New copolymer of acrylamide with allyl methacrylate and its capacity for the removal of azo dyes
Yildirim, Yeliz; Yilmaz, Habibe; Ak, Guliz; Sanlier, Senay Hamarat
http://dx.doi.org/10.1590/0104-1428.1615
Polímeros: Ciência e Tecnologia, vol.25, n2, p.137-145, 2015
Abstract
The copolymerization reactions of Acrylamide (AA) with the different mole ratios of allyl methacrylate (AMA) such as 25/75, 50/50 and 75/25 were studied by radical polymerization under argon atmosphere using 2,2’-Azobis (isobutyronitri1e) (AIBN) as initiator. The copolymers were characterized with Fourier transform infrared spectroscopy (FTIR) and thermogravimetric analysis (TG). FTIR spectra showed that the C=O, C-N and N-H groups in copolymers remained during the copolymerization. It is concluded from the thermograms that Poly(AA-co-AMA) copolymers which contained different ratios of monomer and comonomer exhibit similar thermal behavior. Adsorption capacity, kinetic and isotherm studies of Direct Brown 2 onto the copolymers have been evaluated. Different factors such as the monomer ratio, pH, initial dye concentration, copolymer dosage and contact time affecting the removal process were studied. It was found that the adsorption process agreed with the Freundlich and Dubinin-Raduskevich model and the adsorption of Direct Brown 2 depended on the acrylamide content and pH of the solution. The standard Gibb’s free energy was determined as - 14.7 kJ/mol, which means that adsorption occurred spontaneously and the process is feasible. Increasing the acrylamide content led to increased adsorption of Direct Brown 2 on the copolymer. Moreover, adsorption kinetic studies showed that the adsorption followed a pseudo-second-order kinetic model, indicating that the chemical adsorption was the rate-limiting step. These results show that Poly(AA-co-AMA) can be used as adsorbent for water pollutants such as Direct Brown 2 and has potential applications in related industrial and environmental areas.
Keywords
acrylamide, allyl methacrylate, azo dye, adsorption isotherm, adsorption kinetics.
References
1. Solpan, D., & Kolge, Z. (2006). Adsorption of Methyl Violet in aque-ous solutions by poly(N-vinylpyrrolidone-co-methacrylic acied) hydrogels. Radiation Physics and Chemistry, 75(1), 120128. http://dx.doi.org/10.1016/j.radphyschem.2005.06.005.
2. Vivek, A. V., & Dhamodharan, R. (2008). Amphiphilic polystyrene- graft-poly (N,N-dimethylamino-2-ethyl methacrylate) hydrogels synthesized via room temperature ATRP: Studies on swelling behaviour and dye sorption. Reactive & Functional Polymers, 68(5), 967-973. http://dx.doi.org/10.1016/j.reactfunctpolym.2008.02.006.
3. Homayon, A. P., Marjaneh, S. Z., Simin, T., Elham, M., & Jahanbakhsh, G. (2012). Nickel adsorption from environmental samples by ion imprinted aniline-formaldehyde polymer. Iranian Journal of Chemistry and Chemical Engineering, 31(3), 35-44. Retrieved from http://www.ijcce.ac.ir/article_5949_1204.html
4. Solpan, D., Duran, S., & Torun, M. (2008). Removal of cationic dyes by poly(acrylamide-co-acrylic acid) hydrogels in aqueous solutions. Radiation Physics and Chemistry, 77(4), 447-452. http://dx.doi.org/10.1016/j.radphyschem.2007.08.006.
5. Lu, J. L., Wu, M. Y., Yang, X. L., Dong, Z. B., Ye, J. H., Borthakur, D., Sun, Q. L., & Liang, Y. R. (2010). Decaffeination of tea extracts by using poly(acrylamide-co-ethylene glycol dimethylacrylate) as adsorbent. Journal of Food Engineering, 97(4), 555-562. http://dx.doi.org/10.1016/j.jfoodeng.2009.11.018.
