 | 浙江鑫富生化股份有限公司 | Method for preparing D-pantothenic alcohol by using microbial enzyme method |
| CN101851171A (en) * | 2010-05-06 | 2010-10-06 | 北京京卫信康医药科技发展有限公司 | Preparation method of D-panthenol |
-
2020
- 2020-09-27 CN CN202011033252.6A patent/CN112174845B/en active Active
Patent Citations (3)
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|---|---|---|---|---|
| GB646758A (en) * | 1948-07-23 | 1950-11-29 | Hoffmann La Roche | Process for the manufacture of panthenol derivatives |
| CN1367253A (en) * | 2002-01-29 | 2002-09-04 | 浙江鑫富生化股份有限公司 | Method for preparing D-pantothenic alcohol by using microbial enzyme method |
| CN101851171A (en) * | 2010-05-06 | 2010-10-06 | 北京京卫信康医药科技发展有限公司 | Preparation method of D-panthenol |
Non-Patent Citations (2)
| Title |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022219173A1 (en) * | 2021-04-15 | 2022-10-20 | Dsm Ip Assets B.V. | Production of panthenol |
| CN113317512A (en) * | 2021-05-19 | 2021-08-31 | 安徽华恒生物科技股份有限公司 | Preparation method and application of D-panthenol aqueous solution with high stability |
| EP4108654A1 (en) * | 2021-06-23 | 2022-12-28 | DSM IP Assets B.V. | Production of panthenol |
| CN114292203A (en) * | 2021-12-29 | 2022-04-08 | 安徽泰格生物科技有限公司 | Preparation method of DL-panthenol |
| CN114292203B (en) * | 2021-12-29 | 2023-12-01 | 安徽泰格生物科技有限公司 | Preparation method of DL-panthenol |
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| CN112174845B (en) | 2024-01-12 |
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