An Effective and Reusable Hyperbranched Polymer Immobilized Rhodium Catalyst for the Hydroformylation of Olefins

Abstract

The hydroformylation remains the most applied industrial process to produce aldehydes. Much research has been devoted to developing new catalyst systems since aldehydes are highly desired. Supported metal catalyst complexes have drawn renewed attention due to an increased interest in benign and environmental processes. In this paper, NiXantphos has been immobilized on hyperbranched poly(aryleneoxindole) supports, different in linker, via a one-step post-functionalization. Two heterogeneous hyperbranched poly(aryleneoxindole) supported NiXantphos ligands were evaluated in the microwave assisted rhodium catalyzed hydroformylation of olefins. After selecting the best reaction conditions, a variety of functionalized olefins was successfully converted into the desired linear aldehydes working under milder conditions compared to known processes, in terms of syngas pressure (4.8 bar), temperature (75 °C) and reaction times (20 min). The increased activity might emanate from a positive dendritic effect unique to the dendritic nature of the support. Furthermore, the catalyst system was successfully

Polymeric Heterogeneous Catalysts in the Hydroformylation of Unsaturated Compounds

“…The insoluble materials included a polystyrene-based material with isocyanate groups as well as a material obtained from polyglycerol, hexamethylene diisocyanate and Nixantphos ligand, and the catalyst based on the latter material proved to be highly regioselective in octene-1 hydroformylation (97%). The procedure of fi xing the Nixantphos on highly branched poly arylene oxindole is described in [65]; the obtained rhodium catalyst was highly active in fi ve (5) successive reactions, with <0.3 ppm of rhodium washed out (beginning with the second cycle).…”

“…The rhodium catalyst based on this material remained active during four (4) cycles (with octene-1 conversion rate of circa 75%). As the covalent fi xing of phosphines is required to obtain hydroformylation catalysts, the functionalized polyethylene chips containing amino groups [65], and the Nafi on resin, whose sulfo groups were chlorinated to form -SO 2 Cl and subjected to the action of LiPPh 2 [68], can also be used.…”

10-Phenyl-10H-phenoxazine-4,6-diol tetrahydrofuran monosolvate

“…Phenoxazine-based metal complexes have been reported as catalysts in hydroformylation reactions (van der Veen et al, 2000;Verheyen et al, 2019), C-H bond arylations (Li et al, 2016), and aryl chloride cross-couplings (Zhang et al, 2014). One of the most notable phenoxazine ligands is NiXantPhos (Fig.…”

Hyperbranched Poly(ester‐enamine) from Spontaneous Amino‐yne Click Reaction for Stabilization of Gold Nanoparticle Catalysts

“…Hyperbranched polymers (HBPs), as nano-sized highly-branched three-dimensional macromolecular architectures, have been broadly investigated and utilized in various applications including controlling drug delivery, [1][2][3][4][5] sensing, [6,7] and catalysis, [8][9][10] as well as materials science. [11][12][13][14][15] Because of the attractive properties and wide applications of HBPs, the development of new efficient and selective polymerizations to prepare functional HBPs is an invariably theme in polymer science.…”