Abstract
Paracetamol-imprinted silicas were prepared by three sol–gel routes, including two basic-catalyzed gelification and precipitation routes, and an acid-catalyzed route. The resulting materials from basic gelification were subjected to Soxhlet, ultrasound and thermal extractions, and characterized by infrared spectroscopy, elemental analysis, nitrogen porosimetry, scanning electron microscopy, and atomic force microscopy. Ultrasound was shown to be the most efficient for template extraction. The resulting materials showed surface areas between 30 m2 g−1 (for the precipitation route) and 200 m2 g−1 (for the acid-catalyzed route). After paracetamol extraction, the resulting surface area was between 30 m2 g−1 and 290 m2 g−1. The presence of paracetamol was confirmed by the presence of an infrared absorption band at 1546 cm−1, which is assigned to ν (C=O). The adsorption of paracetamol from aqueous and urine matrixes on the imprinted materials produced by the acid-catalyzed route was ca. 60% of the nominal concentration present in such matrixes. In the silica without molecular imprints, the preconcentration was ca. 20%.
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Moctezuma E, Leyva E, Aguilar CA, Luna RA, Montalvo C (2012) Photocatalytic degradation of paracetamol: intermediates and total reaction mechanism. J Hazard Mater 243:130–138
Solé M, Shaw JP, Frickers PE, Readman JW, Hutchinson TH (2010) Effects on feeding rate and biomaker responses of marine mussels experimentally exposed to propranolol and acetaminhophen. Anal Bioanal Chem 96:649–656
Yang L, Yu LE, Ray MB (2008) Photocatalytic oxidation of paracetamol: dominant reactants, intermediates, and reaction mechanisms. Environ Sci Technol 43:460–465
Roberts P, Thomas K (2006) The occurrence of selected pharmaceuticals in wastewater effluent and surface waters of the lower Tyne catchment. Sci Total Environ 356:143–153
Feng MX, Wang GN, Yang K, Liu HZ, Wang JP (2016) Molecularly imprinted polymer-high performance liquid chromatography for the determination of tetracycline drugs in animal derived foods. Food Control 69:171–176
Tang Y, Lan J, Gao X, Liu X, Zhang D, Wei L, Gao Z, Li J (2016) Determination of clenbuterol in pork and potable water samples by molecularly imprinted polymer through the use of covalent imprinting method. Food Chem 190:952–959
Salehi S, Rasoul-Amini S, Adib N, Shekarchi M (2016) Synthesis of molecular imprinted polymers for selective extraction of domperidone from human serum using high performance liquid chromatography with fluorescence detection. J Chromatogr B 1027:165–173
Avnir D, Blum J, Nairoukh Z (2015) The sol–gel handbook: synthesis, characterization, and applications. Wiley-VCH, Weinheim
Ding Y, Yao Q, Li W, Schubert DW (2015) The evaluation of physical properties and in vitro cell behavior of PHB/ PCL/ sol-gel derived silica hybrid scaffolds and PHB/ PCL fumed silica composite scaffolds. Colloids Surf B Biointerfaces 136:93–98
Meyer S, Schubert U, Bardi M, Wiesinger R, Schreiner M, Grohamann T (2014) J Adhes Adhes 51:103–110
Prokopowicz M, Szewczyk A, Sawicki W (2016) Bioactive monolithic composites of silica/polydimethylsiloxane/calcium phosphate obtained at room temperature in sol-gel. Mater Lett 184:239–242
El Beqqali Abdel-Rehim M (2016) Molecularly imprinted polymer-sol-gel tablet toward micro-solid phase extraction: I. Determination of methadone in human plasma utilizing liquid chromatography-tandem mass spectroscopy. Anal Chim Acta 936:116–122
Owens GJ, Singh RK, Foroutan F, Alqaysi M, Han C, Mahapatra C, Kim H (2016) Sol-gel based materials for biomedical applications. Prog Mater Sci 77:1–79
Morais EC, Correa GG, Brambilla R, Livotto PR, Cardoso MB, Santos JHZ (2012) Silica imprinted materials containing pharmaceuticals as a template: textural aspects. J Solgel Sci Technol 64:324–334
Morais EC, Correa GG, Brambilla R, Radtke C, Baibich I, Santos JHZ (2013) The interaction of encapsulated pharmaceutical drugs with a silica matrix. Colloids Surf B Biointerfaces 103:422–429
Ilavsky J, Jemian PR (2009) Irena: tool suite for modeling and analysis of small-angle scattering. J Appl Crystallogr 42:347–353
Kline SR (2006) Reduction and analysis of SANS and USANS data using IGOR Pro. J Appl Crystallogr 39:895–900
Beaucage G (1995) Approximations leading to a unified exponential/power-law approach to small-angle scattering. J Appl Crystallogr 28:717–728
Beaucage G (1996) Small-angle scattering from polymeric mass fractals of arbitrary mass-fractal dimension. J Appl Crystallogr 29:134–146
Silva RC, Airoldi C (1997) Acid and base catalysts in the hybrid silica sol-gel process. Acid and base catalysts in the hybrid silica sol–gel process. J Colloid Interface Sci 195:381–387
Frost RL, Mendelovici E (2006) Modification of fibrous silicates surfaces with organic derivatives: an infrared spectroscopic study. J Colloid Interface Sci 294:47–52
Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquérol J, Siemienieska T (1985) Reporting physisorption data for gas/ solid system. Pure Appl Chem 57:603–619
Elimelech E, Avnir D (2014) Covalent materials porous from hybrid silica particles. J Colloid Interface Sci 431:157–164
Williams DH, Fleming I (1966) Spectroscopic methods in organic chemistry. McGraw-Hill, London
Coates J (2000) Interpretation of infrared spectra, a practical approach. R.A. Meyers, Chichester
Colthup NB, Daly LH, Wiberley SE (1975) Introduction to infrared and Raman spectroscopy. Academic, New York, NY
Dzherayan TG, Bukov IV, Kostitsyna MV, Shipulo EV, Petrukhin DM, Dunaeva AA, Vladimirova EV (2010) Study of a gentamicin-selective membrane polymer matrix by infrared spectroscopy. J Anal Chem 65:726–731
McManusy JC, Harano Y, Low MJD (1969) Infrared study of the interactions of acetone and siliceous surfaces. Can J Chem 47:2545
Morais EC, Correa GG, Brambilla R, Fisch AG, Santos JHZ (2013) Selective silica-based sorbent materials synthesized by molecular imprinting for adsorption of pharmaceuticals in aqueous matrices. J Sep Sci 36:636–643
Acknowledgements
This work was partially financed by CNPq (Project 448397/2014-5). E. C. Morais thanks FAURGS for the grant. The authors are thankful to the LNLS (Project D11A-SAXS19926) for the measurements performed using the SAXS beamline.
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Morais, E.C., Brambilla, R., Correa, G.G. et al. Imprinted silicas for paracetamol preconcentration prepared by the sol–gel process. J Sol-Gel Sci Technol 83, 90–99 (2017). https://doi.org/10.1007/s10971-017-4399-7
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DOI: https://doi.org/10.1007/s10971-017-4399-7