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Journal of Polymer Research
Published in:

01-02-2025 | Original Paper

Preparation of hyper-crosslinked polymers containing pyrene for adsorption of 1-naphthylamine and 1-naphthol

Authors: Liang Zhang, Xiaomeng Hu, Feng Zhang, Qiuxuan Zhou, Shiyuan Zhou, Peiyang Gu

Published in: Journal of Polymer Research | Issue 2/2025

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Abstract

The study focuses on the synthesis of hyper-crosslinked polymers (HCPs) containing pyrene through Friedel–Crafts reactions. These polymers, named CaHe-2, show exceptional adsorption capacities for aromatic pollutants such as 1-naphthylamine and 1-naphthol, with remarkable removal efficiencies of 93.8% and 90.6% within 20 minutes, respectively. The polymers exhibit a high surface area and mesoporous structure, enhancing their adsorption performance through π–π interactions. The study also includes detailed characterization of the polymers, adsorption kinetics, isotherms, and thermodynamics, as well as regeneration experiments demonstrating the polymers' stability and recyclability. This work proposes a novel method for preparing highly effective adsorbents for aromatic pollutants, making it a significant contribution to the field of water treatment and environmental remediation.
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Literature
1.
Watharkar AD, Kadam SK, Khandare RV, Kolekar PD, Jeon BH, Jadhav JP, Govindwar SP (2018) Asparagus densiflorus in a vertical subsurface flow phytoreactor for treatment of real textile effluent: a lab to land approach for in situ soil remediation. Ecotox Environ Safe 161, 70–77.
2.
Shen X, Faheem M, Matsuo Y, Aziz S, Zhang X, Li Y, Song J, Tian Y, Zhu G (2019) Polarity engineering of porous aromatic frameworks for specific water contaminant capture. J Mater Chem A 7:2507–2512
3.
Alsbaiee A, Smith BJ, Xiao L, Ling Y, Helbling DE, Dichtel WR (2015) Rapid removal of organic micropollutants from water by a porous β-cyclodextrin polymer. Nature 529:190–194PubMed
4.
Mahmoud SA, Atia BM, Amin LG, Abdalla M (2025) Innovative preparation of multi-dentate Schiff base adsorbent for the adsorption of silver and its application on nano silver particles preparation from liquid photographic wastes. J Chem Technol Biotechnol 100:448–465
5.
Gado MA (2024) Efficient adsorption of thorium and cerium from Rosetta monazite concentrate using a novel phosphorylated Schiff-base adsorbent. J Radioanal Nucl Chem 333:5025–5048
6.
Abdalla M (2024) Adsorption of vanadium using a new anionic Schiff Base adsorbent and its application to vanadium separation from boiler ash. J Chem Technol Biotechnol 99:2434–2453
7.
8.
Zhao G, Jiang L, He Y, Li J, Dong H, Wang X, Hu W (2011) Sulfonated Graphene for Persistent Aromatic Pollutant Management. Adv Mater 23:3959–3963PubMed
9.
Yang K, Wu W, Jing Q, Zhu L (2008) Aqueous adsorption of aniline, phenol, and their substitutes by multi-walled carbon nanotubes. Environ Sci Technol Lett 42:7931–7936
10.
11.
Tan L, Tan B (2017) Hypercrosslinked porous polymer materials: design, synthesis, and applications. Chem Soc Rev 46:3322–3356PubMed
12.
Waheed A, Baig N, Ullah N, Falath W (2021) Removal of hazardous dyes, toxic metal ions and organic pollutants from wastewater by using porous hyper-cross-linked polymeric materials: A review of recent advances. J Environ Manage 287:112360PubMed
13.
Li C, Che W, Liu SY, Liao G (2023) Hypercrosslinked microporous polystyrene: from synthesis to properties to applications. Mater Today Chem 29, 101392
14.
Gan Y, Chen G, Sang Y, Zhou F, Man R, Huang J (2019) Oxygen-rich hyper-cross-linked polymers with hierarchical porosity for aniline adsorption. Chem Eng J 368:29–36
15.
Wang X, Mao X, Huang J (2018) Hierarchical porous hyper-cross-linked polymers modified with phenolic hydroxyl groups and their efficient adsorption of aniline from aqueous solution. Colloid. Surfaces A 558:80–87
16.
Yuan X, Li X, Zhu E, Hu J, Sheng W, Cao C (2008) A novel hypercrosslinked polymeric adsorbent modified by phenolic hydroxyl group of 2-naphthol with bromoethane as crosslinking reagent. Carbohyd Polyme 74:468–473
17.
Xu Z, Rong M, Meng Q, Yao H, Ni S, Wang L, Xing H, Qu H, Yang L, Liu H (2020) Fabrication of hypercrosslinked hydroxyl-rich solid phase extractants for cesium separation from the salt lake brine. Chem Eng J 400:125991
