CN109785908A - The method of three zone asynchronised handover Simulation moving beds separation vanillic aldehyde and isovanillin - Google Patents
The method of three zone asynchronised handover Simulation moving beds separation vanillic aldehyde and isovanillin Download PDFInfo
- Publication number
- CN109785908A CN109785908A CN201811609443.5A CN201811609443A CN109785908A CN 109785908 A CN109785908 A CN 109785908A CN 201811609443 A CN201811609443 A CN 201811609443A CN 109785908 A CN109785908 A CN 109785908A
- Authority
- CN
- China
- Prior art keywords
- isovanillin
- vanillic aldehyde
- eluent
- moving bed
- sample liquid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
The method that three zone asynchronised handover Simulation moving beds separate vanillic aldehyde and isovanillin, is related to vanillic aldehyde and isovanillin.Prepare eluent；Prepare vanillic aldehyde and isovanillin sample liquid；Obtained vanillic aldehyde is separated with isovanillin sample liquid using asynchronised handover simulated moving bed chromatography system, obtains vanillic aldehyde and isovanillin.Using asynchronised handover simulated moving bed chromatography system, vanillic aldehyde and isovanillin have been had successfully been isolated, has realized that the preparation of serialization and scale splits purpose.In the case where not increasing equipment investment and solvent consumption, increase feed rate, obtain the rate of recovery, purity be above 99.0% vanillic aldehyde and isovanillin.The present invention has many advantages, such as that yield is high, solvent consumption is low, automatic continuous production, and the stable product of quality can be made, be a kind of isolation technics of great commercial applications prospect.
Description
Technical field
The present invention relates to vanillic aldehydes and isovanillin, separate chinese cymbidium more particularly, to three zone asynchronised handover Simulation moving beds
The method of element and isovanillin.
Background technique
Vanillic aldehyde (Vanillin), the entitled Vanillin of chemistry, molecular formula C8H8O3, molecular weight is
152.15g/mol is white under normality to pale yellow crystals, and fusing point is 81 DEG C, molecular structural formula are as follows:
Vanillic aldehyde is the current maximum synthetic perfume of supply and demand amount in the world, is widely used in food additives, chemicals, tobacco
The flavoring agent or fixastive of industry also can be used as the starting material for synthesizing certain important fine chemicals, while also because it is anti-
Oxidisability and antibiotic property, it is also possible to make food preservative ([1] Yang Wenwen, Wu Qiulin, Tang Hongzhi waits " fragrance queen " --- day
Progress [J] the microbiology notification of right vanillic aldehyde biosynthesis, 2013,06): 1087-1095；[2]Fache M,
Boutevin B,Caillol S.Vanillin production from lignin and its use as a
renewable chemical[J].ACS Sustainable Chemistry&Engineering,2016,4(1):35-46)。
In addition, vanillic aldehyde can be used for the standard reagent of organic analysis, such as examine protein phloroglucin.
A large amount of by-product can be generated during artificial synthesized vanillic aldehyde simultaneously, using guaiacol or lignin as raw material
Synthesis technology in, Ethyl vanillin, syringaldehyde, O-VANILLIN, isovanillin etc. be common by-product, influence vanillic aldehyde production
Product quality ([3] Walton N J, Mayer M J, Narbad A.Vanillin [J] .Phytochemistry, 2003,63
(5):505-515).These by-products have similar physicochemical property with vanillic aldehyde mostly, and conventional method is pure in progress vanillic aldehyde
Efficiency when change is relatively low.Most researchers use last procedure of crystallisation as purifying vanillin product, pass through
The dissolubility difference of different material in a solvent, as temperature reduces, the low substance of solubility can be crystallized out first, reach separation
Purpose.
Summary of the invention
In order to overcome the drawbacks described above of the prior art, the purpose of the present invention is to provide achievable vanillic aldehyde and isovanillin
Height purity separation three zone asynchronised handover Simulation moving beds separation vanillic aldehyde and isovanillin method.
