CN110776484A - Preparation method of vitamin C palmitate - Google Patents
Preparation method of vitamin C palmitate Download PDFInfo
- Publication number
- CN110776484A CN110776484A CN201911070506.9A CN201911070506A CN110776484A CN 110776484 A CN110776484 A CN 110776484A CN 201911070506 A CN201911070506 A CN 201911070506A CN 110776484 A CN110776484 A CN 110776484A
- Authority
- CN
- China
- Prior art keywords
- water
- vitamin
- palmitate
- organic solvent
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of vitamin C palmitate, which specifically comprises the steps of taking vitamin C and palmitic acid as raw materials, adopting a double-solvent system of an organic solvent and water, taking dilute sulfuric acid as a catalyst, rectifying and separating water in the reaction process, stopping the reaction when no water is carried out any more, washing with a small amount of water, and concentrating and crystallizing an organic phase to obtain the vitamin C palmitate.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of vitamin C palmitate
Background
Vitamin C palmitate, also known as L-ascorbyl palmitate, LAP for short, white to yellowish powder, insoluble in water, slightly soluble in vegetable oil, soluble in ethanol, and having a structural formula shown in formula I below:
LAP is a novel multifunctional antioxidant, is evaluated by the food addition committee of the world health organization as a nutritional, non-toxic, efficient and safe-to-use food additive, is collected by British and United states pharmacopoeia, and is widely applied to the fields of food, medicine, cosmetics and the like.
At present, the main processes for preparing the vitamin C palmitate comprise the following steps: direct esterification, acid chloride, and ester exchange.
The vitamin C palmitate is prepared by a direct esterification method, concentrated sulfuric acid is generally used as a reaction solvent and a reaction catalyst, and the operation is simple and convenient. The use of a large amount of concentrated sulfuric acid can enable the whole reaction system to become a homogeneous system, and can absorb part of water generated by the esterification reaction, so that the esterification balance is favorable for moving to the positive direction. However, during the post-treatment process, a large amount of ice water is required to be added to wash the reaction system to form dilute acid aqueous solution, which is conventional in industry: the ratio of concentrated sulfuric acid to raw material is about 10:1, and the acid water brings great environmental protection pressure. Meanwhile, in the washing process, a large amount of heat is released, so that potential safety hazards exist.
Patent CN201710149720.8 proposes that ethyl acetate is added in the esterification reaction liquid as a buffer, so that the temperature of the reaction liquid can be well controlled, but the heat release in the process of diluting sulfuric acid is very large, the potential safety hazard still inevitably exists, and the method does not solve the problem of environment-friendly treatment of dilute acid water.
With the rise of lipase in recent years, many scholars use lipase to catalyze the esterification reaction of vitamin C and palmitic acid under anhydrous conditions, for example, bradoo in JAOCS, and aggregate in journal of molecular biology b, related research articles are published. However, lipase is used as a catalyst, most alcohols are used as a solvent, and a by-product of the esterification reaction of palmitic acid and the solvent is obtained, so that the difficulty of subsequent separation and purification is increased. On the other hand, the lipase is used as a catalyst, and the conversion per pass is lower than that of a sulfuric acid process, so that a molecular sieve is generally added as a water absorbent in the operation process, which also increases the post-treatment process and causes the problem of recycling of the molecular sieve.
Two other methods: the acyl chloride method requires harsh reaction conditions and special reactors, is not beneficial to industrial production, and uses thionyl chloride in the process of preparing the palmitic acid acyl chloride, so that the problem of environmental protection exists; the ester exchange method requires that the palmitic acid is firstly subjected to esterification reaction with other alcohols and then subjected to ester exchange reaction with the vitamin C, so that the operation process and the treatment complexity are inevitably increased.
Therefore, the development of a more excellent method for industrially producing vitamin C palmitate, which solves the problems existing in the prior art, is a target constantly pursued by numerous scholars and enterprises.
