CN104262137B - Alkali extraction and acid precipitation separates dihydroartemisinic acid in qinghaosu production waste - Google Patents
Alkali extraction and acid precipitation separates dihydroartemisinic acid in qinghaosu production waste Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- 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
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- 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
- C07C51/50—Use of additives, e.g. for stabilisation
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- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
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Abstract
A kind of alkali extraction and acid precipitation separates dihydroartemisinic acid from qinghaosu production waste, to produce waste liquid or useless cream as raw material taking qinghaosu, Vacuum Concentration volatilizes the residual solvent of producing in waste liquid or useless cream, first uses the ultrasonic extraction of alkaline solution, merges extract, go precipitation, get supernatant, in supernatant extract, add acid solution, collecting precipitation, by clean distilled water flushing precipitation, freeze drying obtains dry dihydroartemisinic acid product. The present invention has set up the method that separates dihydroartemisinic acid from qinghaosu production waste first, adopts ultrasonic wave assisted Extraction to follow the example of, and effectively improves extraction efficiency and the rate of recovery; And adopt freeze-drying, and efficiently solving the problem of the dihydroartemisinic acid product degraded that traditional drying method causes, product purity reaches more than 72%, and the rate of recovery is high, reaches more than 90%; Output is large, easily realizes industrialization and produces.
Description
Technical field
The present invention relates to a kind of preparation method of dihydroartemisinic acid, be specifically related to a kind of adopt alkali extraction and acid precipitation fromIn qinghaosu production waste, separate the method for dihydroartemisinic acid.
Background technology
Qinghaosu be China find first by natural drug internationally recognized and independent intellectual property right that have,The only Chinese medicine of developing by Western medicine research standard of being approved by WHO of Ye Shi China. Qinghaosu in the marketProduce by China, the development of China's Chinese Medicine Industry is played to importantly impetus. From the World Health OrganizationQinghaosu is regarded as to the most safe and effective antimalarial agent at present, and as treatment malaria first after medication,The market demand sharp increase of qinghaosu. Malaria is that Epidemic Scope is the widest, history is the longest, endangers maximum peopleClass parasitic infection is that third world countries' the highest disease of M & M is planted it for a long time alwaysOne. According to the report of the World Health Organization, the whole world has at least 2,500,000,000 populations to live in malaria district at present, annualThe number that malaria is died from the whole world exceedes 3,000,000 (wherein half is 5 years old following children). Along with Global Temperature becomesThe reasons such as warm and environmental disruption aggravation, the incidence of disease of malaria is in rising trend in recent years. WHO basis is to Anti-MalarialThe demand supposition of thing, the annual sales volume of artemisine medicine is 1,500,000,000 dollars. But because artemislnin content is low,Cause that qinghaosu production cost is high, the market price is high, the developing countries such as Africa, Southeast Asia, the Middle East largePart malaria patients are unable purchase artemisine medicine at all, so caused qinghaosu to answer aspect anti-malarialWith being very limited. Therefore China's qinghaosu industry is also had a strong impact on, the market price of qinghaosu from7000 yuan of per kilograms fall to less than 2000 yuan, and qinghaosu enterprise even loses in profitless space, much green grass or young cropsArtemisin manufacturer forces and stops production or change the line of production. Meanwhile, especially southern national the falling in Africa of developing countryEnter the predicament of antimalarial agent critical shortage.