The present invention the following steps are included:
1) eluent is prepared；
In step 1), the specific method for preparing eluent can are as follows: mixes second alcohol and water, at filtering, ultrasound
Reason, obtains eluent；The volume ratio that the second alcohol and water is pressed can be 35 ︰ 65；The condition of the ultrasound can be 30~50kHz, 10~
20min。
2) vanillic aldehyde and isovanillin sample liquid are prepared；
In step 2), the specific method for preparing vanillic aldehyde and isovanillin sample liquid can are as follows: by vanillic aldehyde with it is different
The vanillic aldehyde eluent that step 1) is prepared dissolves, and obtains sample liquid；The quality of vanillic aldehyde and isovanillin in gained sample liquid
Concentration can be 0.5g/L；
3) use asynchronised handover simulated moving bed chromatography system by the obtained vanillic aldehyde of step 2) and isovanillin sample
Liquid separation, obtains vanillic aldehyde and isovanillin.
In step 3), the stationary phase of the asynchronised handover simulated moving bed chromatography system is reverse phase C18Filler, mobile phase
The eluent prepared for step 1)；Asynchronised handover simulated moving bed chromatography system is mainly by 4 preparation chromatographic columns, 3 constant currents
Pump, 4 solenoid valves, 4 check valves, 4 singlechip controllers and several connecting lines form three zone Simulation moving bed of open loop
System realizes exchange-column shift by the control program of computer installation, every to pass through a switching time, real by electronics Vavle switching
A mobile pillar unit in existing each port mobile phase.4 pillars are divided into I, II, III 3 area, wherein Ith area includes 1 chromatography
Column is located between eluent entrance and extract liquor outlet, and IIth area includes 1 root chromatogram column, exports to enter with sample liquid positioned at extract liquor
Between mouthful, IIIth area includes 2 root chromatogram columns, between sample liquid entrance and raffinate outlet.I area's major function is eluted product
Isovanillin；II area's major function is to realize isovanillin concentration；III area's major function is enriched product vanillic aldehyde.
The eluent that the prepared sample liquid of step 2) and step 1) are prepared is entered from sample liquid entrance and eluent respectively
Mouth injects chromatographic system, sample liquid entrance, eluent entrance, extract liquor outlet, raffinate outlet by sampling pump and elution pump
It is asynchronous to switch to next root chromatogram column along eluent flow direction, the extract liquor containing isovanillin and the raffinate containing vanillic aldehyde
Respectively from extract liquor outlet and raffinate outlet outflow system.
The Parameter Conditions of the fractured operation of the asynchronised handover simulated moving bed chromatography system are as follows: eluent flow rate 2mL/
Min, sample liquid flow velocity are 0.471mL/min, and extract liquor flow velocity is 0.962mL/min, and 18min is divided between switching time, are operated
Temperature is 25 DEG C.
Beneficial effects of the present invention are as follows:
The present invention uses asynchronised handover simulated moving bed chromatography system, has had successfully been isolated vanillic aldehyde and isovanillin, real
The preparation of existing serialization and scale splits purpose.In the case where not increasing equipment investment and solvent consumption, charging is increased
Flow, obtain the rate of recovery, purity be above 99.0% vanillic aldehyde and isovanillin.The present invention has yield height, solvent consumption
The advantages that low, automatic continuous production, the stable product of quality can be made, be a kind of separation skill of great commercial applications prospect
Art.
Detailed description of the invention
Fig. 1 is the structure composition schematic diagram of asynchronised handover simulated moving bed chromatography system of the present invention.
Fig. 2 is extract liquor outlet of the present invention, raffinate outlet, sample liquid entrance, eluent entrance are cut by asynchronous
Change the schematic diagram that strategy switches to mobile phase flow direction.In Fig. 2, original area band is configured as 1/1/2.
Specific embodiment
The present invention is further illustrated below with reference to separation embodiment and attached drawing.