6. Dragan, E. S., Perju, M. M., & Dinu, M. V. (2012). Preparation and characterization of IPN composite hydrogels based on polyacrylamide and chitosan and their interaction with ionic dyes. Carbohydrate Polymers, 88(1), 270-281. http://dx.doi.org/10.1016/j.carbpol.2011.12.002.
7. Shao, D., Ren, X., Hu, J., Chen, Y., & Wang, X. (2010). Preconcentration of Pb2+ from aqueous solution using poly(acrylamide) and poly(N,N-dimethylacrylamide) grafted multiwalled carbon nanotubes. Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 360(1-3), 74-84. http://dx.doi.org/10.1016/j.colsurfa.2010.02.013.
8. Wang, Y., Zeng, L., Ren, X., Song, H., & Wang, A. (2010). Removal of methyl violet from aqueous solutions using poly (acrylic acid-co-acrylamide)/attapulgite composite. Journal of Environmental Sciences, 22(1), 7-14. http://dx.doi.org/10.1016/S1001-0742(09)60068-1. PMid:20397381
9. Işik, M., & Sponza, D. T. (2007). Fate and toxicity of azo dye metabolites under batch long-term anaerobic incubations. Enzyme and Microbial Technology, 40(4), 934-939. http://dx.doi.org/10.1016/j.enzmictec.2006.07.032.
10. Lučić, M., Milosavljević, N., Radetić, M., Šaponjić, Z., Radoičić, M., & Krušić, M. K. (2014). The potential application of TiO2/hydrogel nanocomposite for removal of various textile azo dyes. Separation and Purification Technology, 122, 206-216. http://dx.doi.org/10.1016/j.seppur.2013.11.002.
11. Sanlier, S. H., Ak, G., Yilmaz, H., Ozbakir, G., & Cagliyan, O. (2013). Removal of textile dye, direct red 23, with glutaraldehyde cross-linked magnetic chitosan beads. Preparative Biochemistry & Biotechnology, 43(2), 163-176. http://dx.doi.org/10.1080/10826068.2012.712937. PMid:23302104
12. Mittal, A., Gajbe, V., & Mittal, J. (2008). Removal and recovery of hazardous triphenylmethane dye, Methyl Violet through adsorption over granulated waste materials. Journal of Hazardous Materials, 150(2), 364-375. http://dx.doi.org/10.1016/j.jhazmat.2007.04.117. PMid:17543448
13. Şolpan, D., Torun, M., & Güven, O. (2008). The usability of (sodium alginate/acrylamide) semi-interpenetrating polymer networks on removal of some textile dyes. Journal of Applied Polymer Science, 108(6), 3787-3795. http://dx.doi.org/10.1002/app.27945.
New copolymer of acrylamide with allyl methacrylate and its capacity for the removal of azo dyes
14. Vardareli, T. K., Keskin, S., & Usanmaz, A. (2008). Synthesis and Characterization of Poly(allyl methacrylate) Obtained by Free Radical Initiator. Journal of Macromolecular Science: Pure & Applied Chemistry, 45(4), 302-311. http://dx.doi.org/10.1080/10601320701863783.
15. Zulfiqar, S., Piracha, A., & Masud, K. (1996). The thermal degradation of poly(allyl methacrylate). Polymer Degradation & Stability, 52(1), 89-93. http://dx.doi.org/10.1016/01413910(95)00237-5.
16. Dulman, V., & Cucu-Man, S. M. (2009). Sorption of some textile dyes by beech wood sawdust. Journal of Hazardous Materials, 162(2-3), 1457-1464. http://dx.doi.org/10.1016/j.jhazmat.2008.06.046. PMid:18656305
17. Senthil Kumar, P., Ramalingam, S., Senthamarai, C., Niranjanaa, M., Vijayalakshmi, P., & Sivanesan, S. (2010). Adsorption of dye from aqueous solution by cashew nut shell: Studies on equilibrium isotherm, kinetics and thermodynamics of interactions. Desalination, 261(1-2), 52-60. http://dx.doi.org/10.1016/j.desal.2010.05.032.
