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Crystallization-Induced Deracemization: Experiments and Modeling

[Image: see text] Inspired by deracemization via temperature cycles, which enables the collection of crystals of the desired enantiomer from an initially racemic mixture, we focus in this work on an alternative batch process, namely crystallization-induced deracemization. This process starts with a...

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Autores principales: Bodák, Brigitta, Breveglieri, Francesca, Mazzotti, Marco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8815077/
https://www.ncbi.nlm.nih.gov/pubmed/35140549
http://dx.doi.org/10.1021/acs.cgd.1c01374
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author Bodák, Brigitta
Breveglieri, Francesca
Mazzotti, Marco
author_facet Bodák, Brigitta
Breveglieri, Francesca
Mazzotti, Marco
author_sort Bodák, Brigitta
collection PubMed
description [Image: see text] Inspired by deracemization via temperature cycles, which enables the collection of crystals of the desired enantiomer from an initially racemic mixture, we focus in this work on an alternative batch process, namely crystallization-induced deracemization. This process starts with a suspension of enantiomerically pure crystals, which undergoes a simple cooling crystallization, coupled with liquid-phase racemization. The experimental and model-based analysis of such a process, carried out here, revealed that: (i) deracemization via temperature cycles is a safe choice to operate with high enantiomeric purity, although its throughput is limited by the suspension density; (ii) if the distomer is less prone to nucleation, crystallization-induced deracemization is a simple process; however, its performance is strongly limited by the solubility; (iii) the purity achieved with crystallization-induced deracemization can be increased by utilizing large seed mass and by optimizing the cooling profile or catalyst concentration. Alternatively, the purity increases via partial dissolution of the seeds, which resembles the heating part of the deracemization process via temperature cycles.
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spelling pubmed-88150772022-02-07 Crystallization-Induced Deracemization: Experiments and Modeling Bodák, Brigitta Breveglieri, Francesca Mazzotti, Marco Cryst Growth Des [Image: see text] Inspired by deracemization via temperature cycles, which enables the collection of crystals of the desired enantiomer from an initially racemic mixture, we focus in this work on an alternative batch process, namely crystallization-induced deracemization. This process starts with a suspension of enantiomerically pure crystals, which undergoes a simple cooling crystallization, coupled with liquid-phase racemization. The experimental and model-based analysis of such a process, carried out here, revealed that: (i) deracemization via temperature cycles is a safe choice to operate with high enantiomeric purity, although its throughput is limited by the suspension density; (ii) if the distomer is less prone to nucleation, crystallization-induced deracemization is a simple process; however, its performance is strongly limited by the solubility; (iii) the purity achieved with crystallization-induced deracemization can be increased by utilizing large seed mass and by optimizing the cooling profile or catalyst concentration. Alternatively, the purity increases via partial dissolution of the seeds, which resembles the heating part of the deracemization process via temperature cycles. American Chemical Society 2022-01-06 2022-02-02 /pmc/articles/PMC8815077/ /pubmed/35140549 http://dx.doi.org/10.1021/acs.cgd.1c01374 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Bodák, Brigitta
Breveglieri, Francesca
Mazzotti, Marco
Crystallization-Induced Deracemization: Experiments and Modeling
title Crystallization-Induced Deracemization: Experiments and Modeling
title_full Crystallization-Induced Deracemization: Experiments and Modeling
title_fullStr Crystallization-Induced Deracemization: Experiments and Modeling
title_full_unstemmed Crystallization-Induced Deracemization: Experiments and Modeling
title_short Crystallization-Induced Deracemization: Experiments and Modeling
title_sort crystallization-induced deracemization: experiments and modeling
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8815077/
https://www.ncbi.nlm.nih.gov/pubmed/35140549
http://dx.doi.org/10.1021/acs.cgd.1c01374
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