CN101575531A - Method for synthesizing biodiesel by using high-speed counter-flow reactor - Google Patents

Method for synthesizing biodiesel by using high-speed counter-flow reactor Download PDF

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Publication number
CN101575531A
CN101575531A CNA2008101060042A CN200810106004A CN101575531A CN 101575531 A CN101575531 A CN 101575531A CN A2008101060042 A CNA2008101060042 A CN A2008101060042A CN 200810106004 A CN200810106004 A CN 200810106004A CN 101575531 A CN101575531 A CN 101575531A
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phase
enzyme
flow reactor
speed counter
liquid
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张晓鸥
顾铭
苏志国
欧阳藩
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Institute of Process Engineering of CAS
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Institute of Process Engineering of CAS
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

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  • Apparatus Associated With Microorganisms And Enzymes (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention relates to a method for synthesizing biodiesel by using high-speed counter-flow reactor. A reaction system has liquid/liquid two phases or liquid/liquid/solid three phases; when the reaction system has two phases, a solution of free enzyme (a water phase) forms a fixed phase or moving phase; and when the reaction system has three phases, fixed enzyme and water (a moving liquid phase) form the fixed phase or moving phase. On one hand, the two liquid phases are mixed and clarified at high frequency under the coaction of an acting force which periodically changes in intensity and direction and is generated by the planetary centrifugal motion of a spirally wound pipe columns and a force periodically changing in radial and axial directions in a corrugated pipe to strengthen the contact of the enzyme or microorganisms with a fatty acid substrate and a transmission speed and improve the conversion rate of the substrate; and on the other hand, the selection of an operation mode and the coupling of an extraction process and a back extraction process reduce enzyme activity suppression caused by high-concentration substrate or product accumulation, speed up reaction and improve the conversion rate of the substrate. Meanwhile, the invention provides improvement on apparatus during the implementation of scale-up production.

Description

A kind of method of utilizing the high-speed counter-flow reactor biodiesel synthesis
Technical field
The present invention relates to a kind of method of utilizing the high-speed counter-flow reactor biodiesel synthesis.
Background technology
(high speed counter current chromatography is by Yoichiro doctor Ito of NIH (NIH) a kind of chromatographic separation and purification technology in the invention eighties in last century HSCCC) to high speed adverse current chromatogram.This chromatogram arrangement is wound in spiral tube by light and handy polyfluortetraethylene pipe, there is not the solid support thing in the pipe, spiral tube is in rotation, hollow shaft rotation around angled with the axis of rotation (parallel, vertical or angled), produced periodically variable centrifuge field, the two-phase liquid in the pipe constantly mixes, clarifies under the effect of Archimedean screw power, wherein one is kept mutually, and another is constantly released from the end of pipeline by pump system as moving phase.Target product and impurity is in two alternate distribution of liquid/liquid, realizes separating according to the difference of partition ratio.High speed adverse current chromatogram has been widely used in every field such as biology, medicine, agricultural, the energy, environment, chemical industry, ocean science as a kind of separating and purifying technology at present.
High speed adverse current chromatogram separation and purification device is used as the biocatalytic reaction device, has following advantage:
1) simple in structure, be convenient to amplify.High speed adverse current chromatogram is liquid/liquid distribution system, there is not the solid support thing, with light and handy soft spiral blank pipe as reaction column, stationary phase and moving phase all are fluids, just reaction can be amplified as long as prolong spiral tube simply, also can increase caliber in addition, can improve the retention rate of stationary phase like this, preparation type high-speed counter-current equipment is by innovation, and caliber can reach 20mm, the general 0.3m of equipment volume 3, maximum also less than 2m 3, help multimachine production, expand the scale of production;
2) feeding manner is flexible, and rate of mass transfer is fast.The raw material thing does not need strict pre-treatment, can handle the material of band suspended solid, reactor is one group of spiral blank pipe, no internals, the mixing of phase and clarification are that the strong vibration of leaning on the strong centrifugal force of axial flow and radially cycle variation to produce two-way multi-angle realizes, rate of mass transfer is fast and be easy to by flow rate of mobile phase and spiral tube speed adjustment, two-phase has four import and export, can conveniently form adverse current, cocurrent cooling operation, stationary phase can be selected mutually light or heavy phase, therefore can multiplely make up in the operation, handiness is big;
3) do not have machinery and stir no solid phase carrier.Do not have churned mechanically reactor and be applied to enzymic catalytic reaction, help prolonging the life-span of enzyme, keep enzyme to live, and do not have solid phase carrier, avoided sample to be separated to contact and issuable chemical modification and irreversible adsorption, thereby reduced cost with solid phase carrier.
