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

Journal of agricultural and food chemistry (2009-09-02)
Atanu Biswas, Brajendra K Sharma, Kenneth M Doll, Sevim Z Erhan, Julious L Willett, H N Cheng
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methyl oleate, 99%
Supelco
Methyl oleate, analytical standard
Sigma-Aldrich
Methyl oleate, technical grade, 70%
Sigma-Aldrich
Methyl elaidate, ≥99% (capillary GC)
Supelco
cis-9-Octadecenoic acid methyl ester, certified reference material, 10 mg/mL in heptane
Supelco
Methyl elaidate, analytical standard