CN114292203A - Preparation method of DL-panthenol - Google Patents
Preparation method of DL-panthenol Download PDFInfo
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- CN114292203A CN114292203A CN202111647321.7A CN202111647321A CN114292203A CN 114292203 A CN114292203 A CN 114292203A CN 202111647321 A CN202111647321 A CN 202111647321A CN 114292203 A CN114292203 A CN 114292203A
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- panthenol
- aminopropanol
- solution
- temperature
- cooling
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- SNPLKNRPJHDVJA-UHFFFAOYSA-N dl-panthenol Chemical compound OCC(C)(C)C(O)C(=O)NCCCO SNPLKNRPJHDVJA-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 238000002360 preparation method Methods 0.000 title abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000001816 cooling Methods 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 15
- -1 DL-pantoic acid lactone Chemical class 0.000 claims abstract description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims abstract description 9
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000005917 acylation reaction Methods 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 9
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 238000002425 crystallisation Methods 0.000 claims description 17
- 230000008025 crystallization Effects 0.000 claims description 16
- 239000013078 crystal Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 14
- SERHXTVXHNVDKA-UHFFFAOYSA-N pantolactone Chemical compound CC1(C)COC(=O)C1O SERHXTVXHNVDKA-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 3
- 239000011703 D-panthenol Substances 0.000 description 3
- 235000004866 D-panthenol Nutrition 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 229960003949 dexpanthenol Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MRAMPOPITCOOIN-SECBINFHSA-N (2s)-n-(3-ethoxypropyl)-2,4-dihydroxy-3,3-dimethylbutanamide Chemical compound CCOCCCNC(=O)[C@@H](O)C(C)(C)CO MRAMPOPITCOOIN-SECBINFHSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- SNPLKNRPJHDVJA-SSDOTTSWSA-N (2s)-2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethylbutanamide Chemical compound OCC(C)(C)[C@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-SSDOTTSWSA-N 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- 229930003571 Vitamin B5 Natural products 0.000 description 1
- 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 1
- 229960002079 calcium pantothenate Drugs 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011675 vitamin B5 Substances 0.000 description 1
- 235000009492 vitamin B5 Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of DL-panthenol, which comprises the following steps: taking DL-pantoic acid lactone and 3-aminopropanol as raw materials, and carrying out acylation reaction in ethyl acetate or methyl isobutyl ketone to obtain DL-panthenol solution; and cooling and crystallizing the DL-panthenol solution, carrying out solid-liquid separation, and drying to obtain DL-panthenol solid. The method provided by the invention can be used for reaction at a lower temperature, and the obtained DL-panthenol has higher purity and yield.
Description
Technical Field
The invention belongs to the technical field of chemical production, and particularly relates to a preparation method of DL-panthenol.
Background
DL-panthenol is a precursor of vitamin B5, and is a white powdery solid with a slight off-note odor and is hygroscopic. DL-panthenol is readily soluble in water, ethanol, methanol and propylene glycol, soluble in chloroform and ether, slightly soluble in glycerol, and insoluble in vegetable oils, mineral oils and fats. Is relatively stable in air and under light.
DL-panthenol, D-panthenol and D-panthenol ethyl ether are widely applied to cosmetics series, wherein the D-panthenol and the D-panthenol ethyl ether are in liquid state, and the DL-panthenol can exist in solid form, is convenient to use and transport and is widely concerned. DL-panthenol is racemic mixture of L-panthenol and D-panthenol and may be used widely in medicine, food and cosmetics. In the pharmaceutical industry, it is used as vitamin B medicine and can be directly added into cosmetics.
Currently, DL-panthenol is usually produced industrially by acylation reaction of DL-pantolactone and 3-aminopropanol in an alcohol solvent such as methanol and ethanol, followed by crystallization and purification. For example, CN110835309A discloses a crystallization method of DL-panthenol, which adopts DL-pantoic acid lactone and 3-aminopropanol to react in absolute ethanol at 65-85 ℃ to synthesize DL-panthenol, and then prepares a high-purity DL-panthenol solid product by optimizing crystallization conditions, but the yield of DL-panthenol is only 77% at most. Therefore, a method for producing DL-panthenol with a higher yield has been studied.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a preparation method of DL-panthenol. The method can be used for reaction at a lower temperature, and the obtained DL-panthenol has higher purity and yield.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a preparation method of DL-panthenol, which comprises the following steps:
(1) taking DL-pantoic acid lactone and 3-aminopropanol as raw materials, and carrying out acylation reaction in ethyl acetate or methyl isobutyl ketone to obtain DL-panthenol solution;
(2) and cooling and crystallizing the DL-panthenol solution, carrying out solid-liquid separation, and drying to obtain DL-panthenol solid.
