Synthesis, characterization, and performance comparison of boron using adsorbents based on N-methyl-D-glucosamine

doi:10.1016/j.cjche.2023.01.012

Abstract

Abstract: Using N-methyl-D-glucosamine (NMDG) as the functional monomer, glycidyl methacrylate (GMA) as the connecting monomer, functionalized Fe₃O₄ nano-particles (NPs) as the support, three adsorbents were prepared including direct polymer GMA-NMDG, magnetic GMA-NMDG polymer (MGN), and boron magnetic ion-imprinted polymer (BMIIP). Based upon the optimization of synthesis conditions, the prepared adsorbents and intermediate products were characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscope, energy dispersive spectroscopy, X-ray diffraction, vibrating sample magnetometer, and Brunauer-Emmett-Teller to investigate the synthesis process, the morphological structure and the functional properties of the materials. The optimum performances of GMA-NMDG, MGN and BMIIP were obtained in the initial neutral solution (pH of 6.5). Moreover, GMA-NMDG and MGN reached the maximum adsorption capacity at 120 min, whereas BMIIP reached adsorption saturation at 60 min. The pseudo-second-order kinetic model was more suitable for the adsorption of boron using the adsorbents. The maximum adsorption capacity of GMA-NMDG was found to be 43.4 mg·g^-1, while those of MGN and BMIIP were 32.5 and 28.3 mg·g^-1, respectively. The Langmuir isotherm model was more appropriate to describe the adsorption process. The adsorbents maintained satisfactory adsorption performance within a certain temperature range. Competing ions had little effect on the adsorption of boron, and would be adsorbed simultaneously, due to which, the effect of co-adsorption can be considered. The adsorption capacity of GMA-NMDG was high, while the adsorption selectivity of BMIIP was much better. Furthermore, BMIIP showed good adsorption after five cycles of adsorption and desorption. The comparison of adsorbents showed that GMA-NMDG had the highest adsorption capacity and was suitable for co-adsorption. MGN had a high adsorption capacity, good comprehensive performance and magnetic properties. BMIIP had better adsorption rate, adsorption selectivity and recyclability. Through the optimization of synthesis conditions, the adsorption capacity of the traditional monomer NMDG polymer was increased, and the magnetism was given to facilitate rapid recovery. Combined with the ion imprinting technology, it showed higher boron adsorption selectivity in the presence of competitive ions.

Key words: Boron, Carbohydrate, Adsorption, Magnetic, Surface imprinting, Carrier

摘要： Using N-methyl-D-glucosamine (NMDG) as the functional monomer, glycidyl methacrylate (GMA) as the connecting monomer, functionalized Fe₃O₄ nano-particles (NPs) as the support, three adsorbents were prepared including direct polymer GMA-NMDG, magnetic GMA-NMDG polymer (MGN), and boron magnetic ion-imprinted polymer (BMIIP). Based upon the optimization of synthesis conditions, the prepared adsorbents and intermediate products were characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscope, energy dispersive spectroscopy, X-ray diffraction, vibrating sample magnetometer, and Brunauer-Emmett-Teller to investigate the synthesis process, the morphological structure and the functional properties of the materials. The optimum performances of GMA-NMDG, MGN and BMIIP were obtained in the initial neutral solution (pH of 6.5). Moreover, GMA-NMDG and MGN reached the maximum adsorption capacity at 120 min, whereas BMIIP reached adsorption saturation at 60 min. The pseudo-second-order kinetic model was more suitable for the adsorption of boron using the adsorbents. The maximum adsorption capacity of GMA-NMDG was found to be 43.4 mg·g^-1, while those of MGN and BMIIP were 32.5 and 28.3 mg·g^-1, respectively. The Langmuir isotherm model was more appropriate to describe the adsorption process. The adsorbents maintained satisfactory adsorption performance within a certain temperature range. Competing ions had little effect on the adsorption of boron, and would be adsorbed simultaneously, due to which, the effect of co-adsorption can be considered. The adsorption capacity of GMA-NMDG was high, while the adsorption selectivity of BMIIP was much better. Furthermore, BMIIP showed good adsorption after five cycles of adsorption and desorption. The comparison of adsorbents showed that GMA-NMDG had the highest adsorption capacity and was suitable for co-adsorption. MGN had a high adsorption capacity, good comprehensive performance and magnetic properties. BMIIP had better adsorption rate, adsorption selectivity and recyclability. Through the optimization of synthesis conditions, the adsorption capacity of the traditional monomer NMDG polymer was increased, and the magnetism was given to facilitate rapid recovery. Combined with the ion imprinting technology, it showed higher boron adsorption selectivity in the presence of competitive ions.

