CN104262137A - Separation of sihydroartemisinic acid from artemisinin production waste by means of alkali dissolution and acid deposition - Google Patents
Separation of sihydroartemisinic acid from artemisinin production waste by means of alkali dissolution and acid deposition Download PDFInfo
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- CN104262137A CN104262137A CN201410486319.XA CN201410486319A CN104262137A CN 104262137 A CN104262137 A CN 104262137A CN 201410486319 A CN201410486319 A CN 201410486319A CN 104262137 A CN104262137 A CN 104262137A
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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
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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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- 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
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
Abstract
The invention discloses separation of sihydroartemisinic acid from artemisinin production waste by means of alkali dissolution and acid deposition. The method comprises the following steps of: concentrating in vacuum to volatilize residual solvents in production waste liquid or waste paste by using the artemisinin production waste liquid or the waste paste as raw materials; ultrasonically extracting by using alkali solution; mixing extracting solution with one another and removing sediments to obtain supernate; adding acid solution into the supernate; collecting sediments; washing the sediments by using clean distilled water; freeze-drying to obtain a dry sihydroartemisinic product. A method for separating sihydroartemisinic from the artemisinin production waste is established at first, and then an ultrasonic-assisted extracting method is adopted, so that the extraction efficiency and the recovery rate are effectively improved; by utilizing a freeze-drying method, the problem of degradation of the sihydroartemisinic acid product caused in the traditional drying method is effectively solved; the purity of the product is more than 72 percent, and the recovery rate is more than 90 percent; moreover, the production capacity is high, and the industrialized production is easily realized.
Description
Technical field
The present invention relates to a kind of preparation method of dihydroartemisinic acid, be specifically related to a kind of method adopting alkali extraction and acid precipitation to be separated dihydroartemisinic acid from Artemisinin processing waste.
Background technology
Artemisinin be China find first by the natural drug of internationally recognized and some independent intellectual property rights, Ye Shi China only by WHO approve by Western medicine research standard exploitation Chinese medicine.Artemisinin is in the market produced by China, plays importantly pushing effect to the development of China's Chinese Medicine Industry.From the World Health Organization, Artemisinin is regarded as the most safe and effective antimalarial agent at present, and as after treatment malaria first medication, the market requirement sharp increase of Artemisinin.Malaria is that Epidemic Scope is the widest, history is the longest, endanger maximum human parasite's transmissible disease, is one of disease kind that third world countries' M & M is the highest for a long time always.According to the report of the World Health Organization, the current whole world has 2,500,000,000 population lives at least in malaria district, and the number of malaria is died from more than 3,000,000 (wherein half is less than 5 years old children) in the annual whole world.Along with reasons such as global air temperature warming and environmental disruption aggravations, the sickness rate of malaria is in rising trend in recent years.WHO infers according to the demand of anti-malaria medicaments, and the annual sales volume of artemisine medicine is 1,500,000,000 dollars.But because artemislnin content is low, cause that Artemisinin production cost is high, market value is high, most of malaria patients unable purchase artemisine medicine at all of the developing countries such as Africa, South East Asia, the Middle East, applies be very limited so causes Artemisinin in anti-malarial.Therefore China's Artemisinin industry is also had a strong impact on, and the market value of Artemisinin falls to less than 2000 yuan from per kilogram 7000 yuan, and Artemisinin enterprise even loses in profitless space, and many Artemisinin manufacturers force and stop production or change the line of production.Meanwhile, especially African southern country of developing country has been absorbed in the predicament of antimalarial agent critical shortage.