According to the invention, ethyl acetate or methyl isobutyl ketone is used as a reaction solvent, so that the reaction can be carried out at a lower temperature (such as 40-50 ℃), the precipitation of DL-panthenol crystals is facilitated during temperature reduction and crystallization, and the precipitation of unreacted DL-pantolactone and 3-aminopropanol is reduced, so that the purity and yield of DL-panthenol products are improved.
In some embodiments of the invention, the molar ratio of DL-pantolactone to 3-aminopropanol is 1-1.05: 1; for example, 1:1, 1.01:1, 1.02:1, 1.03:1, 1.04:1, 1.05:1, etc. may be mentioned.
In some embodiments of the invention, the temperature of the acylation reaction is 40-50 ℃; for example, the temperature may be 40 ℃, 41 ℃, 42 ℃, 43 ℃, 44 ℃, 45 ℃, 46 ℃, 47 ℃, 48 ℃, 49 ℃ or 50 ℃.
In some embodiments of the invention, the time for the acylation reaction is 4 to 6 hours; for example, it may be 4h, 4.2h, 4.5h, 4.8h, 5h, 5.2h, 5.8h, or 6 h.
In some embodiments of the invention, the mass ratio of the total mass of the DL-pantoic acid lactone and 3-aminopropanol to the ethyl acetate or methyl isobutyl ketone is 1 (0.8-2); for example, 1:0.8, 1:0.9, 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, 1:1.6, 1:1.7, 1:1.8, 1:1.9, or 1:2, etc. may be mentioned.
In some embodiments of the invention, the crystallization is performed under stirring conditions.
In some embodiments of the invention, the crystallization temperature is-5 to 5 ℃; for example, the temperature may be-5 deg.C, -4 deg.C, -3 deg.C, -2 deg.C, -1 deg.C, 0 deg.C, 1 deg.C, 2 deg.C, 3 deg.C, 4 deg.C or 5 deg.C.
In some embodiments of the invention, the time for crystallization is from 6 to 8 hours; for example, it may be 6h, 6.2h, 6.5h, 6.8h, 7h, 7.2h, 7.5h, 7.8h, 8h, or the like.
In some embodiments of the invention, a seed crystal is added to the DL-panthenol solution during the cooling.
In some embodiments of the invention, the seed crystals are added while cooling to 10-20 ℃.
In some embodiments of the invention, the seed crystal is DL-panthenol.
By adding a small amount of seed crystals to the DL-panthenol solution, crystal nuclei can be formed and the crystallization of DL-panthenol can be promoted. The amount of the seed crystal to be added in the present invention is not particularly limited, and those skilled in the art can select an appropriate amount according to actual needs.
In some embodiments of the invention, the preparation method comprises the following steps:
(1) mixing DL-pantoic acid lactone and 3-aminopropanol with ethyl acetate or methyl isobutyl ketone, and stirring to react at 40-50 ℃ for 4-6h to obtain DL-panthenol solution;
(2) and cooling the DL-panthenol solution to 10-20 ℃, adding DL-panthenol, then continuously cooling to-5 ℃, keeping the temperature for 6-8 hours under the stirring condition, crystallizing, filtering to obtain a DL-panthenol wet product, and drying in vacuum to obtain a DL-panthenol solid.
Compared with the prior art, the invention has the following beneficial effects:
according to the preparation method provided by the invention, ethyl acetate or methyl isobutyl ketone is used as a reaction solvent, so that the reaction can be carried out at a lower temperature (such as 40-50 ℃), the energy consumption is reduced, the precipitation of DL-panthenol crystals is facilitated during temperature reduction and crystallization, and the precipitation of unreacted DL-pantoic acid lactone and 3-aminopropanol is reduced, so that the purity and the yield of DL-panthenol products are improved. The method is convenient to operate and beneficial to industrial production, and the quality of the product prepared by the method can reach the quality standard of United states Pharmacopeia.
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 specific embodiments are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
This example provides a method for preparing DL-panthenol, comprising the following steps:
(1) adding 820kg of ethyl acetate, 520kg of DL-pantolactone (mass after being converted into purity) and 300kg of 3-aminopropanol (mass after being converted into purity) into a dry and clean 5000L reaction kettle in sequence, heating to 45 ℃, and stirring for reacting for 6 hours to obtain a DL-panthenol solution;
(2) and cooling the DL-panthenol solution to 20 ℃, adding 100g of DL-panthenol, continuously cooling to-5 ℃, keeping the temperature for 6 hours under a stirring condition for crystallization after crystals appear, performing centrifugal separation to obtain a wet DL-panthenol product, and performing vacuum drying to obtain 791kg of DL-panthenol solid.
