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

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 in...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2023-04, Vol.35 (4), p.256-265
Main Authors: Wang, Hou, Yang, Yanning, Qin, Shuping, Hu, Kangyu, Zhong, Changyuan, Ouyang, Junying, Liu, Xiong
Format: Article
Language:English
Subjects:
amino acid
Amino acids
Aqueous solutions
Catalysts
chiral extraction
Coordination compounds
Enantiomers
Extractants
Josiphos
mandelic acid
Mathematical models
Metal complexes
Metal ions
Organic solvents
Palladium
Phenylalanine
Phenylglycine
Response surface methodology
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Summary: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. Josiphos‐Pd exhibits good capabilities to enantioseparate Nphe, Cpheg, and MA.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23534