Biofuel is a kind of form of biomass energy, its main component is the low-carbon alkyl ester mixture of the higher fatty acid that is transformed by animal-plant oil, close with its physical and chemical performance and petrifaction diesel, and can directly replace petrifaction diesel or dissolve each other with arbitrary proportion with common petrifaction diesel replacing petrifaction diesel to use and gaining the name.Compare with the petrifaction diesel that is obtained from oil, the biofuel that is obtained from animal-plant oil has environmental friendliness, in use reduces many-sided environmental protection advantages such as bazardous waste discharging, the oil that in addition accounts for world energy consumption amount 40% is very limited because of stock number, cause crude oil and the jumbo fluctuation of fuel oil market price, biofuel is as a kind of high-quality biomass renewable energy source, since nineteen nineties, worldwide form the research and development upsurge, and formed fast-developing industry.Along with development of biology, adopt the technology of biological enzyme agent biodiesel synthesis to obtain research and development in recent years, and biological enzyme technology also can't reach the industrialization realistic scale, and needs are studied new enzyme and do not used chemical catalyst or use the biofuel greenization production technology that can reclaim catalyzer fully.The such extensive centralized production of development biofuel impossible image-stone oil industry, reason is that resource is various wide with distribution area, raw material is collected processing and is waited cost high relatively, therefore there is report to adopt unification of the motherland standard (China is WKG working also) abroad, disperse to produce, in addition can farm or the individual be productive unit, high-speed counter-flow reactor has been amplified to certain scale now, can reach 20mm as caliber, this will be an excellent popularization unit.Utilize high-speed counter-flow reactor to carry out biofuel synthetic report at present as yet.
Summary of the invention
The objective of the invention is to utilize the liquid of high-speed counter-flow reactor/liquid two-phase to distribute (or liquid/liquid/liquid, liquid/liquid/heterogeneous distribution such as solid, liquid/liquid/gas), for the building-up reactions of biofuel provides a place, be coupled the simultaneously separation and purification process of product is developed continuously, biofuel synthetic production technique efficiently.By two alternate high-frequency mixing and the clarifications of liquid/liquid, increase the contact area of enzyme or microorganism and lipid acid substrate on the one hand, improve substrate and product in two alternate mass-transfer efficiency; The coupling of selection by operating method and extraction, back extraction process on the other hand reduces enzyme that the accumulation of high concentration substrate or product caused and lives and suppress, and accelerated reaction improves transformation efficiency.
When the present invention made industrial unit in amplification, caliber need be amplified to 10～20mm, but high-speed counter-current chromatograph is all used all footpath straight tubes at present, and then disengaging time is long to increase pipe range, increases diameter the rotary drum rotating speed is reduced, and resolving power reduces.Technical scale part among the present invention adopts the coiling of corrugated special pipe, increases periodically variable radial and axial power in the pipe, increase by two mixing that contact, reinforcing mass transfer, the microcosmic residence time of increase moving phase, improve the column efficiency of unit volume, make to amplify to become a reality.
The objective of the invention is to realize by the following technical solutions:
In high-speed counter-flow reactor, carry out the synthetic of biofuel, make biological catalyst if adopt the enzyme of free state, then reaction system is a two-phase, if adopt immobilized enzyme, microorganism as biological catalyst or by the non-water enzymic catalytic reaction of reverse micelle bag quilt, then reaction system is a three-phase, and enzyme is in the performance katalysis of phase interface place.By adjusting the mode of connection of four import and export and pump system, moving phase and stationary phase reversible flow also can and flow, and by adjusting the sense of rotation and the rotating speed of spiral tube, mutually light and heavy phase can be as stationary phase or moving phase, temperature of reaction is operated very flexible by the regulation and control of water-bath chuck.
