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Kinetic study on extractive resolution of tropic acid by hydroxyethyl-β-cyclodextrin

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Abstract

Reactive extraction is proposed as a promising approach to the resolution of tropic acid (TA), where hydroxyethyl-β-cyclodextrin (HE-β-CD) is used as a selective extractant. The reaction between tropic acid and extractant occurred in the aqueous phase, and kinetic studies of reactive extraction have been investigated in a Lewis-type stirred cell. The batch experiments have been performed to study the process parameters affecting the extraction rate including agitation speed, interfacial area, pH value of aqueous phase, initial concentration of tropic acid enantiomers and initial concentration of extractant on the initial extraction rate. The kinetic equation of the forward rate was deduced at the experiment condition: r TA+ = (4.041 × 10−3)[TA+][CD]2; r TA− = (3.1234 × 10−3)[TA−][CD]2.

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References

  • Albals D, Hendrickx A, Clincke L, Chankvetadze B, Heyden YV, Mangelings D (2014) A chiral separation strategy for acidic drugs in capillary electrochromatography using both chlorinated and nonchlorinated polysaccharide-based selectors. Electrophoresis 35:2807–2818. doi:10.1002/elps.201400169

    Article  CAS  Google Scholar 

  • Armstrong DW, Han SM, Han YI (1987) Separation of optical isomers of scopolamine, cocaine, homatropine, and atropine. Anal Biochem 167:261–264. doi:10.1016/0003-2697(87)90161-8

    Article  CAS  Google Scholar 

  • Atuu MR, Hossain MM (2007) Dynamic kinetic resolution of racemic tropic acid ethyl ester and its derivatives. Tetrahedron Lett 48:3875–3878. doi:10.1016/j.tetlet.2007.03.143

    Article  CAS  Google Scholar 

  • Bunke A, Jira T (1998) Use of cationic cyclodextrin for enantioseparation by capillary electrophoresis. J Chromatogr A 798:275–280. doi:10.1016/S0021-9673(97)01197-7

    Article  CAS  Google Scholar 

  • Doraiswamy LK, Sharma MM (1984) Heterogeneous reactions: analysis examples and reactor designvol. 2. Fluid–fluid–solid reactions. Wiley, New York, pp 17–45. doi:10.1016/S0021-9673(97)01197-7

    Google Scholar 

  • Gaidhani HK, Wasewar KL, Pangarkar VG (2002) Intensification of enzymatic hydrolysis of penicillin G: part 1. Equilibria and kinetics of extraction of phenyl acetic acid by Alamine 336. Chem Eng Sci 57:1979–1984. doi:10.1016/S0009-2509(02)00078-7

    Article  CAS  Google Scholar 

  • Holbach A, Godde J, Mahendrarajah R, Kockmann N (2015) Enantioseparation of chiral aromatic acids in process intensified liquid–liquid extraction columns. AIChE J 61:266–276. doi:10.1002/aic.14654

    Article  CAS  Google Scholar 

  • Hurst FJ (1986) Interphase transfer kinetics of uranium between phosphoric acid and DEPA-TOPO extractant using Lewis cell techniques. Hydrometallurgy 16:197–208. doi:10.1016/0304-386X(86)90043-5

    Article  CAS  Google Scholar 

  • Javanshir S, Abdollahy M, Abolghasemi H, Khodadadi Darbanb A (2011) Kinetics of Au(III) extraction by DBC from hydrochloric solution using Lewis cell. Int J Miner Process 98:42–47. doi:10.1016/j.minpro.2010.10.002

    Article  CAS  Google Scholar 

  • Kim KH, Park YH (1998) Enantioselective inclusion between terbutaline enantiomers and hydroxypropyl-β-cyclodextrin. Int J Pharm 175:247–253. doi:10.1016/S0378-5173(98)00278-6

    Article  Google Scholar 

  • Klomp D, Peters JA, Hanefeld U (2005) Enzymatic kinetic resolution of tropic acid. Tetrahedron Asymmetry 16:3892–3896. doi:10.1016/j.tetasy.2005.10.032

    Article  CAS  Google Scholar 

  • Kodama K, Kurozumi N, Shitara H, Hirose T (2014) Solvent-induced dual chirality switching in the optical resolution of tropic acid via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol. Tetrahedron 70:7923–7928. doi:10.1016/j.tet.2014.08.053

    Article  CAS  Google Scholar 

  • Marti ME, Gurkan T, Doraiswamy LK (2011) Equilibrium and kinetic studies on reactive extraction of pyruvic acid with trioctylamine in 1-Octanol. Ind Eng Chem Res 50:13518–13525. doi:10.1021/ie200625q

    Article  CAS  Google Scholar 

  • Niemczewska J, Cierpiszewski R, Szymanowski J (2004) Mass transfer of zinc(II) extraction from hydrochloric acid solution in the Lewis cell. Desalination 162:169–177. doi:10.1016/S0011-9164(04)00040-2

