Recent Development: Enantioselective Extraction in Chiral Separation

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.

Recent Development: Enantio Selective Eextraction in Chiral Separation

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.

Syntéza a HPLC enantioseparácia nových derivátov 3-alkoxy-4-hydroxyfenylalkanónov typu potenciálnych α/β-blokátorov

The present paper reports the synthesis of a series of seven compounds with a hetero aminopropanol chain. The compounds were prepared by the conversion of 3-alkoxy-4-hydroxyphenyl alkanones with 2-chloromethyl oxirane and subsequent reaction of the products with heterocyclic amines (pyrrolidine, azepane, 4-methylpiperazine and 2-methoxyphenyl piperazine). The target compounds were synthesized in the form of racemates. The purity of the products was confirmed by thin layer chromatography and their IR, UV-VIS and 1H-NMR spectra were recorded. Enantioseparation of the racemic products was accomplished by HPLC on a Chiralpak AD chiral chromatographic column with tris(3,5-dimethylphenyl)carbamate as the chiral selector. The efficiency of enantioseparation was determined in relation to the composition of the mobile phase (hexane : ethanol : methanol : ethylethanamine) and to the structure of the prepared compounds. Baseline separation was achieved with all compounds using mobile phases A (78 : 11 : 11 : 0,1 v/v/v/v) and B (80 : 10 : 10 : 0,1 v/v/v/v), with selectivity factor ranging from 1.07 to 1.42 and resolution from 0.76 to 5.47. The mobile phase containing a higher amount of hexane did not allow for successful enantioseparation of the piperazine derivatives.

Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation

The introduction of chiral alkyl substituents into the lower rim of calix[4]arene immobilised in the 1,3-alternate conformation led to a system possessing a preorganised ureido cavity hemmed with chiral alkyl units in the near proximity. As shown by the 1H NMR titration experiments, these compounds can be used as receptors for chiral anions in DMSO-d 6. The chiral recognition ability can be further strengthened by the introduction of another chiral moiety directly onto the urea N atoms. The systems with double chiral units being located around the binding ureido cavity showed better stereodiscrimination, with the highest selectivity factor being 3.33 (K L/K D) achieved for N-acetyl-ʟ-phenylalaninate. The structures of some receptors were confirmed by single crystal X-ray analysis.

Synthesis and Characterisation of a Monolithic Imprinted Column Using a Methacrylic Acid Monomer with Porogen Propanol for Atenolol Analysis

A monolithic imprinted atenolol column was constructed by in situ polymerisation using a methacrylic acid monomer and a 1 : 1 (v/v) porogen of propanol: toluene with two template: monomer: crosslinker combinations, namely, MIP 1 (1 : 4 : 20) and MIP 2 (1 : 5 : 20). Physical characterisation of the monolithic columns consisted of permeability testing, Fourier transform infrared (FTIR) testing, surface area analysis (SAA), and scanning electron microscopy (SEM). The permeability value of four monolithic columns was in the good category: MIP 1 (24.01 mD), NIP 1 (56.43 mD), MIP 2 (23.03 mD), and NIP 2 (14.47 mD). The polymerisation process of these four monolithic imprinted columns was carried out perfectly, as shown by the absence of vinyl groups (1000 cm−1 and 900 cm−1) during FTIR testing. Based on SAA testing, the pores of the four polymers were classified as mesopores. The best monolithic column was MIP 1, as seen from the intercolumn and intracolumn reproducibility values and a % RSD <2.0%. The MIP 1 column was selective towards atenolol, as seen from the selectivity factor, imprinting factor (IF), and resolution (Rs) values. The IF values of MIP 1 were atenolol (204.62), metoprolol (3.36), and propranolol (1.27). The Rs value between atenolol and the analogue compounds was 7.23. The MIP 1 column can be used for the analysis of atenolol in blood serum samples with an average percentage recovery rate of 94.88 ± 4.43%.

Adsorption Equilibrium and Thermodynamic Analysis of CO2 and CH4 on Qinshui Basin Anthracite

Adsorption isotherms of CH4 and CO2 on Qinshui Basin anthracite were obtained at the temperatures of 283 K, 303 K, and 323 K using the gravimetric method. The feasibility of the displacement of CH4 by injecting CO2 on this anthracite was verified by calculating the selectivity factor of CO2 over CH4 (αCO2/CH4), adsorption affinities, and thermodynamic properties of CH4 and CO2. Results show that the values of αCO2/CH4 are more than 4.0. Henry’s constant (KH) of CH4 is smaller than that of CO2, and CH4 has a weaker affinity with coal surface. As temperature improves, KH of CO2 and CH4 decrease. Gibbs free energy change (ΔG) and surface potential (Ω) of CO2 are more negative than those of CH4, indicating that CO2 adsorption on anthracite is more spontaneous and favorable. The absolute values of Ω and ΔG of CH4 and CO2 increase with pressure rises. Isosteric heat of adsorption (Qst) of CH4 is lower than that of CO2. With increasing loading, Qst and entropy loss (ΔS) of CH4 decrease, while Qst and ΔS of CO2 increase. The higher ΔS of CO2 reveals that the adsorbed CO2 molecules constitute a more stable rearrangement than CH4 molecules. High temperature reduces ΔS of CH4 and CO2.

Enzymatic Resolution of 3-oxodicyclopentadiene on a Decagram Scale

The chiral building block 3-oxodicyclopentadiene (1) can be readily resolved on a decagram scale by a short sequence consisting of (1) reduction to the corresponding endo-alcohol, (2) enzymatic oxidative resolution with a ketoreductase enzyme to give (+)-1 and the (+)-form of the endo-alcohol, and (3) reoxidation of the (+)-endo-alcohol with another ketoreductase to give (–)-1. With a selectivity factor of 310, the enantiomeric ratios of the resolved (+)-endo-alcohol and (+)-ketone are both >99:1. Both enzymatic oxidations could be performed with a at least 300:1 substrate/catalyst ratio (w/w).