Therefore, reducing production cost is the core place expanded Artemisinin market, improve product competitiveness.The research of low cost production Artemisinin is subject to domestic and international common concern.Because of in Herba Artemisiae annuae, the content of dihydroartemisinic acid is about 6 times of Artemisinin, if dihydroartemisinic acid is converted into Artemisinin completely, the content of Artemisinin is by raising about 6 times, and Artemisinin production cost will obtain breakthrough reduction.At present, the method that dihydroartemisinic acid transforms Artemisinin achieves impressive progress, Seeberger and L é vesque uses Vapourtec to flow synthesizer as building-up reactions platform, (dihydro) arteannuinic acid vitro conversion is obtained Artemisinin by the such photochemically reactive mode of additional uv irradiating, and this achievement in research is delivered on the internal authority magazine " Angewandte Chemie " of 2012.After (dihydro) arteannuinic acid vitro conversion makes a breakthrough, the mass-producing of (dihydro) arteannuinic acid has been prepared into the key of low cost production Artemisinin.Univ California-Berkeley Jay Keasling teaches and the artemisinin synthesis enzyme (ADS) and novel cytochrome p 450 monooxygenase gene (CYP71AV1) that derive from high sweet wormwood are implanted yeast by his research group, and yeast can be transformed into arteannuinic acid the intermediate compound produced in metabolism.The mevalonate pathway that they utilize yeast natural, this approach produces acetyl-CoA by sugar metabolism under normal circumstances and synthesizes sterol; And in pathways metabolism synthesized by them, mevalonate pathway is used to produce intermediate farnesylpyrophosphate (FPP) in a large number, and next farnesylpyrophosphate can be produced arteannuinic acid by ADS and the CYP71AV1 catalysis expressed in yeast.The difficulty of this work is from the assembling of yeast, sweet wormwood several genes and pathways metabolism thereof and precision control.This achievement in research of Keasling professor was also delivered in world authority's magazine " NATURE " in 2006.2010, Wageningen university Harro teach and research team adopt transgene tobacco (
nicotiana benthamiana) synthesize precursor arteannuinic acid.But, although the method for above-mentioned allos synthesis arteannuinic acid obtains interim progress, because cost height so far not yet can industrialization development.In the production process of Artemisinin, dihydroartemisinic acid is also extracted simultaneously from plant materials, but in the further separation and purification process of Artemisinin, dihydroartemisinic acid is left on to be produced in waste liquid, is not used again, causes a large amount of wastes of resource.Therefore, studying the method being separated dihydroartemisinic acid from Artemisinin production waste liquid has very important meaning to making full use of Herba Artemisiae annuae resource, improving added value of product and reducing Artemisinin production cost, there is no pertinent literature report at present.
Summary of the invention:
Technical problem to be solved by this invention is: for above-mentioned the deficiencies in the prior art, a kind of alkali extraction and acid precipitation is provided to be separated dihydroartemisinic acid from Artemisinin processing waste, this method gets Artemisinin to produce waste liquid or useless cream, volatilizes residual solvent, first use basic solution supersound extraction, united extraction liquid, go precipitation, in extracting solution, add acidic solution, collecting precipitation, by clean distilled water flushing precipitation, lyophilize obtains dry dihydroartemisinic 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 is separated dihydroartemisinic acid in Artemisinin processing waste, and the method comprises the steps, in conjunction with see Fig. 1:
A, with Artemisinin processing waste for raw material, vacuum concentration volatilizes to the residual solvent in processing waste, obtains enriched material; Wherein, above-mentioned Artemisinin processing waste refers to that Artemisinin produces waste liquid or useless cream; It is the method recycling design adopting vacuum concentration that described Artemisinin produces volatilizing of residual solvent in waste liquid, thickening temperature is 33-40 DEG C, vacuum concentration is produced waste liquid and is all volatilized to organic solvent, add isopyknic methyl alcohol or dehydrated alcohol again, at 33-40 DEG C, continue vacuum concentration until solution all volatilizes; It is add isopyknic methyl alcohol or dehydrated alcohol in the useless cream of production that described Artemisinin produces volatilizing of residual solvent in useless cream, and at 33-40 DEG C, vacuum concentration all volatilizes to solution.
