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Hydroformylation in Aqueous Biphasic Media Assisted by Molecular Receptors

  • Frédéric Hapiot
  • Hervé Bricout
  • Sébastien Tilloy
  • Eric Monflier
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 342)

Abstract

The role of molecular receptors in aqueous biphasic hydroformylation of higher olefins is highlighted through a detailed analysis of their molecular recognition properties. The behavior of cyclodextrins and calixarenes as molecular receptors is especially emphasized and discussed. Their supramolecular interactions with the substrates and the water-soluble ligands proved to be an essential parameter guiding the reaction performances. The hydroformylation activity and chemo- and regio-selectivities can thus be accurately controlled by a suitable match between the receptor and the reaction components. Development outlooks are also presented.

Graphical Abstract

Keywords

Biphasic catalysis Calixarenes Cyclodextrins Inclusion complexes Molecular recognition 

Abbreviations

3-α-1

2,3-Dimethyl-6-(3-sulfonato-n-propyl)-α-cyclodextrin potassium salt

3-β-1

2,3-Dimethyl-6-(3-sulfonato-n-propyl)-β-cyclodextrin potassium salt

4-α-1

2,3-Dimethyl-6-(3-sulfonato-n-butyl)-α-cyclodextrin potassium salt

4-β-1

2,3-Dimethyl-6-(3-sulfonato-n-butyl)-β-cyclodextrin potassium salt

4-β-2

2,3-Diethyl-6-(3-sulfonato-n-propyl)-β-cyclodextrin potassium salt

acac

Acetylacetonate

AC-β-CD

2,6-Diacetyl-β-cyclodextrin

BiphTS

Tris(p-sulfonatobiphenyl)phosphine trisodium salt

CRYSME-β-CD

Randomly methylated-β-cyclodextrin (substitution degree = 5)

DIME-α-CD

2,6-Dimethyl-α-cyclodextrin

DIME-β-CD

2,6-Dimethyl-β-cyclodextrin

h

Hour(s)

HP-α-CD

Hydroxypropyl-α-cyclodextrin

HP-β-CD

Hydroxypropyl-β-cyclodextrin

HTMAP-α-CD

O-(2-Hydroxy-3-trimethylammonio-n-propyl)-α-cyclodextrin chloride

HTMAP-β-CD

O-(2-Hydroxy-3-trimethylammonio-n-propyl)-β-cyclodextrin chloride

L

Liter(s)

Me

Methyl

min

Minute(s)

mol

Mole(s)

MTMAP/ME-α-CD

O-(2-Methoxy-3-trimethylammonio-n-propyl)-α-cyclodextrin

Ph

Phenyl

polyNAS

Poly(N-acryloyloxysuccinimide)

RAME-α-CD

Randomly methylated α-cyclodextrin (substitution degree = 10.8)

RAME-β-CD

Randomly methylated-β-cyclodextrin (substitution degree = 12.6)

RASBE/ME-β-CD

Randomly methylsulfobutylether-β-cyclodextrin

RASBE-β-CD

Randomly sulfobutylated-β-CD

SBE-β-CD

Sulfobutylether-β-cyclodextrin

SULFA-β-CD

Sulfated-β-cyclodextrin

t-Bu

tert-Butyl

TPPMS

m-Monosulfonatophenyldiphenylphosphine sodium salt

TPPTS

Tris(m-sulfonatophenyl)phosphine trisodium salt

TRIME-β-CD

2,3,6-Trimethyl-β-cyclodextrin

α-CD

α-Cyclodextrin

α-D-GluP

α-d-Glucopyranose

β-CD

β-Cyclodextrin

γ-CD

γ-Cyclodextrin

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Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Frédéric Hapiot
    • 1
  • Hervé Bricout
    • 1
  • Sébastien Tilloy
    • 1
  • Eric Monflier
    • 1
  1. 1.Unité de Catalyse et de Chimie du Solide, CNRS UMR 8181, Faculté des Sciences Jean PerrinEric Monflier, Université d’ArtoisLens CedexFrance

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