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Recovery of Artemisinin from a Complex Reaction Mixture Using Continuous Chromatography and Crystallization

MPG-Autoren
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Horvath,  Zoltan
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Horosanskaia,  Elena
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
Otto-von-Guericke-Universität Magdeburg, External Organizations;

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Lee,  Ju Weon
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Lorenz,  Heike
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Gilmore,  Kerry
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;
Institute for Chemistry and Biochemistry, Free University Berlin, Berlin, Germany;

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Seidel-Morgenstern,  Andreas
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
Otto-von-Guericke-Universität Magdeburg, External Organizations;

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Zitation

Horvath, Z., Horosanskaia, E., Lee, J. W., Lorenz, H., Gilmore, K., Seeberger, P. H., et al. (2015). Recovery of Artemisinin from a Complex Reaction Mixture Using Continuous Chromatography and Crystallization. Organic Process Research & Development, 19(6), 624-634. doi:10.1021/acs.oprd.5b00048.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-0027-B95E-F
Zusammenfassung
Artemisinin, a secondary metabolite of sweet wormwood, is the basis for the production of the most effective antimalarial drugs. Since the amount of artemisinin currently produced from plants is not sufficient to treat the worldwide malaria cases, an effective semisynthetic method was developed recently that is capable of producing artemisinin from dihydroartemisinic acid (DHAA). DHAA is a byproduct obtained during the extraction of artemisinin from plant leaves. The photocatalytic reaction to convert DHAA to artemisinin can be performed continuously in a tubular reactor using toluene as a solvent. The reactor effluent contains besides artemisinin the photocatalyst (dicyanoanthracene) and several compounds that are structurally similar to artemisinin, including unreacted DHAA starting material. To isolate artemisinin from the reaction mixture, two separation techniques were applied, crystallization and chromatography. The solid obtained by seeded cooling crystallization was highly enriched in artemisinin but contained also traces of the photocatalyst. In contrast, using a variant of continuously operated multicolumn simulated moving bed (SMB) chromatography, which splits the feed into three fractions, we were able to recover efficiently the photocatalyst in the raffinate stream. The extract stream provided already almost pure artemisinin, which could be finally further purified in a simple crystallization step.