Therefore, reducing production costs is the core place of expanding qinghaosu market, improving product competitiveness. LowThe research that cost is produced qinghaosu is subject to domestic and international common concern. Because of in artemisia annua, the containing of dihydroartemisinic acidAmount is 6 times of left and right of qinghaosu, if dihydroartemisinic acid is converted into qinghaosu completely, and the content of qinghaosuTo improve 6 times of left and right, qinghaosu production cost will obtain breakthrough reduction. At present, dihydroartemisinic acid transformsThe method of qinghaosu has obtained impressive progress, and Seeberger and L é vesque use Vapourtec to flow and closeCheng Yi is as synthetic reaction platform, and the such photochemically reactive mode of additional ultraviolet irradiation is by (dihydro) green grass or young cropsArtemisic acid vitro conversion has obtained qinghaosu, and this achievement in research was at the internal authority magazine " Angewandte of 2012Chemie " on deliver. After (dihydro) Arteannuic acid vitro conversion makes a breakthrough, the rule of (dihydro) Arteannuic acidModelling has been prepared into the key of low-cost production qinghaosu. The JayKeasling of Univ California-BerkeleyProfessor and his research group will derive from qinghaosu synzyme (ADS) and the novel cytochrome of high sweet wormwoodP450 monooxygenase gene (CYP71AV1) is implanted yeast, and yeast can change the intermediate compound producing in metabolismCause Arteannuic acid. They utilize the natural mevalonate pathway of yeast, and this approach is under normal circumstances by sugarClass metabolism produces acetyl coenzyme A and synthesizes sterol; And in the metabolic pathway of their synthesized, mevalonic acidApproach is used to produce in a large number intermediate farnesylpyrophosphate (FPP), and farnesylpyrophosphate next can byThe ADS expressing in yeast and CYP71AV1 catalysis produce Arteannuic acid. The difficulty of this work be to fromAssembling and the precision control of yeast, sweet wormwood several genes and metabolic pathway thereof. This of Keasling professor grindsStudying carefully achievement also delivered on world's authority's magazine " NATURE " in 2006. 2010, WageningenThe Harro of university professor and research team thereof adopt transgene tobacco (Nicotianabenthamiana) syntheticPrecursor Arteannuic acid. But, although the method for the synthetic Arteannuic acid of above-mentioned allos obtains interim progress, bySo far not yet can industrialization development in cost height. In the production process of qinghaosu, dihydroartemisinic acid is also by sameIn time, extracts from plant, but in the further separation and purification process of qinghaosu, dihydroartemisinic acid quiltStay and produce in waste liquid, be not used again, caused a large amount of wastes of resource. Therefore, research fromQinghaosu produce the method that separates dihydroartemisinic acid in waste liquid to making full use of artemisia annua resource, to improve product attachedValue added have very important meaning with reduction qinghaosu production cost, there is no at present pertinent literature report.
Summary of the invention:
Technical problem to be solved by this invention is: for above-mentioned the deficiencies in the prior art, provide a kind of alkali to carryThe heavy method of acid separates dihydroartemisinic acid from qinghaosu production waste, and this method is to get qinghaosu to produce waste liquid or useless cream,Volatilize residual solvent, first use the ultrasonic extraction of alkaline solution, merge extract, go precipitation, in extract, addEnter acid solution, collecting precipitation, by clean distilled water flushing precipitation, freeze drying obtains dry dihydroArteannuic acid product. This legal system rate is high, the cycle is short, cost is low.
In order to solve the problems of the technologies described above, the technical solution adopted in the present invention is: a kind of alkali extraction and acid precipitation dividesFrom dihydroartemisinic acid in qinghaosu production waste, the method comprises the steps, in conjunction with referring to Fig. 1:
A, taking qinghaosu production waste as raw material, Vacuum Concentration to the residual solvent in production waste volatilizes,Concentrate; Wherein, above-mentioned qinghaosu production waste refers to qinghaosu production waste liquid or useless cream; Described qinghaosu is rawProducing volatilizing of residual solvent in waste liquid is to adopt the method for Vacuum Concentration to reclaim solvent, and thickening temperature is33-40 DEG C, Vacuum Concentration is produced waste liquid to organic solvent and is all volatilized, then adds isopyknic methyl alcohol or anhydrousEthanol, at 33-40 DEG C, continues Vacuum Concentration until solution all volatilizes; Described qinghaosu is produced in useless cream residualVolatilizing of remaining solvent is to add isopyknic methyl alcohol or absolute ethyl alcohol in producing useless cream, at 33-40 DEG C, and vacuumBeing concentrated into solution all volatilizes.