Through detection, the DL-panthenol product has the specific rotation degree of 0, the residual amount of 3-aminopropanol of less than or equal to 0.1 percent, the melting point of 65 ℃, the drying weight loss of less than or equal to 0.5 percent and the heavy metal content of less than or equal to 10ppm, and the DL-panthenol content of 99.5 percent and the yield of 96.0 percent are detected by a liquid chromatography.
Example 2
This example provides a method for preparing DL-panthenol, comprising the following steps:
(1) adding 845kg of ethyl acetate, 545kg of DL-pantolactone (mass after being converted into purity) and 300kg of 3-aminopropanol (mass after being converted into purity) into a dry and clean 5000L reaction kettle in sequence, heating to 50 ℃, and stirring for reacting for 4 hours to obtain a DL-panthenol solution;
(2) and cooling the DL-panthenol solution to 10 ℃, adding 100g of DL-panthenol, then continuously cooling to 5 ℃, keeping the temperature for 8 hours under a stirring condition for crystallization after crystals appear, carrying out centrifugal separation to obtain a wet DL-panthenol product, and carrying out vacuum drying to obtain 791kg of DL-panthenol solid.
Through detection, the DL-panthenol product has the specific rotation degree of 0, the residual amount of 3-aminopropanol of less than or equal to 0.1 percent, the melting point of 65 ℃, the drying weight loss of less than or equal to 0.5 percent and the heavy metal content of less than or equal to 10ppm, and the DL-panthenol content of 99.3 percent and the yield of 95.8 percent detected by a liquid chromatography.
Example 3
This example provides a method for preparing DL-panthenol, comprising the following steps:
(1) sequentially adding 835.6kg of ethyl acetate, 535.6kg of DL-pantolactone (mass after conversion to purity) and 300kg of 3-aminopropanol (mass after conversion to purity) into a dry and clean 5000L reaction kettle, heating to 40 ℃, and stirring for reacting for 5 hours to obtain a DL-panthenol solution;
(2) and cooling the DL-panthenol solution to 15 ℃, adding 100g of DL-panthenol, then continuously cooling to 0 ℃, keeping the temperature for 7 hours under a stirring condition for crystallization after crystals appear, carrying out centrifugal separation to obtain a wet DL-panthenol product, and carrying out vacuum drying to obtain 796kg of DL-panthenol solid.
Through detection, the DL-panthenol product has the specific rotation degree of 0, the residual amount of 3-aminopropanol of less than or equal to 0.1 percent, the melting point of 65 ℃, the drying weight loss of less than or equal to 0.5 percent and the heavy metal content of less than or equal to 10ppm, and the DL-panthenol content of 99.5 percent and the yield of 96.6 percent detected by a liquid chromatography.
Example 4
This example provides a method for preparing DL-panthenol, comprising the following steps:
(1) adding 830.4kg of ethyl acetate, 530.4kg of DL-pantolactone (mass after being converted into purity) and 300kg of 3-aminopropanol (mass after being converted into purity) into a dry and clean 5000L reaction kettle in sequence, heating to 48 ℃, and stirring for reacting for 4.5 hours to obtain a DL-panthenol solution;
(2) and cooling the DL-panthenol solution to 20 ℃, adding 100g of DL-panthenol, continuously cooling to-2 ℃, keeping the temperature for 6.5 hours under a stirring condition after crystals appear, crystallizing, performing centrifugal separation to obtain a wet DL-panthenol product, and performing vacuum drying to obtain 776.1kg of DL-panthenol solid.
Through detection, the DL-panthenol product has the specific rotation degree of 0, the residual amount of 3-aminopropanol of less than or equal to 0.1 percent, the melting point of 65 ℃, the drying weight loss of less than or equal to 0.5 percent and the heavy metal content of less than or equal to 10ppm, and the DL-panthenol content of 99.3 percent and the yield of 94 percent detected by a liquid chromatography.
Comparative example 1
There is provided a process for producing DL-panthenol, which differs from example 1 only in that methanol is used as a solvent.
This comparative example gave 461.3kg of DL-panthenol as a solid, 93.2% DL-panthenol and 52.3% yield.
Comparative example 2
There is provided a process for producing DL-panthenol, which differs from example 1 only in that the solvent used is methanol and the reaction temperature is 65 ℃.
This comparative example gave 466.6kg of DL-panthenol as a solid, 99.1% of DL-panthenol and 56.4% of yield.
