Enantioselective extraction of terbutaline enantiomers by lipophilic tartaric acid

  • Tang Ke-wen 
  • Zhou Chun-shan 


Distribution behavior of terbutaline enantiomers was examined in the aqueous and organic solvent of a two-phase system containing L-dibenzoyltartaric acid and lipophilic phase transfer reagent of Na-tetraphenylborate. The influences of pH, organic solvents, concentrations of Na-tetraphenylborate and L-dibenzoyltartaric acid on the partition coefficients and enantioselectivity of terbutaline enantiomers, were investigated. The results show that tetraphenylborate lipophilic anion and terbutaline enantiomers form two lipophilic salt complexes, which facilitates the solubility of the enantiomers in the organic phase. L-dibenzoyltartaric acid forms more stable complexes with enantiomer II than with enantiomer I. Enantioselectivity and partition coefficient increase with the addition of the length of alkyl chain of alcohols. pH and concentrations of lipophilic anion and L-dibenzoyltartaric acid influence them obviously and differently.

Key words

L-dibenzoyltartaric acid terbutaline enantiomers chiral extraction 

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  1. [1]
    Rosa H H, Pilar C F. Chromatographic separation of chlothalidone enantiomers using β-cyclodextrins as chiral additives[J]. J Chromatogr (B), 2000, 740: 169–177.CrossRefGoogle Scholar
  2. [2]
    Abolfazl S M, Robert T F. Pharmacokinetics of metoprolol enantiomers following single and mutiple administration of racemate in rat[J]. Internal J pharm, 2000, 22: 97–102.Google Scholar
  3. [3]
    Michael J. Single enantiomer drugs: new strategies and directions[J]. Chemistry & Industry, 1996, 5 (20): 374–378.Google Scholar
  4. [4]
    Miriam L. Membranes make chiral separations simpler[J]. Manufacturing chemist, 1995, 10: 25–32.Google Scholar
  5. [5]
    James E R. Chiral separations[J]. AIChE J, 2001, 47(1): 2–5.CrossRefGoogle Scholar
  6. [6]
    Vladimir P, Miće K, Martin E. Lipophilic tartaric acid esters as enantioselective ionophores [J]. Angew Chem, 1989, 28:1147–1152.CrossRefGoogle Scholar
  7. [7]
    Jérôme L, Catherine G G, Sonya T H. Efficient enantioselective extraction tris(diimine)ruthenium II) complex by chiral, lipophilic trisphat anions[J]. Angew Chem, 2000, 39(20): 3695–3697.CrossRefGoogle Scholar
  8. [8]
    Christian R, Anita F. Cationic β-cyclodextrin: a new versatile chiral additive for separation of drug enantiomers by high-performance liquid chromatography [J]. J Chromatogr A, 1995, 704: 67–74.CrossRefGoogle Scholar

Copyright information

© Central South University 2003

Authors and Affiliations

  • Tang Ke-wen 
    • 1
    • 2
  • Zhou Chun-shan 
    • 1
  1. 1.College of Chemistry and Chemical EngineeringCentral South UniversityChangshaChina
  2. 2.Department of Chemistry and Chemical EngineeringYueyang Normal UniversityYueyangChina

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