CN103588835A - Method for recycling scutellarin from waste liquid of acid sediment - Google Patents
Method for recycling scutellarin from waste liquid of acid sediment Download PDFInfo
- Publication number
- CN103588835A CN103588835A CN201310565420.XA CN201310565420A CN103588835A CN 103588835 A CN103588835 A CN 103588835A CN 201310565420 A CN201310565420 A CN 201310565420A CN 103588835 A CN103588835 A CN 103588835A
- Authority
- CN
- China
- Prior art keywords
- scutellarin
- waste liquid
- acid
- heavy waste
- coarse
- 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.)
- Granted
Links
- DJSISFGPUUYILV-UHFFFAOYSA-N UNPD161792 Natural products O1C(C(O)=O)C(O)C(O)C(O)C1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC(O)=CC=1)O2 DJSISFGPUUYILV-UHFFFAOYSA-N 0.000 title claims abstract description 54
- DJSISFGPUUYILV-ZFORQUDYSA-N scutellarin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC(O)=CC=1)O2 DJSISFGPUUYILV-ZFORQUDYSA-N 0.000 title claims abstract description 54
- NPLTVGMLNDMOQE-UHFFFAOYSA-N carthamidin Natural products C1=CC(O)=CC=C1C1OC2=CC(O)=C(O)C(O)=C2C(=O)C1 NPLTVGMLNDMOQE-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 229930190376 scutellarin Natural products 0.000 title claims abstract description 53
- 239000007788 liquid Substances 0.000 title claims abstract description 44
- 239000002699 waste material Substances 0.000 title claims abstract description 35
- 239000002253 acid Substances 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000013049 sediment Substances 0.000 title abstract 5
- 238000004064 recycling Methods 0.000 title abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000001953 recrystallisation Methods 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 238000001291 vacuum drying Methods 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 238000001556 precipitation Methods 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 4
- 238000000605 extraction Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 239000010842 industrial wastewater Substances 0.000 abstract description 2
- 238000004065 wastewater treatment Methods 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 4
- 238000013094 purity test Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241000132521 Erigeron Species 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention discloses a method for recycling scutellarin from a waste liquid of acid sediment, and belongs to the technical field of extraction separation of plant effective components and the field of industrial wastewater treatment. A certain amount of pure water is added into the waste liquid of the acid sediment for standing, sediment is separated out, filtered and washed, an organic solvent is used for recrystallization, and the high-purity scutellarin is obtained. The method is used for recycling the scutellarin in the waste liquid of the acid sediment, and raw medicinal materials are used further; and the method is simple in operation and low in cost, facilitates industrial production and has certain economic benefit and environmental value.
Description
Technical field
The present invention relates to a kind of method that reclaims scutellarin from the heavy waste liquid of acid, belong to effective ingredients in plant extraction and separation technology field and Industrial Wastewater Treatment field.
Background technology
Herba Erigerontis claims again Herba Erigerontis, herb for the short booth bitter fleabane of composite family bitter fleabane platymiscium, have remove obstruction in channels to relieve pain, promoting blood circulation and removing blood stasis, improve the effects such as blood microcirculation, clinically for the treatment of the diseases such as coronary heart disease, diabetes, ephrosis, apoplexy sequela, stenocardia, eighties of last century eighties, the Zhang Renwei of Yunnan medicine institute etc. are the separated effective constituent that obtained Herba Erigerontis from Herba Erigerontis first---scutellarin (having another name called scutellarin, structure is 4 ', 5,6-trihydroxyflavone-7-
o-glucuronide), the preparations such as Herba Erigerontis tablet, Breviscapine have been researched and developed on this basis, at present, the billions of units of Herba Erigerontis series product annual value of production, Yunnan Province has been classified as focus development Chinese medicinal materials, in Chuxiong, the ground such as Lijing, Red River carries out implant mass exploitation, processing.
< < Chinese Pharmacopoeia (2010 editions) > > regulation Breviscarpine is containing effective constituent---scutellarin need be greater than 90%.For a long time, from Herba Erigerontis medicinal material, the method for extraction separation and purification Breviscarpine mostly is sour heavy, then precipitation is made to scutellarin with recrystallization method; Also can adopt macroporous adsorbing resin for purification total flavones, elutriant acidifying, precipitation obtain Breviscarpine coarse-grain, then obtain highly purified scutellarin by recrystallization.Produce Breviscarpine or scutellarin and all adopted sour heavy technique, produced a large amount of mother liquors, become the heavy waste liquid of acid.The pH of the heavy waste liquid of these acid is 1-2, needs just can reach emission standard with rear in a large amount of alkali, simultaneously, in waste liquid, also remain a part of scutellarin, if can reclaim, can further make full use of herb resource, the BOD, the TOD that reduce the heavy waste liquid of acid are equivalent, are conducive to discharge.Yet, at this, have no on the one hand bibliographical information.