关键词: Boron, Carbohydrate, Adsorption, Magnetic, Surface imprinting, Carrier

Hui Jiang, Zijian Zhao, Ning Yu, Yi Qin, Zhengwei Luo, Wenhua Geng, Jianliang Zhu. Synthesis, characterization, and performance comparison of boron using adsorbents based on N-methyl-D-glucosamine[J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 16-31.

References

[1] Q. Wu, M. Liu, X. Wang, A novel chitosan based adsorbent for boron separation, Sep. Purif. Technol. 211 (2019) 162-169.
[2] M.M. Nasef, M. Nallappan, Z. Ujang, Polymer-based chelating adsorbents for the selective removal of boron from water and wastewater: A review, React. Funct. Polym. 85 (2014) 54-68.
[3] P. Li, C. Liu, L. Zhang, S. Zheng, Y. Zhang, Enhanced boron adsorption onto synthesized MgO nanosheets by ultrasonic method, Ultrason. Sonochem. 34 (2017) 938-946.
[4] S. Nishihama, Y. Sumiyoshi, T. Ookubo, K. Yoshizuka, Adsorption of boron using glucamine-based chelate adsorbents, Desalination 310 (2013) 81-86.
[5] X. Zhang, J. Wang, S. Chen, Z. Bao, H. Xing, Z. Zhang, B. Su, Q. Yang, Y. Yang, Q. Ren, A spherical N-methyl-d-glucamine-based hybrid adsorbent for highly efficient adsorption of boric acid from water, Sep. Purif. Technol. 172 (2017) 43-50.
[6] Z.M. Guan, J. Lv, P. Bai, X. Guo, Boron removal from aqueous solutions by adsorption—A review, Desalination 383 (2016) 29-37.
[7] D. Kavak, Removal of boron from aqueous solutions by batch adsorption on calcined alunite using experimental design, J. Hazard. Mater. 163 (1) (2009) 308-314.
[8] N. Hilal, G.J. Kim, C. Somerfield, Boron removal from saline water: A comprehensive review, Desalination 273 (1) (2011) 23-35.
[9] J. Ren, R.H. Li, Y.L. Liu, Y.R. Cheng, D.Y. Mu, R.J. Zheng, J.C. Liu, C.S. Dai, The impact of aluminum impurity on the regenerated lithium nickel cobalt manganese oxide cathode materials from spent LIBs, New J. Chem. 41 (19) (2017) 10959-10965.
[10] G.L. Guo, Y. Lu, D.D. Yang, X.H. Li, M.M. Gong, Purification of thorium by precipitation, J. Radioanal. Nucl. Chem. 327 (2) (2021) 667-671.
[11] L. Melnyk, V. Goncharuk, I. Butnyk, E. Tsapiuk, Boron removal from natural and wastewaters using combined sorption/membrane process, Desalination 185 (1-3) (2005) 147-157.
[12] A. Farhat, F. Ahmad, N. Hilal, H.A. Arafat, Boron removal in new generation reverse osmosis (RO) membranes using two-pass RO without pH adjustment, Desalination 310 (2013) 50-59.
[13] R. Zhang, Y. Xie, J. Song, L. Xing, D. Kong, X. Li, T. He, Extraction of boron from salt lake brine using 2-ethylhexanol, Hydrometallurgy 160 (2016) 129-136.
[14] N. Öztürk, T.E. Köse, Boron removal from aqueous solutions by ion-exchange resin: Batch studies, Desalination 227 (1-3) (2008) 233-240.