B, alkali lye supersound extraction: with the basic solution of 0.2%-0.6% mass body volume concentrations for extraction agent, the ratio adding 1ml basic solution in 3-5g enriched material carries out supersound extraction 2 times, ultrasonic power 80-115 watt, ultrasonic time 40-60min, and ultrasonic temperature is 30-50 DEG C; Wherein, described basic solution is sodium hydroxide, sodium carbonate, sodium bicarbonate, SODIUM PHOSPHATE, MONOBASIC, SODIUM PHOSPHATE, MONOBASIC or disodium phosphate soln, and this sodium hydroxide, sodium carbonate, sodium bicarbonate, SODIUM PHOSPHATE, MONOBASIC, SODIUM PHOSPHATE, MONOBASIC and disodium phosphate soln are all analytical pure.
C, go precipitation: supersound extraction is complete, merge secondary raffinate, adopt under room temperature condition centrifugal or cross elimination precipitation, collect supernatant liquor, obtain clarify extraction solution; Wherein, centrifugal precipitation of going is with the centrifugal 10-15min of 3000rpm/min, goes precipitation; Crossing elimination precipitation is that vacuum filtration goes precipitation.
D, add Acid precipitation: extract the acidic solution adding 0.3-2mol/L in solution in above-mentioned clarification, and constantly stir, until solution ph is 1.0-4.5, room temperature is placed until precipitation is separated out completely; Wherein, this acidic solution is hydrochloric acid, sulfuric acid or phosphoric acid solution, and this hydrochloric acid, sulfuric acid or phosphoric acid are all analytical pure.
E, flushing precipitation: collecting precipitation, use distilled water flushing to precipitate 2 times, and the ratio that each usage quantity of distilled water adds 2ml distilled water in 1g precipitation is added;
F, drying precipitated: will be deposited in-21 DEG C of pre-freeze 10-24h after rinsing, under vacuum condition, on freeze drier, carry out lyophilize, until product moisture content is lower than 1%, products obtained therefrom is Dihydroartemisinin product.
Tool of the present invention has the following advantages: the present invention, recycles for raw material with Artemisinin processing waste; Establish the method being separated dihydroartemisinic acid from Artemisinin processing waste first, present method adopts ultrasonic-assisted extraction method, effectively improves extraction efficiency and the rate of recovery; And adopt freeze-drying, efficiently solve the problem of the dihydroartemisinic acid product degraded that conventional drying process causes; Product purity reaches more than 72%, and the rate of recovery is high, reaches more than 90%; Cycle is short, cost is low, and turnout is large, easily realizes industrialization and produces.
Accompanying drawing explanation
Fig. 1 is the schema of the inventive method.
Fig. 2 is that dihydroartemisinic acid product content analyzes gas chromatogram.
Embodiment:
Below, the present invention will be further described with embodiment, but the present invention is not limited to any one or similar example of these embodiments.
Embodiment 1
Get Artemisinin and produce waste liquid 20L, 33 DEG C of vacuum concentration volatilize to organic solvent, add 450mL methyl alcohol, and 40 DEG C of vacuum concentration all volatilize to solution, take residue, heavy 2.3Kg, adding 11.5L mass body volume concentrations is the sodium hydroxide solution of 0.2%, 80 watts of supersound extraction 2 times, ultrasonic temperature is 50 DEG C, each 60min, merge No. 2 extracting solutions, the centrifugal 10min of 3000rpm under room temperature, go precipitation, collect supernatant liquor, extraction solution must be clarified, the hydrochloric acid soln adding 1mol/L in solution is extracted in clarification, and constantly stir, until solution ph is 4.5, room temperature is placed until precipitation is separated out completely, remove supernatant liquor, collecting precipitation, 150 mL distilled water flushings precipitate 2 times,-21 DEG C of pre-freeze 10h are deposited in after flushing, vacuum lyophilization, until product moisture content is lower than 1%, obtain Dihydroartemisinin product, weight is 62.53g.
