Equilibrium of chiral extraction of 4-nitro-d,l-phenylalanine with BINAP metal complexes

2014 ◽  
Vol 68 (1) ◽  
Author(s):  
Jia-Jia Liu ◽  
Guo-Hui Wu ◽  
Ke-Wen Tang ◽  
Xiong Liu ◽  
Pan-Liang Zhang
Keyword(s):  
Formation Constants ◽  
Chiral Selector ◽  
Reactive Extraction ◽  
Process Variables ◽  
Extraction Condition ◽  
Metal Precursors ◽  
Enantioselective Extraction ◽  
Chiral Extraction ◽  
Optimal Extraction Condition ◽  
Extraction Model

AbstractThe enantioselective extraction of 4-nitro-phenylalanine (Nphy) was studied with metal-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) complexes as the chiral selector. The complex with palladium (BINAP-Pd) exhibits the highest selectivity out of the selectors studied, which is solubilised in the organic phase and preferentially extracts d-Nphy from the aqueous phase. Efficiency of extraction depends, often substantially, on a number of process variables, including types of organic solvents and metal precursors, concentration of ligand, pH, and temperature. A reactive extraction model was established to interpret the experimental data. The equilibrium formation constants and other important parameters required by the model were determined experimentally. The equilibrium formation constants were 6.73 and 1.93 for d-Nphy and l-Nphy. By way of modelling and experiment, an optimal extraction condition with pH of 7 and BINAP-Pd concentration of 1 mmol L−1 was obtained with enantioselectivity (α) of 3.37, which was close to the maximum of 3.48, and a performance factor (pf) of 0.195. The model was verified experimentally with excellent results.

Enantioselective extraction of hydrophilic 2-chloromandelic acid enantiomers by hydroxypropyl-β-cyclodextrin: experiments and modeling

2013 ◽  
Vol 67 (2) ◽  
Author(s):  
Cong-Shan Zhou ◽  
Ping Xu ◽  
Ke-Wen Tang ◽  
Xin-Yu Jiang ◽  
Tao Yang ◽  
...  
Keyword(s):  
Aqueous Phase ◽  
Extraction Efficiency ◽  
Reactive Extraction ◽  
Phase Reaction ◽  
Important Process ◽  
Process Variables ◽  
Model Data ◽  
Cyclodextrin Derivatives ◽  
Enantioselective Extraction ◽  
Extraction Model

AbstractEnantioselective extraction of hydrophilic 2-chloromandelic acid (CMA) enantiomers from organic to aqueous phase with hydroxypropyl-β-cyclodextrin (HP-β-CD) as the selector was investigated. Equilibrium of the extraction system was modeled using a reactive extraction model with a homogeneous aqueous phase reaction. The influence of important process variables on the extraction efficiency, such as the type of the organic solvent and β-cyclodextrin derivatives (β-CDs), concentration of the selector, pH and temperature, was investigated by experiment and modeling. Important parameters of this model were determined experimentally. Results showed that the experimental data agree with the model prediction perfectly and the model was further applied to accurately predict the extraction efficiency influenced simultaneously by pH and the concentration of HP-β-CD. Combining the experiment and the model data, the best extraction conditions were: pH of 2.5, HP-β-CD concentration of 0.05 mol L−1, and temperature of 5°C, providing the enantioselectivity of 1.285 and the performance factor (pf) of 0.011.

scholarly journals Enantioselective Extraction of Phenylalanine Enantiomers Using Environmentally Friendly Aqueous Two-Phase Systems

Processes ◽  
2018 ◽  
Vol 6 (11) ◽  
pp. 212 ◽  
Author(s):  
Danyu Sun ◽  
Runping Wang ◽  
Fenfang Li ◽  
Lianglei Liu ◽  
Zhijian Tan
Keyword(s):  
Ionic Liquids ◽  
Environmentally Friendly ◽  
Deep Eutectic Solvents ◽  
Chiral Selector ◽  
Extraction Temperature ◽  
Two Phase ◽  
Aqueous Two Phase Systems ◽  
Enantioselective Extraction ◽  
Chiral Extraction ◽  
Phase Systems

