Semi-synthetic artemisinin project progress report
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1 Semi-synthetic artemisinin project progress report Dirk Pohlmann project management MPIKG and CEO ArtemiFlow GmbH , Nairobi, 1
2 SINGLET OXYGEN GENERATION Photochemical generation via photosensitizers green reagent, high atom economy photosensitizer oxygen S 1 T 1 1 O 2 hn 1260 nm 3 O 2 S 0 l=660 nm l=560 nm , Nairobi, 2
3 SCALE-UP OF PHOTOCHEMICAL REACTIONS Light intensity diminishes rapidly with path depth A = ε c d e = M -1 cm , Nairobi, 3
4 L A M P L A M P SCALE-UP OF PHOTOCHEMICAL REACTIONS Decreasing path length: high irradiation intensity Continuous removal of product: prevention of side reactions I/I 0 l Batch Falling film Channel , Nairobi, 4
5 BENEFITS OF FLOW CHEMISTRY Small tubing: high irradiation intensity Excellent control over reaction parameters (time, temperature, mixing, pressure etc.) High surface / volume ratio control exothermic reactions Lower operating volumes safety and reagent consumption In-line analysis Ready scale-up by number-up Easy automation , Nairobi, 5
6 BIPHASIC REACTIONS High gas-liquid interfacial area: enhanced rate of mass transfer Extended pressure increases oxygen solubility Gases: Hydrogen Fluorine Carbon dioxide Carbon monoxide Singlet oxygen Triplet oxygen Ozone , Nairobi, 6
7 BIPHASIC REACTIONS Flow pattern change with gas/liquid flow rate: Plug flow Specific interfacial area (a) 3500 m 2 m -3 Slug flow Liquid phase Gas phase m 2 m -3 Annular flow Thin film of liquid m 2 m -3 Specific interfacial area in batch : 100 m 2 m -3 to 2000 m 2 m -3 Ehrfeld, W.; Hessel, V.; Löwe, H. Microreactors: New Technology for Modern Chemistry, Wiley-VCH, , Nairobi, 7
8 BIPHASIC REACTIONS increasing gas flow rate 1.1 mm tube Chen, L., Tian, Y. S., Karayiannis, T. G. Int. J. Heat Mass Transfer, 2006, 49, , Nairobi, 8
9 SEMI-SYNTHESIS Singlet oxygen reacts with dihydroartemisinic acid, further reactions mediated by acid , Nairobi, 9
10 INITIAL REACTOR 2 Pumps required: delivery of substrate solution, addition of acid 450 W medium pressure mercury lamp for photochemical step Artemisinin yield: 40%, productivity: 200 g/d High energy consumption and low yield Lèvesque, F., Seeberger, P.H. Angew. Chem. Int. Ed., 2012, 51, Lèvesque, F., Seeberger, P.H. Org. Lett., 2011, , 13, Nairobi, 10
11 INITIAL REACTOR , Nairobi, 11
12 ENERGY REQUIREMENTS Mercury lamp 450 W + chiller: 1700 W 200 g/d artemisinin: 200 kwh per kg artemisinin! improvement in energy efficiency required , Nairobi, 12
13 NEW GENERATION PHOTOREACTOR Improved setup: LED lamp matches spectrum of photosensitizer High energy efficiency Less energy required for cooling small footprint 1to per year for industry version Artemisinin yield up to 65% Larger reactor possible , Nairobi, 13
14 NEW GENERATION PHOTOREACTOR Photoreactor: cheap FEP-tubing wrapped around glass/pc plate 7.5 ml volume high transmission of light chemically resistant can be immersed in cooling liquid for thermosetting , Nairobi, 14
15 CONTINUOUS ONE-POT PROCESS Simple setup, small footprint of system , Nairobi, 15
16 YIELD Yield of 65% can be achieved, simplifying purification NMR of crude: mainly artemisinin main side products known: , Nairobi, 16
17 PURIFICATION Recrystallization yields artemisinin of high purity No impurities detected by NMR and HPLC with MS/ELSD detector Minor impurity peaks with UV detection (210 nm) HPLC - UV detection NMR , Nairobi, 17
18 CONTINUOUS PURIFICATION Continuous purification benefical single continuous process yielding pure product Evaluation of two processes: continuous crystallization Simulated Moving Bed (SMB) chromatography Juza, M., Mazzotti, M., Morbidelli, M., Trends Biotechnol. 2000, 18, , Nairobi, 18
19 STARTING MATERIAL Dihydroartemisinic acid present in plant Unused waste compound from extraction process Mother liquor remaining from artemisinin extraction: ~ 8% DHAA (results provided by AnalytiCon) Basic extract: 42% DHAA, can be converted to artemisinin without purification , Nairobi, 19
20 COMPANY ArtemiFlow GmbH, founded in November 2012 Personnel: 3 Prof. Peter Seeberger CSO: Dr. Daniel Kopetzki (Junior Scientist of the Year, Brandenburg 2012) CEO: Dirk Pohlmann Milestones for ArtemiFlow GmbH: funding defined business plan written (waiting for more lab data) clients identified Development company for industry prototype indentified cost estimates known , Nairobi, 20
21 DHAA Artesunate Artemether , Nairobi, 21
22 PLANTS Which plants do we need? First answers: no turbos? young plants up to 3 months fresh dried cheap seeds? Or new seeds=combined ART and DHAA content? max combination of Artimisinin +DHAA after 3 months 3 harvests per year = breaking the pork cycle , Nairobi, 22
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