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Systematic and Model-Assisted Process Design for the Extraction and Purification of Artemisinin from Artemisia Annua L.—Part IV: Crystallization

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Systematic and Model-Assisted Process Design for the Extraction and Purification of Artemisinin from Artemisia Annua L.—Part IV: Crystallization processes Article Systematic and Model-Assisted Process Design for the Extraction and Purification of Artemisinin from Artemisia annua L.—Part IV: Crystallization Maximilian Johannes Huter, Axel Schmidt , Fabian Mestmäcker, Maximilian Sixt and Jochen Strube * Institute for Separation and Process Technology, Clausthal University of Technology, 38678 Clausthal-Zellerfeld, Germany; [email protected] (M.J.H.); [email protected] (A.S.); [email protected] (F.M.); [email protected] (M.S.) * Correspondence: [email protected]; Tel.: +49-5323-72-2355 Received: 30 August 2018; Accepted: 26 September 2018; Published: 2 October 2018 Abstract: In this study, process integration for crystallization of a priori purified Artemisia annua L. is investigated. For this total process, the integration operation boundaries and behavior of the crystals are studied. This is performed focusing on a conceptual process design study for artemisinin, aiming towards the development of a crystallization step under given parameters by process integration. At first, different crystallization systems consisting of ethanol-water or acetone-water mixtures are compared. In subsequent steps, the metastable zone width and the behavior of the crystals regarding agglomeration and breakage are checked. Furthermore, the sensitivities of process variables based on several process parameters are investigated. Additionally, the final process integration of crystallization as a combined purification and isolation step is studied. Keywords: artemisinin; conceptual process design; crystallization 1. Introduction Highly purified substances from natural sources are used to treat various diseases. In addition, the social demand continues to rise [1,2]. To obtain pure substances from plant material, several process steps are necessary. A typical process may include extraction as a capture step, followed by purification steps such as liquid-liquid extraction, chromatography and crystallization [3–6]. The whole study includes a detailed investigation of each process step, a conceptual process design and cost estimation. These aspects are divided into the following five articles: Part 0: Sixt, M.; Strube, J. Systematic and model-assisted evaluation of solvent based- for pressurized hot water extraction for the extraction of Artemisinin from Artemisia annua L. Processes 2017, 5, 86, doi:10.3390/pr5040086 [7]. Part I: Sixt, Schmidt et al. Systematic and model-assisted process design for the extraction and purification of Artemisinin from Artemisia annua L.—Part I: Conceptual process design and cost estimation. Processes 2018, 6, 161, doi:10.3390/pr6090161 [8]. Part II: Schmidt, Sixt et al. Systematic and model-assisted process design for the extraction and purification of Artemisinin from Artemisia annua L.—Part II: Model-based design of agitated and packed columns for multistage extraction and scrubbing. Processes 2018, 6, 179, doi:10.3390/pr6100179 [9]. Part III: Mestmäcker, Schmidt et al. Systematic and model-assisted process design for the extraction and purification of Artemisinin from Artemisia annua L.—Part III: Chromatographic Purification. Processes 2018, 6, 180, doi:10.3390/pr6100180 [10]. Processes 2018, 6, 181; doi:10.3390/pr6100181 www.mdpi.com/journal/processes ProcessesProcesses 2018 2018, 6, 181;, 6, 181;doi: 10.3390/pr6100181doi:10.3390/pr6100181 3 of 173 of 17 becausebecause of the of theinfluences influences of side of side components components on solubilityon solubility and and kinetics kinetics [15 –[17,26,32,42,4315–17,26,32,42,43]. With]. With the the shiftshift of the of thecrystallization crystallization step step to earlier to earlier stages stages, it becomes, it becomes more more affectable affectable by theby thevariability variability of the of the sideside component component spectrum spectrum, which, which is a issignificant a significant factor factor for forplant plant-based-based material material. For. Forthis this reason, reason, the the criticalcritical impurities impurities have have to be to determined be determined and and methods methods for batchfor batch variability variability of the of theplant plant material material have ha ve to beto usedbe used [44 ][.44 To]. crystallizeTo crystallize artemisinin artemisinin, those, those critical critical side side components components that that increase increase the thesolubility solubility havehave to be to removbe removed byed precedingby preceding unit unit operations. operations. In thisIn this study, study, the thecrystallization crystallization of a ofrtemisinin artemisinin is investigated is