As can be seen from the experimental results of the above examples and comparative examples, the preparation method provided by the present invention not only enables the acylation reaction to be carried out at a relatively low temperature (40-50 ℃), but also enables the purity of the obtained DL-panthenol product to be more than 99% and the yield to be more than 94%.
Among them, in comparative example 1, when the reaction was carried out at a low temperature (45 ℃) using methanol as a reaction solvent, the reaction was not sufficient, and in addition, when temperature-lowering crystallization was carried out, precipitation of DL-panthenol was insufficient and a large amount of unreacted raw materials were mixed, and therefore, the purity and yield of the obtained DL-panthenol solid were remarkably lowered. Comparative example 2 using methanol as a reaction solvent, although the reaction was relatively sufficient when the reaction was carried out at a relatively high temperature (65 ℃), the effect of temperature-decreasing crystallization was inferior to that of example 1, and thus the purity and yield of the obtained solid DL-panthenol were higher than those of comparative example 1 but still lower than those of example 1.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A method for preparing DL-panthenol, comprising the steps of:
(1) taking DL-pantoic acid lactone and 3-aminopropanol as raw materials, and carrying out acylation reaction in ethyl acetate or methyl isobutyl ketone to obtain DL-panthenol solution;
(2) and cooling and crystallizing the DL-panthenol solution, carrying out solid-liquid separation, and drying to obtain DL-panthenol solid.
2. The process according to claim 1, wherein the molar ratio of DL-pantolactone to 3-aminopropanol is 1-1.05: 1.
3. The process according to claim 1 or 2, wherein the temperature of the acylation reaction is 40 to 50 ℃.
4. The process according to any one of claims 1 to 3, wherein the time for the acylation reaction is 4 to 6 hours.
5. The production method according to any one of claims 1 to 4, wherein the mass ratio of the total mass of the DL-pantoic acid lactone and 3-aminopropanol to the mass of ethyl acetate or methyl isobutyl ketone is 1 (0.8-2).
6. The production method according to any one of claims 1 to 5, wherein the crystallization is carried out under stirring conditions.
7. The method according to any one of claims 1 to 6, wherein the temperature of the crystallization is-5 to 5 ℃.
8. The method according to claim 7, wherein the crystallization time is 6 to 8 hours.
9. The production method according to any one of claims 1 to 8, wherein a seed crystal is added to the DL-panthenol solution during the cooling;
preferably, the seed crystal is added when the temperature is reduced to 10-20 ℃;
preferably, the seed crystal is DL-panthenol.
10. The production method according to any one of claims 1 to 9, characterized by comprising the steps of:
(1) mixing DL-pantoic acid lactone and 3-aminopropanol with ethyl acetate or methyl isobutyl ketone, and stirring to react at 40-50 ℃ for 4-6h to obtain DL-panthenol solution;
(2) and cooling the DL-panthenol solution to 10-20 ℃, adding DL-panthenol, then continuously cooling to-5 ℃, keeping the temperature for 6-8 hours under the stirring condition, crystallizing, filtering to obtain a DL-panthenol wet product, and drying in vacuum to obtain a DL-panthenol solid.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4378923A1 (en) * | 2022-12-01 | 2024-06-05 | DSM IP Assets B.V. | Production of panthenol |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110835309A (en) * | 2019-11-28 | 2020-02-25 | 安徽泰格生物科技有限公司 | Crystallization method of DL-panthenol |
| CN112047851A (en) * | 2020-08-20 | 2020-12-08 | 山东新和成精化科技有限公司 | Preparation method of D-panthenol |
| CN112174845A (en) * | 2020-09-27 | 2021-01-05 | 安徽泰格生物科技有限公司 | Preparation method of D-panthenol |
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- 2021-12-29 CN CN202111647321.7A patent/CN114292203B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110835309A (en) * | 2019-11-28 | 2020-02-25 | 安徽泰格生物科技有限公司 | Crystallization method of DL-panthenol |
| CN112047851A (en) * | 2020-08-20 | 2020-12-08 | 山东新和成精化科技有限公司 | Preparation method of D-panthenol |
| CN112174845A (en) * | 2020-09-27 | 2021-01-05 | 安徽泰格生物科技有限公司 | Preparation method of D-panthenol |
Non-Patent Citations (1)
| Title |
|---|
| 冯晓亮 等: "D-泛醇的合成", 《现代化工》, vol. 26, pages 186 - 187 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4378923A1 (en) * | 2022-12-01 | 2024-06-05 | DSM IP Assets B.V. | Production of panthenol |
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