Title :

Water-soluble phosphane-substituted cyclodextrin as an effective bifunctional additive in hydroformylation of higher olefins

Author(s) :

Leblond, Jérôme [Auteur]
Potier, Jonathan [Auteur]
Unité Matériaux et Transformations - UMR 8207 [UMET]
Unité Matériaux et Transformations (UMET) - UMR 8207
Menuel, Stephane [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Bricout, Hervé [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Machut-Binkowski, Cécile [Auteur]
Landy, David [Auteur]
Tilloy, Sebastien [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Monflier, Eric [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Hapiot, Frederic [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]

Journal title :

Catal. Sci. Technol.

Volume number :

7

Pages :

3823-3830

Publication date :

2017-07-24

HAL domain(s) :

Chimie/Catalyse

English abstract : [en]

In cyclodextrin (CD)-mediated aqueous biphasic catalysis, favoring contacts between the CD (“host”), the organic substrate (“guest”) and the water-soluble catalyst is crucial for the reaction to proceed efficiently at the ...
Show more >In cyclodextrin (CD)-mediated aqueous biphasic catalysis, favoring contacts between the CD (“host”), the organic substrate (“guest”) and the water-soluble catalyst is crucial for the reaction to proceed efficiently at the aqueous/organic interface. Grafting the catalyst onto the CD backbone thus appears as an attractive approach to favor the molecular recognition of the substrate and its subsequent catalytic conversion into products. In this context, a new water-soluble β-CD-based phosphane was synthesized and characterized by NMR, tensiometric and ITC measurements. The β-CD-based phosphane consisted of a 3,3′-disulfonatodiphenyl phosphane connected to the primary face of β-CD by a dimethyleneamino spacer. Intra- and intermolecular inclusion processes of one of the two sulfophenyl groups into the β-CD cavity were identified in water. However, the association constant (Ka) related to the β-CD/sulfophenyl group couple was low. Accordingly, the inclusion process was easily displaced upon coordination to rhodium complexes. The efficacy of the resulting Rh-complex coordinated by β-CD-based phosphanes was assessed in Rh-catalyzed hydroformylation of higher olefins. The catalytic system proved to be far more successful and efficient than a system consisting of supramolecularly interacting phosphanes and CDs. The catalytic activity was up to 30-fold higher while the chemo- and regioselectivities remain rather unchanged.Show less >

Language :

Anglais

Audience :

Internationale

Popular science :

Non

Administrative institution(s) :

ENSCL
Université de Lille
CNRS
INRA
Centrale Lille
Univ. Artois

Collections :

• Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
• Unité Matériaux et Transformations (UMET) - UMR 8207

Research team(s) :

Catalyse et chimie supramoléculaire (CASU)

Submission date :

2019-09-25T14:05:39Z