(1) Background: The environmentally friendly choline-amino acid ionic liquids (ChAAILs) and deep eutectic solvents (DESs) have been used as excellent alternatives to volatile organic compounds (VOCs) and ionic liquids (ILs) in recent years; (2) Methods: Thus, ChAAILs/salt and DESs/salt aqueous two-phase systems (ATPSs) were developed for the chiral extraction of phenylalanine enantiomers. The optimum ATPS of [Ch][L-Pro]/K3PO4 was chosen, and the influencing parameters were investigated, including ChAAILs concentration, salt concentration, chiral selector concentration, extraction temperature, phenylalanine concentration, and system pH; (3) Results: The phenylalanine enantiomers were mainly extracted into the top phase (ChAAIL-rich phase), meanwhile, the (S)-phenylalanine [(S)-Phe)] was preferentially recognized by the chiral selector in the top phase. The maximum separation factor (α) of 2.05 was obtained under the optimal conditions; and (4) Conclusions: This ATPS that was used for the chiral extraction of enantiomers is much more environmentally friendly, simple, and rapid, and has the potential to be used in the enantioselective extraction of other enantiomers.

scholarly journals Recent Development: Enantio Selective Eextraction in Chiral Separation

2021 ◽  
Vol 7 (1) ◽  
Author(s):  
Mohammad Reza Hadjmohammadi ◽  
◽  
Majidhashemi ◽  
Keyword(s):  
Extraction Method ◽  
Extraction Methods ◽  
Chiral Selector ◽  
Selectivity Factor ◽  
Chiral Compound ◽  
Separation Processes ◽  
Typical Performance ◽  
Enantioselective Extraction ◽  
Major Emphasis ◽  
Complexation Process

This paper discusses the recent development of enantioselective extraction methods. There are several methods in this field. The principles of all of enantioselective extraction methods are presented a focus on twophase extractions, in these methods used a chiral compound that named chiral selector, this compound distinguishes between two chiral isomers in complexation process, then one isomer more captured by chiral selector, and separation processes happen. The chiral selector should dissolve in on phase. In these methods, typical performance data are reported major emphasis on distribution ratio and enantioselectivity value or selectivity factor. In this paper, we introduce types of enantioselective extraction method, and discuss about them with several examples.

Hemicelluloses extraction from giant bamboo (Bambusa balcooa Roxburgh) prior to kraft or soda-AQ pulping and its effect on pulp physical properties

Holzforschung ◽  
2013 ◽  
Vol 67 (8) ◽  
pp. 863-870 ◽  
Author(s):  
Phumla Faith Vena ◽  
Michel Brienzo ◽  
María del Prado García-Aparicio ◽  
Johann F. Görgens ◽  
Tim Rypstra
Keyword(s):  
South Africa ◽  
Kraft Pulping ◽  
Viscosity Reduction ◽  
Pulp Yield ◽  
Statistical Experimental Design ◽  
Dilute Acid ◽  
Extraction Condition ◽  
Bambusa Balcooa ◽  
Optimal Extraction Condition ◽  
Better Than

Abstract The alkaline and acid preextraction of giant bamboo (Bambusa balcooa Roxburgh), grown in South Africa, before kraft and soda-anthraquinone (AQ) pulping was in focus and the effects of NaOH concentration, temperature, and time on hemicelluloses extraction were studied by means of a statistical experimental design. The NaOH concentration exerted the strongest influence, solubilizing up to 20.4% of the available xylan with 2.0 M NaOH at 90°C for 240 min. The optimal extraction condition was achieved with 1 M NaOH at 90°C for 240 min, in the course of which 13.6% of the xylan was removed; the screened pulp yield was 50.4% without viscosity reduction, whereas the burst index of the handsheets was even improved. In the case of dilute acid preextraction before soda-AQ pulping, 11.3% xylan could be removed without affecting the pulp quality. The viscosity of the pulp was even better than that of pulps from nonextracted bamboo. The biorefinery approach, alkaline preextraction in combination with kraft pulping, is superior to the approach, acid prehydrolysis/soda-AQ pulping.

scholarly journals Recent Development: Enantioselective Extraction in Chiral Separation

2021 ◽  
Vol 8 (1) ◽  
Author(s):  
Hashemi M ◽  
◽  
Hadjmohammadi MR ◽  
Keyword(s):  
Extraction Method ◽  
Extraction Methods ◽  
Chiral Selector ◽  
Selectivity Factor ◽  
Chiral Compound ◽  
Separation Processes ◽  
Typical Performance ◽  
Enantioselective Extraction ◽  
Major Emphasis ◽  
Complexation Process

