First efficient catalyst recycling for the iridium-catalysed hydroformylation of 1-octene

Abstract

This paper describes the development of an efficient catalyst recycling concept for the iridium-catalysed hydroformylation of 1-octene through the investigation of biphasic systems, thermomorphic solvent systems and an ex situ extraction. Particularly high selectivities (>90%) towards the desired aldehydes as well as low rates of iridium leaching were observed using the monosulfonated triphenylphosphine ligand (TPPMS). In polar solvents such as propylene carbonate or N,N-dimethylformamide, low rates of catalyst leaching (0.2%) as well as high rates of product separation (nearly 80%) were achieved. High reaction rates and a long-term activity and stability of the catalyst were observed using the solvent N,N-dimethylformamide and the extraction with non-polar solvents.Catal. Sci. Technol. This journal is

A Bifunctional MOF Catalyst Containing Metal–Phosphine and Lewis Acidic Active Sites

“…This atom-economic domino reaction, which starts with hydroformylation of alkenes and is followed by reductive amination, is an important and efficient synthesis of amines. [17] In our chosen exemplar reactionb etween cyclopentene and aniline (Scheme 4) with SulP1-MOF-808(Hf)-Rh (using [Rh-(acac)(CO) 2 ]a st he metal precursor), N-(cyclopentylmethyl)aniline was obtained in good yield (75 %).…”

Novel Ir-Complexes for Hydroformylation of Olefins with H2O as the Hydrogen Source

“…The screening reaction conditions, and 1 H NMR, 13 C NMR spectra for the products of hydroformylation of olefins. CCDC: Ir-L2, 1859529; Ir-L3, 2016248; Ir-L4, 2016247.…”

“…In addition, Beller et al have shown that iridium, as an alternative metal to rhodium, can be used to prepare efficiently catalysts for the homogeneous hydroformylation of olefins. [10][11][12][13] It is well known that iridium-complex catalysts are often active for the hydrogenation of olefins. [14][15][16][17] Therefore an important issue to improve the performance of iridium-complexes for catalytic hydroformylation is to suppress the hydrogenation process.…”

“…A frequently used method is to add lithium salts to the reaction systems to inhibit the hydrogenation of olefins during hydroformylation. [10,13] Another method is to control the amount of H 2 in the reaction system. [18][19] The water-gas shift reaction (WGSR, H 2 O＋CO → H 2 ＋CO 2 ) over the Ir-catalyst reported by Peter in 1984, [20][21] is a good method to inhibit hydrogenation of olefins in hydroformylation [22] by in situ generation of the desired amount of H 2 .…”

Recent Advances Utilized in the Recycling of Homogeneous Catalysis

“…Behr group developed an efficient catalyst recycling concept by TMS system and an ex-situ extraction for hydroformylation of 1-octene by using iridium-catalyst (Scheme 7). [31] Very low iridium leaching (0.2 %) and good selectivities (> 90 %) towards the expected aldehydes were obtained with the monosulfonated triphenylphosphine ligand (TPPMS) in polar solvents like N,N-dimethylformamide or propylene carbonate. The catalyst was recycled for the five times with 0.2 % leaching and about 90 % conversion achieved.…”