CN108017530A - A kind of method that Co-Q10 is continuously separated from bacteria residue - Google Patents
A kind of method that Co-Q10 is continuously separated from bacteria residue Download PDFInfo
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- CN108017530A CN108017530A CN201711317608.7A CN201711317608A CN108017530A CN 108017530 A CN108017530 A CN 108017530A CN 201711317608 A CN201711317608 A CN 201711317608A CN 108017530 A CN108017530 A CN 108017530A
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- bacteria residue
- raffinate
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- flow velocity
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
Abstract
The invention discloses a kind of method that Co-Q10 is continuously separated from bacteria residue, including：(1) Co-Q10 crude extract is dissolved in non-polar organic solvent and is made into feeding liquid；(2) feeding liquid and eluant, eluent are continuously passed through in simulated moving bed chromatography system, raffinate is continuously collected from the raffinate mouth of simulated moving bed chromatography system；(3) dissolved again after raffinate obtained by step (2) is concentrated under reduced pressure, then the Co-Q10 fine work that purity is more than 98% is obtained after crystallized, filtering, drying.This method has the characteristics that yield is high, the rate of recovery is high, solvent consumption is few, production serialization, is adapted to industrialization large-scale promotion application.
Description
Technical field
The invention belongs to technical field of chemical separation, and in particular to a kind of method that Co-Q10 is continuously separated from bacteria residue.
Background technology
Co-Q10 is also known as ubiquinone, is a kind of fat-soluble quinones, is primarily present in the heart, liver, the nephrocyte of animal
In, its chemical name for 2- (3,7,11,15,19,23,27,31,35,39- decamethyls -2,6,10,14,18,22,26,30,
34,38- tetra- ten decene bases) -5,6- dimethoxy -3- methyl-p- benzoquinones, molecular formula C59H90O4, molecular weight 863.34.Coenzyme
Q10, which has, to be removed free radical, improves the important physiological function such as cell internal respiration and strengthen immunity, its market demand constantly expands
Greatly, it is widely used in the fields such as medicine, cosmetics and food additives.
The production method of Co-Q10 mainly has chemical synthesis, cell culture of animals method and microbe fermentation method, its
In, microbe fermentation method has technology stability high, is easy to mass produce, easy to operate, and product bioactivity is high, easy
It is the research hotspot of current Co-Q10 production in absorb the advantages that.By zymotic fluid made from microbe fermentation method through centrifugation,
Bacteria residue is obtained after filtering, lyophilized, crushing, Co-Q10 crude extract is obtained by extraction, processing is further purified and obtains high-purity
Co-Q10 product.Existing extracting method includes solvent extraction, saponification method, supercritical fluid extraction, then in conjunction with silica gel
Co-Q10 crude product is further purified in the technologies such as column chromatography, recrystallization.However, mainly contain in Co-Q10 crude extract
There is the coenzyme Q kind homologue that isoprenyl units number is different on side chain, separating difficulty is larger.
CN103819326A discloses a kind of successively with ultrasonic disruption, organic solvent extraction, silica gel column chromatography and crystallization
To refine the method for Co-Q10.CN101429108A disclose it is a kind of extracted successively with absolute ethyl alcohol, water and n-hexane extraction,
Silica gel column chromatography and crystallization are come the method that purifies Co-Q10.CN102391092A discloses one kind and is extracted with supercritical carbon dioxide
Bacteria residue is taken, then with silica gel column chromatography and crystallization, obtains the Co-Q10 that purity is more than 99.5%.CN101987815A is disclosed
The Co-Q10 that purity is more than 98% is prepared in the method that a kind of absorption resin and silica gel column chromatography combine.These methods all need
Silica gel column chromatography is used, although the Co-Q10 of high-purity can be obtained, the above method is all batch process procedures, is deposited
Big in consumption of organic solvent, preparation amount is few, the problems such as silica gel utilization rate is low, thus technique and uneconomical.
Simulated Moving Bed Chromatography is the current chromatographic technique for preparing for most having industrial prospect, and eluant, eluent entrance, feeding liquid enter
All chromatographic columns are divided into four different areas of flow velocity by four inlet and outlet such as mouth, extract outlet, raffinate outlet, are undertaken respectively
Different functions.The adverse current that it simulates eluant, eluent and stationary phase using the exchange-column shift of four inlet and outlet materials moves, so that real
The serialization of existing input and output material.The mixed solution containing strong absorbed component and eluant, eluent is continuously collected in extract outlet, and in raffinate
Continuously collect the mixed solution containing weakly adsorbed components and eluant, eluent in liquid outlet.On the one hand, which allows continuous sample introduction, thus raw
Production capacity power is high；On the other hand, since eluant circulation uses, solvent consumption is few, can reduce the cost prepared on a large scale.For each area
The suitable flow of design, you can obtain the target components of high-purity.
