CN111333571A - Method for synthesizing vitamin B6 triisopalmitate - Google Patents
Method for synthesizing vitamin B6 triisopalmitate Download PDFInfo
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- CN111333571A CN111333571A CN202010153317.4A CN202010153317A CN111333571A CN 111333571 A CN111333571 A CN 111333571A CN 202010153317 A CN202010153317 A CN 202010153317A CN 111333571 A CN111333571 A CN 111333571A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
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Abstract
The invention is suitable for the field of chemical synthesis, and provides a method for synthesizing vitamin B6 triisopalmitate, which comprises the following steps: mixing vitamin B6 hydrochloride, pyridine and cyclohexane, carrying out ice bath treatment, and then dropwise adding 2-hexyldecanoyl chloride for heat preservation reaction to obtain a reaction solution; standing and layering the reaction solution, and taking the upper layer to obtain an upper layer solution A; adding an oxalic acid aqueous solution into the supernatant A for layering, and taking the supernatant to obtain a supernatant B; adding petroleum ether and a saturated sodium bicarbonate solution into the supernatant liquid B for layering, and then adding a saturated sodium chloride solution for washing to obtain a clear solution; and adding calcium carbonate viscous liquid into the clear solution, stirring, separating liquid, and then adding activated carbon for purification to obtain the vitamin B6 triisopalmitate. The synthesis method provided by the invention has the advantages of simple reaction, high purity of the obtained product, less waste water, waste gas and waste residue, and environmental friendliness.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a method for synthesizing vitamin B6 triisopalmitate.
Background
Vitamin B6 triisopalmitate is a common pharmaceutical intermediate and industrial material, and is generally synthesized by using Vitamin B6(Vitamin B6) as a raw material.
However, the conventional method for synthesizing vitamin B6 triisopalmitate is complex, the price of the raw materials used is not stable, and the method is environmentally friendly because the raw materials are likely to generate more waste gas, waste water and waste residues, so that a low-cost and environmentally-friendly method for synthesizing vitamin B6 triisopalmitate is urgently needed.
Disclosure of Invention
The embodiment of the invention aims to provide a method for synthesizing vitamin B6 triisopalmitate, and aims to solve the problems in the background art.
The embodiment of the invention is realized by a method for synthesizing vitamin B6 triisopalmitate, which comprises the following steps:
mixing vitamin B6 hydrochloride, pyridine and cyclohexane, carrying out ice bath treatment, and then dropwise adding 2-hexyldecanoyl chloride for heat preservation reaction to obtain a reaction solution;
standing and layering the reaction solution, and taking the upper layer to obtain an upper layer solution A;
adding an oxalic acid aqueous solution into the supernatant A for layering, and taking the supernatant to obtain a supernatant B;
adding petroleum ether and a saturated sodium bicarbonate solution into the supernatant liquid B for layering, and then adding a saturated sodium chloride solution for washing to obtain a clear solution;
and adding calcium carbonate viscous liquid into the clear solution, stirring, separating liquid, and then adding activated carbon for purification to obtain the vitamin B6 triisopalmitate.
As a preferable mode of the embodiment of the present invention, in the step, the temperature of the ice bath treatment is not higher than 15 ℃.
As another preferable scheme of the embodiment of the invention, in the step, the temperature of the heat preservation reaction is 20-40 ℃.
In another preferable embodiment of the invention, the molar ratio of the vitamin B6 hydrochloride to the pyridine to the cyclohexane to the 2-hexyldecanoyl chloride is 1 (5-7) to (7-9) to (2-4).
In another preferable embodiment of the invention, the mass concentration of the oxalic acid aqueous solution is 1-3%, and the molar ratio of oxalic acid to vitamin B6 hydrochloride is (2-4): 1.
In another preferable mode of the embodiment of the invention, the molar ratio of the sodium bicarbonate to the petroleum ether and the vitamin B6 hydrochloride in the saturated sodium bicarbonate solution is (2-4): 1.
