Potentielle Anwendungen der Flüssig-Flüssig-Chromatographie in der Lebensmittelindustrie
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1 Potentielle Anwendungen der Flüssig-Flüssig-Chromatographie in der Lebensmittelindustrie Mirjana Minceva Assistant Professorship Biothermodynamics Wissenschaftszentrum Weihenstephan (WZW) Technische Universität München 15. FEI-Kooperationsforum Bonn, 26. April
2 OUTLINE 1. Principles of liquid-liquid chromatography* 2. Ongoing research in our group 3. Potential applications 4. Conclusions * Counter-Current Chromatography (CCC) or Centrifugal Partition Chromatography (CPC) 2
3 LIQUID-LIQUID CHROMATOGRAPHY* Liquid-Liquid chromatography partitioning + stationary phase Liquid-Liquid Extraction partitioning Liquid-Solid Chromatography stationary phase * Centrifugal Partition Chromatography (CPC) oder Countercurrent Chromatography (CCC) 3
4 PRINCIPLE OF LIQUID-LIQUID CHROMATOGRAPHY (LLC) Detector Pump 2 Pump 1 Injection valve LLC Centrifuge Mobile phase (MP) Stationary Phase (SP) Solvent 1 LLC Centrifuge = Column Hardware 2.5 Solvent 2 Solvent 3 Detector signal Best operating region 0.4 Ki 2.5 Partition coefficient: K i c c SP i MP i selection of a biphasic liquid system = selection of the mobile and stationary phase V R (cm 3 ) V=time flow rate
5 THE COLUMN IN LIQUID-LIQUID CHROMATOGRAPHY Hydrodynamic machines (Counter-current chromatography-ccc) with 2 axes of rotation Hydrostatic machines (Centrifugal partition chromatography-cpc) with 1 axis of rotation Column volume: 20 ml - 20 l 5
6 THE COLUMN IN LIQUID-LIQUID CHROMATOGRAPHY Hydrodynamic machines (Counter-current chromatography-ccc) with 2 axes of rotation Hydrostatic machines (Centrifugal partition chromatography-cpc) with 1 axis of rotation Column volume: 20 ml - 20 l 6
7 THE COLUMN IN LIQUID-LIQUID CHROMATOGRAPHY Dynamic extractions, UK Hydrodynamic (CCC) apparatus 18 l column Armen Instruments, France Hydrostatic (CPC) apparatus 12.5 l column Typical production capacity: kg/day 7
8 CONTINOUS LIQUID-LIQUID CHROMATOGRAPHY Cyclic process One cycle (Ascending step + Descending step) Ascending step A + B B Descending step A column 1 column 2 column 1 column 2 A + B B A B B B B A B A B A B A A A U - Upper phase L - Lower phase Feed is introduced continuously; Products are collected sequentially Sequential centrifugal partition chromatography (scpc) 8
9 KEY FEATURES OF THE TECHNOLOGY The user prepares not only the mobile phase but the stationary phase as well The nearly limitless choice of solvents makes the technology extremely versatile and allows for the creation of tailor-made mobile and stationary phases The liquid stationary phase occupies 60-90% of the column volume High sample loading capacity Complete sample recovery (no irreversible adsorption) Low solvent consumption compared to HPLC Both liquid phases can be used as the stationary phase and their roles can be switched during the separation run Easy and predictable scale-up 9
10 SCIENTIFIC PROGRESS Scientific paper published each year 90% of the applications are separations of natural products First production-scale units in the early 2000s Alkaloids Flavonoids Terpenes Tannins Saponins Chlorophylls Carotenoids Anthraquinones Phenolic compounds Fat soluble vitamins Phospholipids Mono/Oligo-saccharides Lignans Antibiotics Amino acids Peptides Proteins.. 10
11 OUTLINE 1. Principles of liquid-liquid chromatography* 2. Ongoing research in our group 3. Potential applications 4. Conclusions 11
12 EQIUPMENT AVAILABLE IN OUR GROUP 1. Lab scale hydrodynamic CCC unit (with 20 ml column) separation method development 2. Preparative hydrostatic CPC unit (with 250 ml column) suitable for extraction and separation of biomolecules (peptides, proteins, DNA, RNA) 3. Continuous hydrostatic CPC unit (with two 125 ml columns) continuous separation of binary mixtures and fractionation of multicomponent mixtures 12
13 SEPARATION EXAMPLES FROM OUR LAB Chlorophylls Capsaicinoids Beta acids healthline.com Tocopherols Carotenoids Benzenediols