The content of the invention
, should for a kind of insufficient existing for above method, method that Co-Q10 is continuously separated from bacteria residue of present invention offer
Method technique is simple, and product preparation amount is big, purity is high, and solvent consumption is few, and production cost is low.
The present invention separates Co-Q10 with crystallization integrated processes by Simulated Moving Bed Chromatography from bacteria residue, and this method is with table
Filler of the face rich in polar group adjusts the species and ratio of eluant, eluent, designs suitable each area's flow velocity and cut as stationary phase
The time is changed, can realize that Co-Q10 is separated with the continuous of impurity using Simulated Moving Bed Chromatography, then by isolated coenzyme
Q10 crystallization for purifying again.
A kind of method that Co-Q10 is continuously separated from bacteria residue, comprises the following steps：
(1) Co-Q10 crude extract is dissolved in non-polar organic solvent and is made into feeding liquid；
(2) feeding liquid and eluant, eluent are continuously passed through in simulated moving bed chromatography system, from simulated moving bed chromatography system
Raffinate mouth continuously collect raffinate；
The simulated moving bed chromatography system is made of 4~32 chromatographic columns equipped with stationary phase, Gong Sige areas, per area
It is in series by 1~8 root chromatogram column.Can connect between each area to disconnect, can also using isocratic operator scheme
Using gradient operation mode.The operating parameters such as each area's flow, switching time, switching times and column temperature are pre-set, are continuously pumped into
Feeding liquid and eluant, eluent, after system reaches stable state, the raffinate rich in Co-Q10 is continuously collected from raffinate mouth.
Before simulated moving bed chromatography system operation, stationary-phase particle size is filled into chromatographic column using wet method dress post method,
Dress column solvent is n-hexane or petroleum ether, and pressure, column effect to each column, solute retention time, separating degree, overall porosity carry out pair
Title property experiment, it is ensured that the performance indicator per root chromatogram column is consistent.Separable area is primarily determined that according to " triangle is theoretical ", adjusts each area
Flow and switching time, are kept completely separate until Co-Q10 reaches with impurity.
(3) by after raffinate concentration removing solvent obtained by step (2), it is firm to solid that organic solvent is added at 20~60 DEG C
Good dissolving, then cool the temperature to -5~5 DEG C, when crystallisation by cooling 12~36 is small after filter, filter cake be washed with water after at 20~40 DEG C
Vacuum drying obtains the Co-Q10 fine work of purity more than 98%.
Co-Q10 crude extract is extracted from the bacteria residue obtained by microbial fermentation in the step (1), specifically can refer to public affairs
The number of opening is the method culture bacterium described in the patent application of CN101314782A, CN101619330A or CN105886562A
Kind, bacteria residue will be obtained after filtering fermentation liquor, drying, crushing；The extracting method that Co-Q10 crude extract is extracted from bacteria residue is diacolation
Extraction method, organic solvent extraction, cell fragmentation or supercritical fluid extraction, specifically can be according to the patent for the number of being disclosed below
Apply for CN106146278A, CN101381747A, CN102391092A or CN104694613A.
The non-polar organic solvent is one kind in n-hexane, hexamethylene, normal heptane, normal octane and petroleum ether or appoints
The mixture of two kinds of meaning.These hydrophobic organic solvents have higher solubility for Co-Q10 crude extract.
The total concentration of the feeding liquid is 5~500g/L, more preferably 50~300g/L.If input concentration mistake
Low, then production capacity reduces, and process economy reduces；If input concentration is excessive, it is kept completely separate area and is reduced significantly, design operation
The difficulty of condition increases, separating difficulty increase.
The stationary phase of the simulated moving bed chromatography system is polar macroporous adsorption resin, ion exchange resin, silica gel
Or aluminium oxide.These stationary phases are rich in hydroxyl isopolarity group, can with the carbon-based formation hydrogen bond in coenzyme Q kind homologue, according to
Hyarogen-bonding is of different sizes, identifies the micro-structure difference between homologue.
