Ionic Liquids in Transition Metal-Catalyzed Hydroformylation Reactions

  • Bernhard Rieger
  • Andriy Plikhta
  • Dante A. Castillo-Molina
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 51)


The latest state of the art in ionic liquid-based hydroformylation is reviewed in detail in this chapter. This multiphase homogenous catalytic system represents a promising strategy in order to reduce catalyst leaching during product separation and achieve the desired ratio of linear-to-branched aldehyde with a high catalytic activity and yield. A series of different catalytic systems, ionic liquids (ILs), and ligands together with their application in the hydroformylation of a variety of alkenes is presented. The features of those ILs derived from their composition and their interactions with substrates and catalysts are also discussed. In addition, recent studies on the catalyst distribution in the bulk and on the surface of ILs are summarized. Herein, the properties of the ligands show an impact in the activity and selectivity of the reaction. Moreover, not only Co and Rh complexes can be applied in the hydroformylation in ILs but also Pt and Ru complexes. On the other hand, the uses of CO2 as chemical C1 feedstock or scCO2 as carrier for the reagents and products in the hydroformylation reaction are commented. Catalytic processes where supported ionic liquid phases (SILPs) and nanocatalysts intervened complement this work.


Alkenes Hydroformylation Ionic liquids scCO2 SILP 



1-N-n-Butyl-4-methylpyridinium chloride


1-Butyl-3-[3-(trimethoxysilyl)propyl]imidazolium chloride


1,2-Dimethyl-3-butylimidazolium hexafluorophosphate


1-n-Butyl-3-methylimidazolium tetrafluoroborate


1-n-Butyl-3-methylimidazolium chloride


1-n-Butyl-3-methylimidazolium tetracarbonylcobaltate


1-n-Butyl-3-methylimidazolium n-dodecylsulfate


1-n-Butyl-3-methylimidazolium n-octylsulfate


1-n-Butyl-3-methylimidazolium para-toluenesulfonate


1-n-Butyl-3-methylimidazolium hexafluorophosphate


1-n-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide


1-n-Butyl-3-methylimidazolium trifluoromethanesulfonate


N-n-Butylpyridinium tetrafluoroborate


N-n-Butylpyridinium bis(trifluoromethylsulfonyl)imide


1,3-Dialkylimidazolium anion


1-Ethyl-3-methylimidazolium ethylsulfate


1-Ethyl-3-methylimidazolium trifluoromethanesulfonate


1-Ethyl-2,3-dimethylimidazolium trifluoromethanesulfonate


1-n-Hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide


1-n-Hexyl-3-methylimidazolium trifluoromethanesulfonate


1-(2-Methyl-n-butyl)-3-methylimidazolium trifluoromethanesulfonate


N-Methyl-guanidinium tetracarbonylcobaltate


1-Methyl-triazolium tetracarbonylcobaltate


N-Benzyltriethylammonium bis(trifluoromethylsulfonyl)imide


Tetra-n-butylammonium tetrafluoroborate


Tetraethylammonium bis(trifluoromethylsulfo-nyl)imide


N-Methyltri-n-octylammonium bis(trifluoromethylsulfonyl)imide


1-n-Octyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide


1-n-Octyl-3-methylimidazolium trifluoromethanesulfonate


Tri(n-butyl)-n-tetradecylphosphonium dodecyl-benzenesulfonate


Tri(n-butyl)ethylphosphonium diethylphosphate


Tri(n-hexyl)-n-tetradecylphosphonium chloride


Tri(n-hexyl)-n-tetradecylphosphonium dicyanamide


Tri(n-hexyl)-n-tetradecylphosphonium bis(tri-fluoromethylsulfonyl)imide


1-(2′-Piperid-1′-yl-ethyl)-3-methylimidazolium hexafluorophosphate


1-(2′-Piperid-1′-yl-ethyl)-2-methyl-3-methylimidazolium hexafluorophosphate


1-n-Propyl-3-methylimidazolium triphenyl-phosphine-3-monosulfonate


1-n-Propyl-3-methylimidazolium triphenyl-phosphine-3,3'-disulfonate


N,N-Tetramethyl-guanidinium tetracarbonylcobaltate


1,2,3-Trimethylimidazolium trifluoromethanesulfonate


2-Diphenylphosphinophenylen-1,3-dimethylimidazolium tetrafluoroborate


1-n-Butyl-2-diphenylphosphino-3-methylimidazolium hexafluorophosphate


1-(2′-Piperid-1′-yl-ethyl)-2-diphenylphosphino-3-methylimidazolium hexafluorophosphate






Carbonyl or carbon monoxide




1,1′-Bis(diphenylphosphino)cobaltocenium hexafluorophosphate


1,1′-Bis(diphenylphosphino)-iso-propylcobaltocenium hexafluorophosphate


Energy-dispersive X-ray spectroscopy


Fourier transform infrared spectroscopy


Ionic liquid crystals




Melting point


Magic angle spinning


Metal-containing ionic liquids


Mesoporous silica nanoparticles


N-heterocyclic carbenes




Nuclear magnetic resonance


Tricesium 3,4-dimethyl-2,5,6-tris(p-sulfonato-phenyl)-1-phosphanorbornadiene








Polyethylene glycol


Phosphine-functionalized phosphonium ILs


Polyether guanidinium methanesulfonates ILs


Phenoxaphosphino-modified Xantphos


Parts per billion




para-Toluene sulfonic acid






Room temperature




Supercritical carbon dioxide


Supercritical fluid


Scanning electron microscopy


Supported ionic liquid phase


Transmission electron microscopy


Glass-transition temperature


1,1,3,3-Tetramethylguanidinium lactate


Turn over frequency


Trioctylmethylammonium chloride


Turn over number




Disodium triphenylphosphine-3,3′-disulfonate


Sodium triphenylphosphine-3-monosulfonate


Tri(1,2-dimethyl-3-n-butyl-imidazolium) triphenylphosphine-3,3′,3″-trisulfonate


Trisodium triphenylphosphine-3,3′,3″-trisulfonate


X‐ray diffractometry


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Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  • Bernhard Rieger
    • 1
  • Andriy Plikhta
    • 1
  • Dante A. Castillo-Molina
    • 1
  1. 1.WACKER-Lehrstuhl für Makromolekulare ChemieTechnische Universität MünchenGarching bei MünchenGermany

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