Concrete steps are as follows:
(1) resolvase solution, solid-support immobilized enzyme suspension, micelle or reverse micelle bag are by the preparation of enzyme liquid;
(2) according to the moiety and the phase-splitting characteristics of biofuel building-up reactions system, determine the composition of stationary phase and moving phase, the easy degree of the viscosity of the dissolving situation of form, substrate and the product that the factor of need considering comprises enzyme in water and organic phase, two-phase fluid and separation time, operation etc.;
(3) prepare stationary phase and the moving phase that does not add zymin respectively, ultrasonic degas 15min, leave standstill more than the 30min, if between stationary phase and the moving phase certain ratio of dissolving each other is arranged, then in advance in separating funnel with the two-phase mixing, more than the standing demix 2h, tell light phase and heavy phase, and then ultrasonic degas is standby;
(4) zymin is joined selected contain enzyme mutually in, be uniformly dispersed, the addition of zymin is lived according to enzyme and is adjusted;
(5) by constant flow pump the flow velocity of stationary phase with 8.0～10.0mL/min pumped in the spiral tube of high-speed counter-flow reactor, full until pump, and from the outlet outflow;
(6) beginning high speed rotating spiral tube, the phase time that gently fixes mutually is rotated in the forward, the heavy phase phase time reverse rotation that fixes, rotating speed 300～900rpm carries out the rotating speed adjustment according to stationary phase reservation situation;
(7) go into moving phase with the flow pump of 0.5～2.0mL/min, keep situation and finish the needed reaction times of target conversion according to stationary phase and carry out the flow rate of mobile phase adjustment;
(8) for solving the limited problem of existing installation theoretical plate number, moving phase adopts reflux operation;
(9) behind the reaction certain hour, extract or back extraction, perhaps directly collect the liquid that contains product, volatilize solvent or remove moisture, obtain product and also carry out the transformation efficiency analysis according to the needs of technology.
The method of high-speed counter-flow reactor biodiesel synthesis provided by the invention is applicable to and utilizes various free or immobilized enzymes, from monoglyceride, triglyceride and longer chain fatty acid and the low-carbon alcohol biodiesel synthesis of animal-plant oil and conversion thereof.
The method of high-speed counter-flow reactor biodiesel synthesis provided by the invention, compare with reaction units such as conventional mechanical stirring, fluidization, air lift type, liquid lift-types, have and simple in structurely be easy to that scale is amplified, feeding manner is flexible, rate of mass transfer is fast, enzyme is lived and keep higher and advantage such as the substrate irreversible adsorption is low.Operation has been simplified in reaction process and sepn process coupling, and has reduced high concentration substrate and the inhibition of product to enzyme work, has improved transformation efficiency.
Embodiment
Embodiment 1, in high-speed counter-flow reactor, carry out the reaction of lipase-catalyzed oleic acid and methyl alcohol biodiesel synthesis, on be stationary phase mutually.
Equipment and instrument: high-speed counter-flow reactor, straight tube, bore 5.0mm, column volume 300mL
Bath temperature: 40 ℃
Reaction system: (pH 7.8,0.02M Na for sherwood oil-phosphoric acid buffer 2HPO 4/ NaH 2PO 4) system NOVO Lipozyme TL 100L, 30,000U/mL enzyme liquid
Last phase composite: 350g oleic acid and 50mL methyl alcohol are dissolved in 1L sherwood oil (60～90 ℃).
Following phase composite: 1mL enzyme liquid is dissolved in the 1L phosphoric acid buffer, and (pH 7.8,0.02MNa 2HPO 4/ NaH 2PO 4).
Moving phase adopts reflux operation, improves transformation efficiency.
