Simulated Moving Bed and Related Techniques

Pais, L.S.; Mata, Vera G.; Rodrigues, Alı́rio E.

doi:10.1002/9780470988428.ch7

Cited by 11 publications

(8 citation statements)

References 23 publications

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“…It is also interesting to note that the use of a pure ethanol mobile phase (100:0.3 ethanol‐DEA) allows the first stereoisomer to elute almost completely separated from the other three, since the second and third stereoisomers eluted together. This could be useful for a preparative ternary separation (1; 2 + 3; 4) using a SMB‐related technique such as the JO process …”

Section: Resultsmentioning

confidence: 99%

Separation of Nadolol Stereoisomers by Chiral Liquid Chromatography at Analytical and Preparative Scales

2013

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The separation of the four nadolol stereoisomers on Chiralpak® AD by chiral liquid chromatography was carried out at both analytical and preparative scales. A screening of possible mobile-phase compositions was performed using different alcohol-hydrocarbon mixtures. The results obtained confirm the use of 20:80:0.3 ethanol-hexane-diethylamine reported by McCarthy (1994) but introduce other possibilities for the complete resolution of the four nadolol stereoisomers at analytical scale, namely, the mixtures 30-40:70-60:0.3 ethanol-heptane-diethylamine. Additionally, this work describes how retention and resolution depend on the ethanol content in hexane and heptane mixtures. The separation of nadolol stereoisomers is also carried out at preparative scale and different alcohol-hydrocarbon compositions are proposed, depending on the target component to be obtained. Particularly, this work presents the experimental separation of the more retained nadolol stereoisomer (RSR-nadolol) by simulated moving bed (SMB) chromatography using an 80:20:0.3 ethanol-heptane-diethylamine mobile phase. For a 2 g/l feed concentration, RSR-nadolol is 100% recovered at the extract outlet stream, 100% pure, and with a system productivity of 0.65 g(RSR-nadolol)/(l(bed)(.)h) and a solvent consumption of 9.6 l(solvent)/g(RSR-nadolol).

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Section: Resultsmentioning

confidence: 99%

Separation of Nadolol Stereoisomers by Chiral Liquid Chromatography at Analytical and Preparative Scales

2013

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“…This method is based on the assumptions that mass transfer resistances and axial dispersion are negligible, and the adsorption equilibrium can be described by a Langmuir isotherm model (LG3) or by a linear -þ Langmuir isotherm model (LLG4). However, when mass transfer resistances and axial dispersion cannot be neglected, the critical values are more restrictive and should be evaluated through simulation using more precise models (6,23,(26)(27)(28)(29).…”

Section: Smb Design Toolsmentioning

confidence: 99%

“…Regardless, there is considerable evidence that R(À)ketoprofen and S(þ)ketoprofen enantiomers have important and different therapeutic actions (3,4), and the narrow international legislation concerning ketoprofen safety (5) still allows its commercialization in the form of racemic mixture. Over the last decade, an important improvement on the performance of Simulated Moving Bed (SMB) technology has been noticed, mostly due to academic community contributions exploring and developing new nonconventional and more efficient modes of operation (6)(7)(8)(9). Its practical advantages over other classical techniques allowed SMB technology to become an attractive method for large scale process separation in several industry fields such as biotechnology, pharmaceutics, and fine chemical products.…”

Section: Introductionmentioning

confidence: 99%

Chiral Separation of Ketoprofen Enantiomers by Preparative and Simulated Moving Bed Chromatography

Ribeiro

Gomes

Pais

et al. 2011

Separation Science and Technology

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The pharmaceutical industry is now directed to the market of more safety and efficient drugs, based on single enantiomers. Ketoprofen, still used as a racemic pharmaceutical drug, belongs to the profens class, one of the most representative of the non-steroidal anti-inflammatory drugs. This work presents the chiral separation of ketoprofen enantiomers by simulated moving bed technology, using a laboratory scale unit (the FlexSMB-LSRE 1 ) with six columns, packed with the Chiralpak AD 1 stationary phase (20 lm). A comparative study between a mobile phase composed of a traditional high hydrocarbon content (10%ethanol=90%n-hexane=0-.01%TFA) and a strong polar organic composition (100%ethanol= 0.01%TFA) is presented. The study includes the measurement of the adsorption isotherms, elution, and frontal chromatography experiments, carried out on a SMB column for both compositions. The results obtained allowed the prediction and optimization of the SMB operation. Using pure ethanol as solvent and a racemic feed concentration of 40 g=L, purities above 98.6% on both outlet streams were obtained, with a productivity of 3.84 g feed =(L bed .hr) and a solvent consumption of 0.78 L solvent =g feed . The results obtained in the experimental separation of ketoprofen enantiomers by SMB chromatography indicates that pure ethanol presents better performances than the classic high hydrocarbon content composition.

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“…For more information concerning SMB modeling and simulation, through the equilibrium theory and other more precise SMB models, see references [9][10][11][12][13][14]. Fig.…”

Section: Simulated Moving Bed Simulationsmentioning

confidence: 99%

Preparative separation of ketoprofen enantiomers: Choice of mobile phase composition and measurement of competitive adsorption isotherms

Ribeiro

Graça

Pais

et al. 2008

Separation and Purification Technology

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The present work intends to investigate how mobile phase composition influences the adsorption behavior of ketoprofen enantiomers (a nonsteroidal anti-inflammatory drug) on an amylose-based chiral stationary phase (Chiralpak AD). Three mobile phase compositions were studied: the usual 20% ethanol/80% n-hexane mixture and two pure mobile phases; methanol and ethanol. Pulse and breakthrough experiments under preparative conditions were carried out in order to measure and test adsorption isotherms. The results obtained show that, for preparative separations, pure ethanol is a better mobile phase than the usual 20% ethanol/80% n-hexane mixture: it allows higher solubility of the racemate, lower retention times, and also a higher selectivity at high enantiomer concentrations. These are aspects of crucial importance when the final goal is to achieve high productivity preparative separations, as it is shown for the simulated moving bed (SMB) operation.

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Simulated Moving Bed and Related Techniques

Cited by 11 publications

References 23 publications

Separation of Nadolol Stereoisomers by Chiral Liquid Chromatography at Analytical and Preparative Scales

Separation of Nadolol Stereoisomers by Chiral Liquid Chromatography at Analytical and Preparative Scales

Chiral Separation of Ketoprofen Enantiomers by Preparative and Simulated Moving Bed Chromatography

Preparative separation of ketoprofen enantiomers: Choice of mobile phase composition and measurement of competitive adsorption isotherms

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