In another preferable embodiment of the invention, the molar ratio of sodium chloride to vitamin B6 hydrochloride in the saturated sodium chloride solution is (2-4): 1.
In another preferable embodiment of the invention, the molar ratio of calcium carbonate to vitamin B6 hydrochloride in the calcium carbonate viscous liquid is (0.05-0.2): 1.
As another preferable scheme of the embodiment of the invention, the adding mass of the activated carbon is 4-6% of that of the clear solution.
As another preferable mode of the embodiment of the present invention, in the step, the purification method includes the steps of:
and adding calcium carbonate viscous liquid into the clear solution, stirring, separating liquid, adding activated carbon, placing at the temperature of 60-70 ℃ for refluxing, and performing suction filtration and reduced pressure distillation treatment to obtain the vitamin B6 triisopalmitate.
The synthesis method of the vitamin B6 triisopalmitate provided by the embodiment of the invention has the advantages that the reaction is simple and one-step, the waste water, the waste gas and the waste residue are less, and the method is beneficial to the environment; in addition, the synthesis method has low requirement on equipment, and the production cost of the conventional equipment is low, so that the method is suitable for industrial production; and the obtained product has high purity and basically consistent performance compared with foreign high-quality products.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
The embodiment provides a method for synthesizing vitamin B6 triisopalmitate, which comprises the following steps:
(1) mixing 1mol of vitamin B6 hydrochloride, 5mol of pyridine and 7mol of cyclohexane for 30min, placing the mixture at the temperature of 15 ℃ for ice bath treatment, then dropwise adding 2mol of 2-hexyldecanoyl chloride (the dropwise addition is controlled within 4 h), and carrying out heat preservation reaction for 24h to obtain a reaction solution.
(2) And pouring the reaction solution into a separating funnel, standing for layering for 0.1h, and taking the upper layer to obtain upper layer solution A.
(3) Adding oxalic acid aqueous solution with the mass concentration of 1% into the supernatant A for layering, and taking the supernatant to obtain a supernatant B; wherein the molar mass of the oxalic acid in the oxalic acid water solution is 2 mol.
(4) Adding 2mol of petroleum ether and a saturated sodium bicarbonate solution into the supernatant liquid B for layering, and then adding a saturated sodium chloride solution for washing to obtain a clear solution; wherein the molar mass of the sodium bicarbonate in the saturated sodium bicarbonate solution is 2 mol; the molar mass of sodium chloride in the saturated sodium chloride solution was 2 mol.
(5) And adding calcium carbonate viscous liquid into the clear solution, stirring, separating liquid, adding activated carbon, refluxing at 60 ℃ for 1h, and performing suction filtration and reduced pressure distillation to obtain the vitamin B6 triisopalmitate. Wherein the molar mass of the calcium carbonate in the calcium carbonate viscous liquid is 0.05mol, and the adding mass of the activated carbon is 4% of that of the clear solution.
Example 2
The embodiment provides a method for synthesizing vitamin B6 triisopalmitate, which comprises the following steps:
(1) mixing 1mol of vitamin B6 hydrochloride, 7mol of pyridine and 9mol of cyclohexane for 30min, placing the mixture at the temperature of 5 ℃ for ice bath treatment, then dropwise adding 4mol of 2-hexyldecanoyl chloride (the dropwise addition is controlled within 4 h), and carrying out heat preservation reaction for 24h to obtain a reaction solution.
(2) And pouring the reaction solution into a separating funnel, standing for layering for 1h, and taking the upper layer to obtain an upper layer solution A.
(3) Adding oxalic acid aqueous solution with the mass concentration of 3% into the supernatant A for layering, and taking the supernatant to obtain a supernatant B; wherein the molar mass of oxalic acid in the oxalic acid water solution is 4 mol.
