Green and efficient enantioseparation of amlodipine using a novel pairwise crystallization-circulating extraction coupling method aimed at in situ reuse of mother liquor

Zeng, Leli; Peng, Xiaohui; Liu, Qian; Xu, Tingxuan; Wang, Guoxiang; Bruggen, Bart Van der; Tang, Kewen; Ma, Yan

doi:10.1016/j.seppur.2022.121774

Cited by 6 publications

(8 citation statements)

References 35 publications

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“…Specifically, the above-mentioned coupling techniques, such as ModiCon-VariCol, 99 SFC-SMB, 102 SMB-deracemization, 82,100 ELLE- in situ crystallization, 52 ELLE-membrane-crystallization, 51,147 and ELLE-deracemization, 53 demonstrate that ELLE and chromatography can be integrated with other enantioseparation methods and complement each other.…”

Section: Discussionmentioning

confidence: 99%

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Strategies for chiral separation: from racemate to enantiomer

Sui,

Wang,

Wang

et al. 2023

Chem. Sci.

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Section: Discussionmentioning

confidence: 99%

“…Consequently, crystals with ee values higher than 98% could be consecutively harvested after 15 cycles, and the overall yields reached nearly 100%. 147 Hence, the integration of extraction, crystallization, membrane, and liquid-phase exchange processes shows promise for chiral resolution.…”

Section: Enantioselective Liquid–liquid Extractionmentioning

confidence: 99%

Strategies for chiral separation: from racemate to enantiomer

Sui,

Wang,

Wang

et al. 2023

Chem. Sci.

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“…For instance, ( S )‐ofloxacin is far more active than ( R )‐ofloxacin for antimicrobials 2 . So, researchers have made great efforts to obtain optical pure drugs 3–7 …”

Section: Introductionmentioning

confidence: 99%

“…2 So, researchers have made great efforts to obtain optical pure drugs. [3][4][5][6][7] Asymmetric synthesis, resolution of raceme, and natural chiral sources are the main routes to acquire chiral compounds. Natural sources provide only a narrow range of enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of amino acid and mandelic acid enantiomers using Josiphos‐metal complexes as chiral extractants

Wang

Yang²,

Qin

et al. 2023

Chirality

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The development of new and efficient chiral extractants has always been the research hotspot and difficulty in the field of chiral extraction. Josiphos, a famous ferrocene derivative catalyst, is employed as a chiral extractant in enantioseparation of amino acid and mandelic acid enantiomers. The influences of metal ions, organic solvents, pH of the aqueous solution, extractant concentrations, and extraction temperature on enantioselectivities are systematically studied. The result reveals that Josiphos-Pd has good capabilities to enantioseparate 4-nitro-phenylalanine (Nphe), 3-chloro-phenylglycine (Cpheg), and mandelic acid (MA) with separation factors (α) of 3.30, 2.65, and 2.18, respectively. The pH of the aqueous phase and Josiphos-Pd concentration affect the extraction significantly, whereas extraction temperature shows little influence. After optimizing by response surface method, the mathematical models for extractions are established. And the highest experimental performance factors (pf ) for Nphe, Cpheg, and MA are 0.1843, 0.1335, and 0.08884, respectively.

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“…Diastereoselective crystallization is widely used but tedious and time-consuming. [9][10][11] HPLC and the further developed SMB methods have been shown to be promising and achieved many industrial applications [12][13][14] ; yet, there is still room for improvement due to the expensive equipment and high operational costs. Membrane separation method exhibits excellent separation ability, 15,16 but it is currently only studied in lab-scale applications considering the lower capacity and high-cost issues.…”

mentioning

confidence: 99%

Enhancement of separation performance for ofloxacin enantiomers by a biphasic recognition chiral extraction system

Li,

Cheng,

2024

AIChE Journal

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Despite greatly improved separation performance towards many mixtures, utilizing biphasic recognition chiral extraction (BRCE) systems in enantiomer separation remains challenging due to inadequate comprehension of chiral recognition and biphasic synergism mechanisms. In this work, using ofloxacin enantiomers as a case study, separation performance of BRCE system is systematically examined from experimental and theoretical aspects. The BRCE system, comprising di‐p‐toluoyl‐l‐tartaric acid and β‐cyclodextrin as hydrophobic and hydrophilic selectors, achieves maximum enantioselectivity and enantiomeric excess values of 2.4 and 26% under optimal conditions. Five‐stage counter‐current extraction and reverse extraction significantly improve the enantiomeric excess value up to 91%. Molecular simulations reveal that to construct an enhanced BRCE system, two chiral selectors should have opposite recognition abilities for target enantiomers and weak interactions between themselves. This work provides guidance on selecting suitable selectors for construction of an enhanced BRCE system not only for separating ofloxacin enantiomers but also other enantiomers.

show abstract

Green and efficient enantioseparation of amlodipine using a novel pairwise crystallization-circulating extraction coupling method aimed at in situ reuse of mother liquor

Cited by 6 publications

References 35 publications

Strategies for chiral separation: from racemate to enantiomer

Strategies for chiral separation: from racemate to enantiomer

Enantioseparation of amino acid and mandelic acid enantiomers using Josiphos‐metal complexes as chiral extractants

Enhancement of separation performance for ofloxacin enantiomers by a biphasic recognition chiral extraction system

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