Molecularly Imprinted Polymers Based on Konjac for Selective Caffeine Adsorption in Aqueous Solution

Yıl 2023, Cilt: 10 Sayı: 2, 359 - 370, 31.05.2023

Saranya Wattananon , Samroeng Narakaew , Aphiruk Chaisena

https://doi.org/10.18596/jotcsa.1194200

Cited By: 1

Öz

A number of caffeine extraction methods have been developed, such as microwave assisted extraction and ultrasonic-assisted extraction. The disadvantages of these methods are low selectivity, inconvenience, and inefficiency. Among the existing technologies, molecularly imprinted polymers (MIPs) are one of the most efficient and economical methods for the removal of caffeine contaminants. In this study, the objective was to prepare MIPs for the removal of complicated samples. The obtained materials were used as a sorbent for the extraction of caffeine from coffee brewed in an espresso. The MIPs were prepared using konjac/acrylic acid as a functional monomer, N, N′-methylenebisacrylamide as a cross-linker, and caffeine as a template. The chemical structures of MIPs were characterized by Fourier transform infrared spectroscopy. MIPs exhibited a higher maximum adsorption capacity (87.72 mg/g). The equilibrium adsorption data fit well with the Langmuir adsorption isotherm models, which confirm the monolayer adsorption behaviour of caffeine molecules on the surfaces of the MIPs samples. According to the experimental results of the adsorption capacity of caffeine from aqueous solution, the MIPs showed a higher percentage removal of caffeine (75.66%). Our findings suggest that MIPs are useful adsorbents for the decaffeination of coffee brewed in an espresso.

Anahtar Kelimeler

adsorption, molecularly imprinted polymer, konjac, caffeine, sorbent

Destekleyen Kurum

Lampang Rajabhat University and Center of Excellence for Innovation in Chemistry (PERCH-CIC)

Teşekkür

The authors gratefully acknowledge support of this research by Lampang Rajabhat University and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Ministry of Higher Education, Science, Research and Innovation (MHESI).

