Get access

A more sustainable Wohl–Ziegler bromination: Versatile derivatization of unsaturated FAMEs and synthesis of renewable polyamides

Authors

  • Matthias Winkler,

    1. Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany
    Search for more papers by this author
  • Michael Steinbiß,

    1. Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany
    Search for more papers by this author
  • Michael A. R. Meier

    Corresponding author
    1. Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany
    • Correspondence: Professor Michael A. R. Meier, Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, Building 30.42, 76131 Karlsruhe, Germany

      E-mail: m.a.r.meier@kit.edu

      Fax: +49 721 608 46801

    Search for more papers by this author

  • Dedicated to Frank Gunstone on the occasion of his 90th birthday

Abstract

Within this contribution, a more sustainable procedure for the Wohl–Ziegler bromination of unsaturated fatty acid methyl esters (FAME) was investigated. The resulting allylic bromide functional FAMEs were used for elimination reactions to prepare conjugated fatty acids. Moreover, the fatty acid derived allylic bromides were used as initiators for atom transfer radical polymerization (ATRP). Furthermore, the synthesis of AB-type polyamide monomers was accomplished by a complementary hydrobromination of FAME and subsequent modification. The obtained polyamides were characterized by GPC, NMR, and DSC analysis.

Get access to the full text of this article

Ancillary