The stationary phase is uniform particle sizes, aperture is homogeneous, the spheric granules with high mechanical properties.
The size controlling of the stationary phase is at 5~200 μm, more preferably 10~100 μm.If particle diameter is too big,
Column effect reduces, and is unfavorable for the separation of Co-Q10 and impurity；If particle diameter is too small, column pressure is too high, is unfavorable for operating.
The pore size control of the stationary phase is in 5~100nm, more preferably 10~50nm.If filler aperture is too small,
Then Co-Q10 molecule is not easily accessed inside duct, reduces separating effect；If filler aperture is too big, pore diffusion is slow, mass transfer
Resistance is big.
The eluant, eluent is n-hexane, hexamethylene, normal heptane, normal octane, petroleum ether, acetonitrile, ethyl acetate, tetrahydrochysene furan
Mutter, dimethyl sulfoxide, N,N-dimethylformamide and carbon number are one kind in 1~4 monohydric alcohol or any two kinds of mixing
Thing.Further preferred eluant, eluent is n-hexane and the mixture of ethyl acetate.
Preferably, the percent by volume of ethyl acetate is 1~20% in eluant, eluent.Flowed if the ratio of ethyl acetate is excessive
Dynamic phase polarity is strong, and the separating degree of Co-Q10 and impurity is poor；Mobile phase polarity is weak if the ratio of ethyl acetate is too low, Co-Q10
The retention time in system it is too long, system is difficult to reach stable.
The size of the chromatographic column of the simulated moving bed chromatography system is 5~500mm of diameter, 50~1000mm of length,
More preferably a diameter of 10~100mm, 100~500mm of length.If column size is too small, production capacity is relatively low；If
Column size is excessive, then filler loads difficult, and wall effect is obvious, and the separating capacity of chromatographic column declines.
The operating parameter of the simulated moving bed chromatography system controls：Eluant, eluent 1~1000mL/min of flow velocity, charging
1~100mL/min of flow velocity, extract 1~100mL/min of flow velocity, raffinate 1~100mL/min of flow velocity, switching time 1~
50min.Switching time is more preferably 3~10min, if switching time is too short, switching valve is easily damaged；If switching time
Long, then system is difficult to reach stable state.
The separation temperature of the simulated moving bed chromatography system is 0~60 DEG C, more preferably 20~50 DEG C.It is if warm
Spend low, then the solubility of Co-Q10 in a solvent substantially reduces, and the concentration of feeding liquid is restricted；It is auxiliary if temperature is excessive
Enzyme Q10 easy oxidation deteriorations in separation process.
The organic solvent be carbon number be 1~4 monohydric alcohol, acetonitrile, acetone, ethyl acetate, n-hexane and just
One kind or any two kinds of mixture in heptane.
The volume mass ratio of obtained solid is 20~80L/kg after the organic solvent addition and raffinate concentration.
Compared with prior art, the invention has the advantages that：
1. using continuous chromatography technology, the utilization rate of stationary phase is improved, reduces the consumption of stationary phase.
2. realizing the continuous production of Co-Q10, production process is full-automatic, and labor intensity is low, and production cost is low.
3. the Co-Q10 purity that the purification process of the present invention obtains reaches more than 98%, yield is high, and solvent consumption is few, fits
Promoted and applied in large-scale.
Brief description of the drawings
Fig. 1 is the liquid chromatogram of Co-Q10 product in the embodiment of the present invention 1.
Embodiment
For a further understanding of the present invention, one kind provided by the invention is continuously separated from bacteria residue with reference to embodiment
The method of Co-Q10 is specifically described, but the present invention is not limited to these embodiments, field technology personnel are in core of the present invention
The non-intrinsically safe modifications and adaptations made under heart guiding theory, still fall within protection scope of the present invention.
For Simulation moving bed device using Germany CESP C9116 (Nore, Germany), it assembles more mouthfuls of rotations in following embodiments
Rotary valve, can at most connect 16 root chromatogram columns, identical per area's chromatographic column number, be changed in 1~4；Equipped with 4 S-100 type liquid phase pumps,
Wherein feed 0~10mL/min of flow rate pump, 0~50mL/min of flow velocity of eluant, eluent pump, extraction liquid pump and raffinate liquid pump.Eluant, eluent
Injected between 4th area and 1st area, feeding liquid injects between 2nd area and 3rd area, raffinate outlet of the Co-Q10 between 3rd area and 4th area
Collect, extract outlet of the impurity 10 between 1st area and 2nd area is collected.Every a switching time (note：This switching time is
It is adjustable), chromatographic column switches a position towards eluent stream in the opposite direction.
