CN101053596A - Supercritical carbon dioxide method for extracting high purity rhubarb free anthraquinones - Google Patents
Supercritical carbon dioxide method for extracting high purity rhubarb free anthraquinones Download PDFInfo
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- CN101053596A CN101053596A CN 200710068891 CN200710068891A CN101053596A CN 101053596 A CN101053596 A CN 101053596A CN 200710068891 CN200710068891 CN 200710068891 CN 200710068891 A CN200710068891 A CN 200710068891A CN 101053596 A CN101053596 A CN 101053596A
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Abstract
The invention discloses a method for extracting highly purified rhubarb dissociated anthraquinone by a hypercritical CO2 extraction method, including leaching the material with organic solvent to get leaching liquid, hydrolyzing the combined anthraquinone, balancing out the superfluous acid with inorganic alkali or acid after hydrolytic reaction, getting hydrolytic leaching liquid; injecting the hydrolytic leaching liquid into the extraction vessel for a hypercritical CO2 extraction, entering to the separation vessel after the extraction; recycling separated CO2, collecting discharging rhubarb dissociated anthraquinone and organic solvent, steaming out the organic solvent decompressly, obtaining the rhubarb dissociated anthraquinone powder. The invention adopts the liquid feed to effectively control the material liquid acidity in the extraction vessel and prevent the equipment corrosion and potential safety problems; meanwhile, it does not need install and detach the extraction vessel by entrainer pump liquid feed so that the extraction is processed continuously and greatly saves the extraction time and improve the output in unit time.
Description
Technical field
The present invention relates to the supercritical carbon dioxide extraction field, especially adopt supercritical carbon dioxide fluid to extract Radix Et Rhizoma Rhei powder, obtain the method for high purity rhubarb free anthraquinones.
Background technology
Radix Et Rhizoma Rhei is the dry root and rhizome of polygonum rheum palmatum Rheum palmatum L., Rheum tanguticum Rheumtanguticum Maxim.ex Balf. or Rheum officinale Rheum officinale Baill., be one of the most widely used Chinese herbal medicine in China's Chinese medicine prescription, its main effective ingredient is anthraquinone analog compound and glucosides thereof such as emodin, chrysophanol, aloe-emodin, physcione and chrysophanic acid.These composition has a broad antifungal spectrum, antibacterial action is strong, and various bacteria and pathogenic fungus are had stronger antibacterial action.Wherein the antibacterial action with free aglycons such as chrysophanic acid, emodin, aloe-emodins is the strongest.
The general anthraquinone effective constituents that adopts in the solvent extraction extraction Radix Et Rhizoma Rhei.As in the Chinese invention patent 01134161.0 with Radix Et Rhizoma Rhei decoction piece by 1: the dense ethanol of 4-8 mixes, and reflux, extract, three times is made extractum, finally obtains purity and be the Radix Et Rhizoma Rhei anthraquinone product more than 50%; In the Chinese invention patent 00125405.7 Radix Et Rhizoma Rhei is ground into coarse powder, add 6-12 40-95% soak with ethanol 4-20h doubly, heating and refluxing extraction three times, return time is 0.5-2h, elimination medicinal residues, merge extractive liquid,, add the 0.5-50mL diluted acid by the 100g crude drug and add acid, at 35-80 ℃ of following concentrating under reduced pressure, get Radix Et Rhizoma Rhei anthraquinone extractum, wherein dissociated anthraquinone content＞50% at last; Neutralize with alkali after adopting acid hydrolysis among the Chinese invention patent 99114211.x, advance the anion macroporous resin then, eluent boils off the alcohol back and promptly gets Radix Et Rhizoma Rhei total free anthraquinones with acid hydrolysis.But it is big to adopt these class methods to have a machine solvent-oil ratio, and complex operation, production cost are higher relatively, and the not high shortcoming of the purity of Radix Et Rhizoma Rhei anthraquinone.
