Integration of reactive membrane extraction with lipase-hydrolysis dynamic kinetic resolution of naproxen 2,2,2-trifluoroethyl thioester in isooctane.
Lipases immobilized on polypropylene powders have been used as the biocatalyst in the enantioselective hydrolysis of (S)-naproxen from racemic naproxen thioesters in isooctane, in which trioctylamine was added to perform in situ racemization of the remaining (R)-thioester substrate. A detailed study of the kinetics for hydrolysis and racemization indicates that increasing the trioctylamine concentration can activate and stabilize the lipase as well as enhance the racemization and non-stereoselective hydrolysis of the thioester. Effects of the aqueous pH value and trioctylamine concentration on (S)-naproxen dissociation and partitioning in the aqueous phase as well as the transportation in a hollow fiber membrane were further investigated. Good agreements between the experimental data and theoretical results were obtained when the dynamic kinetic resolution process was integrated with a hollow fiber membrane to reactively extract the desired (S)-naproxen out of the reaction medium.
Department of Chemical Engineering, National Cheng Kung University, Tainan, Taiwan 70101, Republic of China.
Chu-Hsun
CH
Lu
Yu-Chi
YC
Cheng
Shau-Wei
SW
Tsai
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003198:Computer Simulation; D004800:Enzymes, Immobilized; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D008567:Membranes, Artificial; D008956:Models, Chemical; D009288:Naproxen / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D009795:Octanes / Q000737:chemistry*; D011126:Polypropylenes; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
D000588:Amines; D004800:Enzymes, Immobilized; D008567:Membranes, Artificial; D009795:Octanes; D011126:Polypropylenes; C469960:naproxen 2,2,2-trifluoroethyl thioester; D009288:Naproxen; C038229:tri-N-octylamine; C045798:2,2,4-trimethylpentane