Fig. 1 provides the structure composition schematic diagram of asynchronised handover simulated moving bed chromatography system of the present invention, asynchronised handover
Simulated moving bed chromatography system is equipped with pump 1, chromatographic column 2, pressure limiting valve 3,4,4 four-ways 5 of switching valve and check valve 6, the sample
Liquid and eluent are transported to feeding liquid valve and eluent valve, the feeding liquid by sample introduction liquid constant flow pump and eluent constant flow pump respectively
Valve and eluent valve are 1 into 4 switching valve 4 gone out, and only one outlet of any moment and an import in switching valve 4
It is connected；4 root chromatogram columns 2 are serially connected together, and the input end of every root chromatogram column connects a four-way, the other three of four-way
Mouth connects outlet, sample introduction liquid valve and the eluent valve of a root chromatogram column respectively, and the outlet end of every root chromatogram column also connects one four
Logical, the other three mouth of the four-way is separately connected the import of next root chromatogram column, extract liquor valve and raffinate valve.Extract liquor valve and
Raffinate valve is 4 into 1 switching valves gone out, and the outlet of extract liquor valve connects extract liquor constant flow pump, extract liquor constant flow pump external one
A standby pressure valve；The outlet of raffinate valve is connect with raffinate receiving flask, and check valve 6 is equipped between adjacent four-way；Pass through control four
The chromatographic column number in three zone can be set in the outlet of a switching valve and entrance, to constitute the three zone simulation of open loop
Mobile bed system.
Fig. 2 is extract liquor outlet of the present invention, raffinate outlet, sample liquid entrance, eluent entrance are cut by asynchronous
Change the schematic diagram of strategy.Initial configuration as shown in the figure is 1/1/2, by 0.51tsAfter time, injection port is along the direction of mobile phase
Advance a root chromatogram column, and system is configured as 1/2/1 at this time；By 0.76tsAfterwards, extract liquor outlet is before the direction of mobile phase
Into a root chromatogram column, system is configured as 2/1/1 at this time；By tsAfterwards, eluent import and raffinate outlet are simultaneously along flowing
Advance a root chromatogram column in the direction of phase, completes the switching of a cycle.
The embodiment of the present invention includes following steps:
1) eluent is prepared；Second alcohol and water is mixed, filtered, be ultrasonically treated, obtain eluent；What the second alcohol and water was pressed
Volume ratio can be 35 ︰ 65；The condition of the ultrasound can be 30~50kHz, 10~20min.
2) prepare vanillic aldehyde and isovanillin sample liquid: the eluent that vanillic aldehyde and isovanillin are prepared with step 1) is molten
Solution, obtains sample liquid；The mass concentration of vanillic aldehyde and isovanillin can be 0.5g/L in gained sample liquid；
3) use asynchronised handover simulated moving bed chromatography system by the obtained vanillic aldehyde of step 2) and isovanillin sample
Liquid separation, obtains vanillic aldehyde and isovanillin.The stationary phase of the asynchronised handover simulated moving bed chromatography system is reverse phase C18It fills out
Material, mobile phase are the eluent that step 1) is prepared；Asynchronised handover simulated moving bed chromatography system mainly by: 4 preparation chromatographic columns,
3 constant flow pumps, 4 solenoid valves, 4 check valves, 4 singlechip controllers and composition three zone of the open loop simulation of several connecting lines
Mobile bed system realizes exchange-column shift by the control program of computer installation, every to pass through a switching time, passes through electronic valve
A mobile pillar unit in each port mobile phase is realized in switching.4 pillars are divided into I, II, III 3 area, wherein Ith area includes 1
Root chromatogram column is located between eluent entrance and extract liquor outlet, and IIth area includes 1 root chromatogram column, is located at extract liquor outlet and sample
Between product liquid entrance, IIIth area includes 2 root chromatogram columns, between sample liquid entrance and raffinate outlet.I area's major function is to wash
It is temporarily released from one's regular work object isovanillin；II area's major function is to realize isovanillin concentration；III area's major function is enriched product vanillic aldehyde.
The eluent that the prepared sample liquid of step 2) and step 1) are prepared is entered from sample liquid entrance and eluent respectively
Mouth injects chromatographic system, sample liquid entrance, eluent entrance, extract liquor outlet, raffinate outlet by sampling pump and elution pump
It is asynchronous to switch to next root chromatogram column along eluent flow direction, the extract liquor containing isovanillin and the raffinate containing vanillic aldehyde
Respectively from extract liquor outlet and raffinate outlet outflow system.
The Parameter Conditions of the fractured operation of the asynchronised handover simulated moving bed chromatography system are as follows: eluent flow rate 2mL/
Min, sample liquid flow velocity are 0.471mL/min, and extract liquor flow velocity is 0.962mL/min, and 18min is divided between switching time, are operated
Temperature is 25 DEG C.
Specific embodiment is given below.
