Comparative study of the adsorption performance of NH2-functionalized metal organic frameworks with activated carbon composites for the treatment of phenolic wastewaters

doi:10.1016/j.cjche.2023.05.004

中国化学工程学报 ›› 2023, Vol. 63 ›› Issue (11): 130-139.DOI: 10.1016/j.cjche.2023.05.004

• Full Length Article • 上一篇下一篇

Comparative study of the adsorption performance of NH₂-functionalized metal organic frameworks with activated carbon composites for the treatment of phenolic wastewaters

Bolong Jiang^1,2, Shunjie Shi³, Yanyan Cui³, Jiayou Li³, Nan Jiang¹, Yanguang Chen²

1. Innovation Institute for Sustainable Maritime Architecture Research and Technology, Qingdao University of Technology, Qingdao 266000, China;
2. College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318, China;
3. Institute of Environmental and Municipal Engineering, Qingdao University of Technology, Qingdao 266000, China

收稿日期:2023-01-18 修回日期:2023-05-05 出版日期:2023-11-28 发布日期:2024-01-08
通讯作者: Bolong Jiang,E-mail:jiangbolong@qut.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China (22008134).

Comparative study of the adsorption performance of NH₂-functionalized metal organic frameworks with activated carbon composites for the treatment of phenolic wastewaters

Bolong Jiang^1,2, Shunjie Shi³, Yanyan Cui³, Jiayou Li³, Nan Jiang¹, Yanguang Chen²

1. Innovation Institute for Sustainable Maritime Architecture Research and Technology, Qingdao University of Technology, Qingdao 266000, China;
2. College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318, China;
3. Institute of Environmental and Municipal Engineering, Qingdao University of Technology, Qingdao 266000, China

Received:2023-01-18 Revised:2023-05-05 Online:2023-11-28 Published:2024-01-08
Contact: Bolong Jiang,E-mail:jiangbolong@qut.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (22008134).

摘要/Abstract

摘要： To better understand the role of the —NH₂ group in adsorption process of phenolic wastewaters, NH₂-functionalized MIL-53(Al) composites with activated carbon (NH₂-M(Al)@(B)AC) were prepared. The results showed that the NH₂ group could increase the mesopore volume for composites, which promotes mass transfer and full utilization of active sites, because hierarchical mesopore structure makes the adsorbent easier to enter the internal adsorption sites. Furthermore, the introduction of the NH₂ group can improve the adsorption capacity, decrease the activation energy, and enhance the interaction between the adsorbent and p-nitrophenol, demonstrating that the NH₂ group plays a crucial role in the adsorption of p-nitrophenol. The density functional theory calculation results show that the H-bond interaction between the —NH₂ group in the adsorbent and the NO₂ in the p-nitrophenol (adsorption energy of -35.5 kJ·mol^-1), and base-acid interaction between the primary —NH₂ group in the adsorbent and the acidic OH group in the p-nitrophenol (adsorption energy of -27.3 kJ·mol^-1) are predominant mechanisms for adsorption in terms of the NH₂-functionalized adsorbent. Both NH₂-functionalized M(Al)@AC and M(Al)@BAC composites exhibited higher p-nitrophenol adsorption capacity than corresponding nonfunctionalized composites. Among the composites, the NH₂-M(Al)@BAC had the highest p-nitrophenol adsorption capacity of 474 mg·g^-1.

关键词: NH₂-functionalized adsorbent, Phenolic wastewaters, Adsorption, Mechanism, Density functional theory

