Title :

Rhodium catalyzed selective hydroaminomethylation of biorenewable eugenol under aqueous biphasic condition

Author(s) :

Jagtap, Samadhan A. [Auteur]
Gowalkar, Shilpa P. [Auteur]
Monflier, Eric [Auteur]
UCCS Équipe Catalyse Supramoléculaire
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Ponchel, Anne [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
UCCS Équipe Catalyse Supramoléculaire
Bhanage, Bhalchandra M. [Auteur]

Journal title :

Molecular Catalysis

Volume number :

452

Pages :

108-116

Publisher :

Elsevier

Publication date :

2018-06

English keyword(s) :

Amines
Biphasic hydroaminomethylation
Cyclodextrins
Eugenol
Rhodium
TPPTS

HAL domain(s) :

Chimie/Catalyse

English abstract : [en]

This work reports a highly regioselective hydroaminomethylation of eugenol, anethole and estragole with piperidine in aqueous medium. This catalytic system was composed of rhodium complexes stabilized by trisulfonated ...
Show more >This work reports a highly regioselective hydroaminomethylation of eugenol, anethole and estragole with piperidine in aqueous medium. This catalytic system was composed of rhodium complexes stabilized by trisulfonated triphenylphosphine (TPPTS) and of a native or chemically modified cyclodextrins. Various cyclodextrins such as α-cyclodextrins (α-CD), β-cyclodextrin (β-CD), γ-cyclodextrin (γ-CD), 2-hydroxy-propyl β-cyclodextrin (hp-β-CD) and RAndomly MEthylated β-cyclodextrin (RAME-β-CD) have been tested. The effect of different parameters such as syngas pressure, time, temperature, catalyst precursor/loading and the ratio of Metal/Ligand/Cyclodextrin were also investigated. The addition of cyclodextrins as a mass transfer agent remarkably increased the rate reaction and the selectivity of linear amines, specially in the case of RAME-β-CD. So, the Rh/TPPTS/RAME-β-CD as a catalyst exhibited high conversion (92%) and selectivity (79.2%) towards the linear amine as major product under mild conditions. Finally, the catalytic system was recycled up to five times without a significant loss in activity and selectivity.Show less >

Language :

Anglais

Peer reviewed article :

Oui

Audience :

Internationale

Popular science :

Non

Administrative institution(s) :

ENSCL
CNRS
Centrale Lille
Univ. Artois
Université de Lille

Collections :

• Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181

Research team(s) :

Catalyse et chimie supramoléculaire (CASU)

Submission date :

2019-09-25T14:37:55Z
2021-03-17T14:58:11Z