This paper discusses the recent development of enantioselective extraction methods. There are several methods in this field. The principles of all of enantioselective extraction methods are presented a focus on twophase extractions, in these methods used a chiral compound that named chiral selector, this compound distinguishes between two chiral isomers in complexation process, then one isomer more captured by chiral selector, and separation processes happen. The chiral selector should dissolve in on phase. In these methods, typical performance data are reported major emphasis on distribution ratio and enantioselectivity value or selectivity factor. In this paper, we introduce types of enantioselective extraction method, and discuss about them with several examples.

scholarly journals Optimized Extraction Method for Kleeb Bua Daeng Formula with the Aid of the Experimental Design

2021 ◽  
Vol 2021 ◽  
pp. 1-10
Author(s):  
Nittaya Ngamkhae ◽  
Orawan Monthakantirat ◽  
Yaowared Chulikhit ◽  
Chantana Boonyarat ◽  
Charinya Khamphukdee ◽  
...  
Keyword(s):  
Solvent Extraction ◽  
Active Compound ◽  
Centella Asiatica ◽  
Extraction Process ◽  
Piper Nigrum ◽  
Active Components ◽  
Extraction Condition ◽  
Phytochemical Content ◽  
Phytochemical Compounds ◽  
Optimal Extraction Condition

Kleeb Bua Daeng formula is one of the popular remedies sold in Chao Phya Abhaibhubejhr Hospital, Thailand. This formula contains Piper nigrum L., Nelumbo nucifera Gaertn., and Centella asiatica L. as active components. Owing to getting the highest content of its phytochemical compounds, the conditions of solvent extraction for this formula were optimized. The type of solvent, number of extraction times, and ratio between the material and solvent were varied in this study using the Box–Behnken design. The important phytochemical constituents (total phenolics, flavonoids, carotenoids, and anthocyanins) were also determined. From the result of this study, it was found that the highest content of each total active compound was obtained from different conditions such as the optimal extraction condition of phenolic content was obtained using methanol as solvent, one time of extraction, and the ratio of powder and solvent was 1 : 6. Thus, the variation of solvent extraction condition could affect the phytochemical content. Further studies about the herbal formula involving the extraction process should concern the variation of extraction conditions to get the highest content of the active compound.

Enantioselective extraction of mandelic acid enantiomers by L-dipentyl tartrate and β-cyclodextrin as binary chiral selectors

2007 ◽  
Vol 61 (4) ◽  
Author(s):  
F. Jiao ◽  
X. Chen ◽  
W. Hu ◽  
F. Ning ◽  
K. Huang
Keyword(s):  
Organic Solvent ◽  
Organic Phase ◽  
Mandelic Acid ◽  
Distribution Coefficients ◽  
Chiral Selector ◽  
Optimum Concentration ◽  
Chiral Selectors ◽  
Mandelic Acid Enantiomers ◽  
Enantioselective Extraction

AbstractA new binary chiral selector system effective for the enantioselective extraction of racemic mandelic acid is presented. While L-dipentyl tartrate and β-cyclodextrin had a very low enantioselectivity as single selectors, a preferential extraction of D-mandelic acid to the organic phase was found in the binary selector system. Using decanol as organic solvent and pH of a phoshate buffer equal to 2.3, the distribution coefficients of D-and L-mandelic acids as high as 14.9 and 7.0, respectively, and the enantioselectivity value of 2.1 were found at optimum concentration of β-cyclodextrin.

Enantioselective Separation of Racemic Amlodipine by Two-Phase Chiral Extraction ContainingO,O′-Dibenzoyl-(2S,3S)-Tartaric Acid as Chiral Selector

2013 ◽  
Vol 48 (15) ◽  
pp. 2363-2371 ◽  
Author(s):  
Niti Sunsandee ◽  
Ura Pancharoen ◽  
Paitoon Rashatasakhon ◽  
Prakorn Ramakul ◽  
Natchanun Leepipatpiboon
Keyword(s):  
Tartaric Acid ◽  
Chiral Selector ◽  
Enantioselective Separation ◽  
Two Phase ◽  
Chiral Extraction
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