Coupling Rhodium‐Catalyzed Hydroformylation of 10‐Undecenitrile with Organic Solvent Nanofiltration: Toluene Solution versus Solvent‐Free Processes

March 24, 2020

Title

Coupling Rhodium‐Catalyzed Hydroformylation of 10‐Undecenitrile with Organic Solvent Nanofiltration: Toluene Solution versus Solvent‐Free Processes

Author

Antoine Lejeune, Lucas Le Goanvic, Thierry Renouard, Jean‐Luc Couturier, Jean‐Luc Dubois, Jean‐François Carpentier, Murielle Rabiller‐Baudry

Year

2019

Journal

ChemPlusChem

Abstract

Intensification of the rhodium‐catalyzed hydroformylation process to produce 12‐oxo‐dodecanenitrile from biosourced 10‐undecenitrile was performed by coupling the reaction with organic solvent nanofiltration (OSN) for the recycling of the expensive Rh catalyst and the ligands. Four phosphorus‐based ligands were compared with respect to their catalytic performance and rejection in OSN. Biphephos showed the best compromise and up to 3 reaction‐OSN cycles were performed in toluene. A good recycling of the catalytic system was evidenced arising from the OSN (up to 88 % rejection). In order to develop a greener process, a similar approach was achieved in bulk (i. e. solvent‐free medium), thus proving the catalyst recycling feasibility but also that the optimal OSN conditions are not the same as for toluene. Finally, integration of OSN in the overall production process is discussed, aiming at the proposal of a hybrid separation process involving a combination of OSN and distillation for an energy‐efficient separation step.

Instrument

V-630

Keywords

Absorption, Quantitation, Organic chemistry