    Article  CAS  Google Scholar 

  • Nikhade BP, Pangarkar VG (2005) Equilibria and kinetics of extraction of citric acid from aqueous solutions in alamine 336–cyclohexanone system. Sep Sci Technol 40:2539–2554. doi:10.1080/01496390500267681

    Article  CAS  Google Scholar 

  • Ohashi A, Tsukahara S, Watarai H (1998) Acid-catalyzed interfacial complexation in the extraction kinetics of palladium(II) with 2-(5-bromo-2-pyridylazo)-5- diethylaminophenol. Anal Chim Acta 364:53–62. doi:10.1016/S0003-2670(98)00167-6

    Article  CAS  Google Scholar 

  • Pal D, Keshav A (2015) Kinetics of reactive extraction of pyruvic acid using tributylamine dissolved in n-butyl acetate. Int J Chem React Eng 13:63–69. doi:10.1515/ijcre-2014-0117

    CAS  Google Scholar 

  • Reeve TB, Cros JP, Gennari C, Piarulli U, de Vries JG (2006) A practical approach to the resolution of racemic n-benzyl α-amino acids by liquid–liquid extraction with a lipophilic chiral salen-cobalt(III) complex. Angew Chem 45:2449–2453. doi:10.1002/anie.200504116

    Article  CAS  Google Scholar 

  • Steensma M, Kuipers NJM, de Haan AB, Kwant G (2007) Modelling and experimental evaluation of reaction kinetics in reactive extraction for chiral separation of amines, amino acids and amino-alcohols. Chem Eng Sci 62:1395–1407. doi:10.1016/j.ces.2006.11.043

    Article  CAS  Google Scholar 

  • Tang KW, Miao JB, Zhou T, Liu YB, Song LT (2011a) Reaction kinetics in reactive extraction for chiral separation of α-cyclohexyl-mandelic acid enantiomers with hydroxypropyl-b-cyclodextrin. Chem Eng Sci 66:397–404. doi:10.1016/j.ces.2010.10.044

    Article  CAS  Google Scholar 

  • Tang KW, Zhang PL, Pan CY, Li HJ (2011b) Equilibrium studies on enantioselective extraction of oxybutynin enantiomers by hydrophilic β-cyclodextrin derivatives. AIChE J 57:3027–3036. doi:10.1002/aic.12513

    Article  CAS  Google Scholar 

  • Tong SQ, Zhang H, Yan JZ (2016) Analytical enantioseparation of β-substituted- 2-phenylpropionic acids by high-performance liquid chromatography with hydroxypropyl-β-cyclodextrin as chiral mobile phase additive. J Chromatogr Sci 54:593–597. doi:10.1093/chromsci/bmv192

    Article  CAS  Google Scholar 

  • Uslu H, Datta D, Santos D, Bamufleh HS, Bayat C (2016) Separation of 2, 4, 6-trinitrophenol from aqueous solution by liquid–liquid extraction method: equilibrium, kinetics, thermodynamics and molecular dynamic simulation. Chem Eng J 299:342–352

    Article  CAS  Google Scholar 

  • Valle EMMD (2004) Cyclodextrins and their uses: a review. Process Biochem 39:1033–1046. doi:10.1016/S0032-9592(03)00258-9

    Article  Google Scholar 

  • Wasewar KL, Heesink ABM, Versteeg GF, Pangarkar VG (2002) Reactive extraction of lactic acid using alamine 336 in MIBK: equilibria and kinetics. J Biotechnol 97:59–68. doi:10.1016/S0168-1656(02)00057-3

    Article  CAS  Google Scholar 

  • Xu WF, Wang SC, Dai GL, Tang KW, Zhang PL, Xiong BQ, Liu Y (2017) Construction and application of a model on the resolution of tropic acid enantiomers by enantioselective liquid-liquid extraction in centrifugal contactor separators. Process Biochem. doi:10.1016/j.procbio.2017.05.012

    Google Scholar 

  • Zhu P, Fan ZY, Wu JH, Qian GR, Zhou M (2010) Extraction and stripping kinetics of copper (II) by N902 using single drop technique. J Shanghai Univ (Engl Ed) 14:275–280. doi:10.1007/s11741-010-0643-3

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21376071).

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, 414000, China

    Weifeng Xu, Kewen Tang, Panliang Zhang & Biquan Xiong

  2. College of Chemical Engineering, Xiangtan University, Xiangtan, 411105, China

    Pan Jiang

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  1. Weifeng Xu
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  2. Pan Jiang
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  3. Kewen Tang
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Correspondence to Panliang Zhang or Biquan Xiong.

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Xu, W., Jiang, P., Tang, K. et al. Kinetic study on extractive resolution of tropic acid by hydroxyethyl-β-cyclodextrin. Chem. Pap. 72, 585–591 (2018). https://doi.org/10.1007/s11696-017-0304-7

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