Summary of the invention
The object of the present invention is to provide a kind of method that reclaims scutellarin from the heavy waste liquid of acid, specifically comprise the steps:
(1) ratio that is 1:1 ~ 1:10 in the volume ratio of the heavy waste liquid of acid and pure water adds pure water in the heavy waste liquid of acid, standing 2-12 hour, filtration is precipitated, precipitation distilled water wash 1 ~ 2 time, gained is deposited in 20 ~ 60 ℃ of vacuum-dryings 4 ~ 12 hours, obtains scutellarin coarse-grain;
(2) ratio that is 1:5 ~ 1:20 in the volume ratio of scutellarin coarse-grain and acetone joins the scutellarin coarse-grain obtaining in step (1) in organic solvent, recrystallization 1 ~ 2 time, filter, with identical organic solvent washing, precipitate 1 ~ 2 time, then will be deposited in temperature and be under the condition of 20 ~ 60 ℃ vacuum-drying 4 ~ 12 hours, obtain scutellarin highly finished product.
Organic solvent of the present invention is a kind of in acetone, ethanol or methyl alcohol.
The heavy waste liquid of acid of the present invention is the heavy waste liquid of acid that the heavy explained hereafter Breviscarpine of employing acid or scutellarin produce.
The method for detecting purity of scutellarin sample of the present invention, specifically comprises the following steps:
(1) plant and instrument: Agilent 1200 palette spectrogram instrument, are furnished with quaternary pump, diode-array detector, and automatic sampler, column oven, with Agilent ZORBAX SB-C
18(4.6 * 250mm, 5 μ m) are chromatographic column;
(2) liquid-phase condition: 0.1% phosphate aqueous solution (A)-acetonitrile (B) is moving phase, carries out gradient elution, and gradient is as follows: 0-15 min, 15-40% B; 30 ° of C of column temperature, flow velocity 0.8ml/min; Detect wavelength 335 nm, sample size 10 μ l;
(3) typical curve: Y=30.389c-3.8889 (r=0.9998), Y is peak area, c is scutellarin concentration (μ g/ml);
(4) purity testing formula: scutellarin purity=scutellarin concentration/sample concentration * 100%.
Beneficial effect of the present invention is:
(1) the present invention reclaims the scutellarin in the heavy waste liquid of acid, more makes full use of herb resource;
(2) the present invention just can be recovered to highly purified scutellarin by simple method, with low cost, and easily suitability for industrialized production, has good economic benefit;
(3) committed step of the present invention, for add pure water in the heavy waste liquid of acid, is not polluted environment;
(4) when the present invention makes full use of herb resource, can effectively reduce the organism in the heavy waste liquid of acid, reduce TOD and BOD value, reduce the pollution of waste liquid to environment.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail, but protection domain of the present invention is not limited to described content.
Embodiment 1
Described in the present embodiment, from the heavy waste liquid of acid, reclaim the method for scutellarin, specifically comprise the steps:
(1) ratio that is 1:5 in the volume ratio of the heavy waste liquid of acid and pure water adds pure water in the heavy waste liquid of acid, and standing 2 hours, filtration was precipitated, precipitation distilled water wash 1 time, and gained is deposited in 20 ℃ of vacuum-dryings 12 hours, obtains scutellarin coarse-grain;
(2) ratio that is 1:5 in the volume ratio of scutellarin coarse-grain and acetone joins the scutellarin coarse-grain obtaining in step (1) in acetone, recrystallization 1 time, filter, with identical washing with acetone, precipitate 1 time, then by being deposited in temperature, be vacuum-drying 12 hours under the condition of 20 ℃, obtain scutellarin highly finished product;
(3) preparation of need testing solution: get the heavy waste liquid 10ml of acid, vacuum-drying obtains solid, and being configured to mass percent concentration with methyl alcohol is 100 μ g
/the sample liquid of ml, obtains sample one; Accurately weigh scutellarin coarse-grain 10mg, with methyl alcohol, being mixed with mass percent concentration is 100 μ g
/the sample liquid of ml, obtains sample two; Accurately weigh scutellarin highly finished product 10mg, with methyl alcohol, being mixed with mass percent concentration is 100 μ g
/the sample liquid of ml, obtains sample three;
(4) purity of sample one, two, three is tested, measurement result is as shown in table 1.
