CN111533653A - Method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil - Google Patents
Method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil Download PDFInfo
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- CN111533653A CN111533653A CN202010487344.5A CN202010487344A CN111533653A CN 111533653 A CN111533653 A CN 111533653A CN 202010487344 A CN202010487344 A CN 202010487344A CN 111533653 A CN111533653 A CN 111533653A
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- Prior art keywords
- dihydroartemisinic acid
- wax oil
- artemisinin
- cooling
- petroleum ether
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- JYGAZEJXUVDYHI-DGTMBMJNSA-N dihydroartemisinic acid Chemical compound C1CC(C)=C[C@@H]2[C@H]([C@@H](C)C(O)=O)CC[C@@H](C)[C@@H]21 JYGAZEJXUVDYHI-DGTMBMJNSA-N 0.000 title claims abstract description 108
- JYGAZEJXUVDYHI-UHFFFAOYSA-N dihydroartemisininic acid Natural products C1CC(C)=CC2C(C(C)C(O)=O)CCC(C)C21 JYGAZEJXUVDYHI-UHFFFAOYSA-N 0.000 title claims abstract description 54
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 title claims abstract description 35
- 229960004191 artemisinin Drugs 0.000 title claims abstract description 35
- 229930101531 artemisinin Natural products 0.000 title claims abstract description 35
- 239000002699 waste material Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000001816 cooling Methods 0.000 claims abstract description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000013078 crystal Substances 0.000 claims abstract description 28
- 239000003208 petroleum Substances 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000243 solution Substances 0.000 claims abstract description 25
- 238000003756 stirring Methods 0.000 claims abstract description 24
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 239000007864 aqueous solution Substances 0.000 claims abstract description 15
- 238000000967 suction filtration Methods 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000008213 purified water Substances 0.000 claims abstract description 8
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 230000008025 crystallization Effects 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 2
- 241000049464 Artemisia apiacea Species 0.000 claims 1
- 235000011570 Artemisia caruifolia var apiacea Nutrition 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 11
- 240000000011 Artemisia annua Species 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- HATRDXDCPOXQJX-UHFFFAOYSA-N Thapsigargin Natural products CCCCCCCC(=O)OC1C(OC(O)C(=C/C)C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C HATRDXDCPOXQJX-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229930009674 sesquiterpene lactone Natural products 0.000 description 1
- 150000002107 sesquiterpene lactone derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil, which comprises the following steps: 1) adding purified water into the artemisinin waste wax oil, heating to remove residual organic solvent in the wax oil, cooling, adding petroleum ether, adding alkaline substance to adjust pH, heating, refluxing and stirring; 2) cooling to room temperature for layering, removing the aqueous solution layer, centrifuging and concentrating; 3) adding an acidic substance to adjust the pH value; 4) adding petroleum ether, heating and stirring, cooling, standing and layering, taking the petroleum ether layer, and extracting twice; 5) combining the petroleum ether layers, concentrating under reduced pressure, cooling and crystallizing to obtain white and yellow crude crystals of dihydroartemisinic acid; 6) adding 80% ethanol solution into the white-yellow crude dihydroartemisinic acid crystals, stirring until the white-yellow crude dihydroartemisinic acid crystals are completely dissolved, adding activated carbon, stirring and decoloring, performing suction filtration to remove the activated carbon, recovering ethanol, cooling the residual aqueous solution for crystallization, performing suction filtration and drying to obtain high-purity colorless dihydroartemisinic acid crystals. The method has high separation efficiency, simple separation process, and high purity of the separated dihydroartemisinic acid.
Description
Technical Field
The invention belongs to the technical field of medicinal chemistry, and particularly relates to a method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil.
Background
The artemisinin is a sesquiterpene lactone drug with peroxy groups extracted from stems and leaves of plant artemisia annua, which is the first choice drug for treating malaria at present, but the content of the artemisinin in the artemisia annua plant is lower and far lower than that of a biosynthetic precursor dihydroartemisinic acid, and the dihydroartemisinic acid is also extracted from the artemisia annua plant simultaneously in the extraction process of the artemisinin, but the dihydroartemisinic acid is remained in the artemisinin waste wax oil in the further separation and purification process of the artemisinin, so that resource waste is caused, in order to reduce the production cost of the artemisinin, the waste artemisinin wax oil needs to be separated to separate the dihydroartemisinic acid, but the prior method for separating the dihydroartemisinic acid from the artemisinin waste wax oil has the problems of low separation efficiency, complex separation process, high cost, difficulty in industrial production and low purity of the separated dihydroartemisinic acid.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil, which has the advantages of high separation efficiency, simple separation process, low cost, easiness in industrial production and high purity of the separated dihydroartemisinic acid.