Product checking adopts vapor detection method (method reference [Tian N et al. Simultaneous isolation of artemisinin and its precursors from Artemisia annua L. by preparative RP-HPLC. Biomed Chromatogr. 2012,26 (6): 708-13.]), specific as follows: to take 10 mg products, be dissolved in 50mL acetonitrile, air inlet chromatography detects.Chromatographic condition: fid detector, HP-5.0 fused-silica capillary column (30m × 0.32mm × 0.25 μm), high pure nitrogen (99.999%) is carrier gas, flow velocity 3mL/min, high pure nitrogen 40mL/min tail blows, injector temperature 235 DEG C, detector temperature 285 DEG C, splitting ratio 1:1, sample size 1 μ L, quantified by external standard method.Post heating schedule: initial temperature 180 DEG C, after rising to 220 DEG C, keeps 3 min, rise to 280 DEG C with 30 DEG C/min with 6 DEG C/min, keeps 10min.Detected result shows as shown in Figure 2, and dihydroartemisinic acid content is 81.17%.
Embodiment 2
Get Artemisinin and produce useless cream 5kg, add 410mL dehydrated alcohol, 40 DEG C of vacuum concentration all volatilize to solvent, take residue, heavy 3.7Kg; Adding 11.1L mass body volume concentrations is the sodium hydrogen carbonate solution of 0.6%, 90 watts of supersound extraction 2 times, each 50min, and ultrasonic temperature is 45 DEG C, merges No. 2 extracting solutions, the centrifugal 12min of 3000rpm under room temperature, goes precipitation, collects supernatant liquor, must clarify extraction solution; Extract the sulphuric acid soln adding 0.5mol/L in solution in clarification, and constantly stir, until solution ph is 3.2, room temperature is placed until precipitation is separated out completely, removes supernatant, collecting precipitation, 190mL distilled water flushing precipitates 2 times, by rinse after be deposited in-21 DEG C of pre-freeze 15h, vacuum lyophilization, until product moisture content is lower than 1%, obtain Dihydroartemisinin product, the heavy 85.1g of product, show through gas chromatographic detection (method is identical with embodiment 1), dihydroartemisinic acid content is 73.61%.
Embodiment 3
Get Artemisinin and produce useless cream 4kg, add 350 mL methyl alcohol, 33 DEG C of vacuum concentration all volatilize to solvent, take residue, heavy 2.9Kg, adding 11.6L mass body volume concentrations is the sodium dihydrogen phosphate of 0.5%, 100 watts of supersound extraction 2 times, each 45min, ultrasonic temperature is 40 DEG C, merge No. 2 extracting solutions, the centrifugal 15min of 3000rpm under room temperature, go precipitation, collect supernatant liquor, extracting solution must be clarified, the phosphoric acid solution adding 2mol/L in solution is extracted in clarification, and constantly stir, until solution ph is 1.0, room temperature is placed until precipitation is separated out completely, remove supernatant, collecting precipitation, 150mL distilled water flushing precipitates 2 times, by rinse be deposited in-21 DEG C of pre-freeze 24h, vacuum lyophilization, until product moisture content is lower than 1%, obtain Dihydroartemisinin product, the heavy 72.5g of product, show through gas chromatographic detection (method is identical with embodiment 1), dihydroartemisinic acid content is 78.57%.