The purity testing result of table 1. scutellarin
Embodiment 2
Described in the present embodiment, from the heavy waste liquid of acid, reclaim the method for scutellarin, specifically comprise the steps:
(1) ratio that is 1:10 in the volume ratio of the heavy waste liquid of acid and pure water adds pure water in the heavy waste liquid of acid, and standing 12 hours, filtration was precipitated, precipitation distilled water wash 2 times, and gained is deposited in 40 ℃ of vacuum-dryings 8 hours, obtains scutellarin coarse-grain;
(2) ratio that is 1:10 in the volume ratio of scutellarin coarse-grain and ethanol joins the scutellarin coarse-grain obtaining in step (1) in ethanol, recrystallization 2 times, filter, by identical washing with alcohol, precipitate 2 times, then by being deposited in temperature, be vacuum-drying 9 hours under the condition of 35 ℃, obtain scutellarin highly finished product;
(3) preparation of need testing solution: get the heavy waste liquid 10ml of acid, vacuum-drying obtains solid, and being configured to mass percent concentration with methyl alcohol is 100 μ g
/the sample liquid of ml, obtains sample one; Accurately weigh scutellarin coarse-grain 10mg, with methyl alcohol, being mixed with mass percent concentration is 100 μ g
/the sample liquid of ml, obtains sample two; Accurately weigh scutellarin highly finished product 10mg, with methyl alcohol, being mixed with mass percent concentration is 100 μ g
/the sample liquid of ml, obtains sample three;
(4) purity of sample one, two, three is tested, measurement result is as shown in table 2.
The purity testing result of table 2. scutellarin
Embodiment 3
Described in the present embodiment, from the heavy waste liquid of acid, reclaim the method for scutellarin, specifically comprise the steps:
(1) ratio that is 1:1 in the volume ratio of the heavy waste liquid of acid and pure water adds pure water in the heavy waste liquid of acid, and standing 8 hours, filtration was precipitated, precipitation distilled water wash 2 times, and gained is deposited in 60 ℃ of vacuum-dryings 4 hours, obtains scutellarin coarse-grain;
(2) ratio that is 1:8 in the volume ratio of scutellarin coarse-grain and methyl alcohol joins the scutellarin coarse-grain obtaining in step (1) in methyl alcohol, recrystallization 2 times, filter, by identical methanol wash, precipitate 2 times, then by being deposited in temperature, be vacuum-drying 4 hours under the condition of 60 ℃, obtain scutellarin highly finished product;
(3) preparation of need testing solution: get the heavy waste liquid 10ml of acid, vacuum-drying obtains solid, and being configured to mass percent concentration with methyl alcohol is 100 μ g
/the sample liquid of ml, obtains sample one; Accurately weigh scutellarin coarse-grain 10mg, with methyl alcohol, being mixed with mass percent concentration is 100 μ g
/the sample liquid of ml, obtains sample two; Accurately weigh scutellarin highly finished product 10mg, with methyl alcohol, being mixed with mass percent concentration is 100 μ g
/the sample liquid of ml, obtains sample three;
(4) purity of sample one, two, three is tested, measurement result is as shown in table 3.
The purity testing result of table 3. scutellarin
Claims (2)
1. from the heavy waste liquid of acid, reclaim a method for scutellarin, it is characterized in that specifically comprising the steps:
(1) ratio that is 1:1 ~ 1:10 in the volume ratio of the heavy waste liquid of acid and pure water adds pure water in the heavy waste liquid of acid, standing 2-12 hour, filtration is precipitated, precipitation distilled water wash 1 ~ 2 time, gained is deposited in 20 ~ 60 ℃ of vacuum-dryings 4 ~ 12 hours, obtains scutellarin coarse-grain;
(2) ratio that is 1:5 ~ 1:20 in the volume ratio of scutellarin coarse-grain and organic solvent joins the scutellarin coarse-grain obtaining in step (1) in organic solvent, recrystallization 1 ~ 2 time, filter, with identical organic solvent washing, precipitate 1 ~ 2 time, then will be deposited in temperature and be under the condition of 20 ~ 60 ℃ vacuum-drying 4 ~ 12 hours, obtain scutellarin highly finished product.
