The effects of thermodynamics on mass transfer and enantioseparation of (R,S)-amlodipine across a hollow fiber supported liquid membrane

Sunsandee, Niti; Leepipatpiboon, Natchanun; Ramakul, Prakorn; Wongsawa, Thidarat; Pancharoen, Ura

doi:10.1016/j.seppur.2012.09.027

Cited by 30 publications

(15 citation statements)

References 61 publications

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“…The highest enantioselectivity (α) was 8.38 at a pH of 5.0, as illustrated in Table 1. The results are in agreement with our previous reports (36)(37)(38)(39)(40). Therefore, pH 5.0 was considered to be an …”

Section: Results and Discussion Influence Of Buffer Ph In The Aqueoussupporting

confidence: 93%

“…The value of this knowledge is most important for the chemical and pharmaceutical engineering process such as the liquid membrane process and the hollow fiber supported liquid membrane process. This study used the same initial parameters as in our recent work (36)(37)(38)(39)(40) to confirm that the operating conditions such as the buffer pH in the aqueous phase, type of organic solvents, contact time, and concentration ratio of racemic compound to extractant could influence chiral extraction and enantioseparation efficiency. The parameters studied include the effect of extraction equilibrium time, the influence of different alkyl chains of tartaric acids, types of β-cyclodextrin (β-CD) derivatives, organic solvents, and buffer pH.…”

Section: Introductionmentioning

confidence: 97%

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Selective Enantioseparation of Racemic Amlodipine by Biphasic Recognition Chiral Separation System

Sunsandee

Rashatasakhon

Ramakul

et al. 2014

Separation Science and Technology

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The biphasic recognition chiral extraction process was developed and applied to separate amlodipine enantiomer. The chiral extraction system contained tartaric acid derivatives in the organic phase and β-cyclodextrin derivatives in the aqueous phase. The effect of extraction equilibrium time and the influence of different types of tartaric acids, types of β-cyclodextrin derivatives, organic solvents, and buffer pH were investigated. The results indicated that hydroxypropyl-β-cyclodextrin (HP-β-CD) showed a higher recognition ability toward (S)-amlodipine than (R)-amlodipine while dibenzoyl-D-tartrate demonstrated the strongest ability among tartaric acid derivatives to bind with (R)-amlodipine. The distribution ratios for (S)-amlodipine (k S ) and (R)-amlodipine (k R ) gave optimum values at pH 5.0 of 16.54 and 0.78, respectively. Biphasic chiral recognition extraction has great significance for preparative separation of (S)-amlodipine. It can also be used to design and apply the enantioseparation process.

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Section: Results and Discussion Influence Of Buffer Ph In The Aqueoussupporting

confidence: 93%

Section: Introductionmentioning

confidence: 97%

Selective Enantioseparation of Racemic Amlodipine by Biphasic Recognition Chiral Separation System

Sunsandee

Rashatasakhon

Ramakul

et al. 2014

Separation Science and Technology

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“…At the interface, one enantiomer forms a complex with the chiral carrier preferentially depending upon the nature of carrier. A hollow fiber supported liquid membrane has been used for the enantioseparation of (R,S)-amlodipine and levocetirizine as well as the effects of thermodynamics on mass transfer prediction have been investigated [91,92]. Although studies on liquid membranes indicated very high enantioselectivity for certain isomers, the liquid membranes showed poor stability due to loss of solvent and carrier with time.…”

Section: Optical Resolution Through Liquid Membranesmentioning

confidence: 99%

Methods for separation of organic and pharmaceutical compounds by different polymer materials

Ingole

2014

Korean J. Chem. Eng.

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The discrimination of enantiomers is a challenging task in separation technology, and using a membrane is most promising for separating enantiomers from racemic mixture. The optical resolution of chiral compounds is of interest to researchers working in a variety of fields from analytical, organic and medicinal chemistry, to pharmaceutics and materials, to process engineering for fabricating pharmaceuticals, agrochemicals, fragrances and foods, and so on. There is considerable demand for separation techniques appropriate for the large-scale resolution of chiral molecules. The separation of chiral compounds using chiral or achiral/non-chiral polymeric membranes with or without chiral selector represents a promising system for future commercial applications. This review focuses on an active field of chiral separation, membrane-based enantioseparation technique, which has potential for large-scale production of singleenantiomers. Enantiomeric separation by membrane processes has been studied using various configurations of liquid and solid polymer membranes. Selectivity and permeability of liquid-membranes is reasonably good because the rate of diffusion of solute molecules is high in liquids but has inferior durability and stability. Solid polymer membranes have inferior permeability because diffusion of solute through solids is slow but quite stable and durable; however, commercial application of membrane technology for optical resolution is yet to be realized. Several chiral separation membranes were prepared from chiral polymers where enantioselectivity was generated from chiral carbons in the main chain. However, it is rather tricky to generate excellent chiral separation membranes from chiral polymers alone, because racemic penetrants mainly encounter the flexible side chains of the membrane polymers.

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“…Membrane techniques are promising methods for chiral separations due to their low cost, simple arrangement, low energy consumption, high capacity, and continuous operation [7,8]. A high separation efficiency accompanied by high fluxes through the membrane and a good chemical and mechanical stability are required from enantioselective membranes [9][10][11][12][13][14]. Membranes containing chiral centers are good candidates for the separation of enantiomers [7].…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Behavior of Nafion® Membranes towards (+)‐α‐Pinene and (−)‐α‐Pinene

et al. 2015

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a-Pinene enantiomers were sorbed in Nafion membranes. The membranes included a commercial extruded Nafion 115 membrane as well as membranes prepared by casting a Nafion solution, evaporating the solvent, and a thermal treatment at different temperatures. The microstructure of membranes was studied by small-angle and wide-angle X-ray scattering, and magic-angle spinning nuclear magnetic resonance spectroscopy. The change of membrane weight during the sorption process was determined with a sorption microbalance. Noticeable differences concerning the sorption behavior of the various membranes could be stated. The sorption of (+)-a-pinene and (-)-a-pinene in an extruded Nafion membrane turned out to be rather low.

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The effects of thermodynamics on mass transfer and enantioseparation of (R,S)-amlodipine across a hollow fiber supported liquid membrane

Cited by 30 publications

References 61 publications

Selective Enantioseparation of Racemic Amlodipine by Biphasic Recognition Chiral Separation System

Selective Enantioseparation of Racemic Amlodipine by Biphasic Recognition Chiral Separation System

Methods for separation of organic and pharmaceutical compounds by different polymer materials

Stereoselective Behavior of Nafion® Membranes towards (+)‐α‐Pinene and (−)‐α‐Pinene

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