CN112209819A - Preparation method of D-pantoic acid calcium - Google Patents
Preparation method of D-pantoic acid calcium Download PDFInfo
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- CN112209819A CN112209819A CN202011034914.1A CN202011034914A CN112209819A CN 112209819 A CN112209819 A CN 112209819A CN 202011034914 A CN202011034914 A CN 202011034914A CN 112209819 A CN112209819 A CN 112209819A
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- calcium
- pantoic acid
- pantoate
- preparation
- solution containing
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- 229910052791 calcium Inorganic materials 0.000 title claims abstract description 61
- 239000011575 calcium Substances 0.000 title claims abstract description 61
- OTOIIPJYVQJATP-BYPYZUCNSA-N (R)-pantoic acid Chemical compound OCC(C)(C)[C@@H](O)C(O)=O OTOIIPJYVQJATP-BYPYZUCNSA-N 0.000 title claims abstract description 56
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 26
- 239000011259 mixed solution Substances 0.000 claims abstract description 23
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 22
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 22
- -1 D-pantoic acid lactone Chemical class 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 3
- SERHXTVXHNVDKA-BYPYZUCNSA-N (R)-pantolactone Chemical compound CC1(C)COC(=O)[C@@H]1O SERHXTVXHNVDKA-BYPYZUCNSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 abstract description 7
- 239000012535 impurity Substances 0.000 abstract description 6
- 230000000052 comparative effect Effects 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- MRAMPOPITCOOIN-VIFPVBQESA-N (2r)-n-(3-ethoxypropyl)-2,4-dihydroxy-3,3-dimethylbutanamide Chemical compound CCOCCCNC(=O)[C@H](O)C(C)(C)CO MRAMPOPITCOOIN-VIFPVBQESA-N 0.000 description 1
- 239000011703 D-panthenol Substances 0.000 description 1
- 235000004866 D-panthenol Nutrition 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- 229930003571 Vitamin B5 Natural products 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960002079 calcium pantothenate Drugs 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960003949 dexpanthenol Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011675 vitamin B5 Substances 0.000 description 1
- 235000009492 vitamin B5 Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000002699 waste material Substances 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
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of D-pantoic acid calcium, which comprises the following steps: reacting D-pantoic acid lactone with calcium hydroxide to obtain a mixed solution containing D-pantoic acid calcium. The preparation method provided by the invention is simple and feasible, the solvent is safe and pollution-free, stable crystals can be formed at low temperature, and the obtained D-calcium pantoate crystals are not sticky to the wall and are not agglomerated, and have few impurities and high purity.
Description
Technical Field
The invention belongs to the technical field of chemical production, and relates to a preparation method of D-pantoic acid calcium.
Background
The D-pantoic acid lactone is derived from chiral resolution of DL-pantoic acid lactone, the DL-pantoic acid lactone is an organic chemical, and the D-pantoic acid lactone obtained by chiral resolution can be used for synthesizing D-panthenol or D-panthenyl ethyl ether and the like used for cosmetics. The greatest application of D-pantoic acid lactone is to synthesize D-calcium pantothenate, which is also called pantothenic acid and is also called vitamin B5, and the D-calcium pantothenate is a water-soluble B-group vitamin which is widely used in food, medicine, feed additives and the like.
In the synthesis of calcium D-pantothenate, the presence of calcium D-pantoate is found in both the mother liquor and the product, but since the content thereof is too low, studies on the presence of calcium D-pantoate cannot be made, and the application direction of the calcium D-pantoate cannot be judged, it is necessary to provide a production method capable of obtaining high-quality calcium D-pantoate.
Disclosure of Invention
The invention aims to provide a preparation method of D-calcium pantoate, which is simple and easy to implement, has safe and pollution-free solvent, can form stable crystals at low temperature, and the obtained D-calcium pantoate crystals are not sticky to walls, are not agglomerated, have few impurities and have high purity.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a method for preparing D-pantoic acid calcium, the method comprising: reacting D-pantoic acid lactone with calcium hydroxide to obtain a mixed solution containing D-pantoic acid calcium.
In the present invention, the molar ratio of D-pantolactone to calcium hydroxide is 1 (1-1.2), for example, 1: 1.1.
