Aqueous Biphasic Hydroaminomethylation Enabled by Methylated Cyclodextrins: Sensitivity Analysis for Transfer into a Continuous Process
| Autor: | Chryslain Becquet, Kai U. Künnemann, Thomas Seidensticker, Sébastien Tilloy, Eric Monflier, Dennis Weber, Dieter Vogt |
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| Přispěvatelé: | Faculty of Chemistry and Chemical Biology, TU Dortmund University, Otto-Hahn-Straße 6, 44227 Dortmund, Germany., Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), UCCS Équipe Catalyse Supramoléculaire, Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille-Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Aqueous solution
010405 organic chemistry Renewable Energy Sustainability and the Environment [CHIM.ORGA]Chemical Sciences/Organic chemistry General Chemical Engineering chemistry.chemical_element Homogeneous catalysis General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 12. Responsible consumption 0104 chemical sciences Rhodium Catalysis chemistry Cascade reaction Scientific method Environmental Chemistry [CHIM]Chemical Sciences Amine gas treating |
| Zdroj: | ACS Sustainable Chemistry & Engineering ACS Sustainable Chemistry & Engineering, 2021, ⟨10.1021/acssuschemeng.0c07125⟩ ACS Sustainable Chemistry & Engineering, American Chemical Society, 2021, ⟨10.1021/acssuschemeng.0c07125⟩ |
| ISSN: | 2168-0485 |
| Popis: | International audience; Hydroaminomethylation (HAM) is a highly efficient homogeneously catalyzed autotandem reaction converting alkenes into valuable amine products with water being the only coproduct. This work reports for the first time the scale-up of the highly regioselective HAM of 1-decene with diethylamine for a potential continuous process application in a green and sustainable aqueous biphasic medium. The catalytic system Rh/SulfoXantphos and randomly methylated β-cyclodextrin (RAME-β-CD) were herein dissolved in the plain aqueous phase. The addition of cyclodextrins as a green mass transfer agent remarkably increases the reaction rate as well as the selectivity toward linear amines, but they can also support solid content precipitation in this reaction system due to up-scaling effects. Therefore, parameters such as catalyst concentration, organic volume fraction, cyclodextrin concentration, and recyclability were investigated regarding the stability and activity of the system. Especially the organic volume fraction had a decisive influence on solid content precipitation. High regio- and chemoselectivities of 35 and 82%, respectively, at nearly full conversion were achieved toward the linear product amine. The catalytic system was further recycled in batch and scaled up into a 2100 mL autoclave without loss in activity and selectivity. Finally, a continuous process concept was proposed for an extensive investigation regarding long-term stability of the catalytic system. |
| Databáze: | OpenAIRE |
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