Embodiment 4
Get Artemisinin and produce waste liquid 10L, 40 DEG C of vacuum concentration volatilize to organic solvent, add 220mL dehydrated alcohol, and 33 DEG C of vacuum concentration all volatilize to solution, take residue, heavy 1.5Kg, adding 6.0L mass body volume concentrations is the sodium radio-phosphate,P-32 solution of 0.3%, 95 watts of supersound extraction 2 times, each 55min, ultrasonic temperature is 30 DEG C, united extraction liquid, the centrifugal 13min of 3000rpm under room temperature, go precipitation, collect supernatant liquor, extracting solution must be clarified, the sulphuric acid soln adding 0.3mol/L in solution is extracted in clarification, and constantly stir, until solution ph is 3.0, room temperature is placed until precipitation is separated out completely, remove supernatant, collecting precipitation, 90mL distilled water flushing precipitates 2 times, by rinse after be deposited in-21 DEG C of pre-freeze 20h, vacuum lyophilization, until product moisture content is lower than 1%, obtain Dihydroartemisinin product, the heavy 40.5g of product, show through gas chromatographic detection (method is identical with embodiment 1), dihydroartemisinic acid content is 75.13%.
Embodiment 5
Get Artemisinin and produce useless cream 8kg, add 700mL methyl alcohol, 35 DEG C of vacuum concentration all volatilize to solvent, take residue, heavy 5.7Kg, adding 20.8L mass body volume concentrations is the disodium phosphate soln of 0.4%, 115 watts of supersound extraction 2 times, each 40min, ultrasonic temperature is 50 DEG C, merge No. 2 extracting solutions, vacuum filtration, go precipitation, collect clarified filtrate, the sulphuric acid soln adding 1.2mol/L in solution is extracted in clarification, and constantly stir, until solution ph is 4.5, room temperature is placed until precipitation is separated out completely, remove supernatant, collecting precipitation, 300mL distilled water flushing precipitates 2 times, postprecipitation will be rinsed in-21 DEG C of pre-freeze 10h, vacuum lyophilization, until product moisture content is lower than 1%, obtain Dihydroartemisinin product, the heavy 143.2g of product, show through gas chromatographic detection (method is identical with embodiment 1), dihydroartemisinic acid content is 76.33%.
Embodiment 6
Get Artemisinin and produce useless cream 2kg, add 175mL dehydrated alcohol, 38 DEG C of vacuum concentration all volatilize to solvent, take residue, heavy 1.5Kg, adding 7.5L mass body volume concentrations is the sodium carbonate solution of 0.3%, 85 watts of supersound extraction 2 times, each 50 min, ultrasonic temperature is 40 DEG C, merge No. 2 extracting solutions, the centrifugal 10min of 3000rpm under room temperature, go precipitation, collect supernatant liquor, extraction solution must be clarified, the hydrochloric acid adding 1.7mol/L in solution is extracted in clarification, and constantly stir, until solution ph is 2.5, room temperature is placed until precipitation is separated out completely, remove supernatant, collecting precipitation, 300mL distilled water flushing precipitates 2 times, by rinse after be deposited in-21 DEG C of pre-freeze 20h, vacuum lyophilization, until product moisture content is lower than 1%, obtain Dihydroartemisinin product, the heavy 36.1g of product, show through gas chromatographic detection (method is identical with embodiment 1), dihydroartemisinic acid content is 80.15%.
Claims (9)
1. alkali extraction and acid precipitation is separated a dihydroartemisinic acid in Artemisinin processing waste, and it is characterized in that, the method comprises the steps:
A, with Artemisinin processing waste for raw material, vacuum concentration volatilizes to the residual solvent in processing waste, obtains enriched material;
B, alkali lye supersound extraction: with the basic solution of 0.2%-0.6% mass body volume concentrations for extraction agent, the ratio adding 1ml basic solution in 3-5g enriched material carries out supersound extraction 2 times, ultrasonic power 80-115 watt, ultrasonic time 40-60min, and ultrasonic temperature is 30-50 DEG C;
C, go precipitation: supersound extraction is complete, merges secondary raffinate, and room temperature is gone down precipitation, collects supernatant liquor, obtains the extraction solution of clarification;
D, add Acid precipitation: extract the acidic solution adding 0.3-2mol/L in solution in above-mentioned clarification, and constantly stir, until solution ph is 1.0-4.5, room temperature is placed until precipitation is separated out completely;
E, flushing precipitation: collecting precipitation, use distilled water flushing to precipitate 2 times, and the ratio that each usage quantity of distilled water adds 2ml distilled water in 1g precipitation is added;
F, drying precipitated :-21 DEG C of pre-freeze 10-24h will to be deposited in, vacuum lyophilization, until product moisture content is lower than 1% after rinsing.