Adopt the Radix Et Rhizoma Rhei powder after the technology of supercritical carbon dioxide extraction is extracted acid hydrolysis among the last application for a patent for invention CN 200610001899.4 of the inventor first, obtained purity up to 98.5% dissociated anthraquinone product.This technology at first adopts 2-6molL
-1Concentrated acid hydrolysis combined anthraquinone, with in the calcium carbonate powder and excessive acid, the anthraquinones in the extraction Radix Et Rhizoma Rhei powder in the supercritical carbon dioxide extraction still then.The shortcoming of this technology is when the excessive acid solution of neutralization, calcium carbonate and Rhubarb are difficult to mixing and cause Rhubarb local acid too high, when High Temperature High Pressure, can cause heavy corrosion and shorten life-span of supercritical fluid extraction equipment, and production is brought potential potential safety hazard the rustless steel extraction kettle.Chinese patent application 200610057160.5 also with Radix Et Rhizoma Rhei powder through hydrochloric acid solution handle the back with the ethanol infiltration after, put into the extraction of supercritical carbon dioxide extraction still to obtain dissociated anthraquinone, this technology hydrochloric acid directly enters extraction kettle without neutralization, and is more serious to the corrosion meeting of equipment.In addition, this type of extracting process extraction kettle of Rhubarb need being packed into, and supercritical extraction reactor finite volume are so make that single batch of extract yield is lower; And the non-cutting time of loading, unloading material is longer, has limited the industrialization of this technology.
Summary of the invention
It is simple to the invention provides a kind of technology, and operation saves time, the method for the supercritical carbon dioxide fluid continuous extraction free anthraquinones extracted from rheum that product yield and purity are high.
A kind of employing supercritical CO
2The method of extracting high purity rhubarb free anthraquinone comprises the steps:
(1) be the exsiccant raw material organic solvent soaking extraction of 40-200 purpose with granularity, obtain containing the leaching liquid of free anthraquinones extracted from rheum and combined anthraquinone (glucosides type), leaching temperature is 40～70 ℃, and raw materials quality and organic solvent volume ratio are 1: 8 (g: mL);
(2) leaching liquid in the collection step (1) adds mineral acid, hydrolysis combined anthraquinone wherein, hydrolysising condition is pH=1～3,50～80 ℃ of temperature, time 1～3h, with in inorganic base or the salt and excessive acid, transferring to pH value is 6-8, obtains the hydrolysis leaching liquid behind the hydrolysis;
(3) the hydrolysis leaching liquid is fed extraction kettle continuously and carry out supercritical carbon dioxide extraction, extraction enters separating still after finishing, extracting pressure 15～35MPa, and 35～60 ℃ of extraction temperature, hydrolysis leaching liquid feed flow rates is 20～100mLmin
-1
(4) regulate the temperature and pressure of separating still, isolate carbon dioxide and recycle, free anthraquinones extracted from rheum that is extracted out and organic solvent are discharged from the separating still bottom, separating pressure 4～6MPa, and temperature-15～0 ℃, the carbon dioxide average discharge is 0.2～1Lmin
-1
(5) collect the free anthraquinones extracted from rheum and the organic solvent of discharging in the separating still, remove organic solvent under reduced pressure, obtain the free anthraquinones extracted from rheum powder.
The free anthraquinones extracted from rheum powder purity that obtains is greater than 99%, and its yield is greater than 2.6%, can reach 92.5% corresponding to the total recovery of Radix Et Rhizoma Rhei anthraquinone.
Raw material described in the step (1) is the Chinese crude drug that contains emodin and analog thereof.
Described raw material can be Radix Et Rhizoma Rhei, as sorrel, Xining Radix Et Rhizoma Rhei, Rheum tanguticum or Rheum officinale etc.
Described raw material can also be Rhizoma Polygoni Cuspidati, Aloe, Radix Polygoni Multiflori or Semen Cassiae.
What every technological parameter of the inventive method was primarily aimed at is physics, the chemical property of extracting the object emodin, so the inventive method is equally applicable to the Chinese crude drug that other contain emodin and analog thereof.
Described organic solvent is one or more in methanol, ethanol, acetone or the water, preferred alcohol wherein, and purity of alcohol 99% above effect is better.
The percolation bed that has chuck, leaching liquid flow velocity 0.5-3Lh are adopted in leaching described in the step (1)
-1
Mineral acid described in the step (2) is sulphuric acid, hydrochloric acid or phosphoric acid, and described inorganic base or salt are sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate or calcium carbonate.
Compare with the solvent extraction method of routine, it is simple that the present invention has technology, and operation saves time, product yield and purity advantages of higher; Compare with existing other supercritical extraction techniques, the present invention adopts the liquid charging, controls the acidity of material liquid in the extraction kettle effectively, has prevented equipment corrosion and potential safety hazard; Simultaneously, do not need the loading, unloading extraction kettle, make extraction process to carry out continuously, greatly saved the extraction time, improved yield of unit time, help large-scale industrial production by the charging of entrainer pump liquid.