Kaynakça

• 1. James JE. Caffeine and cognitive performance: persistent methodological challenges in caffeine research. Pharmacol Biochem Behav. 2014;124:117-122.
• 2. Rodriguez RS, Haugen R, Rueber A, Huang CC. Reversible neuronal and muscular toxicity of caffeine in developing vertebrates. Comp Biochem Physiol C. Pharmacol Toxicol. 2014;163:47-54.
• 3. Silvarolla MB, Mazzafera P, Fazuoli LC. Plant biochemistry: a naturally decaffeinated arabica coffee. Nature. 2004;429:826-826.
• 4. Bichsel B. Diffusion phenomena during the decaffeination of coffee beans. Food Chemistry. 1979;4(1):53-62.
• 5. Zosel K. Separation with supercritical gases: practical applications, Angewandte Chemie International Edition in English. 1978;17(10):702-709.
• 6. Udaya sankar K, Manohar B, Chokkalingam AA. A note on supercritical carbon dioxide decaffeination of coffee. J Food Sci Technol. 1986;23(6):326-328.
• 7. Ramalakshmi K, Raghavan B. Caffeine in coffee: its removal Why and how. Crit Rev Food Sci Nutr. 1999;39(5):441-456.
• 8. Birtigh A, Liu K, Johannsen M. Regeneration methods for caffeine-loaded CO2. Sep Sci Technol. 1995;30(17):3265-3286.
• 9. Farah A, Paulis T, Moreira D. P. Chlorogenic acids and lactones in regular and water-decaffeinated arabica coffees. J Agric Food Chem. 2006;54(2):374-381.
• 10. Machmudah S, Kitada K, Sasaki M. Simultaneous extraction and separation process for coffee beans with supercritical CO2 and water. Ind Eng Chem Res. 2011;50(4):2227-2235.
• 11. He CY, Liu F, Li KA, Liu HW. Molecularly imprinted polymer film grafted from porous silica for selective recognition of testosterone. Anal Lett. 2006;39(2):275-286.
• 12. Yang HH, Zhang SQ, Tan F, Zhuang ZX, Wang XR. Surface molecularly imprinted nanowires for biorecognition. J Am Chem Soc. 2005;127(5):1378-1379.
• 13. Sun Y. Molecularly imprinted polymer for 2, 4-dichlorophenoxyacetic acid prepared by a sol-gel method. J Chem Sci. 2014;126(4):1005-1011.
• 14. Tadi KK, Motghare RV. Computational and experimental studies on oxalic acid imprinted polymer. J Chem Sci. 2013;125(2):413-418.
• 15. Sellergren B. Molecularly Imprinted Polymers, Man made mimics of antibodies and their applications in analytical chemistry, Techniques and Instrumentation in Analytical Chemistry. Elsevier Publishers. 2001;23.
• 16. Kupai J, Razali M, Büyüktiryaki S, Keçili R, Szekely G. Long-term stability and reusability of molecularly imprinted polymers. Polym Chem. 2017;8:666-673.
• 17. Suravajhala R, Burri H R, Malik B. Development of highly specific and selectively recognizing caffeine imprinted polymer nanomaterials with EGDMA crosslinker. Current Nanomaterials, 2022;7(1):65-72.
• 18. Theodoridis G, Manesiotis P. Selective solid-phase extraction sorbent for caffeine made by molecular imprinting. J Chromatogr A. 2002;948(1-2):163-169.
• 19. Farrington K, Magnerb E, Regan F. Predicting the performance of molecularly imprinted polymers: Selective extraction of caffeine by molecularly imprinted solid phase extraction. Anal Chim Acta. 2006;566:60-68.
• 20. He C, Long Y, Pan J, Li K, Liu F. Application of molecularly imprinted polymers to solid-phase extraction of analytes from real samples. J Biochem Biophys. Methods. 2007;70(2):133-150.
• 21. Saloni J, Lipkowski P, Dasary SSR, Anjaneyulu Y, Yu H, Hill GJr. Theoretical study of molecular interactions of TNT, acrylic acid, and ethylene glycol dimethacrylate-elements of molecularly imprinted polymer modelling process. Polymer. 2011;52(4):1206-1216.
• 22. Ge Y, Butler B, Mirza F, Habib-Ullah S, Fei D. Smart molecularly imprinted polymers: Recent developments and applications. Macromol Rapid Commun. 2013;34(11):903-915.
• 23. Piletsky SA, Andersson HS, Nicholls A. The rational use of hydrophobic effect-based recognition in molecularly imprinted polymers. J Mol Recog. 1998;11(1-6):94-97.
• 24. Sreenivasan K. Synthesis and evaluation of a Beta cyclodextrinbased molecularly imprinted copolymer. J Appl Polym Sci. 1998;70(1):15-18.
