Rhodium/Trialkylamines Catalyzed Reductive Hydroformylation in Ionic Liquid/Heptane Medium: An Unexpected Concept for Catalyst Recycling in Batch and Continuous Flow Processes
We report here the rhodium catalyzed reductive hydroformylation of methyl 10-undecenoate. Our approach is based on an ionic liquid/heptane biphasic system associated with commercially available trialkylamines. The effects of various reaction parameters such as amine type, amine amount, temperature, syngas pressure and composition were studied in order to minimize the rhodium leaching and increase the production of primary alcohols. Although the amine is less soluble in the ionic liquid than in heptane, the catalytic system is efficiently maintained in the ionic liquid phase. For the optimized conditions, the catalytic ionic liquid layer can be recycled at least nine times by keeping an alcohol yield over 50 % and by limiting the rhodium leaching. As an extension of this system and to examine the long-term stability, this batch system was transferred to a miniplant for a continuous flow process. A pilot plant was operated for 45 h of total reaction time, reaching a TTON of 232 for alcohol production.
Authors
- Hervé Bricout (ORCID: https://orcid.org/0000-0002-4895-1636)
- Éric Monflier (ORCID: https://orcid.org/0000-0001-5865-0979)
- Michel Ferreira (ORCID: https://orcid.org/0000-0003-4898-0290)
- Andreas J. Vorholt (ORCID: https://orcid.org/0000-0001-9302-2273)
- Jérémy Ternel (ORCID: https://orcid.org/0000-0002-6559-1564)
- Sébastien Tilloy (ORCID: https://orcid.org/0000-0002-3494-4734)
- Mohammed Lahcini (ORCID: https://orcid.org/0000-0003-1049-7906)
- Abdelghani El Mouat
- Sven Stoertte
- Hannah Stieber
- Walid Abdallah (ORCID: https://orcid.org/0009-0006-2346-3771)
Institutions
- Cadi Ayyad University (MA)
- Centre National de la Recherche Scientifique (FR)
- Université de Lille (FR)
- Max Planck Institute for Chemical Energy Conversion (DE)
- Université Mohammed VI Polytechnique (MA)
- Unité de catalyse et de chimie du solide de Lille (FR)
- Université d'Artois (FR)
- École Centrale de Lille (FR)
Publication Details
- Journal
- ChemSusChem
- Published
- 2024-09-26
- DOI
- https://doi.org/10.1002/cssc.202401384
- Citations
- 7
- Primary Topic
- Ionic liquids properties and applications
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Max-Planck-Gesellschaft
- Ministère de l'Enseignement Supérieur et de la Recherche
- Centre National pour la Recherche Scientifique et Technique
- Région Hauts-de-France