2. from the heavy waste liquid of acid, reclaim according to claim 1 the method for scutellarin, it is characterized in that: described organic solvent is a kind of in acetone, ethanol or methyl alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310565420.XA CN103588835B (en) | 2013-11-14 | 2013-11-14 | A kind of method reclaiming scutellarin from waste liquid is sunk in acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310565420.XA CN103588835B (en) | 2013-11-14 | 2013-11-14 | A kind of method reclaiming scutellarin from waste liquid is sunk in acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103588835A true CN103588835A (en) | 2014-02-19 |
| CN103588835B CN103588835B (en) | 2016-02-24 |
Family
ID=50079186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310565420.XA Expired - Fee Related CN103588835B (en) | 2013-11-14 | 2013-11-14 | A kind of method reclaiming scutellarin from waste liquid is sunk in acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103588835B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113801174A (en) * | 2021-11-01 | 2021-12-17 | 湖南恒生制药股份有限公司 | Process for recovering breviscapine from breviscapine acid precipitation waste liquid |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1462620A (en) * | 2003-04-22 | 2003-12-24 | 中国科学院昆明植物研究所 | Powder of flenabane and its preparation method as well as application in making drugs |
| CN101249125A (en) * | 2007-12-29 | 2008-08-27 | 重庆希尔安药业有限公司 | Herbicide composition and its preparation and application, medicament use |
| CN102188440A (en) * | 2010-03-16 | 2011-09-21 | 万生联合制药有限公司 | Preparation method of high-purity breviscapinun material used by breviscapinun injection |
| CN102614240A (en) * | 2012-04-26 | 2012-08-01 | 王祥红 | Extract containing breviscapine and preparation method thereof |
-
2013
- 2013-11-14 CN CN201310565420.XA patent/CN103588835B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1462620A (en) * | 2003-04-22 | 2003-12-24 | 中国科学院昆明植物研究所 | Powder of flenabane and its preparation method as well as application in making drugs |
| CN101249125A (en) * | 2007-12-29 | 2008-08-27 | 重庆希尔安药业有限公司 | Herbicide composition and its preparation and application, medicament use |
| CN102188440A (en) * | 2010-03-16 | 2011-09-21 | 万生联合制药有限公司 | Preparation method of high-purity breviscapinun material used by breviscapinun injection |
| CN102614240A (en) * | 2012-04-26 | 2012-08-01 | 王祥红 | Extract containing breviscapine and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 金利泰 主编: "《天然药物提取分离工艺》", 31 October 2011 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113801174A (en) * | 2021-11-01 | 2021-12-17 | 湖南恒生制药股份有限公司 | Process for recovering breviscapine from breviscapine acid precipitation waste liquid |
| CN113801174B (en) * | 2021-11-01 | 2024-03-19 | 湖南恒生制药股份有限公司 | Process for recovering breviscapine from breviscapine acid precipitation waste liquid |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103588835B (en) | 2016-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2020119001A1 (en) | Method for preparing cannabidiol by means of high-speed countercurrent chromatography separation and purification | |
| CN103342628B (en) | Method for simultaneously extracting and separating solanesol and nicotine from tobacco | |
| CN100338017C (en) | Method for preparing high-purity chlorogenic acid from honeysuckle crude extract | |
| CN105130796A (en) | Diterpenoid compound and preparing method and application thereof | |
| CN105294628A (en) | Method for preparing flavonoid component by separating wild chrysanthemum flower | |
| CN1935798B (en) | Method for preparing and rographalide | |
| CN104402854A (en) | Method for extracting quercetin from mulberry leaves by utilizing ultrasonic waves | |
| US20130231469A1 (en) | Method for preparing albiflorin and paeoniflorin | |
| CN104628731B (en) | Method for extracting peganum harmala alkaloid under microwave assistance | |
| CN104447910A (en) | Method for preparation of loganin from traditional Chinese medicine Cornus officinalis | |
| CN103040945B (en) | Preparation and detection method of gangsong general flavones | |
| CN105106252A (en) | Method for extracting and separating flavonoid compounds from hypericum japonicum | |
| CN103588835B (en) | A kind of method reclaiming scutellarin from waste liquid is sunk in acid | |
| CN102659861B (en) | Purification method of rhubarb stilbene glucoside | |
| Wu et al. | Preparation of paeoniflorin from the stems and leaves of Paeonia lactiflora Pall.‘Zhongjiang’through green efficient microwave-assisted extraction and subcritical water extraction | |
| CN104844547B (en) | A kind of high efficiency extraction of barbaloin and grading purification method | |
| CN105175426A (en) | Method of extracting and purifying bergenin from cissus pteroclada hayata | |
| CN102250174A (en) | Method for extracting jasminin from winter jasmine leaves | |
| CN102532111A (en) | Method for extracting puerarin from traditional Chinese medicine kudzu | |
| CN104877037A (en) | Separation and purification method, products and application of Christia vespertilionis polysaccharides | |
| CN104352562A (en) | Preparation method of total flavonoids of schizonepeta tenuifolia briq and application of total flavonoids of schizonepeta tenuifolia briq to resistance to tumors | |
| CN105348364B (en) | Method for extraction of oleanolic acid from fructus ligustri lucidi | |
| CN102093210A (en) | Purified preparation method of six ginkgoic acid monomers | |
| CN102603819A (en) | Preparation method of rosavin | |
| CN102190665B (en) | Method for separating and purifying artemisinin by activated charcoal column chromatography employing nonaqueous system |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160224 Termination date: 20211114 |