The purpose of the invention is realized as follows:
a method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil comprises the following steps:
1) adding purified water into the artemisinin waste wax oil, heating at 65-80 ℃ to remove organic solvent remained in the wax oil separated due to production, cooling, adding petroleum ether, adding an alkaline substance to adjust the pH value to 9-10, and heating, refluxing and stirring at 65-80 ℃ for 20-40 min;
2) cooling to room temperature for layering, removing the aqueous solution layer, centrifuging to obtain an orange aqueous solution, and concentrating to obtain a concentrated solution;
3) adding an acidic substance into the concentrated solution obtained in the step 2), and adjusting the pH value to 3-5;
4) adding petroleum ether into the acidified concentrated solution obtained in the step 3), heating and stirring at 35-50 ℃ for 20-40min, cooling, standing, layering, taking a petroleum ether layer, and extracting twice by the same method;
5) combining the petroleum ether layers obtained in the step 4) twice, performing reduced pressure concentration at 50 ℃ by using a rotary evaporator, and performing cooling crystallization to obtain white and yellow crude crystals of dihydroartemisinic acid;
6) adding 80% ethanol solution into the white-yellow crude dihydroartemisinic acid crystals obtained in the step 5), stirring until the crude dihydroartemisinic acid crystals are completely dissolved, adding activated carbon, stirring and decoloring, then performing suction filtration to remove the activated carbon, performing ethanol recovery by using a rotary evaporator at 70-75 ℃, cooling the residual aqueous solution for crystallization, performing suction filtration and drying to obtain the high-purity colorless dihydroartemisinic acid crystals.
In the step 1), the volume of purified water is as follows: the mass of the artemisinin waste wax oil is 3-5ml:1 g.
In the step 1), the volume of petroleum ether is as follows: the mass of the artemisinin waste wax oil is 1-3ml:1 g.
In the step 1), the alkaline substance is flake caustic soda, sodium bicarbonate or sodium hydroxide.
In the step 3), the acidic substance is hydrochloric acid, glacial acetic acid or sulfuric acid.
In the step 4), the volume of petroleum ether added each time is as follows: the volume of the concentrated solution is 0.7-1.4: 1.
In the step 6), the mass ratio of the activated carbon to the white-yellow crude dihydroartemisinic acid crystal is 0.1-0.2: 1.
The invention has the following beneficial effects:
the invention discloses a method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil, which is used for recycling the artemisinin waste wax oil, saving resources and reducing the pollution of the waste wax oil to the environment.
The invention adopts extraction, concentration and decoloration technologies, improves the separation efficiency, reduces the separation cost, has simple separation process and is easy for industrial production.
The invention recovers the ethanol, reduces the usage amount of the organic solvent; the purity of the dihydroartemisinic acid separated by the method is as high as 95-98%.
Detailed Description
Example 1
A method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil comprises the following steps:
1) adding 2000mL of purified water into 500g of artemisinin waste wax oil, heating at 70 ℃ to remove organic solvent remained in the wax oil separated due to production, cooling, adding 500mL of petroleum ether, adding sodium bicarbonate to adjust the pH value to 10, heating at 70 ℃, refluxing and stirring for 30 min;
2) cooling to room temperature for layering, removing the aqueous solution layer, centrifuging to obtain an orange aqueous solution, and concentrating to obtain 700mL of a concentrated solution;
3) adding hydrochloric acid into the concentrated solution obtained in the step 2), and adjusting the pH value to 4;
4) adding 500mL of petroleum ether into the acidified concentrated solution obtained in the step 3), heating and stirring at 40 ℃ for 30min, cooling, standing, layering, taking a petroleum ether layer, and extracting twice by the same method;
5) combining the petroleum ether layers obtained in the step 4) twice to obtain 1000mL in total, performing reduced pressure concentration at 50 ℃ by using a rotary evaporator, concentrating to 50mL, and cooling and crystallizing to obtain 25g of white and yellow crude crystals of dihydroartemisinic acid;
6) adding 80% ethanol solution into 25g of the white-yellow crude dihydroartemisinic acid crystals obtained in the step 5), stirring until the white-yellow crude dihydroartemisinic acid crystals are completely dissolved, adding 5g of activated carbon, stirring and decoloring, then performing suction filtration to remove the activated carbon, recovering ethanol at 70 ℃ by using a rotary evaporator, cooling the residual water solution for crystallization, performing suction filtration and drying to obtain 19g of high-purity colorless dihydroartemisinic acid crystals.