B, the ultrasonic extraction of alkali lye: taking the alkaline solution of 0.2%-0.6% mass body volume concentrations as extractant, by 3-5gConcentrate adds the ratio of 1ml alkaline solution and carries out ultrasonic extraction 2 times, and ultrasonic power 80-115 watt, when ultrasonicBetween 40-60min, ultrasonic temperature is 30-50 DEG C; Wherein, described alkaline solution be NaOH, sodium carbonate,Sodium acid carbonate, sodium dihydrogen phosphate or disodium phosphate soln, this NaOH, sodium carbonate, sodium acid carbonate,It is pure that sodium dihydrogen phosphate and disodium phosphate soln are all analysis.
C, go precipitation: ultrasonic extraction is complete, merge secondary raffinate, under room temperature condition, adopt centrifugal or filterGo precipitation, collect supernatant, obtain the extraction solution of clarification; Wherein, centrifugal go precipitation be with 3000rpm/minCentrifugal 10-15min, goes precipitation; Crossing elimination precipitation is that vacuum filtration goes precipitation.
D, acid adding precipitation: extract in above-mentioned clarification the acid solution that adds 0.3-2mol/L in solution, noDisconnected stirring, until pH is 1.0-4.5, room temperature is placed until precipitation is separated out completely; Wherein, this acidProperty solution be hydrochloric acid, sulfuric acid or phosphoric acid solution, this hydrochloric acid, sulfuric acid or phosphoric acid be all analyze pure.
E, flushing precipitation: collecting precipitation, uses distilled water flushing precipitation 2 times, each use amount of distilled waterThe ratio that adds 2ml distilled water in 1g precipitation is added;
F, drying precipitated: by-21 DEG C of pre-freeze 10-24h that are deposited in after rinsing, under vacuum condition, in freezingOn drying machine, carry out freeze drying, until product moisture content is lower than 1%, products obtained therefrom is dihydroartemisinineProduct.
Tool of the present invention has the following advantages: the present invention, taking qinghaosu production waste as raw material, recycles;Set up first the method that separates dihydroartemisinic acid from qinghaosu production waste, this method adopts ultrasonic wave auxiliaryHelp extraction method, effectively improve extraction efficiency and the rate of recovery; And adopt freeze-drying, efficiently solve traditionThe problem of the dihydroartemisinic acid product degraded that drying means causes; Product purity reaches more than 72%, and the rate of recovery is high,Reach more than 90%; Cycle is short, cost is low, and output is large, easily realizes industrialization and produces.
Brief description of the drawings
Fig. 1 is the flow chart of the inventive method.
Fig. 2 is that dihydroartemisinic acid product content is analyzed gas chromatogram.
Detailed description of the invention:
Below, the present invention will be further described with embodiment, but the present invention is not limited to theseAny of embodiment or similar example.
Embodiment 1
Get qinghaosu and produce waste liquid 20L, 33 DEG C of Vacuum Concentration to organic solvents volatilize, and add 450mL methyl alcohol,40 DEG C of Vacuum Concentration to solution all volatilize, and take residue, heavy 2.3Kg; Add 11.5L quality volume denseDegree is 0.2% sodium hydroxide solution, 80 watts of ultrasonic extractions 2 times, and ultrasonic temperature is 50 DEG C, each 60min,Merge No. 2 times extract, the centrifugal 10min of 3000rpm under room temperature, goes precipitation, collects supernatant, must clarify and carryGet solution, extract in clarification the hydrochloric acid solution that adds 1mol/L in solution, and constantly stir, until pH value of solutionValue is 4.5, and room temperature is placed until precipitation is separated out completely, removes supernatant, collecting precipitation, 150mL distillationWater rinses precipitation 2 times, being deposited in after flushing-21 DEG C pre-freeze 10h, and vacuum freeze drying, until product waterDivide content lower than 1%, obtain dihydroartemisinine product, weight is 62.53g.
