Process modeling of the lipase-catalyzed dynamic kinetic resolution of (R, S)-suprofen 2,2,2-trifluoroethyl thioester in a hollow-fiber membrane.
A Candida rugosa lipase immobilized on polypropylene powder was employed as the biocatalyst for the enantioselective hydrolysis of (R, S)-suprofen 2,2,2-trifluorothioester in cyclohexane, in which trioctylamine was added as the catalyst to perform in situ racemization of the remaining (R)-thioester. A hollow-fiber membrane was also integrated with the dynamic kinetic resolution process in order to continuously extract the desired (S)-suprofen into an aqueous solution containing NaOH. A kinetic model for the whole process (operating in batch and feed-batch modes) was developed, in which enzymatic hydrolysis and deactivation, lipase activation, racemization and non-enantioselective hydrolysis of the substrate by trioctylamine, and reactive extraction of (R)- and (S)-suprofen into the aqueous phase in the membrane were considered. Theoretical predictions from the model for the time-course variations of substrate and product concentrations in each phase were compared with experimental data.
Wang
L W
LW
Department of Chemical Engineering, National Cheng Kung University, Tainan, 70101, Taiwan.
Cheng
Y C
YC
Tsai
S W
SW
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D005591:Chemical Fractionation / Q000379:methods; D003198:Computer Simulation; D004789:Enzyme Activation; D004800:Enzymes, Immobilized / Q000737:chemistry; D005656:Fungal Proteins; D007536:Isomerism; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D008567:Membranes, Artificial; D044085:Microfluidics / Q000379:methods*; D008956:Models, Chemical; D013496:Suprofen / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification*; D014462:Ultrafiltration / Q000379:methods*
D000588:Amines; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D008567:Membranes, Artificial; C501728:suprofen 2,2,2-trifluoroethyl thioester; D013496:Suprofen; D008049:Lipase; C431349:lipase B, Candida antarctica; C038229:tri-N-octylamine