Operation method:
By the constant flow pump system, use to fix with the 8.0mL/min flow velocity and be full of the reaction column jecket mutually, begin to rotate the spiral tube in the main frame then, be rotated in the forward 850rpm, pump into down phase moving phase with the 1.0mL/min flow velocity.Collection exports effusive reaction mixture from spiral tube, standing demix, and every 2h tells containing enzyme moving phase mutually under effusive, is back to reactor inlet, continues to recycle.
Stop the main frame rotation behind the reaction 24h, termination of pumping blows out all reaction mixtures in the spiral tube with nitrogen, and standing demix detects the oleic amount that reduces in the phase organic phase that goes up with the titrating method of NaOH, calculates transformation efficiency.The rate of recovery that water lipase enzyme is lived before and after the olive oil hydrolysis method detection reaction.
Operation result:
On fix and keep 55～60% mutually, 24h esterification yield 76%, enzyme are lived and are reclaimed 92%.
Embodiment 2, carrying out the reaction of lipase-catalyzed oleic acid and methyl alcohol biodiesel synthesis in high-speed counter-flow reactor, is stationary phase down mutually.
Equipment and instrument: high-speed counter-flow reactor, straight tube, bore 5.0mm, column volume 300mL
Bath temperature: 40 ℃
Reaction system: (pH 7.8,0.02M Na for sherwood oil-phosphoric acid buffer 2HPO 4/ NaH 2PO 4) system NOVO Lipozyme TL 100L, 30,000U/mL enzyme liquid
Last phase composite: 350g oleic acid and 50mL methyl alcohol are dissolved in 1L sherwood oil (60～90 ℃).
Following phase composite: 1mL enzyme liquid is dissolved in the 1L phosphoric acid buffer, and (pH 7.8,0.02MNa 2HPO 4/ NaH 2PO 4).
Moving phase adopts reflux operation, improves the utilization ratio of enzyme, reduces the consumption of enzyme.
Operation method:
By the constant flow pump system, with the 8.0mL/min flow velocity with under fix and be full of the reaction column jecket mutually, begin to rotate the spiral tube in the main frame then, reverse rotation 750rpm pumps into phase moving phase with the 0.8mL/min flow velocity.Treat that the spiral tube outlet has outflow mutually on the successive, directly effluent liquid is back to reactor inlet, improve reaction conversion ratio, every 2h, from the reactor outlet moving phase sample that takes a morsel, the oleic amount that reduces with the titrating method monitoring of NaOH, calculate transformation efficiency, thus the monitoring reaction process.
Stop the main frame rotation behind the reaction 24h, termination of pumping blows out all reaction mixtures in the spiral tube with nitrogen, and standing demix detects the oleic amount that reduces in the phase organic phase that goes up with the titrating method of NaOH, calculates total conversion rate.The rate of recovery that water lipase enzyme is lived before and after the olive oil hydrolysis method detection reaction.
Operation result:
Under fix and keep 34～37% mutually, esterification yield 11% behind first 2h, the total esterification yield 85% of 24h, enzyme are lived and are reclaimed 96%.
Embodiment 3, in high-speed counter-flow reactor, carry out the reaction of fixed lipase catalyzed palmitinic acid and ethanol biodiesel synthesis, on be stationary phase mutually.
Equipment and instrument: high-speed counter-flow reactor, corrugated tube, bore 10.0mm, column volume 350mL
Bath temperature: 40 ℃
Reaction system: (pH 7.8,0.02M Na for octane-iso-phosphoric acid buffer 2HPO 4/ NaH 2PO 4) system Novyzym 4352,500U/g immobilized enzyme particle, particle diameter 0.3mm
Last phase composite: acid of 200g palmitinic acid and 30mL ethanol are dissolved in the 1L octane-iso.
Following phase composite: the 4.0g immobilized enzyme particle is suspended in the 1L phosphoric acid buffer, and (pH 7.8,0.02MNa 2HPO 4/ NaH 2PO 4).
Moving phase adopts reflux operation, improves transformation efficiency.