Disclosure of Invention
In order to solve the technical problem, the invention provides a preparation method of vitamin C palmitate, which comprises the steps of taking vitamin C and palmitic acid as raw materials, dissolving the palmitic acid by using an organic solvent, using dilute sulfuric acid as a catalyst, rectifying and dividing water in the reaction process, stopping the reaction when no water is carried out, washing by using a small amount of water, and concentrating and crystallizing an organic phase to obtain the vitamin C palmitate.
The preparation method comprises the following steps:
1) mixing the vitamin C, the palmitic acid and the organic solvent, adding a dilute sulfuric acid catalyst, heating and refluxing, and carrying out azeotropic water separation on the organic solvent and water;
2) after the reaction in the step 1) is finished, cooling the reaction liquid to normal temperature, and washing the reaction liquid with water to obtain an organic phase and a water phase;
3) and 2) recovering part of the organic solvent from the organic phase obtained in the step 2), cooling, crystallizing, filtering and drying to obtain the vitamin C palmitate solid.
In the above method for preparing vitamin C palmitate, the organic solvent is selected from ethers, esters and hydrocarbons, the ethers are selected from one or more of methyl tert-butyl ether, diethyl ether or isopropyl ether; the esters are selected from one or more of sec-butyl acetate or n-butyl acetate; the hydrocarbon is one or more of toluene or cyclohexane. Azeotropic composition of isopropyl ether with water: the water content is 6 percent, the isopropyl ether is 94 percent, and the water carrying capacity is strong; azeotropic composition of methyl tert-butyl ether, diethyl ether and water: the water content is less than 3%.
In the preparation method of the vitamin C palmitate, the azeotropic temperature of the organic solvent and the water in the step 1) is 40-55 ℃. Experiments have shown that temperatures above 55 ℃ affect the purity of the product.
In the above process for producing vitamin C palmitate, the palmitic acid in the palmitic acid organic solvent is present in an amount of 20 to 50% by mass, preferably 25 to 35% by mass. The reason for the range of the mass fraction of palmitic acid is that the increased concentration of palmitic acid tends to cause foaming during distillation, which is detrimental to the stability of distillation.
In the above process for producing vitamin C palmitate, the ratio of vitamin C: the molar ratio of palmitic acid is 1: 1-2, preferably 1:1.3-1.5, to ensure complete conversion of VC.
In the above method for preparing vitamin C palmitate, the concentration of the dilute sulphuric acid is 5-20%, preferably 10-15%, wherein the mass of the pure sulphuric acid is 20-40%, preferably 25-35% of the mass of the vitamin C.
In the preparation method of the vitamin C palmitate, the reaction is finished when no new water is generated.
In the above method for preparing vitamin C palmitate, the organic solvent recovery process in step 2) is preferably distillation concentration, the distillation temperature is controlled at 50-80 deg.C, preferably 55-60 deg.C, and the concentration is carried out until the mass content of vitamin C palmitate is more than 50%, preferably more than 60%, and less than 70%. When the concentration is continued, the viscosity of the vitamin C palmitate is high, and the vitamin C palmitate is not suitable for continuous desolventizing because the vitamin C palmitate wraps an organic solvent.
In the above process for preparing vitamin C palmitate, the drying temperature in step 3) is 30-50 deg.C, preferably 35-45 deg.C. When the drying temperature is higher than 50 ℃, the vitamin C palmitate can deteriorate; when the temperature is lower than 30 ℃, the drying efficiency is low.
In the above method for preparing vitamin C palmitate, the method further comprises: step 4) recycling the water phase in the step 2) for use in the catalytic reaction in the step 1); recycling the crystallized mother liquor obtained after the crystallization in the step 3), combining the crystallized mother liquor with the partially recovered organic solvent in the step 3), and dissolving the next batch of palmitic acid.
Wherein, after water washing, the concentration of sulfuric acid contained in the water phase obtained in the step 2) is close to the use concentration of the dilute sulfuric acid as a catalyst, so that the method can be directly applied to the catalytic reaction in the step 1).