investigated with with a focus a focus on processon process integration integration intointo a conceptual a conceptual process process design design. Therefore,. Therefore, critical critical variables variables, boundaries, boundaries and and sensitivities sensitivities of theof the crystallizationcrystallization process process are areresearched researched, creating, creating a process a process design design space space for anfor organican organic molecule molecule out outof of a multicomponenta multicomponent mixture mixture. This. This includes includes separation separation, and, and tests tests mechanic mechanical andal and thermodynamic thermodynamic influencesinfluences with with a reduced a reduced number number of experiments of experiments. Furthermore. Furthermore, this, this study study is executed is executed focusing focusing on on the themodeling modeling of a ofrtemisinin artemisinin crystallization crystallization. For. Forthis this modeling modeling and and the thecrystallization crystallization process process itself, itself, severalseveral effects effects are areseparated separated in orderin order to createto create a predicti a predictive model.ve model. The The modeling modeling itself itself will will be be publishedProcessespublished 2018in a in,nother6, a 181nother manuscript manuscript, as ,it as would it would exceed exceed the thelimits limits of this of this paper. paper. 2 of 16 In addition,In addition, other other process process positions positions with within thein thedescribed described process process design design (see (see Figure Figure 1) are 1) aretested tested as aasPart combined a combined IV: Huter, purification purification Schmidt and et and al.isolation Systematic isolation step step in and order in model-assisted order to reduce to reduce the process thenumber number design of process of process for the steps extractionsteps and and save save and costscosts. This. This ispurification performed is performed of with Artemisinin with a focus a focus o fromn creatingonArtemisia creating a process annuaa processL.—Part design design field IV: field Crystallization. that that enables enables a (thiscontrolled a controlled article). crystallizationcrystallization with with the theaid aidof modelling of modelling. It .should It should contain contain predictive predictive particle particle size size distribution distribution and and ensureensure theA model-basedtheproduct product quality quality optimization attributes attributes forof the theof theproduct extraction product that step that are was adesiredre performeddesired in a in crystallized a in crystallized a previous product product study [41 by ][.41 the]. ThisinstituteThis should should, [ 7on]., The theon the generalone one hand concepthand, increase, increase is based the theyield on yield the of examplethe of thepharmaceutical pharmaceutical of 10-deacetylbaccatin substance substance, III,and, whichand on theon is the obtainedother other handfromhand, the,yew. thecrystals crystals The should process should become flow become sheetmore more andadjustable adjustable the target for forsubsequent component subsequent steps are steps depictedsuch such as filtering, as in filtering, Figures drying1 dryingand and2[ and 6]. formulationAformulation detailed in process general,in general, description as theseas these andsubsequent asubsequent summary steps ofsteps properties are areaffected affected are givenby bythe in the Partparticle particle 1 This size articlesize distribution distribution focusses on [25,32,41the[25,32,41 crystallization]. ]. step of this conceptual process design. FigureFigure 1. Basic 1.1. Basic process process design design for plant for plant-basedplant-based-based substances substances (LLE, (LLE,(LLE, liquid liquid-liquidliquid-liquid-liquid extraction) extraction)extraction) [8]. [[88].]. FigureFigure 2. Structure 2.2. Structure of artemisinin of artemisinin [8]. [[8].]. 2. Material2. MaterialCrystallization and and Methods Methods is a typical final purification and isolation step preparing for formulation steps of plant-based or semi-synthetical processes, e.g., artemisinin [11–23]. The crystallization step itself is 2.1.affected 2.1Raw. Raw and inandPurified various Purified Material ways, Material based on mechanical and thermodynamic influences, e.g., [24]. The main driving force for crystallization is the solid-liquid equilibrium and, therefore, the solubility of the target Raw Artemisia annua L. and purified artemisinin (CfM Oskar Tropitzsch, Markredwitz, componentRaw Artemisia in a system.annua L. This and solubility purified isartemisinin measurable (CfM viadifferent Oskar Tropitzsch, methods like Markredwitz, the isothermal Germany) are used for this study. The raw plant material is ground to approximately 1 mm with a Germany)excess methodare used orfor the this polythermal study. The raw method, plant material e.g., [25]. is ground
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