(4) Adding 4mol of petroleum ether and a saturated sodium bicarbonate solution into the supernatant liquid B for layering, and then adding a saturated sodium chloride solution for washing to obtain a clear solution; wherein the molar mass of the sodium bicarbonate in the saturated sodium bicarbonate solution is 4 mol; the molar mass of sodium chloride in the saturated sodium chloride solution was 4 mol.
(5) And adding calcium carbonate viscous liquid into the clear solution, stirring, separating liquid, adding activated carbon, refluxing at 70 ℃ for 1h, and performing suction filtration and reduced pressure distillation to obtain the vitamin B6 triisopalmitate. Wherein the molar mass of calcium carbonate in the calcium carbonate viscous liquid is 0.2mol, and the adding mass of the activated carbon is 6% of that of the clear solution.
Example 3
The embodiment provides a method for synthesizing vitamin B6 triisopalmitate, which comprises the following steps:
(1) mixing 1mol of vitamin B6 hydrochloride, 6mol of pyridine and 8mol of cyclohexane for 30min, placing the mixture at the temperature of 10 ℃ for ice bath treatment, then dropwise adding 3mol of 2-hexyldecanoyl chloride (the dropwise addition is controlled within 4 h), and carrying out heat preservation reaction for 24h to obtain a reaction solution.
(2) And pouring the reaction solution into a separating funnel, standing for layering for 0.5h, and taking the upper layer to obtain upper layer solution A.
(3) Adding an oxalic acid aqueous solution with the mass concentration of 2% into the supernatant A for layering, and taking the supernatant to obtain a supernatant B; wherein the molar mass of oxalic acid in the oxalic acid water solution is 3 mol.
(4) Adding 3mol of petroleum ether and a saturated sodium bicarbonate solution into the supernatant liquid B for layering, and then adding a saturated sodium chloride solution for washing to obtain a clear solution; wherein the molar mass of the sodium bicarbonate in the saturated sodium bicarbonate solution is 3 mol; the molar mass of sodium chloride in the saturated sodium chloride solution was 3 mol.
(5) And adding calcium carbonate viscous liquid into the clear solution, stirring, separating liquid, adding activated carbon, refluxing at 65 ℃ for 1h, and performing suction filtration and reduced pressure distillation to obtain the vitamin B6 triisopalmitate. Wherein the molar mass of calcium carbonate in the calcium carbonate viscous liquid is 0.1mol, and the adding mass of the activated carbon is 5% of that of the clear solution.
The performance indexes of a batch of vitamin B6 triisopalmitate obtained according to the enhanced synthesis method of example 3 are shown in table 1 below.
TABLE 1
| Appearance of characters | Colorless to pale yellow oily liquid |
| Refractive index | 1.468-1.474 |
| pH value | 5.0-6.0 |
| Specific gravity (g/ml) | 0.942-0.948 |
| Loss on drying (%) | ≤0.3 |
| Burning residue (%) | ≤0.10 |
| Heavy Metal content (ppm) | ≤20 |
| Purity (%) | ≥99.0 |
| Solvent residue (ppm) | ≤100 |
As can be seen from the above Table 1, the product synthesized by the example of the present invention has higher purity. In addition, the synthesis method provided by the embodiment of the invention has the advantages of simple reaction, easily obtained raw materials, low production cost, less generated waste water, waste gas and waste residues and environmental friendliness.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. A method for synthesizing vitamin B6 triisopalmitate is characterized by comprising the following steps:
mixing vitamin B6 hydrochloride, pyridine and cyclohexane, carrying out ice bath treatment, and then dropwise adding 2-hexyldecanoyl chloride for heat preservation reaction to obtain a reaction solution;
standing and layering the reaction solution, and taking the upper layer to obtain an upper layer solution A;
adding an oxalic acid aqueous solution into the supernatant A for layering, and taking the supernatant to obtain a supernatant B;
adding petroleum ether and a saturated sodium bicarbonate solution into the supernatant liquid B for layering, and then adding a saturated sodium chloride solution for washing to obtain a clear solution;
and adding calcium carbonate viscous liquid into the clear solution, stirring, separating liquid, and then adding activated carbon for purification to obtain the vitamin B6 triisopalmitate.