Description of drawings
Fig. 1 supercritical carbon dioxide method for extracting device of the present invention flow chart is among the figure
1 carbon dioxide steel cylinder, 2 gas purifiers, 3 entrainer jars
4 carbon dioxide storage tanks, the 5 spinner flowmeter 6a plunger displacement pump that boosts
6b entrainer pump 7 blenders 8 extraction kettles
9 separating stills, 10 effusion meters, 11 valves
12 valves, 13 valves, 14 valves
The specific embodiment
Embodiment 1
Referring to accompanying drawing 1, during supercritical carbon dioxide fluid continuous extraction free anthraquinones extracted from rheum, at first material powder is leached acquisition Radix Et Rhizoma Rhei leaching liquid with organic solvent; With diluted acid the combined anthraquinone in the leaching liquid is hydrolyzed then, and neutralizes with alkali subsequently.Heating extraction kettle 8 and separating still 9 are opened the plunger displacement pump 6a that boosts simultaneously extraction kettle 8 are forced into setting pressure (closing separating still 9 early gates 11 this moment) to design temperature.To pour entrainer jar 3 into through acid hydrolysis, Radix Et Rhizoma Rhei leaching liquid that the alkali neutralisation treatment is good, 6b is continuously pumped into extraction kettle 8 with certain flow with it by the entrainer pump.Open separating still 9 early gates 11 this moment, the flow of control circulate carbon dioxide makes Radix Et Rhizoma Rhei anthraquinone and organic solvent continuously flow into separating still 9 with certain speed from extraction kettle 8.Can collect Radix Et Rhizoma Rhei anthraquinone and organic solvent by opening separating still 9 bottom valves 13, carbon dioxide then carries out cycling extraction through valve 14.Collect the water solublity waste liquid by opening extraction kettle 8 bottom valves 12.
According to above-mentioned technological process, get 80-100 order Radix Et Rhizoma Rhei crude drug powder 250 grams (total Radix Et Rhizoma Rhei anthraquinone 2.81g/100g Radix Et Rhizoma Rhei powder), add in the percolation bed of φ 4 * 80cm.Under 40 ℃, carry out the percolation leaching with methanol.Methanol usage 2000mL, flow velocity 0.9Lh
-1, approximately finish leaching behind the 2h, collect methanol leaching liquid 1750mL;
Adding 20mL concentrated hydrochloric acid in the methanol leaching liquid (36%, w/w), mixing, 60 ℃ of following hydrolysis 1.5 hours, the Radix Et Rhizoma Rhei combined anthraquinone was converted into free type fully after testing.Finish reaction, add 25 gram calcium carbonate powders in reactant liquor, transferring reacting liquid pH value is 6.5.
The extraction kettle temperature of regulating supercritical carbon dioxide extraction equipment is 60 ℃, and pressure is 30MPa, and the separating still temperature is-5 ℃, and pressure is 4.0MPa, with hydrolyzed solution with 20mLmin
-1Mean Speed pump into extraction kettle from the entrainer jar by the entrainer pump, regulating the average circular flow of carbon dioxide is 0.2Lmin
-1Extraction process discontinuous unlatching extraction kettle and separating still bottom valve finish extraction to collect the methanol solution (from separating still) of water solublity waste liquid (from extraction kettle) and free anthraquinones extracted from rheum behind about 1.5h.Collect the methanol solution product of 1680mL Radix Et Rhizoma Rhei anthraquinone altogether,, get free anthraquinones extracted from rheum powder 6.5g through vacuum rotary steam.Detecting its purity through HPLC is 98.5%, and wherein the relative amount of emodin, chrysophanol, aloe-emodin, physcione and chrysophanic acid is respectively: 24.2%, 38.1%, 8.5%, 19.1%, 10.1%.Corresponding Radix Et Rhizoma Rhei anthraquinone yield is 91.5%.
