Palladium-based telomerization of 1,3-butadiene with glycerol using methoxy-functionalized triphenylphosphine ligands

Chemistry : a European Journal
Regina PalkovitsBert M Weckhuysen

Abstract

Glycerol is considered a potential renewable building block for the synthesis of existing as well as new chemicals. A promising route is the telomerization of 1,3-butadiene with glycerol leading to C8 chain ethers of glycerol with applications in, for example, surfactant chemistry. Recently, we reported a new set of palladium-based homogeneous catalytic systems for the telomerization of 1,3-butadiene with glycerol and found that palladium complexes bearing methoxy-functionalized triphenylphosphine ligands are highly active catalysts capable of converting crude glycerol without any significant loss of activity. Herein, we present a detailed account of these investigations by reporting on the influence of the butadiene/glycerol ratio, temperature, and reaction time on product selectivity and activity allowing further optimization of catalyst performance. Maximum activity and yield were reached for high 1,3-butadiene/glycerol ratios at a temperature of 90 degrees C, whereas the selectivity for mono- and diethers of glycerol could be optimized by combining high reaction temperatures and short reaction times with low butadiene/glycerol ratios. Variation of the PdII metal precursors and the metal/ligand ratio showed that palladium pr...Continue Reading

References

Aug 19, 2004·Chemistry : a European Journal·Ralf JackstellMatthias Beller
May 10, 2006·Angewandte Chemie·Ricardo R SoaresJames A Dumesic
May 2, 2007·Angewandte Chemie·Mario PagliaroCristina Della Pina
May 31, 2007·Chemical Reviews·Avelino CormaAlexandra Velty
Jul 5, 2007·Angewandte Chemie·George W Huber, Avelino Corma

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Citations

Sep 14, 2010·Angewandte Chemie·Peter J C HausoulRobertus J M Klein Gebbink
Jun 25, 2020·Angewandte Chemie·Joseph BecicaDavid C Leitch
Jun 11, 2011·Macromolecular Rapid Communications·Marcus Rose, Regina Palkovits

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