The measure of Co-Q10 content is operated according to the method described in Chinese Pharmacopoeia in following embodiments of the present invention,
The analysis condition of liquid chromatography is：Waters Atlantis T3 analytical columns (250mm × 4.6mm, 5 μm), with methanol-anhydrous
Ethanol (1:1) it is mobile phase, flow 1mL/min, 20 μ L of sample size, detector is UV detector, Detection wavelength 275nm.
The computational methods of Co-Q10 purity are：A small amount of sample is taken to be dissolved with absolute ethyl alcohol the Co-Q10 product being collected into
And the solution that the Co-Q10 containing about 0.2mg in every 1mL is made is diluted, external standard method is used with its purity of calculated by peak area.
The computational methods of purity and the rate of recovery of the present invention are as follows：
Gross mass × 100% of the quality ÷ products of Co-Q10 in purity=product
In the rate of recovery=product in the quality ÷ raw materials of Co-Q10 Co-Q10 quality × 100%.
Embodiment 1
Co-Q10 crude extract is dissolved in n-hexane, is configured to the feeding liquid of solid concentration 50g/L, wherein coenzyme
The content of Q10 is about 62.3%.
Simulation moving bed is equipped with 8 root chromatogram columns, size 1cm × 25cm；Stationary phase is silica gel, 45 μm of its particle diameter, aperture
10nm；Eluant, eluent is n-hexane and the mixture of ethyl acetate, and the wherein percent by volume of ethyl acetate is 10%；Operation temperature
30℃；Operating parameter is optimized to be determined as：Eluant, eluent flow velocity 16mL/min, feeds flow velocity 2mL/min, extract flow velocity
9.5mL/min, raffinate flow velocity 8.5mL/min, switching time 5min.After continuously switching 32 times, system reaches balance, from raffinate
Liquid outlet is collected into the solution rich in Co-Q10.Analysis shows, the content of Co-Q10 is 95.6% in raffinate.
Raffinate is condensed into solid, ethanol is added at 50 DEG C to being just completely dissolved, solid-to-liquid ratio 1:50, by temperature by
5 DEG C are stepped back down to, is filtered after crystallisation by cooling 24h, 30 DEG C of dry 24h in vacuum drying chamber is put into and obtains Co-Q10 fine work.With liquid phase color
The purity that spectrum analysis obtains Co-Q10 product is 99.2%, and the rate of recovery of whole technique is 95.5%.
Embodiment 2
Co-Q10 crude extract is dissolved in n-hexane, is configured to the feeding liquid of solid concentration 100g/L, wherein coenzyme
The content of Q10 is about 68.7%.
Simulation moving bed is equipped with 8 root chromatogram columns, size 1cm × 25cm；Stationary phase is silica gel, 20 μm of its particle diameter, aperture
22nm；Eluant, eluent is n-hexane and the mixture of ethanol, and the wherein percent by volume of ethanol is 5%；30 DEG C of operation temperature；Operation
Parameter is optimized to be determined as：Eluant, eluent flow velocity 15.4mL/min, feeds flow velocity 1.5mL/min, extract flow velocity 8.9mL/
Min, raffinate flow velocity 8.0mL/min, switching time 4min.After continuously switching 32 times, system reaches balance, from raffinate outlet
It is collected into the solution rich in Co-Q10.Analysis shows, the content of Co-Q10 is 96.5% in raffinate.
Raffinate is condensed into solid, ethyl acetate is added at 30 DEG C to being just completely dissolved, solid-to-liquid ratio 1:20, by temperature
Degree is progressively down to 0 DEG C, is filtered after crystallisation by cooling 24h, is put into 30 DEG C of dry 24h in vacuum drying chamber and obtains Co-Q10 fine work.Use liquid
The purity that analysis of hplc obtains Co-Q10 product is 99.2%, and the rate of recovery of whole technique is 95.9%.
Embodiment 3
Co-Q10 crude extract is dissolved in n-hexane, is configured to the feeding liquid of solid concentration 80g/L, wherein coenzyme
The content of Q10 is about 70.3%.
