Synthesis of an amine-oleate derivative using an ionic liquid catalyst.
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.
Biswas
Atanu
A
Plant Polymer Research, National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, Peoria, Illinois 61604, USA. Atanu.biswas@ars.usda.gov
Sharma
Brajendra K
BK
Doll
Kenneth M
KM
Erhan
Sevim Z
SZ
Willett
Julious L
JL
Cheng
H N
HN
D000814:Aniline Compounds / Q000737:chemistry*; D001881:Borates; D002384:Catalysis; D005561:Formates / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006861:Hydrogen Peroxide / Q000737:chemistry; D007093:Imidazoles; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009829:Oleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D012996:Solutions; D013228:Stearates / Q000737:chemistry
D000814:Aniline Compounds; D001881:Borates; D005561:Formates; D007093:Imidazoles; D007202:Indicators and Reagents; D009829:Oleic Acids; D012996:Solutions; D013228:Stearates; C493603:imidazolium tetrafluoroborate; C030544:formic acid; C026824:methyl 9,10-epoxystearate; C005576:methyl oleate; D006861:Hydrogen Peroxide; C023650:aniline