CN112174845B - Preparation method of D-panthenol - Google Patents
Preparation method of D-panthenol Download PDFInfo
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- CN112174845B CN112174845B CN202011033252.6A CN202011033252A CN112174845B CN 112174845 B CN112174845 B CN 112174845B CN 202011033252 A CN202011033252 A CN 202011033252A CN 112174845 B CN112174845 B CN 112174845B
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- Prior art keywords
- panthenol
- solvent
- pantolactone
- aminopropanol
- reaction
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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 48
- 239000011703 D-panthenol Substances 0.000 title claims abstract description 45
- 235000004866 D-panthenol Nutrition 0.000 title claims abstract description 44
- 229960003949 dexpanthenol Drugs 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 22
- SERHXTVXHNVDKA-BYPYZUCNSA-N (R)-pantolactone Chemical compound CC1(C)COC(=O)[C@@H]1O SERHXTVXHNVDKA-BYPYZUCNSA-N 0.000 claims abstract description 19
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000005917 acylation reaction Methods 0.000 claims abstract description 14
- 239000011259 mixed solution Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000001914 filtration Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000007790 scraping Methods 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 230000000474 nursing effect Effects 0.000 description 2
- 229940101267 panthenol Drugs 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
- 235000020957 pantothenol Nutrition 0.000 description 2
- 239000011619 pantothenol Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000011084 recovery 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
- 102000003839 Human Proteins Human genes 0.000 description 1
- 108090000144 Human Proteins Proteins 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
- 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
- 239000003623 enhancer Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000003906 humectant Substances 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
- 230000003752 improving hair 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
- 230000003020 moisturizing effect Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method 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 obtained by the preparation method provided by the invention has higher yield and higher purity; meanwhile, the recycled solvent can be continuously used, so that 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 B 5 The three forms can be classified into DL-form, D-form and L-form 3, wherein only D-form has biological activity and L-form has no biological activity; d-panthenol is an optically active stereoisomer of panthenol.
D-panthenol is an equivalent of D-pantothenic acid and is widely used in the pharmaceutical, food, feed, and cosmetic industries. In the food industry, the product is used as a nutritional supplement and an enhancer, and can promote metabolism of human proteins, fats and saccharides, keep skin and mucous membranes, improve hair luster, improve immunity and prevent diseases; in the cosmetic industry, the nursing effect on the skin is represented by a deeply penetrating humectant, stimulates the growth of epithelial cells, promotes wound healing and plays an anti-inflammatory role; the care effect on the hair is expressed as a lasting moisturizing function, so that the hair is prevented from being split and damaged, the density of the hair is increased, and the luster of the hair is improved; the nursing of the nails is characterized by improving the hydration of the nails and imparting flexibility to the nails.
At present, in the synthetic method of D-panthenol, it is reported that D-pantolactone and 3-aminopropanol react in a reaction kettle under the condition of taking ethanol as a solvent, and then D-panthenol is obtained by vacuum concentration in the reaction kettle; in addition, CN101851171a discloses a method for preparing D-panthenol, which reacts D-pantolactone with 3-aminopropanol under the condition of no solvent to obtain D-panthenol, and although the solvent is omitted and the step of vacuum concentration for removing the solvent is omitted, the reaction requirement is high, and the quality requirements for raw materials D-pantolactone and 3-aminopropanol are too high; and because the D-panthenol is thicker and reacts under the condition of no solvent addition, along with the increasing thickness of the generated material of the D-panthenol, partial 3-aminopropanol is not contacted with the D-pantolactone and the reaction is insufficient, the obtained D-panthenol has poor quality and high raw material residue, and the obtained product cannot meet the application requirement on the purity of the D-panthenol.
Therefore, there is a need to develop a process for preparing D-panthenol with higher yield and higher product purity.
Disclosure of Invention
The invention aims to provide a preparation method of D-panthenol, and the D-panthenol obtained by the preparation method has higher yield and higher purity; meanwhile, the recycled solvent can be continuously used, so that 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 method for preparing D-panthenol, the method 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 acylation reaction temperature of 10-35 ℃, and the reaction can be completed in a short time at the temperature, so that side reactions can be avoided, the impurity content in the product is reduced, and the product quality is improved. If the reaction temperature is too high, the unreacted raw materials in the finally obtained product are more, 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 results in poor production efficiency.
As a preferred embodiment of the present invention, the reaction temperature of the acylation reaction is 20 to 30℃such as 22℃24℃25℃26℃28 ℃.
The reaction temperature of 20-30 ℃ is preferable, namely, the reaction is carried out at room temperature, the process of heating or cooling is avoided, the reaction time is shorter, and the product quality is higher.
In order to further increase 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 with a resin column.
As a preferable technical scheme of the invention, the resin filled in the resin column is ester adsorption resin, preferably ester adsorption resin FB-02.
The filtration is carried out by adopting a resin column filled with ester adsorption resin, and the invention limits that the D-pantolactone is slightly excessive and the filtration is carried out in combination, thus ensuring the complete reaction of 3-aminopropanol, ensuring the better yield of the final D-panthenol and removing the D-pantolactone which is not completely reacted so as to ensure the final product to have higher purity; and the resin column filtration also has the decoloring effect.
