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Palladium-Catalyzed Telomerization of Butadiene with Polyols: From Mono to Polysaccharides

  • Sandrine Bouquillon
  • Jacques Muzart
  • Catherine PinelEmail author
  • Franck Rataboul
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 295)

Abstract

The telomerization of butadiene with alcohols is an elegant way to synthesize ethers with minimal environmental impact since this reaction is 100% atom efficient. Besides telomerization of butadiene with methanol and water that is industrially developed, the modification of polyols is still under development. Recently, a series of new substrates has been involved in this reaction, including diols, pure or crude glycerol, protected or unprotected monosaccharides, as well as polysaccharides. This opens up the formation of new products having specific physicochemical properties. We will describe recent advances in this field, focusing on the reaction of renewable products and more specifically on saccharides. The efficient catalytic systems as well as the optimized reaction conditions will be described and some physicochemical properties of the products will be reported.

Keywords

Hydrophobic starch Octadienyl ether Palladium Surfactant Telomerization Water catalyzed reaction 

Abbreviations

CMC

Critical micelle concentration

CTAB

Cetyltrimethyl ammonium bromide

dba

Dibenzylideneacetone

DMAc

Dimethyacetamide

DMI

Dimethyl isosorbide

DPPM

Diphenylphosphine methane

DS

Degree of substitution

HLB

Hydrophilic lipophilic balance

IMes.HCl

1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride

MEK

Methyl ethyl ketone

MIBK

Methyl isobutyl ketone

PEG

Poly ethylene glycol

POEA

Polyethoxylated tallow amine

TOMPP

Tris(2-methoxyphenyl)phosphine

TON

Turnover number

TPPMS

(m-Sulfonato-phenyl) diphenyl phosphine monosodium salt

TPPTS

Tris(m-sulfonato-phenyl) phosphine trisodium salt

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Copyright information

© Springer 2010

Authors and Affiliations

  • Sandrine Bouquillon
    • 1
  • Jacques Muzart
    • 1
  • Catherine Pinel
    • 2
    • 3
    Email author
  • Franck Rataboul
    • 2
    • 3
  1. 1.Institut de Chimie Moléculaire de ReimsUMR 6229/CNRS – Université de Reims Champagne-ArdenneReims Cedex 2France
  2. 2.Université de LyonLyonFrance
  3. 3.Institut de Recherches sur la Catalyse et l’Environnement de LyonUniversité Lyon 1 CNRS, UMR 5256VilleurbanneFrance

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