Get access

Poly-α,β-unsaturated aldehydes derived from castor oil via ADMET polymerization

Authors

  • Oliver Kreye,

    1. Laboratory for Sustainable Organic Synthesis, University of Potsdam, Institute of Chemistry, Potsdam, Germany
    Search for more papers by this author
  • Tommy Tóth,

    1. Laboratory for Sustainable Organic Synthesis, University of Potsdam, Institute of Chemistry, Potsdam, Germany
    Search for more papers by this author
  • Michael A. R. Meier

    Corresponding author
    1. Laboratory for Sustainable Organic Synthesis, University of Potsdam, Institute of Chemistry, Potsdam, Germany
    • Laboratory for Sustainable Organic Synthesis, University of Potsdam, Institute of Chemistry, Karl-Liebknecht-Str. 24-25, 14476 Golm/Potsdam, Germany Fax: +49-331-977-5056.
    Search for more papers by this author

Abstract

10-Undecenal, derived by pyrolysis and reduction from castor oil, was almost quantitatively transformed into the corresponding aldol condensation product under basic conditions. This α,ω-diene monomer was polymerized using acyclic diene metathesis (ADMET) polymerization. In a catalyst screening, four of nine different ruthenium-based metathesis catalysts showed good reactivity under neat conditions at 80°C in the presence of 1,4-benzoquinone and polymers with molecular weights up to 11 kDa were formed. Furthermore, the 1H NMR spectra showed that the metathesis catalysts tolerate the α,β-unsaturated aldehyde function and due to the addition of benzoquinone, the degree of double bond isomerization was low. Further experiments investigating reduced catalyst amounts (down to 0.2 mol%) and the temperature dependence of these ADMET polymerizations gave also satisfying results for the formation of poly-α,β-unsaturated aldehydes. Moreover, ADMET polymerizations with different amounts of methyl 10-undecenoate as chain-stopper were performed and the integrals of the corresponding 1H NMR spectra allowed the determination of an absolute degree of polymerization. Finally, a reduction of a poly-α,β-unsaturated aldehyde with sodium borohydride was accomplished. The resulting poly-(allyl alcohol) could be a useful compound in the generation of polymer networks like polyesters, polyurethanes, and polycarbonates and thus be of high interest in materials research.

Get access to the full text of this article

Ancillary