14 SEPARATION OF BETA ACIDS Beta acids from hops (total amount 2-10 %) Name Residual Content / % pk s Colupulon (Co) -CH(CH₃)₂ n-lupulon (n) -CH₂CH(CH₃)₂ Adlupulon (Ad) -CH(CH₃)CH₂CH₃ Source: Wilson(2012): Hops and Beer Bitter taste in beer, antidepressant, anticarcinogenic, antimicrobial Biphasic system: Toluol : (0.2 M DEA in Water/Methanol (80/20 v/v), ph = 9.75 adjusted with H 3 PO 4 ) = 1:2 (v/v) Colupulon n-lupulon Adlupulon Collaboration with Prof. Kristina Friedland, Uni. Erlangen 14
15 SEPARATION OF CHLOROPHYLLS Chlorophyll a Chlorophyll b Chlorophyll a Chlorophyll b Chlorophyll a Chlorophyll b Biphasic system: heptane/ethanol/acetonitrile/water = 10:8:1:1 (v/v) Collaboration with Prof. Stefan Berger, Uni. Leipzig 15
16 SEPARATION OF CAPSAICINOIDS Product 1 Product 2 Capsaicin Dihydrocapsaicin Dihydrocapsaicin 1700 rpm Capsaicin Continuous separation J. Goll, A. Frey, M. Minceva J. Chromatogr. A, 1284 (2013)
17 RESEARCH IN FOCUS 1. A priori screening and selection of biphasic solvent systems 2. Model-based design of liquid-liquid separation processes 3. Alternative operation modes for multicomponent mixtures (extraction, fractionation and separation) 4. Novel biphasic liquid systems with ionic liquids and deep eutectic solvents 17
18 OUTLINE 1. Principles of liquid-liquid chromatography* 2. Ongoing research in our group 3. Potential applications 4. Conclusions 18
19 POSSIBLE APPLICATIONS Raw materials High added value compounds? Process CCC/ CPC Where in the process? - after high-throughput low-selective separation steps: extraction, precipitation, membrane separations - replace high cost chromatographic steps Products CCC/CPC New product Waste High added value compounds? CCC/CPC New product Possible application fields: - food additives, functional foods, dietary supplement, (bio-)pharmaceuticals and cosmetics 19
20 CONCLUSIONS 1. Liquid-liquid chromatography is a highly selective and versatile separation tool 2. Separation of compounds with similar molecular structure possible 3. Typical production capacity in a single unit is 1 g - 1 kg per day 4. Continuous operation possible 5. Model-based process design applicable 20
21 M.Sc. Raena Morley M.Sc. Franziska Bezold M.Sc. Simon Röhrer Dipl.-Ing. Johannes Goll M.Sc. Martin Hübner web: 21
22 PUBLICATIONS 1. Roehrer S., Bezold F., García E. M., Minceva M. Deep Eutectic Solvents in Countercurrent and Centrifugal Partition Chromatography, Journal of Chromatography A, 2016, 1434, Goll J., Audo G., Minceva M. Comparison of twin-cell centrifugal partition chromatographic columns with different cell volume, Journal of Chromatography A, 2015, 1406, Bezold F., Goll J., Minceva M. Study of the applicability of non-conventional aqueous two-phase systems in counter-current and centrifugal partition chromatography, Journal of Chromatography A, 2015, 1388, Frey A., Hopmann E., Minceva M. Selection of Biphasic Liquid Systems in Liquid-Liquid Chromatography Using Predictive Thermodynamic Models, Chemical Engineering & Technology, 2014, 37 (10) J. Goll, A. Frey, M. Minceva, Study of the separation limits of continuous solid support free liquid-liquid chromatography: Separation of capsaicin and dihydrocapsaicin by centrifugal partition chromatography, Journal of Chromatography A, 1284, 59-68, J. Völkl, W. Arlt, M. Minceva Theoretical study of sequential centrifugal partition chromatography AIChE J, 59 (1), , E. Hopmann, A. Frey, M. Minceva A priori selection of the mobile and stationary phase in centrifugal partition chromatography and counter-current chromatography Journal of Chromatography A, 1238, 68 76, E. Hopmann, M. Minceva Separation of a binary mixture by sequential centrifugal partition chromatography Journal of Chromatography A, 1229, , E. Hopmann, J. Goll, M. Minceva, Sequential centrifugal partition chromatography: a new continuous chromatographic technology, Chemical Engineering & Technology., 35 (1), 72-82, E. Hopmann, W. Arlt, M. Minceva Solvent system selection in counter-current chromatography using conductor-like screening model for real solvents Journal of Chromatography A, 1218 (2) ,
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