Recovery of (−)-praziquantel from racemic mixtures by continuous chromatography and crystallisation

Lim, Bee-Gim; Ching, Chi-Bun; Tan, Reginald B. H.; Ng, Siu‐Choon

doi:10.1016/0009-2509(95)00082-g

Cited by 58 publications

(36 citation statements)

References 9 publications

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“…The SMB technology was a breakthrough in increasing the productivity of chromatographic separations; however, a significative decrease in productivity can still be observed as the level of purification increases. For this reason, some authors have been pursuing the use of hybrid processes, combining SMB chromatography and crystallization in order to obtain an increase in productivity (Lim et al, 1995;Lorenz et al, 2001;Bléhaut et al, 2001;Gedicke, 2005;Lorenz et al, 2006). The general concept of the hybrid process is based on using chromatography as a prepurification stage, followed by a crystallization step to achieve the final purification.…”

Section: Enantioseparation Via Chromatography and Crystallizationmentioning

confidence: 99%

Ternary phase diagram of ketamine ((R,S)-2-(2-chlorophenyl)-2methylaminocyclohexanone) in ethanol and preliminary studies aiming at Enantioselective Crystallization of S-ketamine

Barros

Tamagawa

Santana

et al. 2009

Braz. J. Chem. Eng.

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-Crystallization is an important industrial-scale process for the purification of enantiomers that depends on a phase diagram. In this work, the ternary phase diagram of R-and S-ketamine in ethanol was determined. The eutectic point indicated that crystallization of pure enantiomers from solutions containing more than 75% of the desired enantiomer is feasible. Solubility studies showed the feasibility of using temperature control to conduct the process. Batch crystallization of ketamine (S/R:80/20) solutions at 25°C provided the isolation of S-ketamine (purity of 100%) with a yield from 65 to 70% and a productivity of 6.5 g/(l h).

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Section: Enantioseparation Via Chromatography and Crystallizationmentioning

confidence: 99%

Ternary phase diagram of ketamine ((R,S)-2-(2-chlorophenyl)-2methylaminocyclohexanone) in ethanol and preliminary studies aiming at Enantioselective Crystallization of S-ketamine

Barros

Tamagawa

Santana

et al. 2009

Braz. J. Chem. Eng.

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“…2 (region II and III). The mother liquor (ML) attains in this case eutectic composition in point E. As described earlier [3,[5][6][7][8], this operating policy delivers the maximum amount of pure crystalline product with respect to the amount of this enantiomer in FC. But it is quite clear that operating the process at this boundary would be extremely delicate since the smallest disturbance in the wrong direction would move the process into the three-phase region, causing crystallization of the undesired enantiomer and violation of the product specifications.…”

Section: Steady-state Designmentioning

confidence: 96%

“…Application of the hybrid separation process SMB-crystallization has been discussed for different SLEs. Investigated systems are, e.g., praziquantel [5], mandelic acid [1,3,7], Tröger's base [8], threonine [3], methionine [9], bicalutamide [10], as well as the epimers of a diastereomeric compound [11].…”

Section: Introductionmentioning

confidence: 99%

Dynamics and Control of Coupled Continuous Chromatography and Crystallization Processes for the Production of Pure Enantiomers

Swernath¹,

Kaspereit²,

Kienle³

2013

Chem Eng & Technol

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The combination of continuous chromatographic processes and subsequent crystallization with a recycle of the mother liquor can improve significantly the efficiency of separation processes for the production of enantiomers if compared to the stand-alone chromatographic process. For the first time, dynamic operability and plantwide control of such a process combination is investigated. In the first step, the effect of disturbances on the open loop dynamics is evaluated. In a second step, a simple plantwide control strategy is proposed in order to ensure a robust process operation. It is demonstrated that the direct control of the simulated moving bed (SMB) unit is not required to stabilize the process combination while maintaining the desired product specifications. Instead, this can be achieved easily by controlling the amount of solvent removed or added to the system.

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“…This process combination was investigated for different systems [64,[67][68][69][70]. It was found that its performance can be significantly better than that of stand-alone separations by SMB chromatography.…”

Section: E2 Smb Chromatography In Process Combinationsmentioning

confidence: 98%

“…10 (left) shows an example where it can be very beneficial to use a SMB process at limited outlet purities. In this process, originally suggested by Lim et al [67], one or two pure enantiomers are obtained from a racemic mixture by combining the SMB unit with a crystallization step. The SMB unit delivers one or two only partially purified streams; the final product purity of 100 % is then obtained by selective crystallization.…”

Section: E1 Smb Processes For Limited Product Puritiesmentioning

confidence: 99%

New Developments in Simulated Moving Bed Chromatography

2008

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Chromatographic separation processes are widely used to isolate and purify value added products. Most frequently, such separation processes are performed exploiting the principles of injecting samples of the feed mixture in a repetitive periodic manner and collecting the target products batchwise. In the early 1960s, an alternative operation principle based on using several columns connected in series and exploiting a continuous countercurrent movement between the mobile and stationary phases initiated significant improvements in performing specific separation processes in the petrochemical and sugar industries. In the last decade, the so-called simulated moving bed (SMB) chromatography has rapidly entered the pharmaceutical industry. In particular enantioseparations using chiral stationary phases have become a strong driving force to develop more sophisticated concepts of continuous chromatography. Currently, the growing interest in efficient methods for the downstream processing of biomolecules enhances interest in SMB processes. This paper gives a brief overview of the new suggestions and trends. © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim [accessed July 4, 2008

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Recovery of (−)-praziquantel from racemic mixtures by continuous chromatography and crystallisation

Cited by 58 publications

References 9 publications

Ternary phase diagram of ketamine ((R,S)-2-(2-chlorophenyl)-2methylaminocyclohexanone) in ethanol and preliminary studies aiming at Enantioselective Crystallization of S-ketamine

Ternary phase diagram of ketamine ((R,S)-2-(2-chlorophenyl)-2methylaminocyclohexanone) in ethanol and preliminary studies aiming at Enantioselective Crystallization of S-ketamine

Dynamics and Control of Coupled Continuous Chromatography and Crystallization Processes for the Production of Pure Enantiomers

New Developments in Simulated Moving Bed Chromatography

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