The invention has the beneficial effects that:
the invention discloses a process for preparing vitamin C palmitate. The invention mixes vitamin C, palmitic acid and organic solvent, uses dilute sulphuric acid as catalyst, and prepares vitamin C palmitate by directly esterifying vitamin C and palmitic acid. The process method has the advantages of few raw material types, simplicity, easy obtaining, safe and reliable operation process, and the sulfuric acid catalyst can be used mechanically, so that the problem of environmental protection is solved, and the process method is one of innovativeness. The invention has the other innovativeness that the use amount of sulfuric acid is obviously reduced, other organic solvents can be repeatedly used, the cost is greatly reduced on the basis of ensuring the effect, the one-way conversion rate of the vitamin C is more than 98%, the yield is more than 95%, and the product purity is more than 99%.
Detailed Description
The following experimental examples are intended to further illustrate the invention but not to limit it. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
Example 1
Respectively adding 67g of vitamin C, 126g of palmitic acid, 235g of methyl tert-butyl ether (MTBE) and 220g of dilute sulfuric acid (9%) into a 1L four-mouth reaction bottle, adopting a 80cm glass spring packed tower, adding a water separator, cooling by cooling water, heating the materials under stirring to 40 ℃ and starting to reflux, wherein the MTBE and the water are subjected to azeotropic distillation at the moment, solvent water and water generated by the reaction are continuously taken out, obvious water and oil phases are formed in the water separator, after the reflux reaction is carried out for 48 hours, the water level in the water separator is not increased, cooling to normal temperature, adding 210g of water into the reaction liquid, stirring, standing and layering, and the total mass of the water phase is 230g and is reserved for application; recovering MTBE 125g from oil phase under normal pressure (heating in water bath at 80 deg.C), cooling to-20 deg.C, crystallizing, filtering, and oven drying (40 deg.C) to obtain 149.9g vitamin C palmitate. The yield of the obtained vitamin C palmitate is 95.1 percent, the conversion rate of the vitamin C is about 98.5 percent, and the product purity is 99.2 percent.
Example 2
Respectively adding 64.2g of vitamin C, 131g of palmitic acid, 306g of isopropyl ether and 172.5g of dilute sulfuric acid (13%) into a 1L four-mouth reaction bottle, adopting a 80cm glass spring packed tower, adding a water separator, cooling by cooling water, heating the materials to 54 ℃ under the stirring condition, starting to reflux, carrying out azeotropic boiling on the isopropyl ether and water at the moment, continuously taking out solvent water and water generated by the reaction, forming obvious water and oil phases in the water separator, after reflux reaction for 30 hours, no increase of the water level in the water separator, cooling to normal temperature, adding 157g of water into the reaction liquid, stirring, standing and layering; recovering 150g isopropyl ether from oil phase under normal pressure (heating in water bath at 80 deg.C), cooling to-10 deg.C, crystallizing, filtering, and oven drying (40 deg.C) to obtain 144.5g vitamin C palmitate. The yield of the obtained vitamin C palmitate is 95.6 percent, the conversion rate of the vitamin C is about 98.9 percent, and the product purity is 99.5 percent.
Example 3
Respectively adding 69.2g of vitamin C, 141.5g of palmitic acid, 285g of ether and 198.6g of dilute sulfuric acid (9.3%) into a 1L four-mouth reaction bottle, adopting a 80cm glass spring packed tower, adding a water separator, cooling by cooling water, heating the materials to 34 ℃ under the stirring condition, starting refluxing, enabling the ether and the water to perform azeotropic distillation, continuously carrying out solvent water and water generated by the reaction, enabling the water separator to have obvious water-oil two phases, after the reflux reaction is carried out for 78 hours, enabling the water level in the water separator not to increase, cooling to the normal temperature, adding 178g of water into the reaction liquid, stirring, standing and layering; recovering 170g of diethyl ether from the oil phase under normal pressure (heating in water bath at 60 ℃), cooling to-10 ℃, crystallizing, filtering, and drying at 40 ℃ to obtain 156.1g of vitamin C palmitate. The yield of the obtained vitamin C palmitate is 96.1 percent, the conversion rate of the vitamin C is about 99 percent, and the product purity is 99.2 percent.