Product detects and adopts vapor detection method (method bibliography [TianNetal.SimultaneousisolationofartemisininanditsprecursorsfromArtemisiaannuaL.byPreparativeRP-HPLC.BiomedChromatogr.2012,26 (6): 708-13.]), concrete asUnder: take 10mg product, be dissolved in 50mL acetonitrile, air inlet chromatography detects. Chromatographic condition: FIDDetector, HP-5.0 fused-silica capillary column (30m × 0.32mm × 0.25 μ m), high pure nitrogen (99.999%)For carrier gas, flow velocity 3mL/min, high pure nitrogen 40mL/min tail blows, 235 DEG C of injector temperatures, detector285 DEG C of temperature, split ratio 1:1, sample size 1 μ L, external standard method is quantitative. Post heating schedule: initial temperature180 DEG C, rise to after 220 DEG C with 6 DEG C/min, keep 3min, rise to 280 DEG C with 30 DEG C/min, keep10min. Testing result shows as shown in Figure 2, and dihydroartemisinic acid content is 81.17%.
Embodiment 2
Get qinghaosu and produce useless cream 5kg, add 410mL absolute ethyl alcohol, 40 DEG C of Vacuum Concentration to solvents are all wavedDry, take residue, heavy 3.7Kg; Add the sodium bicarbonate solution that 11.1L mass body volume concentrations is 0.6%,90 watts of ultrasonic extractions 2 times, each 50min, ultrasonic temperature is 45 DEG C, merges No. 2 times extract, under room temperatureThe centrifugal 12min of 3000rpm, goes precipitation, collects supernatant, must clarify and extract solution; Extract solution in clarificationIn add the sulfuric acid solution of 0.5mol/L, and constantly stir, until pH is 3.2, room temperature is placed straightSeparate out completely to precipitation, remove supernatant, collecting precipitation, 190mL distilled water flushing precipitation 2 times, after rinsingBe deposited in-21 DEG C of pre-freeze 15h, vacuum freeze drying, until product moisture content is lower than 1%, obtains dihydroQinghaosu product, the heavy 85.1g of product, shows two through gas chromatographic detection (method is identical with embodiment 1)Hydrogen Arteannuic acid content is 73.61%.
Embodiment 3
Get qinghaosu and produce useless cream 4kg, add 350mL methyl alcohol, 33 DEG C of Vacuum Concentration to solvents all volatilize,Take residue, heavy 2.9Kg; Add the sodium dihydrogen phosphate that 11.6L mass body volume concentrations is 0.5%, 100Watt ultrasonic extraction 2 times, each 45min, ultrasonic temperature is 40 DEG C, merges No. 2 times extract, 3000rpm under room temperatureCentrifugal 15min, goes precipitation, collects supernatant, obtains clarification extract, extracts in solution and adds 2mol/L in clarificationPhosphoric acid solution, and constantly stir, until pH is 1.0, room temperature place until precipitation separate out completely,Remove supernatant, collecting precipitation, 150mL distilled water flushing precipitation 2 times, by rinse be deposited in-21 DEG C pre-Freeze 24h, vacuum freeze drying, until product moisture content, lower than 1%, obtains dihydroartemisinine product, producesThe heavy 72.5g of product, shows through gas chromatographic detection (method is identical with embodiment 1), dihydroartemisinic acid content is 78.57％。
Embodiment 4
Get qinghaosu and produce waste liquid 10L, 40 DEG C of Vacuum Concentration to organic solvents volatilize, and add the anhydrous second of 220mLAlcohol, 33 DEG C of Vacuum Concentration to solution all volatilize, and take residue, heavy 1.5Kg; Add 6.0L quality volumeConcentration is 0.3% sodium radio-phosphate,P-32 solution, 95 watts of ultrasonic extractions 2 times, and each 55min, ultrasonic temperature is 30 DEG C,Merge extract, the centrifugal 13min of 3000rpm under room temperature, goes precipitation, collects supernatant, obtains clarification extract,Extract in clarification the sulfuric acid solution that adds 0.3mol/L in solution, and constantly stir, until pH is3.0, room temperature is placed until precipitation is separated out completely, removes supernatant, collecting precipitation, 90mL distilled water flushing precipitation2 times, by-21 DEG C of pre-freeze 20h that are deposited in after rinsing, vacuum freeze drying, until product moisture content is lowIn 1%, obtain dihydroartemisinine product, the heavy 40.5g of product, through gas chromatographic detection (method and embodiment 1Identical) show, dihydroartemisinic acid content is 75.13%.