Embodiment 2
According to the technological process of embodiment 1, get 80-100 order Radix Et Rhizoma Rhei crude drug powder 250 grams (total Radix Et Rhizoma Rhei anthraquinone 2.81g/100g Radix Et Rhizoma Rhei powder), add in the percolation bed of φ 4 * 80cm.Under 60 ℃, carry out the percolation leaching with ethanol.Ethanol consumption 2000mL, flow velocity 1.2Lh
-1, approximately finish leaching behind the 1.67h, collect ethanol leaching liquid 1770mL;
Adding 20mL concentrated hydrochloric acid in the ethanol leaching liquid (36%, w/w), mixing, 70 ℃ of following hydrolysis 2 hours, the Radix Et Rhizoma Rhei combined anthraquinone was converted into free type fully after testing.Finish reaction, add 25 gram calcium carbonate powders in reactant liquor, transferring reacting liquid pH value is 6.6.
The extraction kettle temperature of regulating supercritical carbon dioxide extraction equipment is 50 ℃, and pressure is 25MPa, and the separating still temperature is-15 ℃, and pressure is 4.0MPa, with hydrolyzed solution with 30mLmin
-1Mean Speed pump into extraction kettle from the entrainer jar by the entrainer pump, regulating the average circular flow of carbon dioxide is 0.5lmin
-1Extraction process discontinuous unlatching extraction kettle and separating still bottom valve finish extraction to collect the alcoholic solution (from separating still) of water solublity waste liquid (from extraction kettle) and free anthraquinones extracted from rheum behind about 1h.Collect the methanol solution product of 1700mL Radix Et Rhizoma Rhei anthraquinone altogether,, get free anthraquinones extracted from rheum powder 6.6g through vacuum rotary steam.Detecting its purity through HPLC is 98.5%, and corresponding Radix Et Rhizoma Rhei anthraquinone yield is 92.5%.
Embodiment 3
According to the technological process of embodiment 1, get 80-100 order Radix Et Rhizoma Rhei crude drug powder 250 grams (total Radix Et Rhizoma Rhei anthraquinone 2.81g/100g Radix Et Rhizoma Rhei powder), add in the percolation bed of φ 4 * 80cm.Under 40 ℃, carry out the percolation leaching with ethanol.Ethanol consumption 2000mL, flow velocity 1.0Lh
-1, approximately finish leaching behind the 2h, collect ethanol leaching liquid 1800mL;
Adding 20mL concentrated hydrochloric acid in the ethanol leaching liquid (36%, w/w), mixing, 50 ℃ of following hydrolysis 2 hours, the Radix Et Rhizoma Rhei combined anthraquinone was converted into free type fully after testing.Finish reaction, add 25 gram calcium carbonate powders in reactant liquor, transferring reacting liquid pH value is 6.8.
The extraction kettle temperature of regulating supercritical carbon dioxide extraction equipment is 50 ℃, and pressure is 15MPa, and the separating still temperature is-15 ℃, and pressure is 4.0MPa, with hydrolyzed solution with 100mLmin
-1Mean Speed pump into extraction kettle from the entrainer jar by the entrainer pump, regulating the average circular flow of carbon dioxide is 1lmin
-1Extraction process discontinuous unlatching extraction kettle and separating still bottom valve finish extraction to collect the alcoholic solution (from separating still) of water solublity waste liquid (from extraction kettle) and free anthraquinones extracted from rheum behind about 0.5h.Collect the methanol solution product of 1680mL Radix Et Rhizoma Rhei anthraquinone altogether,, get free anthraquinones extracted from rheum powder 6.4g through vacuum rotary steam.Detecting its purity through HPLC is 98.7%, and corresponding Radix Et Rhizoma Rhei anthraquinone yield is 90.2%.
Claims (9)
1, a kind of employing supercritical CO
2The method of extracting high purity rhubarb free anthraquinone is characterized in that comprising the steps:
(1) be the exsiccant raw material organic solvent soaking extraction of 40-200 purpose with granularity, obtain containing the leaching liquid of free anthraquinones extracted from rheum and combined anthraquinone, leaching temperature is 40～70 ℃, and raw materials quality and organic solvent volume ratio are 1: 8;
(2) leaching liquid in the collection step (1) adds mineral acid, hydrolysis combined anthraquinone wherein, hydrolysising condition is pH=1～3,50～80 ℃ of temperature, time 1～3h, with in inorganic base or the salt and excessive acid, transferring to pH value is 6-8, obtains the hydrolysis leaching liquid behind the hydrolysis;
(3) the hydrolysis leaching liquid is fed extraction kettle continuously and carry out supercritical carbon dioxide extraction, extraction enters separating still after finishing, extracting pressure 15～35MPa, and 35～60 ℃ of extraction temperature, hydrolysis leaching liquid feed flow rates is 20～100mLmin
-1
(4) regulate the temperature and pressure of separating still, isolate carbon dioxide and recycle, free anthraquinones extracted from rheum that is extracted out and organic solvent are discharged from the separating still bottom, separating pressure 4～6MPa, and temperature-15～0 ℃, the carbon dioxide average discharge is 0.2～1Lmin
-1
(5) collect the free anthraquinones extracted from rheum and the organic solvent of discharging in the separating still, remove organic solvent under reduced pressure, obtain the free anthraquinones extracted from rheum powder.
