Dynamic kinetic resolution: alternative approach in optimizing S-ibuprofen production.
A lipase catalysed enantioselective hydrolysis process under in situ racemization of the remaining (R)-ibuprofen ester substrate with sodium hydroxide as the catalyst was developed for the production of S-ibuprofen from (R,S)-ibuprofen ester in isooctane. Detailed investigations on parameters study indicated that 0.5 M NaOH, addition of 20% (v/v) co-solvent (dimethyl sulphoxide), operating temperature of 45 degrees C, and 40 mmol/L substrate gave 86% conversion and 99.4% optical purity of S-ibuprofen in dynamic kinetic resolution. Meanwhile, in common enzymatic kinetic resolution process, only 42% conversion of the racemate and 93% enantiomeric excess of the product was obtained which are of lower values as compared to dynamic kinetic resolution. The S-ibuprofen produced during each process was evaluated and approximately 50% increment in concentration of S-acid product was produced when dynamic kinetic resolution was applied into the process.
Fazlena
H
H
School of Chemical Engineering, Universiti Sains Malaysia, 14300, Nibong Tebal, Seberang Prai Selatan, Penang, Malaysia.
Kamaruddin
A H
AH
Zulkali
M M D
MM
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003198:Computer Simulation; D006868:Hydrolysis; D007052:Ibuprofen / Q000138:chemical synthesis*; D007536:Isomerism; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D008956:Models, Chemical; D012972:Sodium Hydroxide / Q000737:chemistry*; D013696:Temperature
D012972:Sodium Hydroxide; D008049:Lipase; D007052:Ibuprofen