Embodiment 5
Get qinghaosu and produce useless cream 8kg, add 700mL methyl alcohol, 35 DEG C of Vacuum Concentration to solvents all volatilize,Take residue, heavy 5.7Kg; Add the disodium phosphate soln that 20.8L mass body volume concentrations is 0.4%, 115Watt ultrasonic extraction 2 times, each 40min, ultrasonic temperature is 50 DEG C, merges No. 2 times extract, vacuum filtration,Go precipitation, collect clarification filtration liquid, extract in clarification the sulfuric acid solution that adds 1.2mol/L in solution, noDisconnected stirring, until pH is 4.5, room temperature is placed until precipitation is separated out completely, removes supernatant, collectsPrecipitation, 300mL distilled water flushing precipitation 2 times, will rinse postprecipitation in-21 DEG C of pre-freeze 10h, vacuum refrigerationDry, until product moisture content, lower than 1%, obtains dihydroartemisinine product, the heavy 143.2g of product, through gasPhase chromatogram detects (method is identical with embodiment 1) and shows, dihydroartemisinic acid content is 76.33%.
Embodiment 6
Get qinghaosu and produce useless cream 2kg, add 175mL absolute ethyl alcohol, 38 DEG C of Vacuum Concentration to solvents are all wavedDry, take residue, heavy 1.5Kg; Add the sodium carbonate liquor that 7.5L mass body volume concentrations is 0.3%, 85 wattsUltrasonic extraction 2 times, each 50min, ultrasonic temperature is 40 DEG C, merges No. 2 times extract, 3000rpm under room temperatureCentrifugal 10min, goes precipitation, collects supernatant, must clarify and extract solution, extracts in solution and adds in clarificationThe hydrochloric acid of 1.7mol/L, and constantly stir, until pH is 2.5, room temperature is placed until precipitation is completeSeparate out, remove supernatant, collecting precipitation, 300mL distilled water flushing precipitation 2 times, will be deposited in-21 DEG C after rinsingPre-freeze 20h, vacuum freeze drying, until product moisture content, lower than 1%, obtains dihydroartemisinine product,The heavy 36.1g of product, shows dihydroartemisinic acid content through gas chromatographic detection (method is identical with embodiment 1)Be 80.15%.
Claims (9)
1. alkali extraction and acid precipitation separates a dihydroartemisinic acid in qinghaosu production waste, it is characterized in that the partyMethod comprises the steps:
A, taking qinghaosu production waste as raw material, under methyl alcohol or absolute ethyl alcohol effect, Vacuum Concentration is useless to producingResidual solvent in material volatilizes, and obtains concentrate;
B, the ultrasonic extraction of alkali lye: taking the alkaline solution of 0.2%-0.6% mass body volume concentrations as extractant, by 3-5gConcentrate adds the ratio of 1ml alkaline solution and carries out ultrasonic extraction 2 times, and ultrasonic power 80-115 watt, when ultrasonicBetween 40-60min, ultrasonic temperature is 30-50 DEG C;
C, go precipitation: ultrasonic extraction is complete, merges secondary raffinate, the room temperature precipitation of going down, collection supernatant,Obtain the extraction solution of clarification;
D, acid adding precipitation: extract in above-mentioned clarification the acid solution that adds 0.3-2mol/L in solution, noDisconnected stirring, until pH is 1.0-4.5, room temperature is placed until precipitation is separated out completely;
E, flushing precipitation: collecting precipitation, uses distilled water flushing precipitation 2 times, each use amount of distilled waterThe ratio that adds 2ml distilled water in 1g precipitation is added;
F, drying precipitated: by-21 DEG C of pre-freeze 10-24h that are deposited in after rinsing, vacuum freeze drying, untilProduct moisture content is lower than 1%.
