NDLI: Rhodium(i) diphenylphosphine complexes supported on porous organic polymers as efficient and recyclable catalysts for alkene hydrogenation

Content Provider	Royal Society of Chemistry (RSC)
Author	Campos, Cristian H. Alderete, Joel B. Torres, Cecilia C. Urbano, Bruno F. Belmar, Julio B. Jeria, Solange E.
Copyright Year	2017
Abstract	This paper describes the synthesis and characterization of porous polymeric materials as a support for rhodium(I) cationic coordination compounds and their use as heterogeneous catalysts for alkene hydrogenation. The synthetic strategy was the insertion of a vinyl-moiety in a bis(2-chloroethyl)amine precursor to provide highly porous resins with an enriched modifiable surface. The precursors synthesized were N,N-bis(2-chloroethyl)prop-2-en-1-amine (Alk-POL) and N,N-bis(2-chloroethyl)acrylamide (Acy-POL). The resins were obtained through suspension polymerization of methyl acrylate and divinylbenzene as a co-polymer and cross-linker, respectively. The resin surfaces were functionalized with diphenylphosphine groups followed by Rh(I) metal deposition using [Rh(COD)2]BF4 (COD = 1,5-cyclooctadiene) as the catalyst precursor. The Rh-catalysts were characterized by different physicochemical techniques and assessed for their catalytic performances in the heterogeneous hydrogenation of styrene and its derivatives. It was found that the catalytic activities and selectivity of the heterogenized rhodium complex (Rh-Alk-POL and Rh-Acy-POL) in the hydrogenation reactions were comparable to its homogeneous analogue. Analysis of the spent homogeneous resin Rh-Alk-POL catalyst after the first reaction cycle showed the presence of metallic Rh nanoparticles arising from the reduction of the Rh complex. Extensive recycling and Rh leaching studies were carried out for the Rh-Acy-POL catalyst. Both the activity and selectivity could be maintained for at least seven reaction runs and without metal leaching during the reaction cycles. We have also studied the liquid-phase hydrogenation reaction of various styrene m-substituted derivatives. The Rh-Acy-POL catalyst exhibits excellent catalytic activity for hydrogenation of the substrates and only vinyl-group hydrogenation was detected. Finally, the presence of electron-donating/-withdrawing substituents at the meta-position resulted in different rates of vinyl group hydrogenation. This effect was quantified in terms of the Hammett relationship, in which the catalyst displayed a linear correlation between the Hammett substituent constant (σmeta) and the hydrogenation rate.
Starting Page	3398
Ending Page	3407
Page Count	10
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	7
Issue Number	6
Journal	RSC Advances
DOI	10.1039/c6ra26104c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Divinylbenzene Vinyl group Substituent Hydrogenation Diphenylphosphine Acrylamide Alkene Rhodium Prop- Resin 1,5-Cyclooctadiene Styrene Hammett equation Methyl acrylate Suspension polymerization
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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