[15] A. Hussain, R. Sharma, J. Minier-Matar, Z. Hirani, S. Adham, Application of emerging ion exchange resin for boron removal from saline groundwater, J. Water Process. Eng. 32 (2019) 100906.
[16] Y.A. Jarma, E. Çermikli, D. İpekçi, E. Altıok, N. Kabay, Comparison of two electrodialysis stacks having different ion exchange and bipolar membranes for simultaneous separation of boron and lithium from aqueous solution, Desalination 500 (2021) 114850.
[17] L.L. Hao, P. Wang, S. Valiyaveettil, Successive extraction of As(V), Cu(II) and P(V) ions from water using spent coffee powder as renewable bioadsorbents, Sci. Rep. 7 (2017) 42881.
[18] T. Kameda, J. Oba, T. Yoshioka, New treatment method for boron in aqueous solutions using Mg-Al layered double hydroxide: Kinetics and equilibrium studies, J. Hazard. Mater. 293 (2015) 54-63.
[19] C.Y. Sun, F. Zhang, A. Wang, S. Li, F. Cheng, Direct synthesis of mesoporous aluminosilicate using natural clay from low-grade potash ores of a salt lake in Qinghai, China, and its use in octadecylamine adsorption, Appl. Clay Sci. 108 (2015) 123-127.
[20] M. Hosseini Talari, N.S. Tabrizi, V. Babaeipour, F. Halek, Adsorptive removal of organic pollutants from water by carbon fiber aerogel derived from bacterial cellulose, J. Sol Gel Sci. Technol. 101 (2) (2022) 345-355.
[21] N. Bicak, M. Gazi, B.F. Senkal, Polymer supported amino bis-(cis-propan 2, 3 diol) functions for removal of trace boron from water, React. Funct. Polym. 65 (1-2) (2005) 143-148.
[22] M. Gazi, N. Bicak, Selective boron extraction by polymer supported 2-hydroxylethylamino propylene glycol functions, React. Funct. Polym. 67 (10) (2007) 936-942.
[23] Y. Miyazaki, H. Matsuo, T. Fujimori, H. Takemura, S. Matsuoka, T. Okobira, K. Uezu, K. Yoshimura, Interaction of boric acid with salicyl derivatives as an anchor group of boron-selective adsorbents, Polyhedron 27 (13) (2008) 2785-2790.
[24] H. Iwasaki, M. Yoshikawa, Molecularly imprinted polyacrylonitrile adsorbents for the capture of Cs+ ions, Polym. J. 48 (12) (2016) 1151-1156.
[25] M. Taghizadeh, S. Hassanpour, Selective adsorption of Cr(VI) ions from aqueous solutions using a Cr(VI)-imprinted polymer supported by magnetic multiwall carbon nanotubes, Polymer 132 (2017) 1-11.
[26] Y.B. Li, B.J. Gao, R.K. Du, Studies on preparation and recognition characteristic of surface-ion imprinting material IIP-PEI/SiO₂ of chromate anion, Sep. Sci. Technol. 46 (9) (2011) 1472-1481.
[27] D. Kong, N. Wang, N. Qiao, Q. Wang, Z. Wang, Z. Zhou, Z. Ren, Facile preparation of ion-imprinted chitosan microspheres enwrapping Fe₃O₄ and graphene oxide by inverse suspension cross-linking for highly selective removal of copper(II), ACS Sustain. Chem. Eng. 5 (8) (2017) 7401-7409.
[28] Y. Huang, R. Wang, Highly effective and low-cost ion-imprinted polymers loaded on pretreated vermiculite for lithium recovery, Ind. Eng. Chem. Res. 58 (27) (2019) 12216-12225.
[29] Y.C. Zhan, X.B. Luo, S.S. Nie, Y.N. Huang, X.M. Tu, S.L. Luo, Selective separation of Cu(II) from aqueous solution with a novel Cu(II) surface magnetic ion-imprinted polymer, Ind. Eng. Chem. Res. 50 (10) (2011) 6355-6361.