Example 4
Respectively adding 65.2g of vitamin C, 131g of palmitic acid, 298g of sec-butyl acetate and 168.5g of dilute sulfuric acid (15.7%) into a 1L four-mouth reaction bottle, adopting an 80cm glass spring packed tower, adding a water separator, cooling by cooling water, controlling the system pressure to be 25kpa, heating the material to 56 ℃ under the stirring condition, starting refluxing, enabling the sec-butyl acetate and water to be subjected to azeotropic distillation, continuously carrying out solvent water and reaction generated water, enabling the water separator to be in an obvious water-oil two phase state, after refluxing reaction for 34h, enabling the water level in the water separator not to increase, cooling to normal temperature, adding 147g of water into the reaction liquid, stirring, standing and layering; recovering about 287g of sec-butyl acetate from the oil phase under reduced pressure (heating in water bath at 80 ℃), cooling to-10 ℃, crystallizing, filtering, and drying (at 40 ℃) to obtain 147.8g of vitamin C palmitate. The yield of the obtained vitamin C palmitate is 96.4%, the conversion rate of the vitamin C is about 98.7%, and the product purity is 99.6%.
Example 5
Respectively adding 68.7g of vitamin C, 134g of palmitic acid, 279g of n-butyl acetate and 163.5g of dilute sulfuric acid (14.3%) into a 1L four-mouth reaction bottle, adopting an 80cm glass spring packed tower, adding a water separator, cooling by cooling water, controlling the system pressure to be 45kpa, heating the material to 57 ℃ under the stirring condition, starting refluxing, carrying out azeotropic boiling on the n-butyl acetate and water, continuously carrying out solvent water and water generated by the reaction, forming obvious water-oil two phases in the water separator, after refluxing reaction for 54h, keeping the water level in the water separator from increasing, cooling to normal temperature, adding 144g of water into the reaction liquid, stirring, standing and layering; recovering n-butyl acetate under reduced pressure (80 deg.C in water bath), cooling to-10 deg.C, crystallizing, filtering, and oven drying (40 deg.C) to obtain 156.9g vitamin C palmitate. The yield of the obtained vitamin C palmitate is 97.1 percent, the conversion rate of the vitamin C is about 99.0 percent, and the product purity is 99.4 percent.
Example 6
Respectively adding 67.7g of vitamin C, 130g of palmitic acid, 420g of toluene and 160.5g of dilute sulfuric acid (12.7%) into a 1L four-mouth reaction bottle, adopting a 80cm glass spring packed tower, adding a water separator, cooling by cooling water, controlling the system pressure to be 56kpa, heating the material to 50 ℃ under the stirring condition, starting refluxing, enabling the toluene and the water to be subjected to azeotropic distillation, continuously taking out solvent water and water generated by the reaction, enabling the water separator to be in an obvious water-oil two-phase state, after refluxing reaction for 46 hours, enabling the water level in the water separator not to be increased, cooling to normal temperature, adding 132g of water into the reaction liquid, stirring, standing and layering; recovering toluene under reduced pressure from oil phase at about 412g (80 deg.C in water bath), cooling to-10 deg.C, crystallizing, filtering, and oven drying (40 deg.C) to obtain 154.2g vitamin C palmitate. The yield of the obtained vitamin C palmitate is 96.8 percent, the conversion rate of the vitamin C is about 99.3 percent, and the product purity is 99.4 percent.
Example 7
Adding 61.2g of vitamin C, 122g of palmitic acid, 220g of cyclohexane and 132.5g of dilute sulfuric acid (16.9%) into a 1L four-mouth reaction bottle respectively, heating the materials to 57 ℃ by adopting a 80cm glass spring packed tower and a water separator, cooling the materials by cooling water, and starting to reflux under the condition of normal-pressure stirring, wherein the cyclohexane and the water are subjected to azeotropic distillation at the moment, the solvent water and the water generated by the reaction are continuously taken out, an obvious water-oil two phase is formed in the water separator, after reflux reaction is carried out for 23 hours, the water level in the water separator is not increased, cooling the water to normal temperature, adding 112g of water into the reaction liquid, stirring, standing and layering; recovering cyclohexane under reduced pressure from oil phase at about 214g (heating in water bath at 80 deg.C), cooling to-10 deg.C, crystallizing, filtering, and oven drying (40 deg.C) to obtain 140.1 g vitamin C palmitate. The yield of the obtained vitamin C palmitate is 97.3 percent, the conversion rate of the vitamin C is about 99.2 percent, and the product purity is 99.2 percent.