In the present invention, the reaction is carried out in a solvent, and the solvent in the present invention is water.
The invention preferably selects water as solvent, and has the advantages of safety and environmental protection.
In order to avoid waste of the solvent and ensure easy handling of the D-pantoic acid calcium, the mass ratio of the solvent to the D-pantoic acid lactone is (2-5: 1), such as 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1 and the like.
The calcium hydroxide is dropwise added into a reaction system in the form of a calcium hydroxide aqueous solution.
If the calcium hydroxide (or the calcium hydroxide aqueous solution) is directly added into a reaction system, implosion can be caused, rapid crystallization and precipitation can be carried out during the reaction, and the crystals are stirred and instantly locked, so that the impurities of the crystals are more, the purity is lower, and the separation is difficult.
In a preferred embodiment of the present invention, the concentration of the aqueous calcium hydroxide solution is 15 to 30 wt%, such as 16 wt%, 18 wt%, 20 wt%, 22 wt%, 25 wt%, 28 wt%, etc.
The concentration of the calcium hydroxide aqueous solution is preferably 15-30 wt%, within the range, the reaction rate is moderate, and the reaction time is suitable.
The dropping rate of the invention is 5-10mL/min, such as 6mL/min, 7mL/min, 8mL/min, 9mL/min and the like.
In order to ensure the yield and purity of the final product, the reaction temperature is 60-80 deg.C, such as 62 deg.C, 65 deg.C, 68 deg.C, 70 deg.C, 72 deg.C, 75 deg.C, 78 deg.C, etc.
The reaction temperature of 60-80 ℃ is optimized in the invention, the reaction rate is moderate within the reaction temperature range, and the finally obtained D-calcium pantoate has few impurities and high purity.
The reaction time of the invention is 1-3h, such as 1.2h, 1.5h, 1.8h, 2.0h, 2.2h, 2.5h, 2.8h and the like.
As a preferable technical solution of the present invention, the preparation method further comprises: and cooling the mixed solution containing the D-calcium pantoate for crystallization, and then filtering and drying to obtain the D-calcium pantoate.
The temperature reduction is carried out under the condition of stirring.
As a preferred technical scheme, the preparation method provided by the invention comprises the following steps:
(1) dropwise adding a calcium hydroxide aqueous solution into a D-pantoic acid lactone aqueous solution for reaction to obtain a mixed solution containing D-pantoic acid calcium;
(2) and cooling the mixed solution containing the D-calcium pantoate under the stirring condition for crystallization, filtering and drying to obtain the D-calcium pantoate.
Compared with the prior art, the invention has the following beneficial effects:
(1) the preparation method provided by the invention is simple and feasible, and the raw materials are easy to obtain;
(2) by controlling the concentration, the dropping speed, the reaction temperature and other conditions of the calcium hydroxide aqueous solution, the finally obtained D-calcium pantoate has less impurities, high purity and higher yield.
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 preparation method of D-pantoic acid calcium comprises the following steps:
(1) sequentially adding 100g of deionized water and 50g of D-pantoic acid lactone with the specific rotation degree of +46 degrees into a clean 500mL single-mouth bottle, stirring and dissolving, then dropwise adding 114g of 25 wt% calcium hydroxide aqueous solution, and reacting for 1h at 60 ℃ to obtain mixed solution containing D-pantoic acid calcium;
(2) and (3) cooling the mixed solution containing the D-calcium pantoate to-5 ℃ under stirring, preserving heat, crystallizing, filtering and drying to obtain the D-calcium pantoate.
Example 2
A preparation method of D-pantoic acid calcium comprises the following steps:
(1) sequentially adding 100g of deionized water and 50g of D-pantoic acid lactone with the specific rotation degree of +46 degrees into a clean 500mL single-mouth bottle, stirring and dissolving, then dropwise adding 114g of 25 wt% calcium hydroxide aqueous solution, and reacting for 1h at 80 ℃ to obtain mixed solution containing D-pantoic acid calcium;
(2) and (3) cooling the mixed solution containing the D-calcium pantoate to-5 ℃ under stirring, preserving heat, crystallizing, filtering and drying to obtain the D-calcium pantoate.