Abstract: To better understand the role of the —NH₂ group in adsorption process of phenolic wastewaters, NH₂-functionalized MIL-53(Al) composites with activated carbon (NH₂-M(Al)@(B)AC) were prepared. The results showed that the NH₂ group could increase the mesopore volume for composites, which promotes mass transfer and full utilization of active sites, because hierarchical mesopore structure makes the adsorbent easier to enter the internal adsorption sites. Furthermore, the introduction of the NH₂ group can improve the adsorption capacity, decrease the activation energy, and enhance the interaction between the adsorbent and p-nitrophenol, demonstrating that the NH₂ group plays a crucial role in the adsorption of p-nitrophenol. The density functional theory calculation results show that the H-bond interaction between the —NH₂ group in the adsorbent and the NO₂ in the p-nitrophenol (adsorption energy of -35.5 kJ·mol^-1), and base-acid interaction between the primary —NH₂ group in the adsorbent and the acidic OH group in the p-nitrophenol (adsorption energy of -27.3 kJ·mol^-1) are predominant mechanisms for adsorption in terms of the NH₂-functionalized adsorbent. Both NH₂-functionalized M(Al)@AC and M(Al)@BAC composites exhibited higher p-nitrophenol adsorption capacity than corresponding nonfunctionalized composites. Among the composites, the NH₂-M(Al)@BAC had the highest p-nitrophenol adsorption capacity of 474 mg·g^-1.

Key words: NH₂-functionalized adsorbent, Phenolic wastewaters, Adsorption, Mechanism, Density functional theory

Bolong Jiang, Shunjie Shi, Yanyan Cui, Jiayou Li, Nan Jiang, Yanguang Chen. Comparative study of the adsorption performance of NH₂-functionalized metal organic frameworks with activated carbon composites for the treatment of phenolic wastewaters[J]. 中国化学工程学报, 2023, 63(11): 130-139.

