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Ionic Liquids (ILs) in Organometallic Catalysis pp 95–144Cite as

Ionic Liquids in Transition Metal-Catalyzed Hydroformylation Reactions

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 51))

Abstract

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.

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Abbreviations

[4-mbpy][Cl]:

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

[b((MeOSi)3p)im][Cl]:

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

[bdmim][PF6]:

1,2-Dimethyl-3-butylimidazolium hexafluorophosphate

[bmim][BF4]:

1-n-Butyl-3-methylimidazolium tetrafluoroborate

[bmim][Cl]:

1-n-Butyl-3-methylimidazolium chloride

[bmim][Co(CO)4]:

1-n-Butyl-3-methylimidazolium tetracarbonylcobaltate

[bmim][n-C12H25OSO3]:

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

[bmim][n-C8H17OSO3]:

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

[bmim][p-C6H4SO3]:

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

[bmim][PF6]:

1-n-Butyl-3-methylimidazolium hexafluorophosphate

[bmim][Tf2N]:

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

[bmim][TfO]:

1-n-Butyl-3-methylimidazolium trifluoromethanesulfonate

[bpy][BF4]:

N-n-Butylpyridinium tetrafluoroborate

[bpy][Tf2N]:

N-n-Butylpyridinium bis(trifluoromethylsulfonyl)imide

[daim][An]:

1,3-Dialkylimidazolium anion

[emim][C2H5OSO3]:

1-Ethyl-3-methylimidazolium ethylsulfate

[emim][TfO]:

1-Ethyl-3-methylimidazolium trifluoromethanesulfonate

[emmim][TfO]:

1-Ethyl-2,3-dimethylimidazolium trifluoromethanesulfonate

[hmim][Tf2N]:

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

[hmim][TfO]:

1-n-Hexyl-3-methylimidazolium trifluoromethanesulfonate

[mbmim][TfO]:

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

[mg][Co(CO)4]:

N-Methyl-guanidinium tetracarbonylcobaltate

[mtr][Co(CO)4]:

1-Methyl-triazolium tetracarbonylcobaltate

[NBnEt3][Tf2N]:

N-Benzyltriethylammonium bis(trifluoromethylsulfonyl)imide

[NBu4][BF4]:

Tetra-n-butylammonium tetrafluoroborate

[NEt4][Tf2N]:

Tetraethylammonium bis(trifluoromethylsulfo-nyl)imide

[NOc3Me][Tf2N]:

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

[omim][Tf2N]:

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

[omim][TfO]:

1-n-Octyl-3-methylimidazolium trifluoromethanesulfonate

[P(C4H9)3(C14H29)][DBS]:

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

[P(C4H9)3(C2H5)][DEP]:

Tri(n-butyl)ethylphosphonium diethylphosphate

[P(C6H13)3(C14H29)][Cl]:

Tri(n-hexyl)-n-tetradecylphosphonium chloride

[P(C6H13)3(C14H29)][DCA]:

Tri(n-hexyl)-n-tetradecylphosphonium dicyanamide

[P(C6H13)3(C14H29)][Tf2N]:

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

[PEmim][PF6]:

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

[PEmmim][PF6]:

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

[prmim][TPPMS]:

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

[prmim]2[TPPDS]:

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

[tmg][Co(CO)4]:

N,N-Tetramethyl-guanidinium tetracarbonylcobaltate

[tmim][TfO]:

1,2,3-Trimethylimidazolium trifluoromethanesulfonate

2-(DPP-C6H4)-[mmim][BF4]:

2-Diphenylphosphinophenylen-1,3-dimethylimidazolium tetrafluoroborate

2-DPP-[mbim][PF6]:

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

2-DPP-[PEmmim][PF6]:

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

bim(B(C6H5)3):

(3-n-Butylimidazole)triphenylboron

Co:

Cobalt

CO:

Carbonyl or carbon monoxide

COD:

Cycloocta-1,5-diene

DPP-Cobaltocene:

1,1′-Bis(diphenylphosphino)cobaltocenium hexafluorophosphate

DPPiPr-Cobaltocene:

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

EDX:

Energy-dispersive X-ray spectroscopy

FTIR:

Fourier transform infrared spectroscopy

ILCs:

Ionic liquid crystals

IR:

Infrared

m.p.:

Melting point

MAS:

Magic angle spinning

MCILs:

Metal-containing ionic liquids

MCM-41:

Mesoporous silica nanoparticles

NHCs:

N-heterocyclic carbenes

nm:

Nanometer

NMR:

Nuclear magnetic resonance

NORBOS-Cs3 :

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

NPs:

Nanoparticles

OPGPP:

Octylpolyethyleneglycol-phenylene-phosphite

P:

Phosphorus

PEG:

Polyethylene glycol

PFILs:

Phosphine-functionalized phosphonium ILs

PGMILs:

Polyether guanidinium methanesulfonates ILs

POP-Xantphos-2[mmim][PF6]:

Phenoxaphosphino-modified Xantphos

ppb:

Parts per billion

Pt:

Platinum

PTSA:

para-Toluene sulfonic acid

Rh:

Rhodium

Rh(CO)2(acac):

(Acetylacetonato)dicarbonylrhodium(I)

rt:

Room temperature

Ru:

Ruthenium

scCO2 :

Supercritical carbon dioxide

SCF:

Supercritical fluid

SEM:

Scanning electron microscopy

SILP:

Supported ionic liquid phase

TEM:

Transmission electron microscopy

T g :

Glass-transition temperature

TMGL:

1,1,3,3-Tetramethylguanidinium lactate

TOF:

Turn over frequency

TOMAC:

Trioctylmethylammonium chloride

TON:

Turn over number

TPP, PPh3 :

Triphenylphosphine

TPPDS:

Disodium triphenylphosphine-3,3′-disulfonate

TPPMS:

Sodium triphenylphosphine-3-monosulfonate

TPPTI:

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

TPPTS:

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

XRD:

X‐ray diffractometry

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Authors and Affiliations

  1. WACKER-Lehrstuhl für Makromolekulare Chemie, Technische Universität München, Lichtenbergstraße 4, 85747, Garching bei München, Germany

    Bernhard Rieger, Andriy Plikhta & Dante A. Castillo-Molina

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  1. Bernhard Rieger
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  2. Andriy Plikhta
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  3. Dante A. Castillo-Molina
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Correspondence to Bernhard Rieger .

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Editors and Affiliations

  1. Institute of Chemistry - UFRGS, Porto Alegre, Brazil

    Jairton Dupont

  2. Department of Inorganic Chemistry, Institute of Chemistry, University of Pecs, Pécs, Hungary

    László Kollár

Appendix

Appendix

Table 3 Summary of Rh- and Co-based hydroformylations in ILs
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Rieger, B., Plikhta, A., Castillo-Molina, D.A. (2014). Ionic Liquids in Transition Metal-Catalyzed Hydroformylation Reactions. In: Dupont, J., Kollár, L. (eds) Ionic Liquids (ILs) in Organometallic Catalysis. Topics in Organometallic Chemistry, vol 51. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2014_86

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