Example 3
A preparation method of D-pantoic acid calcium comprises the following steps:
(1) sequentially adding 100g of deionized water and 50g of D-pantoic acid lactone with the specific rotation degree of +46 degrees into a clean 500mL single-mouth bottle, stirring and dissolving, then dropwise adding 190g of 15 wt% calcium hydroxide aqueous solution, and reacting for 3h at 80 ℃ to obtain mixed solution containing D-pantoic acid calcium;
(2) and (3) cooling the mixed solution containing the D-calcium pantoate to-5 ℃ under stirring, preserving heat, crystallizing for 6 hours, filtering and drying to obtain the D-calcium pantoate.
Example 4
A preparation method of D-pantoic acid calcium comprises the following steps:
(1) sequentially adding 100g of deionized water and 50g of D-pantoic acid lactone with the specific rotation degree of +46 degrees into a clean 500mL single-mouth bottle, stirring and dissolving, then dropwise adding 142.5g of 20 wt% calcium hydroxide aqueous solution, and reacting for 1h at 60 ℃ to obtain mixed solution containing D-pantoic acid calcium;
(2) and (3) cooling the mixed solution containing the D-calcium pantoate to-5 ℃ under stirring, preserving heat, crystallizing, filtering and drying to obtain the D-calcium pantoate.
Comparative example 1
A preparation method of D-pantoic acid calcium comprises the following steps:
(1) sequentially adding 100g of deionized water and 50g of D-pantoic acid lactone with the specific rotation degree of +46 degrees into a clean 500mL single-mouth bottle, stirring and dissolving, then dropwise adding 95g of 40 wt% calcium hydroxide aqueous solution, and reacting for 1h at 80 ℃ to obtain mixed solution containing D-pantoic acid calcium;
(2) and (3) cooling the mixed solution containing the D-calcium pantoate to-5 ℃ under stirring, preserving heat, crystallizing, filtering and drying to obtain the D-calcium pantoate.
Comparative example 2
A preparation method of D-pantoic acid calcium comprises the following steps:
(1) sequentially adding 100g of methanol and 50g of D-pantoic acid lactone with the specific rotation degree of +46 degrees into a clean 500mL single-mouth bottle, stirring and dissolving, then dropwise adding 142.5g of 20 wt% calcium hydroxide aqueous solution, and reacting for 1h at 60 ℃ to obtain mixed solution containing D-pantoic acid calcium;
(2) and (3) cooling the mixed solution containing the D-calcium pantoate to-5 ℃ under stirring, preserving heat, crystallizing, filtering and drying to obtain the D-calcium pantoate.
Comparative example 3
A preparation method of D-pantoic acid calcium comprises the following steps:
(1) adding 100g of methanol into a clean 500mL single-mouth bottle, adding 50g of D-pantoic acid lactone with the specific rotation degree of +46 ℃ and 142.5g of 20 wt% calcium hydroxide aqueous solution under stirring, and reacting for 1h at 60 ℃ to obtain a mixed solution containing D-pantoic acid calcium;
(2) and (3) cooling the mixed solution containing the D-calcium pantoate to-5 ℃ under stirring, preserving heat, crystallizing, filtering and drying to obtain the D-calcium pantoate.
Performance testing
The samples provided in examples 1 to 4 and comparative examples 1 to 3 were weighed and the yield thereof was calculated, and the results are shown in table 1:
TABLE 1
Note: comparative example 1 suddenly agglomerates and adheres to the reaction vessel in the process of temperature reduction, loose particles cannot be formed, impurities are more, and separation is difficult, so that the particles are not recovered; comparative example 3 was already imploded in the reaction vessel at the beginning of the reaction and no subsequent steps could be performed.
The embodiment and the performance test show that the preparation method provided by the invention is simple and feasible, the prepared D-calcium pantoate is a stable crystal, does not stick to the wall, is easy to carry out subsequent treatment, and has high purity and high yield of the product.
As can be seen from the comparison of examples 2-3 with comparative example 1, the concentration of the aqueous calcium hydroxide solution provided by the present invention needs to be in the range of 15-30 wt% to obtain D-pantoic acid calcium which is not sticky to the wall and is easy for subsequent treatment; as can be seen from the comparison between example 4 and comparative example 2, the method can adopt water as a solvent to prepare the D-pantoic acid calcium, and the water as the solvent is safe and environment-friendly; as can be seen from a comparison of example 4 and comparative example 3, the calcium hydroxide solvent of the present invention is required to react with D-pantoic acid lactone in the form of a dropwise addition.