18. Chowdhury, S., Chakraborty, S., & Saha, P. (2011). Biosorption of Basic Green 4 from aqueous solution by Ananas comosus (pineapple) leaf powder. Colloids and Surfaces. B, Biointerfaces, 84(2), 520-527. http://dx.doi.org/10.1016/j.colsurfb.2011.02.009. PMid:21349693
19. Mittal, A. (2006). Use of hen feathers as potential adsorbent for the removal of a hazardous dye, Brilliant Blue FCF, from wastewater. Journal of Hazardous Materials, 128(2-3), 233-239. http://dx.doi.org/10.1016/j.jhazmat.2005.08.043. PMid:16221529
20. Ofokansi, K., Winter, G., Fricker, G., & Coester, C. (2010). Matrix-loaded biodegradable gelatin nanoparticles as new approach to improve drug loading and delivery. European Journal of Pharmaceutics and Biopharmaceutics, 76(1), 1-9. http://dx.doi.org/10.1016/j.ejpb.2010.04.008. PMid:20420904
21. Mittal, A., Gajbe, V., & Mittal, J. (2008). Removal and recovery of hazardous triphenylmethane dye, Methyl Violet through adsorption over granulated waste materials. Journal of Hazardous Materials, 150(2), 364-375. http://dx.doi.org/10.1016/j.jhazmat.2007.04.117. PMid:17543448
22. Ngah, W. S. W., & Fatinathan, S. (2008). Adsorption of Cu(II) ions in aqueous solution using chitosan beads, chitosan–GLA beads and chitosan–alginate beads. Chemical Engineering Journal, 143(1-3), 62-72. http://dx.doi.org/10.1016/j.cej.2007.12.006.
23. Akçay, G., Kılınç, E., & Akçay, M. (2009). The equilibrium and kinetics studies of flurbiprofen adsorption onto tetrabutylammonium montmorillonite (TBAM). Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 335(1–3), 189-193. http://dx.doi.org/10.1016/j.colsurfa.2008.11.009.
24. Rastogi, R., Gulati, N., Kotnala, R. K., Sharma, U., Jayasundar, R., & Koul, V. (2011). Evaluation of folate conjugated pegylated thermosensitive magnetic nanocomposites for tumor imaging and therapy. Colloids and Surfaces. B, Biointerfaces, 82(1), 160-167. http://dx.doi.org/10.1016/j.colsurfb.2010.08.037.PMid:20851578
25. Chiou, M. S., Ho, P. Y., & Li, H. Y. (2004). Adsorption of anionic dyes in acid solutions using chemically cross-linked chitosan beads. Dyes and Pigments, 60(1), 69-84. http://dx.doi.org/10.1016/S0143-7208(03)00140-2.
26. Deniz, F., & Saygıdeğer, S. D. (2011). Removal of a hazardous azo dye (Basic Red 46) from aqueous solution by princess tree leaf. Desalination, 268(1-3), 6-11. http://dx.doi.org/10.1016/j.desal.2010.09.043.
2. Vivek, A. V., & Dhamodharan, R. (2008). Amphiphilic polystyrene- graft-poly (N,N-dimethylamino-2-ethyl methacrylate) hydrogels synthesized via room temperature ATRP: Studies on swelling behaviour and dye sorption. Reactive & Functional Polymers, 68(5), 967-973. http://dx.doi.org/10.1016/j.reactfunctpolym.2008.02.006.
3. Homayon, A. P., Marjaneh, S. Z., Simin, T., Elham, M., & Jahanbakhsh, G. (2012). Nickel adsorption from environmental samples by ion imprinted aniline-formaldehyde polymer. Iranian Journal of Chemistry and Chemical Engineering, 31(3), 35-44. Retrieved from http://www.ijcce.ac.ir/article_5949_1204.html
4. Solpan, D., Duran, S., & Torun, M. (2008). Removal of cationic dyes by poly(acrylamide-co-acrylic acid) hydrogels in aqueous solutions. Radiation Physics and Chemistry, 77(4), 447-452. http://dx.doi.org/10.1016/j.radphyschem.2007.08.006.