[30] M. Shamsipur, J. Fasihi, K. Ashtari, Grafting of ion-imprinted polymers on the surface of silica gel particles through covalently surface-bound initiators: A selective sorbent for uranyl ion, Anal. Chem. 79 (18) (2007) 7116-7123.
[31] A. Islam, H. Javed, A. Chauhan, I. Ahmad, S. Rais, Triethylenetetramine-grafted magnetite graphene oxide-based surface-imprinted polymer for the adsorption of Ni(II) in food samples, J. Chem. Eng. Data 66 (1) (2021) 456-465.
[32] L. Zhang, J. Xue, X. Zhou, X. Fei, Y. Wang, Y. Zhou, L. Zhong, X. Han, Adsorption of molybdate on molybdate-imprinted chitosan/triethanolamine gel beads, Carbohydr. Polym. 114 (2014) 514-520.
[33] D.J. Li, Y. Chen, Z. Liu, Boronate affinity materials for separation and molecular recognition: Structure, properties and applications, Chem. Soc. Rev. 44 (22) (2015) 8097-8123.
[34] E. Kanao, Y. Tsuchiya, K. Tanaka, Y. Masuda, T. Tanigawa, T. Naito, T. Sano, T. Kubo, K. Otsuka, Poly(ethylene glycol) hydrogels with a boronic acid monomer via molecular imprinting for selective removal of quinic acid gamma-lactone in coffee, ACS Appl. Polym. Mater. 3 (1) (2021) 226-232.
[35] X.Y. Hou, B.L. Guo, Y.K. Tong, M.M. Tian, Using self-polymerization synthesis of boronate-affinity hollow stannic oxide based fragment template molecularly imprinted polymers for the selective recognition of polyphenols, J. Chromatogr. A 1612 (2020) 460631.
[36] S. Liu, J. Liu, J. Pan, J. Luo, X. Niu, T. Zhang, F. Qiu, Two are better than one: Halloysite nanotubes-supported surface imprinted nanoparticles using synergy of metal chelating and low pKa boronic acid monomers for highly specific luteolin binding under neutral condition, ACS Appl. Mater. Interfaces 9 (38) (2017) 33191-33202.
[37] Q. Wang, X.T. Liu, M.H. Zhang, Z. Wang, Z.Y. Zhou, Z.Q. Ren, Facile preparation of novel ion-imprinted polymers for selective extraction of Br(I) ions from aqueous solution, Ind. Eng. Chem. Res. 58 (16) (2019) 6670-6678.
[38] H.J. Zhu, H. Yao, K. Xia, J. Liu, X. Yin, W. Zhang, J. Pan, Magnetic nanoparticles combining teamed boronate affinity and surface imprinting for efficient selective recognition of glycoproteins under physiological pH, Chem. Eng. J. 346 (2018) 317-328.
[39] B.S. Zhao, M. He, B.B. Chen, B. Hu, Fe₃O₄ nanoparticles coated with double imprinted polymers for magnetic solid phase extraction of lead(II) from biological and environmental samples, Mikrochim. Acta 186 (12) (2019) 775.
[40] H. Zhang, D. Fang, Z. Kong, J. Wei, X. Wu, S. Shen, W. Cui, Y. Zhu, Enhanced adsorption of phthalic acid esters (PAEs) from aqueous solution by alkylbenzene-functionalized polypropylene nonwoven and its adsorption mechanism insight, Chem. Eng. J. 331 (2018) 406-415.
[41] X.Y. Zhou, J. Wei, H. Zhang, K. Liu, H. Wang, Adsorption of phthalic acid esters (PAEs) by amphiphilic polypropylene nonwoven from aqueous solution: The study of hydrophilic and hydrophobic microdomain, J. Hazard. Mater. 273 (2014) 61-69.
[42] T. Qi, A. Sonoda, Y. Makita, H. Kanoh, K. Ooi, T. Hirotsu, Synthesis and borate uptake of two novel chelating resins, Ind. Eng. Chem. Res. 41 (2) (2002) 133-138.