• 25. Wang Y, Wang E, Wu Z, Li H, Zhu Z, Zhu X, et al. Synthesis of chitosan molecularly imprinted polymers for solid-phase extraction of methandrostenolone. Carbohydr Polym. 2014;101:517-523.
• 26. Zhang YL, Zhang J, Dai CM, Zhou XF, Liu SG. Sorption of carbamazepine from water by magnetic molecularly imprinted polymers based on chitosan-Fe3O4. Carbohydr Polym. 2013;97(2):809-816.
• 27. Yıldırım A, Acay H, Baran A. Synthesis and characterization of molecularly imprinted composite as a novel adsorbent and competition with non-imprinting composite for removal of dye. J. Turk. Chem. Soc., Sect. A: Chem. 2021;8(2):609-622.
• 28. Lin Y, Tang SQ, Mao X, Bao LJ. Protein recognition via molecularly imprinted agarose gel membrane. J Biomed Mater Res A. 2008;85(3):573-581.
• 29. Zhao KY, Cheng GX, Huang JJ, Ying, XG. Rebinding and recognition properties of protein-macromolecularly imprinted calcium phosphate/alginate hybrid polymer microspheres. React Funct Polym. 2008;68(3):732-741.
• 30. Brenner T, Wang Z, Achayuthakan P, Nakajima T, Nishinari K. Rheology and synergy of κ-carrageenan/locust bean gum/konjac glucomannan gels. Carbohydr Polym. 2013;98(1):754-760.
• 31. Ratcliffe I, Williams PA, English RJ, Meadows J. Small stain deformation measurements of konjac glucomannan solutions and influence of borate cross-linking. Carbohydr Polym. 2013;95(1):272-281.
• 32. Tian DT, Li SR, Liu XP, Wang JS, Hu S, Liu CM. Synthesis and properties of konjac glucomannangraft-poly(acrylic acid-co-trimethylallyl ammonium chloride) as a novel polyampholytic superabsorbent. Adv Polyml Tech. 2013;32(S1):E131-E140.
• 33. Wu WT, Yang LC, Chen HL. Effects of konjac glucomannan, inulin and cellulose on acute colonic responses to genotoxic azoxymethane. Food Chem. 2014;155:304-310.
• 34. Zhang C, Chen JD, Yang FQ. Konjac glucomannan, a promising polysaccharide for OCDDS. Carbohydr Polym. 2014;104:175-181.
• 35. Da-Ting T, Yu-Ch, Z, Ling X, Fang-Ting L. Synthesis and properties of caffeine molecularly imprinted polymers based on konjac glucomannan. Adv Polym Techno. 2017; 36(1):68-76.
• 36. Tan CJ, Wangrangsimakul S, Bai R, Tong YW. Defining the Interactions between Proteins and Surfactants for Nanoparticle Surface Imprinting through Miniemulsion Polymerization. Chem Mater. 2008;20(1):118-127.
• 37. Clarke RJ. In Proceedings of the 9th Coll. ASIC. 1980;467-472.
• 38. Rofti J. In Proceedings of the 5th Coll. ASIC. 1971;179-200.
• 39. Kai A, Huiting K, Lilei Z, Lianxiong G, Dating T. Preparation and properties of thermosensitive molecularly imprinted polymer based on konjac glucomannan and its controlled recognition and delivery of 5-fluorouracil. J Drug Deliv Sci Technol. 2020;60:101977.
• 40. Atia AA, Donia AM, Yousif AM. Removal of some hazardous heavy metals from aqueous solution using magnetic chelating resin with iminodiacetate functionality. Sep Purif Technol. 2008;61(3):348-357.
• 41. Demirel G, Özçetin G, Turan E, Çaykara T. pH/temperature-sensitive imprinted ionic poly (N-tert-butylacrylamide-co-acrylamide/maleic acid) hydrogels for bovine serum albumin. Macromol Biosci. 2005;5(10):1032-1037.
• 42. Kimhi O, Bianco-Peled H. Study of the interactions between protein-imprinted hydrogels and their templates. Langmuir. 2007;23(11):6329-6335.
• 43. Li N, Ng TB, Wong JH, Qiao JX, Zhang YN, Zhou R, et al. Separation and purification of the antioxidant compounds, caffeic acid phenethyl ester and caffeic acid from mushrooms by molecularly imprinted polymer. Food Chem. 2013;139(1-4):1161-1167.
• 44. Wei S-L, Guo X-J, Wang H-W, Tian Y-X, Yan Z-J. Preparation of caffeine molecularly imprinted polymers and application on solid phase extraction. Chinese J Anal Chem. 2012;40(07):1071-1075.
• 45. Yinzhe J, Dae-Ki C, Kyung H R. Adsorption isotherms of caffeine on molecular imprinted polymer. Korean J. Chem. Eng. 2008;25(4):816-818.