Continuous chiral resolution of racemic Ibuprofen by diastereomeric salt formation in a Couette-Taylor crystallizer

Green and Strategic Approach for Chiral Resolution by Diastereomeric Salt Formation: The Study of Racemic Ibuprofen

“…Therefore, the overall recovery rate of S -IBU is (6.7 g × 90%)/9 g × 100% = 67% (≈56% × 70% × 95% × 90%) (i.e., S -IBU percentage)/0.5 (i.e., only half S -IBU in Rac-IBU). The present study shows greater process efficiency as compared to the published works with definite results or figures, which gave 36.8%ee and an overall averaged yield of 50% in the three steps (IPA was used as the solvent for recrystallization) and 71%de but a very low yield of <10% in a continuous Couette–Taylor crystallizer using a cosolvent of EtOH-water (4/1, v/v) …”

“…In the present study, S -MBA and KOH were selected as the resolving agent and nonchiral agent, respectively, based on the literature survey and our preliminary results. According to the literature, the resolution of Rac-IBU had been performed by diastereomeric salt formation with several resolving agents, such as l -lysine, N -methyl- d -glucamine, and R - , and S -MBA. , l -Arginine had also been used as a chiral selector in thin-layer chromatography …”

“…The present study shows greater process efficiency as compared to the published works with definite results or figures, which gave 36.8%ee and an overall averaged yield of 50% in the three steps (IPA was used as the solvent for recrystallization) 43 and 71%de but a very low yield of <10% in a continuous Couette−Taylor crystallizer using a cosolvent of EtOH-water (4/1, v/v). 44 Guidelines for the Development of Chiral Resolution Processes by Diastereomeric Salt Formation. According to the present study, guidelines for the late-stage development of a chiral resolution process by diastereomeric salt formation are provided.…”

Design of diastereomeric salt resolutionviamulticomponent system characterization: a case study with hydrate formation

“…4 Contrary to other methods like preferential crystallization and solid-state deracemization, it can be applied to any material that has acidic/basic functional group. 5 Therefore, its application in intensively researched innovative crystallization procedures (e.g., continuous crystallization 6 and Viedma-ripening 7 ) is actively studied as well. Knowledge about the physicochemical properties of our system is the key to the development of an efficient resolution process.…”

“…5 Therefore, its application in intensively researched innovative crystallization procedures ( e.g. , continuous crystallization 6 and Viedma-ripening 7 ) is actively studied as well.…”