[43] Z.J. Zhao, H. Jiang, L. Wu, N. Yu, Z.W. Luo, W.H. Geng, Preparation of magnetic surface ion-imprinted polymer based on functionalized Fe₃O₄ for fast and selective adsorption of cobalt ions from water, Water 14 (2) (2022) 261.
[44] J. Qian, S. Zhang, Y. Zhou, P. Dong, D.B. Hua, Synthesis of surface ion-imprinted magnetic microspheres by locating polymerization for rapid and selective separation of uranium(VI), RSC Adv. 5 (6) (2015) 4153-4161.
[45] A. Sabarudin, K. Oshita, M. Oshima, S. Motomizu, Synthesis of cross-linked chitosan possessing N-methyl-d-glucamine moiety (CCTS-NMDG) for adsorption/concentration of boron in water samples and its accurate measurement by ICP-MS and ICP-AES, Talanta 66 (1) (2005) 136-144.
[46] C.S. Xie, X. Huang, S. Wei, C. Xiao, J. Cao, Z. Wang, Novel dual-template magnetic ion imprinted polymer for separation and analysis of Cd²⁺ and Pb²⁺ in soil and food, J. Clean. Prod. 262 (2020) 121387.
[47] N. Khoddami, F. Shemirani, A new magnetic ion-imprinted polymer as a highly selective sorbent for determination of cobalt in biological and environmental samples, Talanta 146 (2016) 244-252.
[48] Z.Y. Zhou, X.T. Liu, M.H. Zhang, J. Jiao, H.W. Zhang, J. Du, B. Zhang, Z.Q. Ren, Preparation of highly efficient ion-imprinted polymers with Fe₃O₄ nanoparticles as carrier for removal of Cr(VI) from aqueous solution, Sci. Total Environ. 699 (2020) 134334.
[49] H. Guo, Y. Tang, Y. Yu, L. Xue, J.Q. Qian, Covalent immobilization of α-amylase on magnetic particles as catalyst for hydrolysis of high-amylose starch, Int. J. Biol. Macromol. 87 (2016) 537-544.
[50] G.Y. Liu, H. Wang, X. Yang, L. Li, Synthesis of tri-layer hybrid microspheres with magnetic core and functional polymer shell, Eur. Polym. J. 45 (7) (2009) 2023-2032.
[51] F. Shafizadeh, M. Taghizadeh, S. Hassanpour, Preparation of a novel magnetic Pd(II) ion-imprinted polymer for the fast and selective adsorption of palladium ions from aqueous solutions, Environ. Sci. Pollut. Res. 26 (18) (2019) 18493-18508.
[52] X.Y. Zheng, H.L. Zheng, R. Zhao, Y.J. Sun, Q. Sun, S.X. Zhang, Y.Z. Liu, Polymer-functionalized magnetic nanoparticles: Synthesis, characterization, and methylene blue adsorption, Materials 11 (8) (2018) 1312.
[53] M. Fayazi, M.A. Taher, D. Afzali, A. Mostafavi, M. Ghanei-Motlagh, Synthesis and application of novel ion-imprinted polymer coated magnetic multi-walled carbon nanotubes for selective solid phase extraction of lead(II) ions, Mater. Sci. Eng. C 60 (2016) 365-373.
[54] M.A. Al-Ghouti, S.S. Dib, Utilization of nano-olive stones in environmental remediation of methylene blue from water, J. Environ. Health Sci. Eng. 18 (1) (2020) 63-77.
[55] B.Q. Lu, Y.J. Zhu, H.Y. Ao, C. Qi, F. Chen, Synthesis and characterization of magnetic iron oxide/calcium silicate mesoporous nanocomposites as a promising vehicle for drug delivery, ACS Appl. Mater. Interfaces 4 (12) (2012) 6969-6974.
[56] S. Akbarnejad, A.A. Amooey, S. Ghasemi, High effective adsorption of acid fuchsin dye using magnetic biodegradable polymer-based nanocomposite from aqueous solutions, Microchem. J. 149 (2019) 103966.