5. Lu, J. L., Wu, M. Y., Yang, X. L., Dong, Z. B., Ye, J. H., Borthakur, D., Sun, Q. L., & Liang, Y. R. (2010). Decaffeination of tea extracts by using poly(acrylamide-co-ethylene glycol dimethylacrylate) as adsorbent. Journal of Food Engineering, 97(4), 555-562. http://dx.doi.org/10.1016/j.jfoodeng.2009.11.018.
6. Dragan, E. S., Perju, M. M., & Dinu, M. V. (2012). Preparation and characterization of IPN composite hydrogels based on polyacrylamide and chitosan and their interaction with ionic dyes. Carbohydrate Polymers, 88(1), 270-281. http://dx.doi.org/10.1016/j.carbpol.2011.12.002.
7. Shao, D., Ren, X., Hu, J., Chen, Y., & Wang, X. (2010). Preconcentration of Pb2+ from aqueous solution using poly(acrylamide) and poly(N,N-dimethylacrylamide) grafted multiwalled carbon nanotubes. Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 360(1-3), 74-84. http://dx.doi.org/10.1016/j.colsurfa.2010.02.013.
8. Wang, Y., Zeng, L., Ren, X., Song, H., & Wang, A. (2010). Removal of methyl violet from aqueous solutions using poly (acrylic acid-co-acrylamide)/attapulgite composite. Journal of Environmental Sciences, 22(1), 7-14. http://dx.doi.org/10.1016/S1001-0742(09)60068-1. PMid:20397381
9. Işik, M., & Sponza, D. T. (2007). Fate and toxicity of azo dye metabolites under batch long-term anaerobic incubations. Enzyme and Microbial Technology, 40(4), 934-939. http://dx.doi.org/10.1016/j.enzmictec.2006.07.032.
10. Lučić, M., Milosavljević, N., Radetić, M., Šaponjić, Z., Radoičić, M., & Krušić, M. K. (2014). The potential application of TiO2/hydrogel nanocomposite for removal of various textile azo dyes. Separation and Purification Technology, 122, 206-216. http://dx.doi.org/10.1016/j.seppur.2013.11.002.
11. Sanlier, S. H., Ak, G., Yilmaz, H., Ozbakir, G., & Cagliyan, O. (2013). Removal of textile dye, direct red 23, with glutaraldehyde cross-linked magnetic chitosan beads. Preparative Biochemistry & Biotechnology, 43(2), 163-176. http://dx.doi.org/10.1080/10826068.2012.712937. PMid:23302104
12. Mittal, A., Gajbe, V., & Mittal, J. (2008). Removal and recovery of hazardous triphenylmethane dye, Methyl Violet through adsorption over granulated waste materials. Journal of Hazardous Materials, 150(2), 364-375. http://dx.doi.org/10.1016/j.jhazmat.2007.04.117. PMid:17543448
13. Şolpan, D., Torun, M., & Güven, O. (2008). The usability of (sodium alginate/acrylamide) semi-interpenetrating polymer networks on removal of some textile dyes. Journal of Applied Polymer Science, 108(6), 3787-3795. http://dx.doi.org/10.1002/app.27945.
New copolymer of acrylamide with allyl methacrylate and its capacity for the removal of azo dyes
14. Vardareli, T. K., Keskin, S., & Usanmaz, A. (2008). Synthesis and Characterization of Poly(allyl methacrylate) Obtained by Free Radical Initiator. Journal of Macromolecular Science: Pure & Applied Chemistry, 45(4), 302-311. http://dx.doi.org/10.1080/10601320701863783.
