Process optimization of continuous liquid–liquid extraction in centrifugal contactor separators for separation of oxybutynin enantiomers

Tang, Kewen; Wang, Yaqiong; Huang, Yan Yan Shery; Dai, Guilin

doi:10.1016/j.seppur.2015.06.027

Cited by 17 publications

(13 citation statements)

References 35 publications

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“…Modified cyclodextrines have been reported frequently in the recent liquid–liquid separation literature, often exhibiting improved solubility and selectivity (e.g. β‐hydroxypropyl‐cyclodextrines, having a significantly increased water solubility of 450 mg mL ‐1 compared with β‐CD (50 mg mL ‐1 )) …”

Section: Chiral Liquid–liquid Systems (Clls)mentioning

confidence: 99%

“…As mentioned above in the section on CDs, tartrates have been applied extensively in biphasic systems using both CDs and tartrate selectors, e.g. Tang and his team confirmed enantioselectivity for a range of pharmaceutical components, such as flurbiprofen, amlodipine, oxybutynin, and pantoprazole …”

Section: Chiral Liquid–liquid Systems (Clls)mentioning

confidence: 99%

“…-hydroxypropyl-cyclodextrines, having a significantly increased water solubility of 450 mg mL -1 compared with -CD (50 mg mL -1 )). [98][99][100][101][102][103][104][105] Next to applications in liquid-liquid systems, important developments on aqueous cyclic chiral selectors have been reported by Armstrong and co-workers for HPLC and capillary electrophoresis (CE). 106 Twelve different CD and cyclofructan derivatives were used on a set of 17 racemic tetrahydrobenzimidazoles ( Fig.…”

Section: Cyclodextrines and Cyclofructansmentioning

confidence: 99%

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Enantioseparation with liquid membranes

Gössi

Riedl

Schuur

2017

J of Chemical Tech & Biotech

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Chiral resolution of racemic products is a challenging and important task in the pharmaceutical, agrochemical, flavor, polymer and fragrances industries. One of the options for these challenging separations is to use liquid membranes. Although liquid membranes have been known for almost four decades and have been used for optical resolutions, no comprehensive review has been published about the use of this technology for enantioseparations. In this review, the various liquid membrane‐related technologies are described and compared, including bulk liquid membranes, emulsion liquid membranes, micelle‐extraction and micellar enhanced ultrafiltration, as well as supported liquid membranes. Next to technological advances, an overview of recent developments in chiral recognition chemistry in liquid–liquid equilibria is presented. The following extractant classes have recently been reported in conjunction with chiral separation: cyclodextrines, BINOL's, calixarenes, crown ethers, BINAP's, tartaric acids and ionic liquids. The use of two supported (non‐liquid) membranes with an inner loop of extract phase appears to be the most stable liquid membrane configuration, allowing for a large degree of freedom in operational conditions such as solvent to feed ratio. The library of solvents still needs broadening to make the technology more versatile and based on the variety of successes with catalytically active organometallic complexes, development of new chiral selector systems based on asymmetric catalysis literature is suggested for future selector screening studies. © 2017 Society of Chemical Industry

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Section: Chiral Liquid–liquid Systems (Clls)mentioning

confidence: 99%

Section: Chiral Liquid–liquid Systems (Clls)mentioning

confidence: 99%

Section: Cyclodextrines and Cyclofructansmentioning

confidence: 99%

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Enantioseparation with liquid membranes

Gössi

Riedl

Schuur

2017

J of Chemical Tech & Biotech

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“…CCS has been successfully used for the synthesis and refining of biodiesel, for separation of ionic liquid dispersions, for oil‐water separation, and for several other extraction processes . Although the separation of enantiomers by multistage ELLE in CCS has attracted increasing attention in recent years, studies on experimental and modeling of the multistage ELLE have been rarely reported …”

mentioning

confidence: 99%

“…27,28 Although the separation of enantiomers by multistage ELLE in CCS has attracted increasing attention in recent years, studies on experimental and modeling of the multistage ELLE have been rarely reported. 22,[29][30][31][32] 2-Phenylpropionic acid ( Figure 1) is an important 2arylpropionic acid class which is widely used to synthesize chiral drugs such as loxoprfen. It has been revealed that 2-arylpropionic acid enantiomers have their main pharmacological activity on the (S)-enantiomer, while the (R)-enantiomer is inactive.…”

mentioning

confidence: 99%

Experimental and Model Studies on Continuous Separation of 2‐Phenylpropionic Acid Enantiomers by Enantioselective Liquid–Liquid Extraction in Centrifugal Contactor Separators

et al. 2016

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Multistage enantioselective liquid-liquid extraction (ELLE) of 2-phenylpropionic acid (2-PPA) enantiomers using hydroxypropyl-β-cyclodextrin (HP-β-CD) as extractant was studied experimentally in a counter-current cascade of centrifugal contactor separators (CCSs). Performance of the process was evaluated by purity (enantiomeric excess, ee) and yield (Y). A multistage equilibrium model was established on the basis of single-stage model for chiral extraction of 2-PPA enantiomers and the law of mass conservation. A series of experiments on the extract phase/washing phase ratio (W/O ratio), extractant concentration, the pH value of aqueous phase, and the number of stages was conducted to verify the multistage equilibrium model. It was found that model predictions were in good agreement with the experimental results. The model was applied to predict and optimize the symmetrical separation of 2-PPA enantiomers. The optimal conditions for symmetric separation involves a W/O ratio of 0.6, pH of 2.5, and HP-β-CD concentration of 0.1 mol L(-1) at a temperature of 278 K, where eeeq (equal enantiomeric excess) can reach up to 37% and Yeq (equal yield) to 69%. By simulation and optimization, the minimum number of stages was evaluated at 98 and 106 for eeeq > 95% and eeeq > 97%.

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Liquid‐Liquid Centrifugal Extractors: Types and Recent Applications – a Review

Hamamah

Grützner

2022

ChemBioEng Reviews

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In light of the elevating pressures toward adopting intensifying technologies, centrifugal extractors are increasingly drawing attention as a promising alternative to traditional extraction equipment. Recently, many fields have applied them in research and that resulted in a considerable amount of information that may be hard to follow. To keep interested researchers updated, this work presents the state‐of‐the‐art status of those devices. That is, the different types of centrifugal extractors are first surveyed with emphasis on those available on the market nowadays. Then, their recent applications are covered with exclusion of two fields: oil‐water separations and nuclear industry, as the purpose is to accent centrifugal extractors' potential and compatibility with the widest possible range of applications beyond traditional ones. A further section addresses the hydrodynamics of annular centrifugal contactors that form a major subfamily of centrifugal extractors. Those annular variants have received special focus throughout this work, since not only are they the most encountered devices in literature but also still to date under development with latest versions being 3D‐printed.

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Process optimization of continuous liquid–liquid extraction in centrifugal contactor separators for separation of oxybutynin enantiomers

Cited by 17 publications

References 35 publications

Enantioseparation with liquid membranes

Enantioseparation with liquid membranes

Experimental and Model Studies on Continuous Separation of 2‐Phenylpropionic Acid Enantiomers by Enantioselective Liquid–Liquid Extraction in Centrifugal Contactor Separators

Liquid‐Liquid Centrifugal Extractors: Types and Recent Applications – a Review

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