Operation method:
By the constant flow pump system, use to fix with the 8.0mL/min flow velocity and be full of the reaction column jecket mutually, begin to rotate the spiral tube in the main frame then, be rotated in the forward 800rpm, pump into down phase moving phase with the 0.5mL/min flow velocity.Collection exports effusive reaction mixture from spiral tube, standing demix, and every 2h tells containing enzyme moving phase mutually under effusive, is back to reactor inlet, continues to recycle.
Stop the main frame rotation behind the reaction 24h, termination of pumping blows out all reaction mixtures in the spiral tube with nitrogen, and standing demix detects the amount that goes up the palmitinic acid acid that reduces in the phase organic phase with the titrating method of NaOH, calculates transformation efficiency.The rate of recovery that water lipase enzyme is lived before and after the olive oil hydrolysis method detection reaction.
Operation result:
On fix and keep 64～69% mutually, 24h esterification yield 80%, enzyme are lived and are reclaimed 96%.
Embodiment 4, carrying out the reaction of fixed lipase catalyzed palmitinic acid and ethanol biodiesel synthesis in high-speed counter-flow reactor, is stationary phase down mutually.
Equipment and instrument: high-speed counter-flow reactor, corrugated tube, bore 10.0mm, column volume 350mL
Bath temperature: 40 ℃
Reaction system: (pH 7.8,0.02M Na for octane-iso-phosphoric acid buffer 2HPO 4/ NaH 2PO 4) system Novyzym 4352,500U/g immobilized enzyme particle, particle diameter 0.3mm
Last phase composite: acid of 200g palmitinic acid and 30mL ethanol are dissolved in the 1L octane-iso.
Following phase composite: the 4.0g immobilized enzyme particle is suspended in the 1L phosphoric acid buffer, and (pH 7.8,0.02MNa 2HPO 4/ NaH 2PO 4).
Moving phase adopts reflux operation, improves the utilization ratio of enzyme, reduces the consumption of enzyme.
Operation method:
By the constant flow pump system, with the 8.0mL/min flow velocity with under fix and be full of the reaction column jecket mutually, begin to rotate the spiral tube in the main frame then, reverse rotation 700rpm pumps into phase moving phase with the 0.5mL/min flow velocity.Treat that the spiral tube outlet has outflow mutually on the successive, directly effluent liquid is back to reactor inlet, improve reaction conversion ratio, every 2h, from the reactor outlet moving phase sample that takes a morsel, the amount of the palmitinic acid that reduces with the titrating method monitoring of NaOH, calculate transformation efficiency, thus the monitoring reaction process.
Stop the main frame rotation behind the reaction 24h, termination of pumping blows out all reaction mixtures in the spiral tube with nitrogen, and standing demix detects the amount that goes up the palmitinic acid that reduces in the phase organic phase with the titrating method of NaOH, calculates total conversion rate.The rate of recovery that water lipase enzyme is lived before and after the olive oil hydrolysis method detection reaction.
Operation result:
Under fix and keep 30～33% mutually, esterification yield 8% behind first 2h, the total esterification yield 92% of 24h, enzyme are lived and are reclaimed 99%.

Claims (8)

1. a method of utilizing the high-speed counter-flow reactor biodiesel synthesis comprises the steps:
(1) resolvase solution, solid-support immobilized enzyme suspension, micelle or reverse micelle bag are by the preparation of enzyme liquid;
(2) according to the moiety and the phase-splitting characteristics of biofuel building-up reactions system, determine the composition of stationary phase and moving phase, easy degree of the viscosity of the dissolving situation of form, substrate and the product that comprises enzyme in water and organic phase, two-phase fluid and separation time, operation etc.;
(3) prepare stationary phase and the moving phase that does not add zymin respectively, ultrasonic degas 15min, leave standstill more than the 30min, for the solvent that certain ratio of dissolving each other is arranged between stationary phase and the moving phase, in separating funnel with the two-phase mixing, more than the standing demix 2h, tell light phase and heavy phase, and then ultrasonic degas is standby;
(4) zymin is joined selected contain enzyme mutually in, be uniformly dispersed, live according to enzyme and adjust the zymin addition;
(5) by constant flow pump the flow velocity of stationary phase with 8.0～10.0mL/min pumped in the spiral tube of high-speed counter-flow reactor, full until pump, and from the outlet outflow;
(6) start the high speed rotating spiral tube, the phase time that gently fixes mutually is rotated in the forward, the heavy phase phase time reverse rotation that fixes, and rotating speed 300～900rpm carries out the rotating speed adjustment according to stationary phase reservation situation;
(7) go into moving phase with the flow pump of 0.5～2.0mL/min, keep situation and finish the needed reaction times adjustment of target conversion flow rate of mobile phase according to stationary phase;
(8) for solving the limited problem of existing installation theoretical plate number, moving phase adopts reflux operation;
(9) behind the reaction certain hour, extraction or back extraction or the direct liquid that contains product of collecting volatilize solvent or remove moisture, obtain product and also carry out the transformation efficiency analysis.