参考文献

[1] Qingjie, Wang, Design of solvent mixtures for removal of phenol from wastewater using a non-linear programming model with a multi-start method, Emerg. Contam. 8 (2022) 39–45.
[2] G. Busca, S. Berardinelli, C. Resini, L. Arrighi, Technologies for the removal of phenol from fluid streams: A short review of recent developments, J. Hazard. Mater. 160 (2–3) (2008) 265–288.
[3] D. Naidu, N. Panigrahi, J. Mishra, N. Sahoo, Assessing the potential of mesoporous MCM-41 nanoparticles for treatment of phenolic wastewater, Int. J. Nano Biomater. 7 (2) (2017) 124.
[4] N.J. Li, J. Jiang, D.Y. Chen, Q.F. Xu, H. Li, J.M. Lu, A reusable immobilization matrix for the biodegradation of phenol at 5000 mg/L, Sci. Rep. 5 (2015) 8628.
[5] Z.X. Wu, D.Y. Zhao, Ordered mesoporous materials as adsorbents, Chem. Commun. 47 (12) (2011) 3332–3338.
[6] Yun, Qu, Magnetic Fe₃O₄/ZIF-8 composite as an effective and recyclable adsorbent for phenol adsorption from wastewater, Sep. Purif. Technol. 294 (2022) 121169.
[7] X.D. Zhao, M.Q. Zheng, X.L. Gao, J. Zhang, E.B. Wang, Z.Q.Gao, The application of MOFs-based materials for antibacterials adsorption, Coord. Chem. Rev. 440 (2021) 213970.
[8] Sufang, Song, Isomerous Al-BDC-NH₂ metal-organic frameworks for metronidazole removal: Effect of topology structure, J. Solid State Chem. 314 (2022) 123376.
[9] B. Mudyawabikwa, H.H. Mungondori, L. Tichagwa, D.M. Katwire, Methylene blue removal using a low-cost activated carbon adsorbent from tobacco stems: Kinetic and equilibrium studies, Water Sci. Technol. 75 (10) (2017) 2390–2402.
[10] Edidiong, Asuquo, Martin, Adsorption of Cd(II) and Pb(II) ions from aqueous solutions using mesoporous activated carbon adsorbent: Equilibrium, kinetics and characterisation studies, J. Environ. Chem. Eng. 5 (1) (2017) 679–698.
[11] N.B. Azmi, M.J.K. Bashir, S. Sethupathi, C.A.Ng, Anaerobic stabilized landfill leachate treatment using chemically activated sugarcane bagasse activated carbon: Kinetic and equilibrium study, Desalination Water Treat. 57 (9) (2016) 3916–3927.
[12] X.D. Zhao, M.Q. Zheng, X.L. Gao, Z.Q. Gao, H.L. Huang, Construction of an anionic porous framework via a post-synthesis strategy to regulate the adsorption behavior of organic pollutants, J. Mater. Sci.55 (30) (2020) 14751–14760.
[13] N.A. Rashidi, S. Yusup, Potential of palm kernel shell as activated carbon precursors through single stage activation technique for carbon dioxide adsorption, J. Clean. Prod. 168 (2017) 474–486.
[14] K. Wilson, H. Yang, C.W. Seo, W.E.Marshall, Select metal adsorption by activated carbon made from peanut shells, Bioresour. Technol. 97 (18) (2006) 2266–2270.
[15] Q.Q. Miao, Y.M. Tang, J. Xu, X.P. Liu, L.R. Xiao, Q.H.Chen, Activated carbon prepared from soybean straw for phenol adsorption, J. Taiwan. Inst. Chem. Eng. 44 (3) (2013) 458–465.
[16] E.R. Abaide, G.L. Dotto, M.V. Tres, G.L. Zabot, M.A.Mazutti, Adsorption of 2-nitrophenol using rice straw and rice husks hydrolyzed by subcritical water, Bioresour. Technol. 284 (2019) 25–35.
[17] S. Wang, Y.R. Lee, H. Kim, Y. Won, S.E. Jeong, D.H. Lee, J.Y. Kim, S.H. Jo, H. Kim, Y.C. Park, H.Nam, Development of high-performance adsorbent using KOH-impregnated rice husk-based activated carbon for indoor CO₂ adsorption, Chem. Eng. J. 437(2022) 135378.
[18] Songlei, Lv, A functional activated carbon for efficient adsorption of phenol derived from pyrolysis of rice husk, KOH-activation and EDTA-4Na-modification, Appl. Surf. Sci. 510 (2020) 145425.
[19] E. Barea, C. Montoro, J.A.R. Navarro, Toxic gas removal-metal-organic frameworks for the capture and degradation of toxic gases and vapours, Chem. Soc. Rev. 43 (16) (2014) 5419–5430.
[20] Yu-Hang, Li, Seignette salt induced defects in Zr-MOFs for boosted Pb(Ⅱ) adsorption: Universal strategy and mechanism insight, Chem. Eng. J. 442 (2022) 136276.
[21] X. Ren, C. Wang, Y. Li, P. Wang, S. Gao, Defective SO₃H-MIL-101(Cr) for capturing different cationic metal ions: Performances and mechanisms. Journal of Hazardous Materials 445(2023) 130552.
[22] S.J. Shi, Y.Y. Cui, N. Jiang, B.L. Jiang, Fabrication of a metal-organic framework composite modified with biomass activated carbon (BAC) and functionalized with NH₂ for efficient p-nitrophenol adsorption, ChemistrySelect 7 (11) (2022) e202104008.