Separate embodiment 1
A, operating condition
Mobile phase: Yi Chun ︰ water volume ratio is 35 ︰, 65 solution；
Sample introduction concentration: vanillic aldehyde is 0.5g/L with isovanillin sample introduction concentration；
Eluent flow rate: Ud=2mL/min；
Extract liquor flow velocity: Ue=0.962mL/min；
Sample introduction flow velocity: Uf=0.471mL/min；
Raffinate flow velocity: Ur=1.509mL/min；
Switching time: Ts=18.0min.
B, separating step
Isovanillin and vanillic aldehyde are sufficiently dissolved, concentration 0.5g/L in prepared mobile phase, sample liquid and is washed
De- liquid successively injects asynchronised handover simulated moving bed chromatography system from injection port and eluent entrance, is simulated and is moved by asynchronised handover
The controller of dynamic bed chromatographic system, after 9.28min, injection port passes through along one root chromatogram column of the direction of mobile phase advance
After 13.7min, extract liquor is exported along one root chromatogram column of the direction of mobile phase advance, after 18min, eluent import and raffinate
Liquid outlet along one root chromatogram column of the direction of mobile phase advance, completes the switching of a cycle simultaneously.
C, check analysis
With reverse phase C18The chromatographic column of filler preparation, chromatographic column specification are i.d.4.6mm × 150mm, and detector is UV230 II
UV detector, mobile phase are Yi Chun ︰ water=35 ︰ 65 (V ︰ V), flow 0.5mL/min, 25 DEG C of column temperature, 20 μ L of sample volume, are examined
Survey wavelength is 260nm, analytical extraction liquid and raffinate composition.Isovanillin product purity reaches 99.3% in extract liquor, recycling
Rate is 99.1%, and raffinate kind vanillic aldehyde product purity reaches 99.0%, the rate of recovery 99.8%.
The present invention uses C18Silica gel is stationary phase, and 35% ethanol water is mobile phase, by sample isovanillin and chinese cymbidium
Element is dissolved in mobile phase, obtains sample liquid, and resulting sample liquid is continuously separated with three zone simulated moving bed systems are constructed, point
The isovanillin and vanillic aldehyde of single configuration have not been obtained；The present invention uses three zone asynchronised handover Simulated Moving Bed Chromatography systems
System, obtains isovanillin and its isomer vanillic aldehyde, obtained product purity is above 99.0% under antiphasic condition；This
There is yield to increase, reduce stationary phase loss, reduce mobile phase consumption, is automatic in the case where not increasing equipment investment for invention
The advantages that changing continuous production.
Claims (9)
1. the method for three zone asynchronised handover Simulation moving beds separation vanillic aldehyde and isovanillin, it is characterised in that including following step
It is rapid:
1) eluent is prepared；
2) vanillic aldehyde and isovanillin sample liquid are prepared；
3) the obtained vanillic aldehyde of step 2) and isovanillin sample liquid are divided using asynchronised handover simulated moving bed chromatography system
From acquisition vanillic aldehyde and isovanillin.
2. the method for the separation of three zone asynchronised handover Simulation moving bed vanillic aldehyde and isovanillin as described in claim 1, special
It levies and is in step 1), the preparation eluent method particularly includes: second alcohol and water is mixed, filtered, be ultrasonically treated, obtained
Eluent.
3. the method for the separation of three zone asynchronised handover Simulation moving bed vanillic aldehyde and isovanillin as claimed in claim 2, special
Sign be the second alcohol and water by volume ratio be 35 ︰ 65.
4. the method for the separation of three zone asynchronised handover Simulation moving bed vanillic aldehyde and isovanillin as claimed in claim 2, special
Sign is that the condition of the ultrasound is 30~50kHz, 10~20min.
5. the method for the separation of three zone asynchronised handover Simulation moving bed vanillic aldehyde and isovanillin as described in claim 1, special
Sign is in step 2), described to prepare vanillic aldehyde and isovanillin sample liquid method particularly includes: vanillic aldehyde and an unusually sweet smell is blue
The eluent dissolution that element is prepared with step 1), obtains sample liquid；The mass concentration of vanillic aldehyde and isovanillin in gained sample liquid
For 0.5g/L.
