fevereiro 2015 vol. 1 num. 2 - XX Congresso Brasileiro de Engenharia Química

Artigo - Open Access.

Idioma principal

Thermodynamic study of the separation of racemic ibuprofen by chiral liquid chromatography



ABSTRACT: The chiral drug (RS)-2-(4-(2-methylpropyl)phenyl) propanoic acid, known as ibuprofen, is an important non-steroidal anti-inflammatory drug, also notorious for its analgesic and antipyretic properties. This medicine is market in racemic form R-(-)-ibuprofen and S-(+)-ibuprofen, however, in some countries only the second enantiomer is applied. This paper refers to the study of the thermodynamic parameters relative for separation of the racemic mixture in analytical chiral chromatographic columns packed with cellulose tris (3,5-dimethylphenylcarbamate). In this analysis, the enthalpy (ΔH0), entropy (ΔS0), enthalpy difference (ΔΔH0), entropy difference (ΔΔS0), and isoenantioselective temperature (Tiso) was determined by van’t Hoff approach. KEYWORDS: ibuprofen, thermodynamic parameters, chiral separation, adsorption



DOI: 10.5151/chemeng-cobeq2014-1476-19091-177605

Referências bibliográficas
  • [1] ASNIN, L.; KACZMARSKI, K.; FELINGER, A.; GRITTI, F.; GUIOCHON, G. Adsorption of the enantiomers of 3-chloro-1-phenyl-propanol on silica-bonded chiral quinidine carbamate. J. Chromatogr. A, v. 1101, n. 1, p. 158-170, 2006.
  • [2] CHEN, C., S.; SHIEH, W., R.; LU, P., H.; HARRIMAN, S.; CHEN, C., Y. Metabolic stereoisomeric inversion of ibuprofen in mammals. BBA-Protein Struct. M., v. 1078, n. 3, p. 411-417, 1991.
  • [3] COYM, J. Evaluation of ternary mobile phases for reversed-phase liquid chromatography: Effect of composition on retention mechanism. J. Chromatogr. A, v. 1217, n. 38, p. 5957–5964, 2010.
  • [4] CREMASCO, M. A.; HRITZKO, B. J.; XIE, Y.; WANG, N. H. L. Parameters estimation for amino acids adsorption in a fixed bed by moment analysis. Braz. J. Chem. Eng., v. 18, n. 2, p. 181-194, 2001.
  • [5] FERRARI, W. M.; CREMASCO, M. A. Study of the separation conditions of the racemic ibuprofen on high performance liquid chromatography. Anais Eletrônicos do 10º Encontro Brasileiro sobre Adsorção – EBA 2014 JANDERA, P.; COLIN, H.; GUIOCHON, G. Interaction indexes for prediction of retention in reversed-phase liquid chromatography. Anal. Chem., v. 54, n. 3, p. 435-441, 1982.
  • [6] Área temática: Engenharia das Separações e Termodinâmica 7 LÄMMERHOFER, M. Chiral recognition by enantioselective liquid chromatography: mechanisms and modern chiral stationary phases. J. Chromatogr. A, v. 1217, n. 6, p. 814-856, 2010.
  • [7] MIHLBACHLER, K.; KACZMARSKI, K.; SEIDEL-MORGENSTERN, A; GUIOCHON, G. Measurement and modeling of the equilibrium behavior of the Tröger’s base enantiomers on an amylose-based chiral stationary phase. J. Chromatogr. A, v. 955, n. 1, p. 35-52, 2002.
  • [8] MOREIRA, J., V.; NASCIMENTO, A., C.; CREMASCO, M., A. Determination of isoselective temperature and selectivity for the products of piperonal organic synthesis from Piper hispidinervum c. dc by high-performance liquid chromatography on c18 stationary phase VII CBTermo, 2013.
  • [9] NASCIMENTO, A. C.; PERNA, R. F.; CREMASCO, M. A.; SANTANA, C. C. Enantioseparation of Secnidazole by High-Performance Liquid Chromatography using Amylose-based Stationary Phase. Adsorpt. Sci. Technol., 30 (2012), 739-750.
  • [10] OLIVEIRA, C., E., L; CREMASCO, M., A. Estudo termodinâmico da retenção cromatrográfica de uma mistura binária carvacrol-timol utilizando a técnica de cromatografia de alta eficiência. VII CBTermo, 2013.
  • [11] PALMA, C.; DI PAOLA, R.; PERROTTA, C.; MAZZON, E.; CATTANEO, D.; TRABUCCHI, E.; CUZZOCREA, S.; CLEMENTI, E. Ibuprofen–arginine generates nitric oxide and has enhanced anti-inflammatory effects. Pharmacol. Res., v. 60, n. 4, p. 221-228, 2009.
  • [12] PÉTER, A.; TÖRÖK, G.; ARMSTRONG, D. W.; TÓTH, G.; TOURWÉ, D. Effect of temperature on retention of enantiomers of β-methyl amino acids on a teicoplanin chiral stationary phase. J. Chromatogr. A, v. 828, n. 1, p. 177-190, 1998.
  • [13] SCHNEIDER, P.; SMITH, J. M. Adsorption rate constants from chromatography. AlChE J., v.14, n. 5, p. 762-771, 1968.
  • [14] SCHULTE, M.; EPPING, A. Fundamentals and General Terminology in SCHMIDT-TRAUB, H. Preparative Chromatography of Fine Chemicals and Pharmaceutical Agents. Weinheim: Wiley-VCH, 2005.
  • [15] VALDERRAMA, P.; POPPI, R. J. Second order standard addition method and fluorescence spectroscopy in the quantification of ibuprofen enantiomers in biological fluids. Chemometr. Intell. Lab., v. 106, n. 2, p. 160-165, 2011.
  • [16] YOON, J., S.; YOON, D.; OH, J.; KEUN, Y., L.; LEE, H, S.; KOH, Y., Y.; JIN, T., K.; KANG, H., J.; LEE, J., S. The effects and safety of dexibuprofen compared with ibuprofen in febrile children caused by upper respiratory tract infection. Brit. J. Clin. Pharmaco., v. 66, n. 6, p. 854-860, 2008.
Como citar:

FERRARI, W. M.; CREMASCO, M. A.; "Thermodynamic study of the separation of racemic ibuprofen by chiral liquid chromatography", p. 15714-15721 . In: Anais do XX Congresso Brasileiro de Engenharia Química - COBEQ 2014 [= Blucher Chemical Engineering Proceedings, v.1, n.2]. São Paulo: Blucher, 2015.
ISSN 2359-1757, DOI 10.5151/chemeng-cobeq2014-1476-19091-177605

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