Synthesis of an amine-oleate derivative using an ionic liquid catalyst

J Agric Food Chem. 2009 Sep 23;57(18):8136-41. doi: 10.1021/jf901401s.

Abstract

A facile (and environmentally friendly) reaction between epoxidized methyl oleate and aniline to produce an oleate-aniline adduct, without the formation of fatty amide, was discovered. This reaction was carried out neat, with a catalytic amount of an ionic liquid. No solvent was used, no byproducts were produced, and the ionic liquid could be recovered and recycled. The reaction products were fully characterized by NMR and GC-MS.

MeSH terms

  • Aniline Compounds / chemistry*
  • Borates
  • Catalysis
  • Formates / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Hydrogen Peroxide / chemistry
  • Imidazoles
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Oleic Acids / chemical synthesis*
  • Oleic Acids / chemistry
  • Solutions
  • Stearates / chemistry

Substances

  • Aniline Compounds
  • Borates
  • Formates
  • Imidazoles
  • Indicators and Reagents
  • Oleic Acids
  • Solutions
  • Stearates
  • imidazolium tetrafluoroborate
  • formic acid
  • methyl 9,10-epoxystearate
  • methyl oleate
  • Hydrogen Peroxide
  • aniline