The purity of the colorless crystals of the high-purity dihydroartemisinic acid obtained above was 96% by HPLC.
Example 2
A method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil comprises the following steps:
1) adding 1500mL of purified water into 500g of artemisinin waste wax oil, heating at 65 ℃ to remove organic solvent remained in wax oil separated due to production, cooling, adding 1000mL of petroleum ether, adding caustic soda flakes to adjust pH value to 9, heating at 65 ℃, refluxing and stirring for 40 min;
2) cooling to room temperature for layering, removing the aqueous solution layer, centrifuging to obtain an orange aqueous solution, and concentrating to obtain 600mL of a concentrated solution;
3) adding sulfuric acid into the concentrated solution obtained in the step 2), and adjusting the pH value to 5;
4) adding 600mL of petroleum ether into the acidified concentrated solution obtained in the step 3), heating and stirring at 35 ℃ for 40min, cooling, standing and layering, taking a petroleum ether layer, and extracting twice by the same method;
5) combining the petroleum ether layers obtained in the step 4) twice to obtain 1200mL in total, performing reduced pressure concentration at 50 ℃ by using a rotary evaporator, concentrating to 45mL, and cooling and crystallizing to obtain 22g of white and yellow crude crystals of dihydroartemisinic acid;
6) adding 80% ethanol solution into the 20g of the white-yellow crude dihydroartemisinic acid crystals obtained in the step 5), stirring until the white-yellow crude dihydroartemisinic acid crystals are completely dissolved, adding 2.2g of activated carbon, stirring and decoloring, then performing suction filtration to remove the activated carbon, recovering ethanol by using a rotary evaporator at 75 ℃, cooling and crystallizing the residual aqueous solution, performing suction filtration and drying to obtain 16g of high-purity colorless dihydroartemisinic acid crystals.
The purity of the colorless crystals of the high-purity dihydroartemisinic acid obtained above was 95% by HPLC.
Example 3
A method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil comprises the following steps:
1) adding 2500mL of purified water into 500g of artemisinin waste wax oil, heating at 80 ℃ to remove organic solvent remained in production separation wax oil, cooling, adding 1500mL of petroleum ether, adding sodium hydroxide to adjust pH value to 10, heating at 80 ℃, refluxing and stirring for 20 min;
2) cooling to room temperature for layering, removing the aqueous solution layer, centrifuging to obtain an orange aqueous solution, and concentrating to obtain 500mL of a concentrated solution;
3) adding glacial acetic acid into the concentrated solution obtained in the step 2), and adjusting the pH value to 3;
4) adding 700mL of petroleum ether into the acidified concentrated solution obtained in the step 3), heating and stirring at 50 ℃ for 20min, cooling, standing, layering, taking a petroleum ether layer, and extracting twice by the same method;
5) combining the petroleum ether layers obtained in the step 4) twice to obtain 1400mL in total, performing reduced pressure concentration at 50 ℃ by using a rotary evaporator, concentrating to 55mL, and cooling for crystallization to obtain 24g of white-yellow crude crystals of dihydroartemisinic acid;
6) adding 80% ethanol solution into 24g of the white-yellow crude dihydroartemisinic acid crystals obtained in the step 5), stirring until the mixture is completely dissolved, adding 3.6g of activated carbon, stirring and decoloring, then performing suction filtration to remove the activated carbon, recovering ethanol at 72 ℃ by using a rotary evaporator, cooling and crystallizing the residual water solution, performing suction filtration and drying to obtain 18g of high-purity colorless dihydroartemisinic acid crystals.
The purity of the colorless crystals of the high-purity dihydroartemisinic acid obtained above was 98% by HPLC.