2. a kind of according to claim 1 method of utilizing the high-speed counter-flow reactor biodiesel synthesis is characterized in that the column jecket type of high-speed counter-flow reactor comprises straight tube, sinuflo tube, spiral tube and cross section special-shaped pipe etc.
3. a kind of according to claim 1 method of utilizing the high-speed counter-flow reactor biodiesel synthesis is characterized in that the column jecket internal diameter 2.6～20.0mm of high-speed counter-flow reactor.
4. a kind of according to claim 1 method of utilizing the high-speed counter-flow reactor biodiesel synthesis is characterized in that step 2) type of described biofuel building-up reactions comprises esterification, transesterification reaction.
5. a kind of according to claim 1 method of utilizing the high-speed counter-flow reactor biodiesel synthesis is characterized in that step 2) moiety of described reaction substrate triglyceride, monoglyceride, longer chain fatty acid and the various low-carbon alcohol (methyl alcohol, ethanol, propyl alcohol etc.) that comprise various animal-plant oil, be converted by animal-plant oil.
6. a kind of according to claim 1 method of utilizing the high-speed counter-flow reactor biodiesel synthesis is characterized in that step 2) other solvent of described composition stationary phase and moving phase comprises organic solvents commonly used such as various aqueous buffer solutions, sherwood oil, normal hexane, normal heptane, octane-iso, hexanaphthene.
7. a kind of according to claim 1 method of utilizing the high-speed counter-flow reactor biodiesel synthesis is characterized in that step 2) described catalysis comprises lipase, the esterase of various free states or immobilization (solid carrier, micelle, reverse micelle) with enzyme.
8. a kind of according to claim 1 method of utilizing the high-speed counter-flow reactor biodiesel synthesis is characterized in that the described transformation efficiency detection method of step 9) comprises acid base titration, gas chromatographic analysis, liquid-phase chromatographic analysis etc.
CNA2008101060042A 2008-05-07 2008-05-07 Method for synthesizing biodiesel by using high-speed counter-flow reactor Pending CN101575531A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109321609A (en) * 2018-10-29 2019-02-12 南京工业大学 Method for preparing R-mandelic acid by using microchannel reaction device
CN109750075A (en) * 2019-01-25 2019-05-14 山东省分析测试中心 A kind of method for transformation of rare ginsenoside
CN109971801A (en) * 2018-11-28 2019-07-05 山东省分析测试中心 Application of the high-speed counter-current chromatograph in the conversion of glycoside ingredients Biogenic

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109321609A (en) * 2018-10-29 2019-02-12 南京工业大学 Method for preparing R-mandelic acid by using microchannel reaction device
CN109971801A (en) * 2018-11-28 2019-07-05 山东省分析测试中心 Application of the high-speed counter-current chromatograph in the conversion of glycoside ingredients Biogenic
WO2020107629A1 (en) * 2018-11-28 2020-06-04 山东省分析测试中心 Use of high-speed countercurrent chromatograph in bioconversion of glycoside component
CN109750075A (en) * 2019-01-25 2019-05-14 山东省分析测试中心 A kind of method for transformation of rare ginsenoside
CN109750075B (en) * 2019-01-25 2020-12-01 山东省分析测试中心 Method for converting rare ginsenoside

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Application publication date: 20091111