[23] D.D. Feng, D.W. Guo, Y. Zhang, S.Z. Sun, Y.J. Zhao, Q. Shang, H.L. Sun, J.Q. Wu, H.P.Tan, Functionalized construction of biochar with hierarchical pore structures and surface O-/N-containing groups for phenol adsorption, Chem. Eng. J. 410 (2021) 127707.
[24] J.M. Park, H.S. Jhung, A remarkable adsorbent for removal of bisphenol S from water: Aminated metal-organic framework, MIL-101-NH₂, Chem. Eng. J. 396 (2020) 125224.
[25] B.J. Liu, F. Yang, Y.X. Zou, Y.Peng, Adsorption of phenol and p-nitrophenol from aqueous solutions on metal-organic frameworks: Effect of hydrogen bonding, J. Chem. Eng. Data 59 (5) (2014) 1476–1482.
[26] M. Reda, Abdelhameed, Cu-BTC metal-organic framework natural fabric composites for fuel purification, Fuel Process. Technol. 159 (2017) 306–312.
[27] L.H. Qi, H.L. Jiang, T.N. Lin, X.Y. Chang, B.L. Jiang, Fabrication of MIL-53(Al) based composites from biomass activated carbon (AC) for efficient p-nitrophenol adsorption from aqueous solution, J. Taiwan. Inst. Chem. Eng. 127 (2021) 220–227.
[28] B. Seoane, C. Téllez, J. Coronas, C. Staudt, NH₂-MIL-53(Al) and NH₂-MIL-101(Al) in sulfur-containing copolyimide mixed matrix membranes for gas separation, Sep. Purif. Technol. 111 (2013) 72–81.
[29] M. Al Sharabati, R.Sabouni, Selective removal of dual dyes from aqueous solutions using a metal organic framework (MIL-53(Al)), Polyhedron 190 (2020) 114762.
[30] A.M. Aldawsari, I.H. Alsohaimi, H.M.A. Hassan, M.R. Berber, Z.E.A. Abdalla, I. Hassan, E.A.M. Saleh, B.H.Hameed, Activated carbon/MOFs composite: AC/NH₂-MIL-101(Cr), synthesis and application in high performance adsorption of p-nitrophenol, J. Saudi Chem. Soc. 24 (9) (2020) 693–703.
[31] X.P. Quan, Z.Q. Sun, J.L. Xu, S.Y. Liu, Y.D. Han, Y. Xu, H. Meng, J.B. Wu, X.Zhang, Construction of an aminated MIL-53(Al)-functionalized carbon nanotube for the efficient removal of bisphenol AF and metribuzin, Inorg. Chem. 59 (5) (2020) 2667–2679.
[32] L.L. Liu, X.S. Tai, N.N. Zhang, Q.G. Meng, C.L. Xin, Supported Au/MIL-53(Al): A reusable green solid catalyst for the three-component coupling reaction of aldehyde, alkyne, and amine, Reac Kinet Mech Cat 119 (1) (2016) 335–348.
[33] Y.M. Zhang, Z.Q. Ma, Q.S. Zhang, J.Y. Wang, Q.Q. Ma, Y.Y. Yang, X.P. Luo, W.G.Zhang, Comparison of the physicochemical characteristics of bio-char pyrolyzed from moso bamboo and rice husk with different pyrolysis temperatures, BioResources 12 (3) (2017): 4652–4669.
[34] W.P. Xiong, Z.T. Zeng, X. Li, G.M. Zeng, R. Xiao, Z.H. Yang, Y.Y. Zhou, C. Zhang, M. Cheng, L. Hu, C.Y. Zhou, L. Qin, R. Xu, Y.R.Zhang, Multi-walled carbon nanotube/amino-functionalized MIL-53(Fe) composites: Remarkable adsorptive removal of antibiotics from aqueous solutions, Chemosphere 210 (2018) 1061–1069.
[35] B.L. Jiang, T.H. Zhu, N. Jiang, M.Y. Gong, G. Yang, F. Li, H. Song, T.Z.Hao, Ultra-deep adsorptive removal over hierarchically structured AgCeY zeolite from model gasoline with high competitor content, J. Clean. Prod. 297 (2021) 126582.
[36] T. Boontongto, R. Burakham, Evaluation of metal-organic framework NH₂-MIL-101(Fe) as an efficient sorbent for dispersive micro-solid phase extraction of phenolic pollutants in environmental water samples, Heliyon 5 (11) (2019) e02848.
[37] M.P. Li, Y.Y. Wang, Y.X. Liu, H. Wang, H. Song, Preparation of active carbon through one-step NaOH activation of coconut shell biomass for phenolic wastewater treatment, Res Chem Intermed 48 (4) (2022) 1665–1684.
[38] W.M. Zhang, Z.W. Xu, B.C. Pan, Q.J. Zhang, W. Du, Q.R. Zhang, K. Zheng, Q.X. Zhang, J.L.Chen, Adsorption enhancement of laterally interacting phenol/aniline mixtures onto nonpolar adsorbents, Chemosphere 66 (11) (2007) 2044–2049.
[39] Y.L. Xiao, T.T. Han, G. Xiao, Y.P. Ying, H.L. Huang, Q.Y. Yang, D.H. Liu, C.L.Zhong, Highly selective adsorption and separation of aniline/phenol from aqueous solutions by microporous MIL-53(Al): A combined experimental and computational study, Langmuir 30 (41) (2014) 12229–12235.

Comparative study of the adsorption performance of NH₂-functionalized metal organic frameworks with activated carbon composites for the treatment of phenolic wastewaters

Comparative study of the adsorption performance of NH₂-functionalized metal organic frameworks with activated carbon composites for the treatment of phenolic wastewaters

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