Simulation moving bed is equipped with 16 root chromatogram columns, size 1cm × 15cm；Stationary phase is the neutral alumina of 200~300 mesh
Aluminium；Eluant, eluent is n-hexane and the mixture of ethyl acetate, and the wherein percent by volume of ethyl acetate is 10%；Operation temperature 40
℃；Operating parameter is optimized to be determined as：Eluant, eluent flow velocity 3mL/min, feeds flow velocity 1.5mL/min, extract flow velocity
2.2mL/min, raffinate flow velocity 2.3mL/min, switching time 10min.After continuously switching 48 times, system reaches balance, from extraction
Extraction raffinate outlet is collected into the solution rich in Co-Q10.Analysis shows, the content of Co-Q10 is 95.2% in raffinate.
Raffinate is condensed into solid, ethanol is added at 50 DEG C to being just completely dissolved, solid-to-liquid ratio 1:50, by temperature by
5 DEG C are stepped back down to, is filtered after crystallisation by cooling 12h, 35 DEG C of dry 12h in vacuum drying chamber is put into and obtains Co-Q10 fine work.With liquid phase color
The purity that spectrum analysis obtains Co-Q10 product is 98.2%, and the rate of recovery of whole technique is 94.5%.
Embodiment 4
Co-Q10 crude extract is dissolved in hexamethylene, is configured to the feeding liquid of solid concentration 150g/L, wherein coenzyme
The content of Q10 is about 72.7%.
Simulation moving bed is equipped with 16 root chromatogram columns, size 1cm × 15cm；Stationary phase is the neutral alumina of 200~300 mesh
Aluminium；Eluant, eluent is hexamethylene and the mixture of methanol, and the wherein percent by volume of methanol is 5%；20 DEG C of operation temperature；Operation ginseng
Number is optimized to be determined as：Eluant, eluent flow velocity 7mL/min, feeds flow velocity 2mL/min, extract flow velocity 4.8mL/min, raffinate
Flow velocity 4.2mL/min, switching time 5min.After continuously switching 48 times, system reaches balance, is collected into and is rich in from raffinate outlet
The solution of Co-Q10.Analysis shows, the content of Co-Q10 is 95.0% in raffinate.
Raffinate is condensed into solid, acetone is added at 30 DEG C to being just completely dissolved, solid-to-liquid ratio 1:20, by temperature by
5 DEG C are stepped back down to, is filtered after crystallisation by cooling 24h, 35 DEG C of dry 12h in vacuum drying chamber is put into and obtains Co-Q10 fine work.With liquid phase color
The purity that spectrum analysis obtains Co-Q10 product is 98.0%, and the rate of recovery of whole technique is 93.8%.
Claims (9)
1. a kind of method that Co-Q10 is continuously separated from bacteria residue, comprises the following steps：
(1) Co-Q10 crude extract is dissolved in non-polar organic solvent and is made into feeding liquid；
(2) feeding liquid and eluant, eluent are continuously passed through in simulated moving bed chromatography system, from the extraction of simulated moving bed chromatography system
Remaining mouth continuously collects raffinate；
(3) raffinate obtained by step (2) is concentrated after removing solvent, at 20~60 DEG C, then adds organic solvent dissolving, -5~5
Filtered after DEG C 12~36h of crystallisation by cooling, after filter cake is washed with water, 20~40 DEG C of vacuum drying obtain purity be more than 98% it is auxiliary
Enzyme Q10 fine work；
The volume mass ratio of obtained solid is 20~80L/kg after the organic solvent addition and raffinate concentration.
2. the method according to claim 1 that Co-Q10 is continuously separated from bacteria residue, it is characterised in that the non-pole
Property organic solvent be n-hexane, hexamethylene, normal heptane, normal octane and petroleum ether in one kind or any two kinds of mixture.
3. the method according to claim 1 that Co-Q10 is continuously separated from bacteria residue, it is characterised in that the charging
The total concentration of liquid is 5~500g/L.
4. the method according to claim 1 that Co-Q10 is continuously separated from bacteria residue, it is characterised in that the elution
Agent is n-hexane, hexamethylene, normal heptane, normal octane, petroleum ether, acetonitrile, ethyl acetate, tetrahydrofuran, dimethyl sulfoxide, N, N- bis-
Methylformamide and one kind or any two kinds of mixture in the monohydric alcohol that carbon number is 1~4.
5. the method according to claim 4 that Co-Q10 is continuously separated from bacteria residue, it is characterised in that the elution
Agent is n-hexane and the mixture of ethyl acetate, and the wherein percent by volume of ethyl acetate is 1~20%.