2. alkali extraction and acid precipitation as claimed in claim 1 is separated dihydroartemisinic acid in Artemisinin processing waste, it is characterized in that, the Artemisinin processing waste in described step A refers to that Artemisinin produces waste liquid or useless cream.
3. alkali extraction and acid precipitation as claimed in claim 2 is separated dihydroartemisinic acid in Artemisinin processing waste, it is characterized in that, it is in 33-40 DEG C that described Artemisinin produces volatilizing of residual solvent in waste liquid, vacuum concentration is produced waste liquid and is all volatilized to organic solvent, add isopyknic methyl alcohol or dehydrated alcohol again, at 33-40 DEG C, continue vacuum concentration until solution all volatilizes.
4. alkali extraction and acid precipitation as claimed in claim 2 is separated dihydroartemisinic acid in Artemisinin processing waste, it is characterized in that, it is add isopyknic methyl alcohol or dehydrated alcohol in the useless cream of production that described Artemisinin produces volatilizing of residual solvent in useless cream, at 33-40 DEG C, vacuum concentration all volatilizes to solution.
5. alkali extraction and acid precipitation as claimed in claim 1 is separated dihydroartemisinic acid in Artemisinin processing waste, it is characterized in that, basic solution in described step B is sodium hydroxide, sodium carbonate, sodium bicarbonate, SODIUM PHOSPHATE, MONOBASIC, SODIUM PHOSPHATE, MONOBASIC or disodium phosphate soln, wherein, sodium hydroxide, sodium carbonate, sodium bicarbonate, SODIUM PHOSPHATE, MONOBASIC, SODIUM PHOSPHATE, MONOBASIC and disodium phosphate soln are all analytical pure.
6. alkali extraction and acid precipitation as claimed in claim 1 is separated dihydroartemisinic acid in Artemisinin processing waste, it is characterized in that, the precipitation of going down of the room temperature in described step C is under room temperature, adopts centrifugal or crosses elimination precipitation.
7. alkali extraction and acid precipitation as claimed in claim 6 is separated dihydroartemisinic acid in Artemisinin processing waste, and it is characterized in that, described centrifugal precipitation of going is with the centrifugal 10-15min of 3000rpm/min, goes precipitation.
8. alkali extraction and acid precipitation as claimed in claim 6 is separated dihydroartemisinic acid in Artemisinin processing waste, it is characterized in that, described elimination precipitation of crossing is that vacuum filtration goes precipitation.
9. alkali extraction and acid precipitation as claimed in claim 1 is separated dihydroartemisinic acid in Artemisinin processing waste, and it is characterized in that, the acidic solution in described step D is hydrochloric acid, sulfuric acid or phosphoric acid solution, and wherein, hydrochloric acid, sulfuric acid or phosphoric acid are all analytical pure.
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| CN104987341A (en) * | 2015-06-29 | 2015-10-21 | 兰捷 | Method for extracting artemisinin from sweet wormwood |
| 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 |
| CN110563573A (en) * | 2019-05-31 | 2019-12-13 | 长沙艾康生物科技有限公司 | method for removing impurities in production process of high-purity dihydroartemisinic acid |
| 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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Cited By (4)
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| CN104987341A (en) * | 2015-06-29 | 2015-10-21 | 兰捷 | Method for extracting artemisinin from sweet wormwood |
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| CN110563573A (en) * | 2019-05-31 | 2019-12-13 | 长沙艾康生物科技有限公司 | method for removing impurities in production process of high-purity dihydroartemisinic acid |
| 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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