Functionalized Ionic Liquid‐Catalyzed 1‐Feruloyl‐ sn ‐glycerol Synthesis

Feruloyl Glycerol (FG) is a potential antioxidant and UV absorbing ingredient in food and cosmetic industries. Transesterifications of ethyl ferulate (EF) with glycerol to synthesize FG were performed using different functionalized ionic liquids (1‐butylsulfonic‐3‐methylimidazolium tosylate, [BSO 3 HMIM]TS; 1‐propylsulfonic‐3‐methylimidazolium tosylate, [PSO 3 HMIM]TS; 1‐butylsulfonic‐3‐methylimidazolium trifluoromethanesulfonate, [BSO 3 HMIM]OTF; 1‐butylsulfonic‐3‐methylimidazolium hydrogen sulfate, [BSO 3 HMIM]HSO 4 ; N ‐methylimidazolium hydrogen sulfate, [HMIM]HSO 4 ; 1‐butyl‐3‐methylimidazolium hydroxide, [BMIM]OH; 1‐butyl‐3‐methylimidazo tetrachloride molysite, [BMIM]FeCl 4 ; and 1‐hexyl‐3‐methylimidazo tetrachloride molysite, [BMIM]FeCl 4 ) as catalysts, respectively. High EF conversion (98.0 ± 1.5 %), 1‐FG (1‐feruloyl‐ sn ‐glycerol) yield (88.7 ± 1.1 %) and reaction selectivity for 1‐FG (90.5 ± 2.1 %) were obtained using [BSO 3 HMIM]TS as catalyst. The activation energy ( E a ), the Michaelis–Menten kinetic constant ( K m ), and the maximum initial reaction rate ( v max ) of the transesterification are 65.9 ± 3.3 kJ/mol, 1.8 ± 0.1 mol/L, and (1.6 ± 0.4) × 10 −2 mol/(L min), respectively. Effects of catalyst loading, reaction temperature, and the molar ratio of EF to glycerol on EF conversion and reaction selectivity for 1‐FG (1‐FG yield/EF conversion) were also investigated.