6. the method for the separation of three zone asynchronised handover Simulation moving bed vanillic aldehyde and isovanillin as described in claim 1, special
Sign is that in step 3), the stationary phase of the asynchronised handover simulated moving bed chromatography system is reverse phase C18Filler, mobile phase are
The eluent that step 1) is prepared；Asynchronised handover simulated moving bed chromatography system is by 4 preparation chromatographic columns, 3 constant flow pumps, 4 electricity
Magnet valve, 4 check valves, 4 singlechip controllers and several connecting lines form three zone simulated moving bed system of open loop, pass through
The control program of computer installation realizes exchange-column shift, every to pass through a switching time, realizes each end by electronics Vavle switching
A mobile pillar unit in mouth mobile phase；4 pillars are divided into I, II, III 3 area, wherein Ith area includes 1 root chromatogram column, are located at
Between eluent entrance and extract liquor outlet, IIth area includes 1 root chromatogram column, is located between extract liquor outlet and sample liquid entrance,
IIIth area includes 2 root chromatogram columns, between sample liquid entrance and raffinate outlet.
7. the method for the separation of three zone asynchronised handover Simulation moving bed vanillic aldehyde and isovanillin as claimed in claim 6, special
Sign is that Ith area major function is eluted product isovanillin；II area's major function is to realize isovanillin concentration；III area master
Wanting function is enriched product vanillic aldehyde.
8. the method for the separation of three zone asynchronised handover Simulation moving bed vanillic aldehyde and isovanillin as claimed in claim 6, special
Sign is the eluent for preparing the prepared sample liquid of step 2) and step 1) respectively from sample liquid entrance and eluent entrance
By sampling pump and elution pump injection chromatographic system, sample liquid entrance, eluent entrance, extract liquor outlet, raffinate outlet are different
Step switches to next root chromatogram column along eluent flow direction, the extract liquor containing isovanillin and the raffinate containing vanillic aldehyde point
Not from extract liquor outlet and raffinate outlet outflow system.
9. the method for the separation of three zone asynchronised handover Simulation moving bed vanillic aldehyde and isovanillin as claimed in claim 6, special
Sign is the Parameter Conditions of the fractured operation of the asynchronised handover simulated moving bed chromatography system are as follows: eluent flow rate 2mL/
Min, sample liquid flow velocity are 0.471mL/min, and extract liquor flow velocity is 0.962mL/min, and 18min is divided between switching time, are operated
Temperature is 25 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811609443.5A CN109785908A (en) | 2018-12-27 | 2018-12-27 | The method of three zone asynchronised handover Simulation moving beds separation vanillic aldehyde and isovanillin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811609443.5A CN109785908A (en) | 2018-12-27 | 2018-12-27 | The method of three zone asynchronised handover Simulation moving beds separation vanillic aldehyde and isovanillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109785908A true CN109785908A (en) | 2019-05-21 |
Family
ID=66497789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811609443.5A Pending CN109785908A (en) | 2018-12-27 | 2018-12-27 | The method of three zone asynchronised handover Simulation moving beds separation vanillic aldehyde and isovanillin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109785908A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110305129A (en) * | 2019-08-01 | 2019-10-08 | 厦门大学 | The method of three zone asynchronised handover Simulation moving beds separation rutaecarpin and Rutaecarpine |
| CN111705168A (en) * | 2020-07-08 | 2020-09-25 | 江南大学 | Method for purifying xylose hydrolysate by desalting with three zones with simulated moving bed |
| TWI794071B (en) * | 2022-04-01 | 2023-02-21 | 田寮生技數位科技股份有限公司 | A method of vanillin extraction and purification |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105617714A (en) * | 2015-12-31 | 2016-06-01 | 厦门大学 | Asynchronous switching three-zone-belt simulation moving bed |
| CN105985220A (en) * | 2014-11-26 | 2016-10-05 | 义守大学 | Method for purifying alcohol compound |
