Kinetics of reaction extraction separation of 2-phenylbutyric acid enantiomers

被引:0
|
作者
Jiang P. [1 ]
Zhang P. [2 ]
Zeng L. [2 ]
Xu W. [2 ]
Tang K. [2 ]
机构
[1] College of Chemical Engineering, Xiangtan University, Xiangtan, 411105, Hunan
[2] Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, 414006, Hunan
来源
Tang, Kewen (tangkewen@sina.com) | 2017年 / Materials China卷 / 68期
关键词
2-phenylbutyric acid; Chemical reactive; Extraction; Kinetics;
D O I
10.11949/j.issn.0438-1157.20161190
中图分类号
学科分类号
摘要
Kinetics research on the reactive extraction of 2-phenylbutyric acid enantiomers using hydroxyethyl-β-cyclodextrin (HE-β-CD) as extractant was performed in a Lewis cell. A homogeneous reaction model and a two-film theory were employed to describe the mass transfer mechanism of the reactive extraction process. The process parameters affecting the initial extraction rate, including agitation speed, interfacial area, pH value of aqueous phase, initial concentration of 2-phenylbutyric acid (2-PBA) enantiomers and initial concentration of extractant, were separately studied. The results showed that the reaction between hydroxyethyl-β-cyclodextrin and 2-phenylbutyric acid was a fast reaction. It was found that the reaction was first order in 2-phenylbutyric acid and second order in hydroxyethyl-β-cyclodextrin. The forward rate constants for the extraction of (+)-2-phenylbutyric acid and (-)-2-phenylbutyric acid were 2.829×10-4 and 1.803×10-4 m6·mol-2·s-1, respectively. The results were useful for the design and operation of reactive extraction process in large-scale production, and provide scientific basis for equipment design and process intensification. © All Right Reserved.
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页码:163 / 169
页数:6
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共 37 条
  • [1] Hefnawy M.M., Aboul-Enein H.Y., A validated LC method for the determination of vesamicol enantiomers in human plasma using vancomycin chiral stationary phase and solid phase extraction, J. Pharm. Biomed. Anal., 35, 3, pp. 535-543, (2004)
  • [2] Guxman A., Yuste F., Toscano R.A., Et al., Absolute configuration of (-)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-alpha]-pyrrole-l-carboxylic acid, the active enantiomer of ketorolac, J. Med. Chem., 29, 4, pp. 589-591, (1986)
  • [3] Mitscher L.A., Sharma P.N., Chu D.T.W., Et al., Chiral DNA gyrase inhibitors (II): Asymmetric synthesis and biological activity of the enantiomers of 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (ofloxacin), J. Med. Chem., 30, 12, pp. 2283-2286, (1987)
  • [4] Plenge P., Mellerup E.T., Honore T., Et al., The activity of 25 paroxetine/femoxetine structure variants in various reactions, assumed to be important for the effect of antidepressants, J. Pharm. Pharmacol., 39, 11, pp. 877-882, (1987)
  • [5] Shum W.P., Chen J., Cannarsa M.J., Synthesis and enantiomeric purity determination of chiral 3-benzylglycidol, a key synthon for HIV protease inhibitors, Chirality, 6, 8, pp. 681-684, (1994)
  • [6] Halabi A., Ferrayoli C., Palacio M., Et al., Validation of a chiral HPLC assay for (R)-salbutamol sulfate, J. Pharm. Biomed. Anal., 34, 1, pp. 45-51, (2004)
  • [7] Cerletti C., Manarini S., Coloma M., Et al., The (+)-enantiomer is responsible for the antiplatelet and anti-inflammatory activity of (±)-indobufen, J. Pharm. Pharmaco., 42, 12, pp. 885-887, (1990)
  • [8] Viegas R.M.C., Afonso C.A.M., Crespo J.G., Et al., Racemic resolution of propranolol in membrane contactors: modelling and process optimization, J. Membr. Sci., 305, 1-2, pp. 203-214, (2007)
  • [9] Gourlay M.D., Kendrick J., Leusen F.J.J., Predicting the spontaneous chiral resolution by crystallization of a pair of flexible nitroxide radicals, Cryst. Growth. Des., 8, 8, pp. 2899-2905, (2008)
  • [10] Huerta F.F., Backvall J.E., Enantioselective synthesis of β-hydroxy acid derivatives via a one-pot aldol reaction-dynamic kinetic resolution, Org. Lett., 3, 8, pp. 1209-1212, (2001)