Hydrocarboxylation of olefins using an amphiphilic palladium catalyst, activity and recycling properties NMR identification of some reaction intermediates: NMR identification of some reaction intermediates

Magnus Karlsson, Adriana Ionescu, Carlaxel Andersson

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The high solubility in acidic solutions of N-bis(N',N'-diethyl-2-aminoethyl)-4-aminomethylphenyl-diphenylphosphine (N3P) make it a suitable candidate for study and comparison to the more commonly studied trisulfonated triphenylphosphine (TPPTS) ligand in the palladium catalysed aqueous hydrocarboxylation reaction. The catalyst employing N3P shows an inverted regioselectivity compared to the TPPTS system. Non-coordinating anions give the best results in terms of activity and stability of the catalyst. Due to N3P amphiphilic character and contrary to sulfonated phosphines reaction, it is possible to recycle the catalyst, both by extracting the substrate and by extracting the catalyst into an organic solvent. The hydrocarboxylation of styrene, I-octene and 4-penteneoic acid demonstrates that the reaction rate is strongly dependent on the solubility of the substrates. Using the water-soluble 3-buten-1-ol as substrate, two palladium zerovalent complexes, two palladium hydrides, one acyl and one alkyl complexes were identified by means of NMR and IR. (c) 2006 Elsevier B.V. All rights reserved.
Original languageEnglish
JournalJournal of Molecular Catalysis A: Chemical
Volume259
Issue number1-2
Pages (from-to)231-237
ISSN1381-1169
DOIs
Publication statusPublished - 2006
Externally publishedYes

Keywords

  • Catalysis
  • Process Chemistry and Technology
  • Materials Science (miscellaneous)
  • Amphiphilic phosphine
  • Aqueous phase
  • Hydrocarboxylation
  • Palladium
  • Recycling
  • Carboxylation
  • Catalysts
  • Molecular structure
  • Nuclear magnetic resonance
  • Solubility
  • Olefins
  • CHEMISTRY,
  • HYDRIDE COMPLEXES
  • 2-PHASE SYSTEM
  • HYDROXYCARBONYLATION
  • WATER
  • TRIPHENYLPHOSPHINE
  • CONVERSIONS
  • STYRENE
  • TPPTS
  • amphiphilic phosphine
  • aqueous phase
  • hydrocarboxylation
  • palladium
  • recycling
  • PALLADIUM
  • T
  • X

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