Effect of water activity on the lipase catalyzed esterification of geraniol in ionic liquid [bmim]PF6.
Enzymatic reactions in non-aqueous media have been shown to be effective in carrying out chemical transformation where the reactants are insoluble in water or water is a byproduct limiting conversion. Ionic liquids, liquid organic salts with infinitesimal vapor pressure, are potentially useful alternatives to organic solvents. It is known that the thermodynamic water activity is an important variable affecting the activity of enzymes in non-aqueous solvents. This study investigated the influence of water activity on the esterification of geraniol with acetic acid in ionic liquid [bmim]PF6 catalyzed by immobilized Candida antarctica lipase B. The conversion of geraniol in [bmim]PF6 was significant although the reaction rate was slower than in organic solvents. The profile of initial reaction rate-water activity was determined experimentally, and differed from the data reported for other non-aqueous solvents. A maximum in the initial reaction rate was found at aw = 0.6. The pseudo reaction equilibrium constant, Kx, was measured experimentally for the reaction. The average value of Kx in [bmim]PF6 was 12, 20-fold lower than the value reported for the same system in hexane.
Barahona
Donifan
D
Department of Chemical Engineering, Kansas State University, Durland Hall 105, Manhattan, Kansas 66506-5102, USA.
Pfromm
Peter H
PH
Rezac
Mary E
ME
D000080462:Acyclic Monoterpenes; D002384:Catalysis; D004951:Esterification; D005656:Fungal Proteins; D007093:Imidazoles / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
C412621:1-butyl-3-methylimidazolium hexafluorophosphate; D000080462:Acyclic Monoterpenes; D005656:Fungal Proteins; D007093:Imidazoles; D013729:Terpenes; D014867:Water; D008049:Lipase; C431349:lipase B, Candida antarctica; C007836:geraniol