Comparative example 1
Conventional esterification of concentrated sulfuric acid
Respectively adding 65.2g of vitamin C, 131g of palmitic acid and 600g of concentrated sulfuric acid (96%) into a 1L four-mouth reaction bottle, reacting for 50 hours under the condition of stirring at 80 ℃, adding 1500g of water and 1000g of butyl acetate after the reaction is finished, extracting and layering to generate 36% dilute sulfuric acid, decompressing a butyl acetate oil phase, recovering part of an extracting agent (heating in a water bath for 60 ℃), then cooling to-10 ℃, crystallizing, filtering, drying (40 ℃), and obtaining 115g of vitamin C palmitate. The yield of the obtained vitamin C palmitate is 75%, the conversion rate of the vitamin C is about 77%, and the product purity is 96.0%.
Comparative example 2
Respectively adding 65.2g of vitamin C, 131g of palmitic acid and 350g of dilute sulfuric acid (50%) into a 1L four-mouth reaction bottle, reacting for 50 hours under the condition of stirring at 80 ℃, adding 1500g of water and 1000g of butyl acetate after the reaction is finished, extracting and layering to generate 9.4% of dilute sulfuric acid, recovering part of an extracting agent from a butyl acetate oil phase under reduced pressure (heating in a water bath for 60 ℃), then cooling to-10 ℃, crystallizing, filtering and drying (40 ℃), and obtaining 53.6g of vitamin C palmitate. The yield of the obtained vitamin C palmitate is 35%, the conversion rate of the vitamin C is about 56.2%, and the purity of the product is 96.5%.
The results of the above examples and comparative examples show that, on the basis of the concentrated sulfuric acid esterification method, the invention adopts a two-solvent system of an organic solvent and water, and dilute sulfuric acid is used as a catalyst to obtain the vitamin C palmitate. The preparation method has the advantages of simple process flow, convenient operation, high product yield and purity, reduction of environmental protection pressure and potential safety hazard in the post-treatment process, and suitability for industrial production.
Claims (9)
1. The preparation method of the vitamin C palmitate is characterized by comprising the following steps:
1) mixing the vitamin C, the palmitic acid and the organic solvent, adding a dilute sulfuric acid catalyst, heating and refluxing, and carrying out azeotropic water separation on the organic solvent and water;
2) after the reaction in the step 1) is finished, cooling the reaction liquid to normal temperature, and washing the reaction liquid with water to obtain an organic phase and a water phase;
3) and 2) recovering part of the organic solvent from the organic phase obtained in the step 2), cooling, crystallizing, filtering and drying to obtain the vitamin C palmitate solid.
2. The method for preparing vitamin C palmitate according to claim 1, wherein the organic solvent is selected from ethers, esters and hydrocarbons, the ethers are selected from one or more of methyl tert-butyl ether, ethyl ether and isopropyl ether; the esters are selected from one or more of sec-butyl acetate or n-butyl acetate; the hydrocarbon is one or more of toluene or cyclohexane.
3. The method for preparing ascorbyl palmitate as claimed in claim 2, wherein the organic solvent is one or more selected from the group consisting of methyl tert-butyl ether, ethyl ether and isopropyl ether.
4. The process for producing vitamin C palmitate as claimed in claim 3, wherein the organic solvent is isopropyl ether.
5. The method for preparing ascorbyl palmitate according to claim 1, wherein the azeotropic temperature of the organic solvent and water is 40-55 ℃.
6. The method for preparing ascorbyl palmitate according to claim 1, wherein the concentration of the dilute sulfuric acid is 5-20%, and the mass of the pure sulfuric acid is 20-40% of the mass of the ascorbyl palmitate.