2. The method for synthesizing vitamin B6 triisopalmitate as claimed in claim 1, wherein the ice-bath treatment temperature is not higher than 15 ℃.
3. The method for synthesizing vitamin B6 triisopalmitate as claimed in claim 1, wherein the reaction temperature is 20-40 ℃ during the step of heat preservation.
4. The method for synthesizing vitamin B6 triisopalmitate as claimed in claim 1, wherein the molar ratio of the vitamin B6 hydrochloride to the pyridine to the cyclohexane to the 2-hexyldecanoyl chloride is 1 (5-7) to (7-9) to (2-4).
5. The method for synthesizing vitamin B6 triisopalmitate as claimed in claim 4, wherein the mass concentration of the oxalic acid aqueous solution is 1% -3%, and the molar ratio of oxalic acid to vitamin B6 hydrochloride is (2-4): 1.
6. The method for synthesizing vitamin B6 triisopalmitate as claimed in claim 4, wherein the molar ratio of sodium bicarbonate to petroleum ether to vitamin B6 hydrochloride in the saturated sodium bicarbonate solution is (2-4): 1.
7. The method for synthesizing vitamin B6 triisopalmitate as claimed in claim 4, wherein the molar ratio of sodium chloride to vitamin B6 hydrochloride in the saturated sodium chloride solution is (2-4): 1.
8. The method for synthesizing vitamin B6 triisopalmitate as claimed in claim 4, wherein the molar ratio of calcium carbonate to vitamin B6 hydrochloride in the calcium carbonate viscous liquid is (0.05-0.2): 1.
9. The method for synthesizing vitamin B6 triisopalmitate as claimed in claim 1, wherein the added mass of the activated carbon is 4-6% of the clear solution.
10. The method for synthesizing vitamin B6 triisopalmitate according to claim 1, wherein the purification method comprises the following steps:
and adding calcium carbonate viscous liquid into the clear solution, stirring, separating liquid, adding activated carbon, placing at the temperature of 60-70 ℃ for refluxing, and performing suction filtration and reduced pressure distillation treatment to obtain the vitamin B6 triisopalmitate.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117143011A (en) * | 2023-08-30 | 2023-12-01 | 上海克琴科技有限公司 | Synthesis method of vitamin B6 triisopalmitate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003206279A (en) * | 2002-01-08 | 2003-07-22 | Nikko Chemical Co Ltd | Pyridoxine derivative and skin care preparation and hair cosmetic containing the same pyridoxine derivative |
| CN108069926A (en) * | 2017-11-09 | 2018-05-25 | 南京斯拜科生化实业有限公司 | A kind of synthetic method of Ascorbyl Tetraisopalmitate |
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2020
- 2020-03-07 CN CN202010153317.4A patent/CN111333571A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003206279A (en) * | 2002-01-08 | 2003-07-22 | Nikko Chemical Co Ltd | Pyridoxine derivative and skin care preparation and hair cosmetic containing the same pyridoxine derivative |
| CN108069926A (en) * | 2017-11-09 | 2018-05-25 | 南京斯拜科生化实业有限公司 | A kind of synthetic method of Ascorbyl Tetraisopalmitate |
Non-Patent Citations (1)
| Title |
|---|
| 吴梧桐 主编: "《生物制药工艺学 （第三版）》", 30 April 2013, 北京 ：中国医药科技出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117143011A (en) * | 2023-08-30 | 2023-12-01 | 上海克琴科技有限公司 | Synthesis method of vitamin B6 triisopalmitate |
| CN117143011B (en) * | 2023-08-30 | 2024-04-02 | 上海克琴科技有限公司 | Synthesis method of vitamin B6 triisopalmitate |
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