15. Zulfiqar, S., Piracha, A., & Masud, K. (1996). The thermal degradation of poly(allyl methacrylate). Polymer Degradation & Stability, 52(1), 89-93. http://dx.doi.org/10.1016/01413910(95)00237-5.
16. Dulman, V., & Cucu-Man, S. M. (2009). Sorption of some textile dyes by beech wood sawdust. Journal of Hazardous Materials, 162(2-3), 1457-1464. http://dx.doi.org/10.1016/j.jhazmat.2008.06.046. PMid:18656305
17. Senthil Kumar, P., Ramalingam, S., Senthamarai, C., Niranjanaa, M., Vijayalakshmi, P., & Sivanesan, S. (2010). Adsorption of dye from aqueous solution by cashew nut shell: Studies on equilibrium isotherm, kinetics and thermodynamics of interactions. Desalination, 261(1-2), 52-60. http://dx.doi.org/10.1016/j.desal.2010.05.032.
18. Chowdhury, S., Chakraborty, S., & Saha, P. (2011). Biosorption of Basic Green 4 from aqueous solution by Ananas comosus (pineapple) leaf powder. Colloids and Surfaces. B, Biointerfaces, 84(2), 520-527. http://dx.doi.org/10.1016/j.colsurfb.2011.02.009. PMid:21349693
19. Mittal, A. (2006). Use of hen feathers as potential adsorbent for the removal of a hazardous dye, Brilliant Blue FCF, from wastewater. Journal of Hazardous Materials, 128(2-3), 233-239. http://dx.doi.org/10.1016/j.jhazmat.2005.08.043. PMid:16221529
20. Ofokansi, K., Winter, G., Fricker, G., & Coester, C. (2010). Matrix-loaded biodegradable gelatin nanoparticles as new approach to improve drug loading and delivery. European Journal of Pharmaceutics and Biopharmaceutics, 76(1), 1-9. http://dx.doi.org/10.1016/j.ejpb.2010.04.008. PMid:20420904
21. Mittal, A., Gajbe, V., & Mittal, J. (2008). Removal and recovery of hazardous triphenylmethane dye, Methyl Violet through adsorption over granulated waste materials. Journal of Hazardous Materials, 150(2), 364-375. http://dx.doi.org/10.1016/j.jhazmat.2007.04.117. PMid:17543448
22. Ngah, W. S. W., & Fatinathan, S. (2008). Adsorption of Cu(II) ions in aqueous solution using chitosan beads, chitosan–GLA beads and chitosan–alginate beads. Chemical Engineering Journal, 143(1-3), 62-72. http://dx.doi.org/10.1016/j.cej.2007.12.006.
23. Akçay, G., Kılınç, E., & Akçay, M. (2009). The equilibrium and kinetics studies of flurbiprofen adsorption onto tetrabutylammonium montmorillonite (TBAM). Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 335(1–3), 189-193. http://dx.doi.org/10.1016/j.colsurfa.2008.11.009.
24. Rastogi, R., Gulati, N., Kotnala, R. K., Sharma, U., Jayasundar, R., & Koul, V. (2011). Evaluation of folate conjugated pegylated thermosensitive magnetic nanocomposites for tumor imaging and therapy. Colloids and Surfaces. B, Biointerfaces, 82(1), 160-167. http://dx.doi.org/10.1016/j.colsurfb.2010.08.037.PMid:20851578
25. Chiou, M. S., Ho, P. Y., & Li, H. Y. (2004). Adsorption of anionic dyes in acid solutions using chemically cross-linked chitosan beads. Dyes and Pigments, 60(1), 69-84. http://dx.doi.org/10.1016/S0143-7208(03)00140-2.
26. Deniz, F., & Saygıdeğer, S. D. (2011). Removal of a hazardous azo dye (Basic Red 46) from aqueous solution by princess tree leaf. Desalination, 268(1-3), 6-11. http://dx.doi.org/10.1016/j.desal.2010.09.043.
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