Claims (7)
1. A method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil is characterized by comprising the following steps:
1) adding purified water into the artemisinin waste wax oil, heating at 65-80 ℃ to remove organic solvent remained in the wax oil separated due to production, cooling, adding petroleum ether, adding an alkaline substance to adjust the pH value to 9-10, and heating, refluxing and stirring at 65-80 ℃ for 20-40 min;
2) cooling to room temperature for layering, removing the aqueous solution layer, centrifuging to obtain an orange aqueous solution, and concentrating to obtain a concentrated solution;
3) adding an acidic substance into the concentrated solution obtained in the step 2), and adjusting the pH value to 3-5;
4) adding petroleum ether into the acidified concentrated solution obtained in the step 3), heating and stirring at 35-50 ℃ for 20-40min, cooling, standing, layering, taking a petroleum ether layer, and extracting twice by the same method;
5) combining the petroleum ether layers obtained in the step 4) twice, performing reduced pressure concentration at 50 ℃ by using a rotary evaporator, and performing cooling crystallization to obtain white and yellow crude crystals of dihydroartemisinic acid;
6) adding 80% ethanol solution into the white-yellow crude dihydroartemisinic acid crystals obtained in the step 5), stirring until the crude dihydroartemisinic acid crystals are completely dissolved, adding activated carbon, stirring and decoloring, then performing suction filtration to remove the activated carbon, performing ethanol recovery by using a rotary evaporator at 70-75 ℃, cooling the residual aqueous solution for crystallization, performing suction filtration and drying to obtain the high-purity colorless dihydroartemisinic acid crystals.
2. The method for separating and purifying dihydroartemisinic acid from artemisia apiacea waste wax oil as claimed in claim 1, wherein in the step 1), the volume of purified water is as follows: the mass of the artemisinin waste wax oil is 3-5ml:1 g.
3. The method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil as claimed in claim 1, wherein in the step 1), the volume of petroleum ether is: the mass of the artemisinin waste wax oil is 1-3ml:1 g.
4. The method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil as claimed in claim 1, wherein in step 1), the alkaline substance is caustic soda flakes, sodium bicarbonate or sodium hydroxide.
5. The method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil as claimed in claim 1, wherein in step 3), the acidic substance is hydrochloric acid, glacial acetic acid or sulfuric acid.
6. The method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil as claimed in claim 1, wherein in step 4), the volume of petroleum ether added each time: the volume of the concentrated solution is 0.7-1.4: 1.
7. The method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil as claimed in claim 1, wherein in the step 6), the mass ratio of the activated carbon to the white-yellow crude crystals of dihydroartemisinic acid is 0.1-0.2: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010487344.5A CN111533653A (en) | 2020-06-02 | 2020-06-02 | Method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010487344.5A CN111533653A (en) | 2020-06-02 | 2020-06-02 | Method for separating and purifying dihydroartemisinic acid from artemisinin waste wax oil |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6372646A (en) * | 1986-09-16 | 1988-04-02 | Maruzen Kasei Kk | Production of lansic acid |
| CN103694106A (en) * | 2013-12-28 | 2014-04-02 | 湘西自治州奥瑞克医药化工有限责任公司 | Method for extracting and purifying dihydroartemisinic acid from artemisinin wax oil |
| US20140364630A1 (en) * | 2011-08-29 | 2014-12-11 | Max-Planck-Gesellschaft Zur Förderung Der Wissensc | Method and device for the synthesis of artemisinin |
| CN110105195A (en) * | 2019-04-09 | 2019-08-09 | 湖南威嘉生物科技有限公司 | A method of extracting dihydroartemisinic acid from sweet wormwood wax oil |
| CN110256237A (en) * | 2019-05-31 | 2019-09-20 | 长沙艾康生物科技有限公司 | A kind of high-purity dihydroartemisinic acid preparation method of the easy industrialized production of low energy consumption |
-
2020
- 2020-06-02 CN CN202010487344.5A patent/CN111533653A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6372646A (en) * | 1986-09-16 | 1988-04-02 | Maruzen Kasei Kk | Production of lansic acid |
| US20140364630A1 (en) * | 2011-08-29 | 2014-12-11 | Max-Planck-Gesellschaft Zur Förderung Der Wissensc | Method and device for the synthesis of artemisinin |
| CN103694106A (en) * | 2013-12-28 | 2014-04-02 | 湘西自治州奥瑞克医药化工有限责任公司 | Method for extracting and purifying dihydroartemisinic acid from artemisinin wax oil |
| CN110105195A (en) * | 2019-04-09 | 2019-08-09 | 湖南威嘉生物科技有限公司 | A method of extracting dihydroartemisinic acid from sweet wormwood wax oil |
| CN110256237A (en) * | 2019-05-31 | 2019-09-20 | 长沙艾康生物科技有限公司 | A kind of high-purity dihydroartemisinic acid preparation method of the easy industrialized production of low energy consumption |
Non-Patent Citations (1)
| Title |
|---|
| 何树华等主编: "《基础化学实验》", 31 July 2017, 西南交通大学出版社 * |
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Application publication date: 20200814 |
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