2, the method for claim 1 is characterized in that: the raw material described in the step (1) is the Chinese crude drug that contains emodin and analog thereof.
3, method as claimed in claim 2 is characterized in that: described raw material is a Radix Et Rhizoma Rhei.
4, method as claimed in claim 2 is characterized in that: described raw material is Rhizoma Polygoni Cuspidati, Aloe, Radix Polygoni Multiflori or Semen Cassiae.
5, the method for claim 1 is characterized in that: described organic solvent is one or more in methanol, ethanol, acetone or the water.
6, method as claimed in claim 4 is characterized in that: described organic solvent is an ethanol.
7, the method for claim 1 is characterized in that: the percolation bed that has chuck, leaching liquid flow velocity 0.5-3Lh are adopted in the leaching described in the step (1)
-1
8, the method for claim 1 is characterized in that: the mineral acid described in the step (2) is sulphuric acid, hydrochloric acid or phosphoric acid.
9, the method for claim 1 is characterized in that: inorganic base described in the step (2) or salt are sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate or calcium carbonate.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101507760A (en) * | 2009-03-13 | 2009-08-19 | 四川省中医药科学院 | Medicine composite for treating kidney disease |
| CN102240327A (en) * | 2011-04-29 | 2011-11-16 | 栗进才 | Method for extracting total anthraquinone in rhubarb from traditional Chinese medicine rhubarb by supercritical fluid |
| CN104909999A (en) * | 2015-04-16 | 2015-09-16 | 聊城大学 | Method for separating and purifying anthraquinone compound and styrene acid from rhubarb extractive |
| CN105498275A (en) * | 2015-12-01 | 2016-04-20 | 赵金树 | Low-cost low-energy-consumption CO2 supercritical extraction device and process |
| CN105999761A (en) * | 2016-06-27 | 2016-10-12 | 广州纤维产品检测研究院 | Method for rapidly separating polycyclic aromatic hydrocarbons in textiles by using supercritical CO2 fluid |
-
2007
- 2007-05-23 CN CN200710068891A patent/CN100584355C/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101507760A (en) * | 2009-03-13 | 2009-08-19 | 四川省中医药科学院 | Medicine composite for treating kidney disease |
| CN101507760B (en) * | 2009-03-13 | 2013-03-27 | 四川省中医药科学院 | Medicine composite for treating kidney disease |
| CN102240327A (en) * | 2011-04-29 | 2011-11-16 | 栗进才 | Method for extracting total anthraquinone in rhubarb from traditional Chinese medicine rhubarb by supercritical fluid |
| CN104909999A (en) * | 2015-04-16 | 2015-09-16 | 聊城大学 | Method for separating and purifying anthraquinone compound and styrene acid from rhubarb extractive |
| CN104909999B (en) * | 2015-04-16 | 2016-07-20 | 聊城大学 | A kind of isolated and purified anthraquinone analog compound and method of styrene acid from Radix Et Rhizoma Rhei |
| CN105498275A (en) * | 2015-12-01 | 2016-04-20 | 赵金树 | Low-cost low-energy-consumption CO2 supercritical extraction device and process |
| CN105498275B (en) * | 2015-12-01 | 2017-08-11 | 赵金树 | A kind of inexpensive low power consuming carbon dioxide supercritical extraction device and technique |
| CN105999761A (en) * | 2016-06-27 | 2016-10-12 | 广州纤维产品检测研究院 | Method for rapidly separating polycyclic aromatic hydrocarbons in textiles by using supercritical CO2 fluid |
| CN105999761B (en) * | 2016-06-27 | 2018-11-23 | 广州纤维产品检测研究院 | Using supercritical CO2The method of polycyclic aromatic hydrocarbon in fluid quick separating textile |
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