7. The method for preparing ascorbyl palmitate according to claim 1, wherein the partial organic solvent recovery process in the step 2) is preferably distillation concentration, the distillation temperature is controlled to be 50-80 ℃, and the concentration is carried out until the mass fraction of the ascorbyl palmitate reaches more than 50%.
8. The method for preparing ascorbyl palmitate as claimed in claim 1, wherein the drying temperature in the step 3) is 30-50 ℃.
9. The method for preparing ascorbyl palmitate according to claim 1, further comprising:
step 4) recycling the water phase in the step 2) for use in the catalytic reaction in the step 1); recycling the crystallized mother liquor obtained after the crystallization in the step 3), combining the crystallized mother liquor with the partially recovered organic solvent in the step 3), and dissolving the next batch of palmitic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911070506.9A CN110776484A (en) | 2019-11-05 | 2019-11-05 | Preparation method of vitamin C palmitate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911070506.9A CN110776484A (en) | 2019-11-05 | 2019-11-05 | Preparation method of vitamin C palmitate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110776484A true CN110776484A (en) | 2020-02-11 |
Family
ID=69389015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911070506.9A Pending CN110776484A (en) | 2019-11-05 | 2019-11-05 | Preparation method of vitamin C palmitate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110776484A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112608954A (en) * | 2020-11-27 | 2021-04-06 | 安徽泰格生物技术股份有限公司 | Preparation method of vitamin C palmitate |
| CN113441009A (en) * | 2021-06-22 | 2021-09-28 | 黑龙江新和成生物科技有限公司 | Vitamin C bipolar membrane acidification production process and device |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705869A (en) * | 1983-03-12 | 1987-11-10 | Basf Aktiengesellschaft | Preparation of fatty acid esters of ascorbic acid |
| CN101747187A (en) * | 2009-12-25 | 2010-06-23 | 浙江工业大学 | Method for preparing iso-octyl palmitate |
| CN102304109A (en) * | 2011-08-29 | 2012-01-04 | 河北维尔康制药有限公司 | Method for synthesizing L-ascorbyl palmitate |
| CN102558115A (en) * | 2011-12-29 | 2012-07-11 | 蚌埠丰原医药科技发展有限公司 | Preparation method of L-ascorbyl palmitate |
| CN102603583A (en) * | 2012-02-28 | 2012-07-25 | 湘潭大学 | Method for preparing multi-sulfhydryl carboxylic ester |
| CN106883202A (en) * | 2017-03-14 | 2017-06-23 | 深圳市海滨制药有限公司 | A kind of preparation method of L ascorbyl palmitates |
| CN107814716A (en) * | 2017-10-16 | 2018-03-20 | 上海邦高化学有限公司 | A kind of industrial method for producing ethylene glycol diformate |
-
2019
- 2019-11-05 CN CN201911070506.9A patent/CN110776484A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705869A (en) * | 1983-03-12 | 1987-11-10 | Basf Aktiengesellschaft | Preparation of fatty acid esters of ascorbic acid |
| CN101747187A (en) * | 2009-12-25 | 2010-06-23 | 浙江工业大学 | Method for preparing iso-octyl palmitate |
| CN102304109A (en) * | 2011-08-29 | 2012-01-04 | 河北维尔康制药有限公司 | Method for synthesizing L-ascorbyl palmitate |
| CN102558115A (en) * | 2011-12-29 | 2012-07-11 | 蚌埠丰原医药科技发展有限公司 | Preparation method of L-ascorbyl palmitate |
| CN102603583A (en) * | 2012-02-28 | 2012-07-25 | 湘潭大学 | Method for preparing multi-sulfhydryl carboxylic ester |
| CN106883202A (en) * | 2017-03-14 | 2017-06-23 | 深圳市海滨制药有限公司 | A kind of preparation method of L ascorbyl palmitates |