As a preferable technical scheme of the invention, the concentration is water bath scraping plate vacuum concentration.
In order to ensure higher 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 invention adopts the water bath scraping plate to recycle the solvent in vacuum, so that the solvent quantity residue of the product can be ensured to be lower, the recycled solvent can be repeatedly used after simple rectification, the production cost is reduced, the environmental pollution is reduced, in the process of recycling the solvent, the water bath temperature is required to be below 70 ℃, and if the water bath temperature is higher than 70 ℃, the purity of the product can be slightly reduced.
As one of the preferable technical schemes 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) Filtering the mixed solution containing D-panthenol by a resin column to remove unreacted raw materials, and then concentrating in vacuum by a water bath scraping plate to remove the solvent to obtain the D-panthenol.
Compared with the prior art, the invention has the following beneficial effects:
(1) The invention can ensure that the reaction is completed in a shorter time by limiting the reaction temperature of 10-35 ℃, and the impurity of the product is less and the purity is higher;
(2) The invention can ensure that the 3-aminopropanol completely reacts by limiting the D-pantolactone to be slightly excessive and introducing a resin column for filtration, and the unreacted D-pantolactone can be removed by using the resin column while the filtration also has the decoloring effect;
(3) The invention adopts the mode of removing the solvent in vacuum by the water bath scraping plate, the temperature of the water bath is required to be below 70 ℃, and the product can be ensured to have higher purity while removing the solvent.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Example 1
The preparation method of the D-panthenol comprises the following steps:
(1) Taking 1310kg of D-pantolactone, dissolving 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 by a resin column (filled with adsorption ester resin FB-02), and introducing the filtrate into a water bath type scraper concentrator for recovering methanol under reduced pressure, wherein the water bath temperature is 65 ℃, thus obtaining 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
The preparation method of the D-panthenol comprises the following steps:
(1) Taking 1306kg of D-pantolactone, dissolving in 1500L of methanol, adding 750kg of 3-aminopropanol into a reaction kettle, heating to 25 ℃ for acylation reaction for 8 hours to obtain a mixed solution containing D-panthenol;
(2) Filtering the mixed solution by a resin column, feeding the filtrate into a water bath type scraper concentrator for methanol recovery, and recovering the methanol under reduced pressure at the water bath temperature of 68 ℃ to obtain the D-panthenol.
Example 5
The preparation method of the D-panthenol comprises the following steps:
(1) Taking 1300kg of D-pantolactone to be dissolved in 1500L of methanol, adding 750kg of 3-aminopropanol into a reaction kettle, heating to 35 ℃ for carrying out acylation reaction for 6 hours to obtain a mixed solution containing D-panthenol;
(2) Filtering the mixed solution by a resin column, feeding the filtrate into a water bath type scraper concentrator for methanol recovery, and recovering the methanol under reduced pressure at the water bath temperature of 68 ℃ 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 according to cosmetic raw material D-panthenol test standard GB/T33306-2016, and the test results are shown in Table 1:
TABLE 1
The embodiment and the performance test show that the preparation method provided by the invention is simple and easy to implement, the prepared D-panthenol has higher yield and purity, the residual amounts of the solvent and unreacted raw materials are very small, and all indexes of the D-panthenol meet the regulations.
As is clear from the comparison of example 1 and examples 2-3, the molar ratio of D-pantolactone to 3-aminopropanol in the present invention is (1.01-1.05): 1 has a better effect; as can be seen from the comparison of the example 1 and the comparative examples 1-2, the acylation reaction temperature is required to be within the range of 10-35 ℃, and the final product has higher yield and fewer impurities; as is clear from the comparison between example 1 and comparative example 3, the water bath temperature at the time of recovering the solvent needs to be below 70℃to maintain the product at a high purity.
The applicant states that the present invention describes the process for the preparation of D-panthenol according to the invention by means of the examples described above, but the invention is not limited to the detailed processes described above, i.e. it is not meant that the invention must be carried out in dependence of the detailed processes described above. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (1)
1. A method for preparing 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 20-30 ℃, the molar ratio of the D-pantolactone to the 3-aminopropanol is (1.01-1.05): 1, and the solvent is methanol and/or ethanol
The preparation method further comprises the steps of filtering and concentrating the mixed solution containing the D-panthenol to obtain the D-panthenol, wherein the filtering is performed by using a resin column, resin filled in the resin column is ester adsorption resin, the concentration is water bath scraping plate vacuum concentration, and the temperature of the water bath is less than or equal to 70 ℃.
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 CN112174845A (en) | 2021-01-05 |
| CN112174845B true CN112174845B (en) | 2024-01-12 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
Citations (3)
| 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)
| 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 |
Non-Patent Citations (3)
| Title |
|---|
| 中国饮料工业协会编.《饮料制作工》.2010,第521-522页. * |
| 冯晓亮等."D-泛醇的合成".《现代化工》.2006,第26卷第186-188页. * |
| 费成煜，唐培瑜.赤霉素水溶性制剂.《农药》.1994,第33卷(第05期),第17-18页. * |
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