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Enantioselective extraction of terbutaline enantiomers with β-cyclodextrin derivatives as hydrophilic selectors

  • Kewen Tang EMAIL logo and Panliang Zhang
Published/Copyright: March 16, 2011
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Chemical Papers
From the journal Chemical Papers Volume 65 Issue 3

Abstract

Hydrophilic β-cyclodextrin (β-CD) and its derivatives are not soluble in organic liquids but they are highly soluble in water and can interact with enantiomers selectively to form diastereomeric complexes which enable their use as chiral selectors in chiral solvent extraction. In this paper, terbutaline enantiomers were extracted by hydrophilic β-CD derivatives in an aqueous/organic biphasic solvent system with racemic terbutaline in the organic phase and β-CD in the aqueous phase. Five β-CD derivatives, namely: methyl-β-cyclodextrin (Me-β-CD), hydroxyethyl-β-cyclodextrin (HE-β-CD), 2-hydroxyethyl-β-cyclodextrin (2-HE-β-CD), (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD) and (4-sulfobutylether)-β-cyclodextrin (SBE-β-CD) were used as hydrophilic selectors, respectively. Process variables affecting extraction efficiency were investigated, namely influence of the type of organic solvents and β-CD derivatives, concentrations of selectors and terbutaline enantiomers, pH, and temperature. Experimental results show that the efficiency of extraction depends, often strongly, on process variables. All five β-CD derivatives studied preferentially extract the more biologically active (R)-terbutaline from the organic phase; HP-β-CD has the strongest recognition ability. The maximum enantioselectivity (α) of 1.42 was achieved under optimal conditions: pH 7.0 and temperature of 5°C. Utilization of the extraction method for separation of terbutaline enantiomers is expected to be cheap and easy to scale up to commercial scale.

Keywords: chiral separation; reactive extraction; β-cyclodextrin derivatives; terbutaline enantiomers

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Published Online: 2011-3-16
Published in Print: 2011-6-1

© 2011 Institute of Chemistry, Slovak Academy of Sciences

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  3. Enantioselective extraction of terbutaline enantiomers with β-cyclodextrin derivatives as hydrophilic selectors
  4. Effective photocatalytic degradation of an azo dye over nanosized Ag/AgBr-modified TiO2 loaded on zeolite
  5. Photocatalytically-assisted electrochemical degradation of p-aminophenol in aqueous solutions using zeolite-supported TiO2 catalyst
  6. Spectroscopic investigations and physico-chemical characterization of newly synthesized mixed-ligand complexes of 2-methylbenzimidazole with metal ions
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  13. Antimycobacterial 3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones substituted on phenyl and benzoxazine moiety in position 6
  14. Polar constituents of Ligustrum vulgare L. and their effect on lipoxygenase activity
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https://doi.org/10.2478/s11696-011-0011-8
Keywords for this article
chiral separation; reactive extraction; β-cyclodextrin derivatives; terbutaline enantiomers

Articles in the same Issue

  1. Steam-reforming of ethanol for hydrogen production
  2. Polymeric ionic liquid as a background electrolyte modifier enhancing the separation of inorganic anions by capillary electrophoresis
  3. Enantioselective extraction of terbutaline enantiomers with β-cyclodextrin derivatives as hydrophilic selectors
  4. Effective photocatalytic degradation of an azo dye over nanosized Ag/AgBr-modified TiO2 loaded on zeolite
  5. Photocatalytically-assisted electrochemical degradation of p-aminophenol in aqueous solutions using zeolite-supported TiO2 catalyst
  6. Spectroscopic investigations and physico-chemical characterization of newly synthesized mixed-ligand complexes of 2-methylbenzimidazole with metal ions
  7. Synthesis, molecular characterisation, and in vivo study of platinum(IV) coordination compounds against B16 mouse melanoma tumours
  8. Swelling properties of particles in amphoteric polyacrylamide dispersion
  9. Electronic structures and spectroscopic regularities of phenylene-modified SWCNTs
  10. An expeditious, environment-friendly, and microwave-assisted synthesis of 5-isatinylidenerhodanine derivatives
  11. Pd-catalysed conjugate addition of arylboronic acids to α,β-unsaturated ketones under microwave irradiation
  12. Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent
  13. Antimycobacterial 3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones substituted on phenyl and benzoxazine moiety in position 6
  14. Polar constituents of Ligustrum vulgare L. and their effect on lipoxygenase activity
  15. Solubility of methane in pure non-ionic surfactants and pure and mixtures of linear alcohols at 298 K and 101.3 kPa
  16. Theoretical studies on polynitrobicyclo[1.1.1]pentanes in search of novel high energy density materials
  17. Insight into the degradation of a manganese(III)-citrate complex in aqueous solutions
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