| US9534262B2 (en) * | 2013-03-28 | 2017-01-03 | Georgia Tech Research Corporation | Methods and controllers for simulated moving bed chromatography for multicomponent separation |
| CN106390519A (en) * | 2016-09-12 | 2017-02-15 | 华东理工大学 | Method for continuously separating aminoglutethimide racemate through multi-column simulated moving bed chromatography technology |
| CN108129529A (en) * | 2018-01-12 | 2018-06-08 | 厦门大学 | A kind of method for isolating and purifying stevia rebaudianum sugar monomer |
-
2018
- 2018-12-27 CN CN201811609443.5A patent/CN109785908A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9534262B2 (en) * | 2013-03-28 | 2017-01-03 | Georgia Tech Research Corporation | Methods and controllers for simulated moving bed chromatography for multicomponent separation |
| CN105985220A (en) * | 2014-11-26 | 2016-10-05 | 义守大学 | Method for purifying alcohol compound |
| CN105617714A (en) * | 2015-12-31 | 2016-06-01 | 厦门大学 | Asynchronous switching three-zone-belt simulation moving bed |
| CN106390519A (en) * | 2016-09-12 | 2017-02-15 | 华东理工大学 | Method for continuously separating aminoglutethimide racemate through multi-column simulated moving bed chromatography technology |
| CN108129529A (en) * | 2018-01-12 | 2018-06-08 | 厦门大学 | A kind of method for isolating and purifying stevia rebaudianum sugar monomer |
Non-Patent Citations (2)
| Title |
|---|
| 陈金良，姚传义，卢英华: "三区带模拟移动床分离邻香兰素与香兰素", 《厦门大学学报》 * |
| 陈金良: "三区带异步切换模拟移动床分离香兰素与邻香兰素", 《道客巴巴》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110305129A (en) * | 2019-08-01 | 2019-10-08 | 厦门大学 | The method of three zone asynchronised handover Simulation moving beds separation rutaecarpin and Rutaecarpine |
| CN111705168A (en) * | 2020-07-08 | 2020-09-25 | 江南大学 | Method for purifying xylose hydrolysate by desalting with three zones with simulated moving bed |
| TWI794071B (en) * | 2022-04-01 | 2023-02-21 | 田寮生技數位科技股份有限公司 | A method of vanillin extraction and purification |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109785908A (en) | The method of three zone asynchronised handover Simulation moving beds separation vanillic aldehyde and isovanillin | |
| WO2020259565A1 (en) | Industrializable method for rapidly and efficiently extracting xanthophyll and quercetagetin | |
| CN107011308B (en) | The method of polymethoxyflavone class compound is isolated and purified from bowl mandarin orange fruit | |
| CN110483599A (en) | The separation method of flavones ingredient in a kind of manaca leaf | |
| CN105669631B (en) | A kind of potentilla plants extract and the method for therefrom separating four kinds of tanninses compounds | |
| CN105566414B (en) | The method that four kinds of flavone glycosides are isolated and purified from waxberry flesh | |
| Carmali et al. | Recovery of lupanine from Lupinus albus L. leaching waters | |
| CN101190909B (en) | Method for preparing four kinds of theaflavin monomer | |
| CN104356105B (en) | A kind of preparation method of EGCG | |
| CN102010387A (en) | Method for purifying orlistat | |
| CN109021040A (en) | A kind of continuous chromatography isolation and purification method of Gardenoside | |
| CN108084007A (en) | A kind of method of Simulated Moving Bed Chromatography separation Co-Q10 and CoQ1 1 | |
| CN100484931C (en) | Isolation preparing process for a plurality of isoflavones components in astragalus root | |
| CN101024609B (en) | Process for producing shikimic acid | |
| CN105771311B (en) | A method of mixed extract is purified using dynamic axial compression column | |
| CN106986851B (en) | A kind of preparation method of high purity EGCG | |
| CN102002029B (en) | Method for separating and extracting isoflavone by simulated moving bed adsorption | |
| CN101070335A (en) | Process for preparing high-purity gentiopicrin | |
| CN108179169B (en) | A kind of method that microbe transformation method prepares damulin A | |
| CN104672066A (en) | Method for separating and purifying pterostilbene from blueberries | |
| CN110559688A (en) | Method for separating isomers of oleanolic acid and ursolic acid | |
| CN110066306A (en) | A kind of Isorhamnetin-3-O-neohespeidoside preparative liquid chromatography separation method | |
| CN108586435A (en) | The preparation method of Echinulin | |
| CN104230872B (en) | A kind of process for separation and purification of d-Delta-Tocopherol | |
| CN110305129B (en) | Method for separating evodiamine and rutaecarpine by three-zone asynchronous switching simulated moving bed |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190521 |
|
| RJ01 | Rejection of invention patent application after publication |