Lipophilisation of Caffeic Acid through Esterification with Propanol Using Water-tolerable Acidic Ionic Liquid as Catalyst.

Propyl caffeate was synthesized to produce lipophilic antioxidant, which used caffeic acid and propanol as starting materials, acidic ionic liquid as catalyst. The highest yield of propyl caffeate (98.7±0.8%) have been achieved under the optimum as follows: 1-butylsulfonic-3-methylimidazolium tosylate showed the best catalytic performance, molar ratio of caffeic acid to propanol was 1:20, reaction temperature was 90°C and the amount of acidic ionic liquid was 40%. The relationship between temperature and the forward rate constant gave the activation energy of 33.6 kJ mol(-1), which indicated that acidic ionic liquid possesses high catalytic activity in the synthesis of PC. And the activity of acidic ionic liquid was not inhibited by the water produced during the esterification process. More importantly, this reaction system can even proceed smoothly when initial water content was 5%.