6. the method according to claim 1 that Co-Q10 is continuously separated from bacteria residue, it is characterised in that the simulation
The stationary phase of mobile bed chromatic system is polar macroporous adsorption resin, ion exchange resin, silica gel or aluminium oxide, and stationary phase
Size controlling is at 5~200 μm, and pore size control is in 5~100nm.
7. the method according to claim 1 that Co-Q10 is continuously separated from bacteria residue, it is characterised in that the simulation
The size of the chromatographic column of mobile bed chromatic system is 5~500mm of diameter, 50~1000mm of length.
8. the method according to claim 1 that Co-Q10 is continuously separated from bacteria residue, it is characterised in that the simulation
The operating parameter of mobile bed chromatic system controls：Separation temperature is 0~60 DEG C, eluant, eluent 1~1000mL/min of flow velocity, charging
1~100mL/min of flow velocity, extract 1~100mL/min of flow velocity, raffinate 1~100mL/min of flow velocity, switching time 1~
50min。
9. the method according to claim 1 that Co-Q10 is continuously separated from bacteria residue, it is characterised in that in step (3),
The organic solvent is in monohydric alcohol, acetonitrile, acetone, ethyl acetate, n-hexane and the normal heptane that carbon number is 1~4
A kind of or any two kinds of mixture.
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| CN201711317608.7A CN108017530B (en) | 2017-12-12 | 2017-12-12 | Method for continuously separating coenzyme Q10 from mushroom dregs |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110002985A (en) * | 2019-05-15 | 2019-07-12 | 丽珠集团(宁夏)制药有限公司 | One kind is from ubiquinone10Ubiquinone is isolated and purified in mother liquor10Method and ubiquinone10Crude product |
| CN110465114A (en) * | 2019-08-23 | 2019-11-19 | 内蒙古金达威药业有限公司 | A kind of Simulation moving bed continuous chromatography chromatographic system and its application and the method for purifying Co-Q10 |
| CN112920035A (en) * | 2019-12-06 | 2021-06-08 | 中国科学院大连化学物理研究所 | Method for removing Q11 impurity in coenzyme Q10 by using preparation chromatography |
| CN115677468A (en) * | 2022-11-02 | 2023-02-03 | 广东润和生物科技有限公司 | Method for purifying coenzyme Q10 |
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| CN101233095A (en) * | 2005-06-10 | 2008-07-30 | 协和发酵工业株式会社 | Method of purifying ubiquinone-10 |
| CN101987815A (en) * | 2010-09-28 | 2011-03-23 | 华东理工大学 | Purification process for preparing high-purity coenzyme Q10 |
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2017
- 2017-12-12 CN CN201711317608.7A patent/CN108017530B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101233095A (en) * | 2005-06-10 | 2008-07-30 | 协和发酵工业株式会社 | Method of purifying ubiquinone-10 |
| CN101987815A (en) * | 2010-09-28 | 2011-03-23 | 华东理工大学 | Purification process for preparing high-purity coenzyme Q10 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110002985A (en) * | 2019-05-15 | 2019-07-12 | 丽珠集团(宁夏)制药有限公司 | One kind is from ubiquinone10Ubiquinone is isolated and purified in mother liquor10Method and ubiquinone10Crude product |
| CN110465114A (en) * | 2019-08-23 | 2019-11-19 | 内蒙古金达威药业有限公司 | A kind of Simulation moving bed continuous chromatography chromatographic system and its application and the method for purifying Co-Q10 |
| WO2021036386A1 (en) * | 2019-08-23 | 2021-03-04 | 内蒙古金达威药业有限公司 | Simulated moving bed continuous chromatography system and application thereof, and method for purifying coenzyme q10 |
| CN110465114B (en) * | 2019-08-23 | 2021-08-20 | 内蒙古金达威药业有限公司 | Simulated moving bed continuous chromatography chromatographic system, application thereof and method for purifying coenzyme Q10 |
| CN112920035A (en) * | 2019-12-06 | 2021-06-08 | 中国科学院大连化学物理研究所 | Method for removing Q11 impurity in coenzyme Q10 by using preparation chromatography |
| CN115677468A (en) * | 2022-11-02 | 2023-02-03 | 广东润和生物科技有限公司 | Method for purifying coenzyme Q10 |
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| CN108017530B (en) | 2020-10-13 |
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