2. alkali extraction and acid precipitation as claimed in claim 1 separates dihydroartemisinic acid in qinghaosu production waste, itsBe characterised in that, the qinghaosu production waste in described A step refers to qinghaosu production waste liquid or useless cream.
3. alkali extraction and acid precipitation as claimed in claim 2 separates dihydroartemisinic acid in qinghaosu production waste, itsBe characterised in that, it is in 33-40 DEG C that described qinghaosu is produced volatilizing of residual solvent in waste liquid, and Vacuum Concentration is producedWaste liquid to organic solvent all volatilizes, then adds isopyknic methyl alcohol or absolute ethyl alcohol, at 33-40 DEG C, continuesVacuum Concentration until solution all volatilize.
4. alkali extraction and acid precipitation as claimed in claim 2 separates dihydroartemisinic acid in qinghaosu production waste, itsBe characterised in that, it is to add equal-volume in producing useless cream that described qinghaosu is produced volatilizing of residual solvent in useless creamMethyl alcohol or absolute ethyl alcohol, at 33-40 DEG C, Vacuum Concentration to solution all volatilizes.
5. alkali extraction and acid precipitation as claimed in claim 1 separates dihydroartemisinic acid in qinghaosu production waste, itsBe characterised in that, the alkaline solution in described step B is NaOH, sodium carbonate, sodium acid carbonate, di(2-ethylhexyl)phosphateHydrogen sodium or disodium phosphate soln, wherein, NaOH, sodium carbonate, sodium acid carbonate, sodium dihydrogen phosphate andIt is pure that disodium phosphate soln is all analysis.
6. alkali extraction and acid precipitation as claimed in claim 1 separates dihydroartemisinic acid in qinghaosu production waste, itsBe characterised in that, it is under room temperature that the room temperature in described step C goes down to precipitate, and adopts centrifugal or mistake elimination precipitation.
7. alkali extraction and acid precipitation as claimed in claim 6 separates dihydroartemisinic acid in qinghaosu production waste, itsBe characterised in that, described centrifugal go precipitation be with the centrifugal 10-15min of 3000rpm/min, go precipitation.
8. alkali extraction and acid precipitation as claimed in claim 6 separates dihydroartemisinic acid in qinghaosu production waste, itsBe characterised in that, the described elimination precipitation of crossing is that vacuum filtration goes precipitation.
9. alkali extraction and acid precipitation as claimed in claim 1 separates dihydroartemisinic acid in qinghaosu production waste, itsBe characterised in that, the acid solution in described step D is hydrochloric acid, sulfuric acid or phosphoric acid solution, wherein, hydrochloric acid,It is pure that sulfuric acid or phosphoric acid are all analysis.
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| CN110229059A (en) * | 2019-05-31 | 2019-09-13 | 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 |
| CN110143867A (en) * | 2019-05-31 | 2019-08-20 | 湖南农业大学 | A kind of equipment for extracting dihydroartemisinic acid from qinghaosu production waste oil |
| CN110623002A (en) * | 2019-09-18 | 2019-12-31 | 禹州市天源生物科技有限公司 | Preparation method of sweet wormwood wax oil insect repellent |
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