The applicant states that the present invention is illustrated by the above examples to the preparation of the calcium D-pantoate of 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 practiced. 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 preparation method of D-pantoic acid calcium, characterized in that, the preparation method comprises: reacting D-pantoic acid lactone with calcium hydroxide to obtain a mixed solution containing D-pantoic acid calcium.
2. The method according to claim 1, wherein the molar ratio of D-pantolactone to calcium hydroxide is 1 (1-1.2).
3. The method of claim 1 or 2, wherein the reaction is carried out in a solvent.
4. The method according to claim 3, wherein the solvent is water.
5. The production method according to claim 3 or 4, characterized in that the mass ratio of the solvent to the D-pantoic acid lactone is (2-5): 1.
6. The production method according to any one of claims 1 to 5, wherein the calcium hydroxide is added dropwise to the reaction system in the form of an aqueous calcium hydroxide solution.
7. The method according to claim 6, wherein the concentration of the aqueous calcium hydroxide solution is 15 to 30 wt%;
and/or the dropping rate is 5-10 mL/min.
8. The method for preparing according to any one of claims 1 to 7, wherein the temperature of the reaction is 60 to 80 ℃;
and/or the reaction time is 1-3 h.
9. The production method according to any one of claims 1 to 8, further comprising: cooling the mixed solution containing the D-calcium pantoate for crystallization, and then filtering and drying to obtain the D-calcium pantoate;
preferably, the temperature reduction is performed under stirring.
10. The production method according to any one of claims 1 to 8, characterized by comprising:
(1) dropwise adding a calcium hydroxide aqueous solution into a D-pantoic acid lactone aqueous solution for reaction to obtain a mixed solution containing D-pantoic acid calcium;
(2) and cooling the mixed solution containing the D-calcium pantoate under the stirring condition for crystallization, filtering and drying to obtain the D-calcium pantoate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011034914.1A CN112209819A (en) | 2020-09-27 | 2020-09-27 | Preparation method of D-pantoic acid calcium |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011034914.1A CN112209819A (en) | 2020-09-27 | 2020-09-27 | Preparation method of D-pantoic acid calcium |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114394948A (en) * | 2021-12-29 | 2022-04-26 | 安徽泰格生物科技有限公司 | Recycling method of panthenol mother liquor |
| CN116217428A (en) * | 2022-12-22 | 2023-06-06 | 黑龙江新和成生物科技有限公司 | Methanol hydrate crystal of D-calcium pantothenate and process for producing D-calcium pantothenate |
| CN116589437A (en) * | 2023-04-07 | 2023-08-15 | 天津大学 | Continuous crystallization method of D-pantolactone |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110835185A (en) * | 2019-12-02 | 2020-02-25 | 安徽华恒生物科技股份有限公司 | Method for separating acid and ester from mixed solution |
-
2020
- 2020-09-27 CN CN202011034914.1A patent/CN112209819A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110835185A (en) * | 2019-12-02 | 2020-02-25 | 安徽华恒生物科技股份有限公司 | Method for separating acid and ester from mixed solution |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114394948A (en) * | 2021-12-29 | 2022-04-26 | 安徽泰格生物科技有限公司 | Recycling method of panthenol mother liquor |
| CN116217428A (en) * | 2022-12-22 | 2023-06-06 | 黑龙江新和成生物科技有限公司 | Methanol hydrate crystal of D-calcium pantothenate and process for producing D-calcium pantothenate |
| CN116217428B (en) * | 2022-12-22 | 2024-04-02 | 黑龙江新和成生物科技有限公司 | Methanol hydrate crystal of D-calcium pantothenate and process for producing D-calcium pantothenate |
| CN116589437A (en) * | 2023-04-07 | 2023-08-15 | 天津大学 | Continuous crystallization method of D-pantolactone |
| CN116589437B (en) * | 2023-04-07 | 2024-11-15 | 天津大学 | A continuous crystallization method for D-pantolactone |
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