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

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.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0027-B95E-F Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002B-3656-2
Genre: Journal Article

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 Creators:
Horvath, Zoltan1, Author              
Horosanskaia, Elena1, 2, Author              
Lee, Ju Weon1, Author              
Lorenz, Heike1, Author              
Gilmore, Kerry3, Author              
Seeberger, Peter H.3, 4, Author              
Seidel-Morgenstern, Andreas1, 2, Author              
Affiliations:
1Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society, ou_1738150              
2Otto-von-Guericke-Universität Magdeburg, External Organizations, ou_1738156              
3Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_persistent22              
4Institute for Chemistry and Biochemistry, Free University Berlin, Berlin, Germany, ou_persistent22              

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 Abstract: 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.

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Language(s): eng - English
 Dates: 2015
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1021/acs.oprd.5b00048
Other: 5/15
 Degree: -

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Title: Organic Process Research & Development
  Other : Org. Process Res. Dev.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 19 (6) Sequence Number: - Start / End Page: 624 - 634 Identifier: Other: 1083-6160
CoNE: https://pure.mpg.de/cone/journals/resource/1083-6160