| CN107814716A (en) * | 2017-10-16 | 2018-03-20 | 上海邦高化学有限公司 | A kind of industrial method for producing ethylene glycol diformate |
Non-Patent Citations (6)
| Title |
|---|
| 《化工百科全书》编辑委员会编: "《化工百科全书》", 30 September 1998, 化学工业出版社 * |
| BIN WEN等: "Ultrasound accelerated esterification of palmitic acid with vitamin C", 《ULTRASONICS SONOCHEMISTRY》 * |
| 吴济民: "醋酸酐生产技术及衍生物研究进展", 《当代化工》 * |
| 武玉民等: "一缩二乙二醇油酸双酯皮革加脂剂的合成研究", 《皮革化工》 * |
| 王娜等: "新教材中乙酸乙酯制取实验的改进", 《化学教育》 * |
| 祝显虹等: ""一锅法"合成L- 抗坏血酸棕榈酸酯工艺改进", 《化工技术与开发》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112608954A (en) * | 2020-11-27 | 2021-04-06 | 安徽泰格生物技术股份有限公司 | Preparation method of vitamin C palmitate |
| CN112608954B (en) * | 2020-11-27 | 2023-03-10 | 安徽泰格生物技术股份有限公司 | Preparation method of vitamin C palmitate |
| CN113441009A (en) * | 2021-06-22 | 2021-09-28 | 黑龙江新和成生物科技有限公司 | Vitamin C bipolar membrane acidification production process and device |
| CN113441009B (en) * | 2021-06-22 | 2022-07-22 | 黑龙江新和成生物科技有限公司 | Vitamin C bipolar membrane acidification production process and device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109400476B (en) | Preparation method of estolide | |
| CN101863855B (en) | Preparation of temperature sensitive acidic ionic liquid and method of using the same in catalyzing alcoholic acid esterification | |
| CN101215235B (en) | Method for synthesizing hindered phenol antioxidants | |
| CN110776484A (en) | Preparation method of vitamin C palmitate | |
| CN101172253B (en) | Esterification catalysts and esterification process of organic acid | |
| CN110483473B (en) | Method for preparing 1, 3-propane sultone | |
| CN102824929B (en) | Preparation method of dioctyl terephthalate and used catalyst | |
| CN102964495A (en) | Synthetic method of terpene resin | |
| CN104529935B (en) | Method for synthesizing ethyl 2-(3-aldehyde-4-isobutyloxyphenyl)-4-methylthiazole-5-formate | |
| KR20130107472A (en) | Method for preparing high-purified unsaturated fatty acids using waste animal and vegetable oil | |
| CN114920642B (en) | Separation process for obtaining high-purity fatty acid monoglyceride and fatty acid diglyceride | |
| CN107602400B (en) | Method for accelerating synthesis time of mefenamic acid | |
| CN101967081B (en) | Process for recovering water-containing methanol solution produced in production of antioxygen 1010 | |
| CN101709055A (en) | Method for synthesizing ionic liquid | |
| CN102276415B (en) | Method for improving fluorine-containing alkyl alcohol yield | |
| CN102731299B (en) | Liquid-liquid extraction separation method of methyl propionate-methanol-water azeotropic system | |
| CN101838222B (en) | Preparation method of N-(4-ethoxycarbonylphenyl)-N'-ethyl-N'-phenylformamidine | |
| CN1450046A (en) | Method for synthesizing high-recovery and high-optical purity L-butyl lactate | |
| CN104262212A (en) | Method for continuously preparing 2,6-dinonyl naphthalene sulfonic acid | |
| CN113980046A (en) | Preparation method of high-purity isooctyl monomethyltrimercaptoacetate tin heat stabilizer | |
| CN112457228B (en) | Preparation method of thioglycollic acid-2-ethylhexyl ester in fused salt hydrate | |
| CN105541611A (en) | Method for preparing aceto acetoxy ethyl methacrylate | |
| JPS6034558B2 (en) | Method for producing N,N'-bis-trimethylsilyl urea | |
| CN115784929B (en) | Preparation method of crotononitrile | |
| CN109400468B (en) | Preparation method of L-dibenzoyl dimethyl tartrate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200211 |
|
| RJ01 | Rejection of invention patent application after publication |