The exploration of the reversed enantioselectivity of a chitosan functionalized cellulose acetate membranes in an electric field driven process

Zhou, Zhengzhong; Cheng, Jiu Hua; Chung, Tai‐Shung; Hatton, T. Alan

doi:10.1016/j.memsci.2011.11.002

Cited by 23 publications

(6 citation statements)

References 36 publications

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“…The empirical investigation of gas permeation performance of pure and filled polymer as membranes is difficult, time consuming and costly or needs obtaining special parameters in the critical conditions (such as high temperature and high pressure) [32][33][34][35][36]. On the other hand, by applying the considerable improvements in the computational calculations and using this assumption that the motions of atoms can be described by Newtons' laws and the interactions among the atoms can be calculated by using the existing empirical potential functions, the molecular dynamics (MD) simulation has provided a general and high efficient method to simulate various natural processes at the molecular level [36][37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Molecular simulation study of penetrant gas transport properties into the pure and nanosized silica particles filled polysulfone membranes

Golzar

Amjad‐Iranagh

Amani

et al. 2014

Journal of Membrane Science

127

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Section: Introductionmentioning

confidence: 99%

Molecular simulation study of penetrant gas transport properties into the pure and nanosized silica particles filled polysulfone membranes

Golzar

Amjad‐Iranagh

Amani

et al. 2014

Journal of Membrane Science

127

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“…[99] Hatton and co-workers explored the influence of driving force on the chiral separation performance of a chitosan functionalized cellulose acetate membrane. [100] By using racemic tryptophan (Trp) as probe solution, D-Try was selectively transported through the membrane driven by the concentration gradient or hydraulic pressure with ee values of 94% and 66%, respectively. In contrast, when an electric field was applied as the driving force, L-Try was enriched in the permeate chamber, giving rise to a reversed enantioselectivity with ee value of −16%.…”

Section: Polymer-based Chiral Separation Membranesmentioning

confidence: 99%

Emerging Homochiral Porous Materials for Enantiomer Separation

Zhang

Zhu

et al. 2021

Adv Funct Materials

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Efficient resolution of racemates of chiral molecules is of great significance in the pharmaceutical, agrochemical, fragrances, and food additives industries. Emerging homochiral porous materials such as metal-organic frameworks, covalent-organic frameworks, porous-organic cages, and metal-organic cages with ultrahigh surface area, controllable pore chemistry and ample chiral recognition sites are promising for efficient chiral resolution, which display excellent properties for chiral separation applications. This review summarizes the design and synthesis strategies for the construction of homochiral porous materials, including direct synthesis, post-synthesis, and chiral induction synthesis. Following this, applications of emerging homochiral porous materials, including enantioselective adsorption, chiral chromatography, and membrane-based chiral separation are highlighted. Finally, the challenges in this area are discussed, with future perspectives provided.

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“…Conventional chiral resolution methods, including preferential crystallization, stereoselective transformation by an optical resolution agent, high performance liquid chromatography and electrophoresis, have the common shortcomings such as relatively low productivity, expensive chemical consumables, and high energy consumption. 8–10 The use of membrane technology for chiral separations offers several advantages over traditional methods, including low time cost, simplicity of operation, and easy scale-up. 5–10 Furthermore, when using chiral activated membranes only a small quantity of an expensive chiral selector is required.…”

Section: Introductionmentioning

confidence: 99%

“…8–10 The use of membrane technology for chiral separations offers several advantages over traditional methods, including low time cost, simplicity of operation, and easy scale-up. 5–10 Furthermore, when using chiral activated membranes only a small quantity of an expensive chiral selector is required. 8–10 …”

Section: Introductionmentioning

confidence: 99%

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Enantiomeric Selective Adsorption of Amino Acid by Polysaccharide Composite Materials

Duri

Tran

2014

Langmuir

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A composite containing cellulose (CEL) and chitosan (CS) synthesized by a simple and recyclable method by using butylmethylimmidazolium chloride, an ionic liquid, was found to exhibit remarkable enantiomeric selectivity toward adsorption of amino acids. 100%CS shows the highest adsorption capacity and enantiomeric selectivity. A racemic amino acid can be enantiomerically resolved by 100%CS in about 96–120 hrs. Interestingly, adsorption by 50:50 CEL:CS is more similar to that by 100%CS than to 100%CEL. Specifically, while 100% CEL shows lowest adsorption capacity and enantiomeric selectivity, 50:50 CEL:CS has sufficient enantiomeric selectivity to enable it to be used for chiral resolution. This is very significant because in spite of its high enantiomeric selectivity, 100%CS cannot practically be used because it has relatively poor mechanical properties and undergoes extensive swelling. Adding 50% of CEL to CS substantially improves the mechanic properties and reduces its swelling while retains sufficient enantiomeric selectivity to enable it to be used for routine chiral separations. Kinetic results indicate that the enantiomeric selective adsorption is due not to the initial surface adsorption but rather to the subsequent stage in which the adsorbate molecules diffuse into the pores within the particle of the composites and consequently got adsorbed by the interior of each particle. The strong inter- and intramolecular hydrogen bond network in CEL enables it to adopt a very dense structure which makes it difficult for adsorbate molecules to diffuse to its interior thereby leading to low enantiomeric selectivity. Compared to hydroxy group, amino group cannot form strong hydrogen bond. The hydrogen bond network in CS is not as extensive as in CEL, and its inner structure is relatively less dense than CEL. Adsorbate molecules can, therefore, diffuse from the outer surface to its inner structure relatively easier than in CEL, thereby leading to higher enantiomeric selectivity for 100%CS.

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The exploration of the reversed enantioselectivity of a chitosan functionalized cellulose acetate membranes in an electric field driven process

Cited by 23 publications

References 36 publications

Molecular simulation study of penetrant gas transport properties into the pure and nanosized silica particles filled polysulfone membranes

Molecular simulation study of penetrant gas transport properties into the pure and nanosized silica particles filled polysulfone membranes

Emerging Homochiral Porous Materials for Enantiomer Separation

Enantiomeric Selective Adsorption of Amino Acid by Polysaccharide Composite Materials

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