Optimization of the mobile phase composition for preparative chiral separation of flurbiprofen enantiomers

Ribeiro, António E.; Graça, Nuno S.; Pais, L.S.; Rodrigues, Alı́rio E.

doi:10.1016/j.seppur.2009.03.049

Cited by 13 publications

(19 citation statements)

References 37 publications

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“…The simulation of the SMB process was carried out by using the gPROMS software package (Process Systems Enterprise, London, UK) to predict the transient evolution of the nadolol stereoisomer concentrations in both the extract and the raffinate outlet streams and the internal concentration profiles on the set of six SMB columns. The detailed SMB model equations can be found in previous works …”

Section: Methodsmentioning

confidence: 99%

“…From a preparative point of view, a high selectivity of the enantiomers should not be the only goal, as it is frequently followed at analytical scale. In this choice, high solubility and low retention times should also be taken into account, in order to improve the preparative process performance, as has been extensively explicated for the separation of chiral nonsteroidal anti‐inflammatory drugs …”

Section: Introductionmentioning

confidence: 99%

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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: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

2013

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“…The phenomenon could be explained by the fact that the enantioselective complexation between the L‐dioctyl tartrate and R‐enantiomer was achieved at 25 °C and an optimized α value of 2.34 was obtained. Comparatively, the effect of temperature on chiral separation of flurbiprofen enantiomers was quite different from other biphasic recognition extraction systems …”

Section: Resultsmentioning

confidence: 75%

“…Thus, chiral selectors identified the specific enantiomers from the racemic mixture and formed diastereomeric complexes, which could be extracted separately. A variety of chiral selectors such as crown ether, porphyrin, tartaric acid derivatives, cyclodextrins and their derivatives, etc., were selected as chiral selectors in ELLE . Nevertheless, the application of many current chiral selectors is often limited to their solubility for many solvents .…”

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confidence: 99%

Enantioseparation of Racemic Flurbiprofen by Aqueous Two‐Phase Extraction With Binary Chiral Selectors of L‐dioctyl Tartrate and L‐tryptophan

et al. 2015

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A novel method for chiral separation of flurbiprofen enantiomers was developed using aqueous two-phase extraction (ATPE) coupled with biphasic recognition chiral extraction (BRCE). An aqueous two-phase system (ATPS) was used as an extracting solvent which was composed of ethanol (35.0% w/w) and ammonium sulfate (18.0% w/w). The chiral selectors in ATPS for BRCE consideration were L-dioctyl tartrate and L-tryptophan, which were screened from amino acids, β-cyclodextrin derivatives, and L-tartrate esters. Factors such as the amounts of L-dioctyl tartrate and L-tryptophan, pH, flurbiprofen concentration, and the operation temperature were investigated in terms of chiral separation of flurbiprofen enantiomers. The optimum conditions were as follows: L-dioctyl tartrate, 80 mg; L-tryptophan, 40 mg; pH, 4.0; flurbiprofen concentration, 0.10 mmol/L; and temperature, 25 °C. The maximum separation factor α for flurbiprofen enantiomers could reach 2.34. The mechanism of chiral separation of flurbiprofen enantiomers is discussed and studied. The results showed that synergistic extraction has been established by L-dioctyl tartrate and L-tryptophan, which enantioselectively recognized R- and S-enantiomers in top and bottom phases, respectively. Compared to conventional liquid-liquid extraction, ATPE coupled with BRCE possessed higher separation efficiency and enantioselectivity without the use of any other organic solvents. The proposed method is a potential and powerful alternative to conventional extraction for separation of various enantiomers.

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“…Among these methods, mobile phase variables are helpful probes for investigating which interactions are involved [18,19]. Even change of mobile phase composition can lead to the reversal of elution order between enantiomers [20,21].…”

Section: Discussion On the Retention Mechanism Using The Retention Modelmentioning

confidence: 99%

Enantioseparation of Hydrobenzoin and Structurally Related Compounds on β-Cyclodextrin and Hydroxypropyl-β-cyclodextrin Bonded Chiral Stationary Phases

Guo

Xie

et al. 2011

Chromatographia

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A b-cyclodextrin (b-CD) and a hydroxypropylb-cyclodextrin (HP-b-CD) bonded chiral stationary phase (CSP) were prepared. Comparative evaluations of these two CSPs for the enantioseparation of hydrobenzoin, benzoin and a-phenethyl alcohol by reversed-phase liquid chromatography were presented. The effects of buffer composition in the mobile phase on the retention and enantioseparation were investigated. The borate buffer had a significant influence on the retention and enantioseparation of hydrobenzoin. Linear solvent strength retention model was used to fit the chromatographic data. Good linearity existed between the logarithm of retention factor (k) and the volume fraction of organic modifier (u). Another retention model, stoichiometric displacement theory for retention, was also tried to fit the chromatographic data. The results showed that not only acetonitrile, but also water molecules participated in the displacing process of the solute.

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Optimization of the mobile phase composition for preparative chiral separation of flurbiprofen enantiomers

Cited by 13 publications

References 37 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

Enantioseparation of Racemic Flurbiprofen by Aqueous Two‐Phase Extraction With Binary Chiral Selectors of L‐dioctyl Tartrate and L‐tryptophan

Enantioseparation of Hydrobenzoin and Structurally Related Compounds on β-Cyclodextrin and Hydroxypropyl-β-cyclodextrin Bonded Chiral Stationary Phases

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