[57] S. Hassan, A.H. Kamel, A.A. Hassan, A. Amr, H. Abd El-Naby, M. Al-Omar, A. Sayed, CuFe₂O₄/polyaniline (PANI) nanocomposite for the hazard mercuric ion removal: Synthesis, characterization, and adsorption properties study, Molecules 25 (12) (2020) 2721.
[58] L.Y. Wang, J. Li, J. Wang, X. Guo, X. Wang, J. Choo, L. Chen, Green multi-functional monomer based ion imprinted polymers for selective removal of copper ions from aqueous solution, J. Colloid Interface Sci. 541 (2019) 376-386.
[59] T. Velempini, K. Pillay, X.Y. Mbianda, O.A. Arotiba, Carboxymethyl cellulose thiol-imprinted polymers: Synthesis, characterization and selective Hg(II) adsorption, J. Environ. Sci. (China) 79 (2019) 280-296.
[60] S.I. Moussa, M.M.S. Ali, R.R. Sheha, The performance of activated carbon/NiFe₂O₄ magnetic composite to retain heavy metal ions from aqueous solution, Chin. J. Chem. Eng. 29 (2021) 135-145.
[61] Y.A.B. Neolaka, Y. Lawa, J.N. Naat, A.A. Pau Riwu, H. Darmokoesoemo, G. Supriyanto, C.I. Holdsworth, A.N. Amenaghawon, H.S. Kusuma, A Cr(VI)-imprinted-poly(4-VP-co-EGDMA) sorbent prepared using precipitation polymerization and its application for selective adsorptive removal and solid phase extraction of Cr(VI) ions from electroplating industrial wastewater, React. Funct. Polym. 147 (2020) 104451.
[62] H. Hoshina, J.H. Chen, H. Amada, N. Seko, Chelating fabrics prepared by an organic solvent-free process for boron removal from water, Polymers 13 (7) (2021) 1163.
[63] X. Li, R. Liu, S. Wu, J. Liu, S. Cai, D. Chen, Efficient removal of boron acid by N-methyl-d-glucamine functionalized silica-polyallylamine composites and its adsorption mechanism, J. Colloid Interface Sci. 361 (1) (2011) 232-237.
[64] P. Fang, W. Xia, Y. Zhou, Z. Ai, W. Yin, M. Xia, J. Yu, R. Chi, Q. Yue, Ion-imprinted mesoporous silica/magnetic graphene oxide composites functionalized with Schiff-base for selective Cu(II) capture and simultaneously being transformed as a robust heterogeneous catalyst, Chem. Eng. J. 385 (2020) 123847.
[65] A.M. Al’Abri, S. Mohamad, S.N. Abdul Halim, N.K. Abu Bakar, Development of magnetic porous coordination polymer adsorbent for the removal and preconcentration of Pb(II) from environmental water samples, Environ. Sci. Pollut. Res. 26 (11) (2019) 11410-11426.
[66] G.Y. Abo El-Reesh, A.A. Farghali, M. Taha, R.K. Mahmoud, Novel synthesis of Ni/Fe layered double hydroxides using urea and glycerol and their enhanced adsorption behavior for Cr(VI) removal, Sci. Rep. 10 (1) (2020) 587.
[67] M. Li, J. Feng, K. Huang, S. Tang, R. Liu, H. Li, F. Ma, X. Meng, Amino group functionalized SiO₂@graphene oxide for efficient removal of Cu(II) from aqueous solutions, Chem. Eng. Res. Des. 145 (2019) 235-244.
[68] I.M. Kenawy, M.A. Ismail, M.A.H. Hafez, M.A. Hashem, Synthesis and characterization of novel ion-imprinted guanyl-modified cellulose for selective extraction of copper ions from geological and municipality sample, Int. J. Biol. Macromol. 115 (2018) 625-634.
[69] O.B. Nchoe, M.J. Klink, F.M. Mtunzi, V.E. Pakade, Synthesis, characterization, and application of β-cyclodextrin-based ion-imprinted polymer for selective sequestration of Cr(VI) ions from aqueous media: Kinetics and isotherm studies, J. Mol. Liq. 298 (2020) 111991.