18.
Zhang D, Chen Y, Wang J, Wang Y, Cao Y, Li J, Zhou F, Huang J, Liu YN (2023) Melamine-functionalization of the carbonyl-rich polymers for iodine vapor and Hg2+ capture. Chem Eng J 460, 141669
19.
Xie G, Lin X, Martinez MR, Wang Z, Lou H, Fu R, Wu D, Matyjaszewski K (2018) Fabrication of Porous Functional Nanonetwork-Structured Polymers with Enhanced Adsorption Performance from Well-Defined Molecular Brush Building Blocks. Chem Mater 30:8624–8629
20.
Wolska J, Frankowski M, Jenczyk J, Wolski L (2024) Highly sulfonated hyper-cross-linked polymers as promising adsorbents for efficient and selective removal of ciprofloxacin from water. Sep Purifi Technol 343:127147
21.
Zhang Y, Wu Y, Fu Y, Qx Jia, Zhang Z (2024) Sulfonated hypercross-linked porous organic polymer based humidity sensor. Sensors. Actuat B: Chem 401:134997
22.
Zeng X, Huang J (2020) Anisole-modified hyper-cross-linked resins for efficient adsorption of aniline from aqueous solution. J Colloid Interf Sci 569:177–183
23.
Bayraç C and Camızcı G  (2019) Adsorptive removal of patulin from apple juice via sulfhydryl-terminated magnetic bead-based separation. J Hazard Mater 366, 413–422.
24.
Wang Y, Cao Y, Zong J, Shu Z, Xiao Q, Wang X, Zhou F, Huang J (2022) Acetamido-functionalized hyper-crosslinked polymers for efficient removal of phenol in aqueous solution. Sep Purifi Technol 287:120566
25.
Cao Y, Wang Y, Zhou F, Huang J, Xu M (2022) Acylamino-functionalized hyper-cross-linked polymers for efficient adsorption removal of phenol in aqueous solution. Sep Purifi Technol 303:122229
26.
Wang X, Wang Y, Shu Z, Cao Y, Wang X, Zhou F, Huang J (2023) Phenolic hydroxyl-functionalized hyper-cross-linked polymers for efficient adsorptive removal of aniline. Sep Purifi Technol. 305:122443
27.
Huang J, Wang X, Wang X, Huang K (2011) Hyper-cross-linked Polystyrene-co-divinylbenzene Resin Modified with Acetanilide: Synthesis, Structure and Adsorptive Removal of Salicylic Acid from Aqueous Solution. Ind Eng Chem Re. 50:2891–2897
28.
Cai Y, Wen X, Wang Y, Song H, Li Z, Cui Y, Li C (2021) Preparation of hyper-crosslinked polymers with hierarchical porous structure from hyperbranched polymers for adsorption of naphthalene and 1-naphthylamine. Sep Purifi Technol 266:118542
29.
Zhang W, Xu Z, Pan B, Zhang Q, Zhang Q, Du W, Pan B, Zhang Q (2007) Cooperative effect of lateral acid–base interaction on 1-naphthol/1-naphthylamine binary adsorption onto nonpolar polymer adsorbents. Sep Purifi Technol 55:141–146
30.
Zhang W, Hong C, Pan B, Xu Z, Zhang Q, Lv L (2008) Removal enhancement of 1-naphthol and 1-naphthylamine in single and binary aqueous phase by acid–basic interactions with polymer adsorbents. J Hazard Mater 158:293–299PubMed
31.
Yang X, Li J, Wen T, Ren X, Huang Y, Wang X (2013) Adsorption of naphthalene and its derivatives on magnetic graphene composites and the mechanism investigation. Colloid Surface A 422:118–125
32.
Ahn JH, Jang JE, Oh CG, Ihm SK, Cortez J, Sherrington DC (2006) Rapid Generation and Control of Microporosity, Bimodal Pore Size Distribution, and Surface Area in Davankov-Type Hyper-Cross-Linked Resins. Macromolecules 36:627–632
33.
Wang J, Zhang P, Liu L, Zhang Y, Yang J, Zeng Z, Deng S (2018) Controllable synthesis of bifunctional porous carbon for efficient gas-mixture separation and high-performance supercapacitor. Chem Eng J 348:57–66
34.
Fenton JL, Burke DW, Qian D, Olvera de la Cruz M, Dichtel WR (2021) Polycrystalline Covalent Organic Framework Films Act as Adsorbents, Not Membranes. J Am Chem Soc 143:1466–1473PubMed
35.
Guo YZ, Gao F, Wang Z, Liu YA, Hu WB, Yang H, Wen K (2021) Highly Branched Pillar[5]arene-Derived Porous Aromatic Frameworks (PAFs) for Removal of Organic Pollutants from Water. ACS Appl Mater Interfaces 13:16507–16515PubMed
36.
Hu X, Xu G, Zhang H, Li M, Tu Y, Xie X, Zhu Y, Jiang L, Zhu X, Ji X, Li Y, Li A (2020) Multifunctional β-Cyclodextrin Polymer for Simultaneous Removal of Natural Organic Matter and Organic Micropollutants and Detrimental Microorganisms from Water. ACS Appl Mater Interfaces 12:12165–12175PubMed
37.
Rizzi V, Gubitosa J, Signorile R, Fini P, Cecone C, Matencio A, Trotta V, Cosma P (2021) Cyclodextrin nanosponges as adsorbent material to remove hazardous pollutants from water: The case of ciprofloxacin. Chem Eng J 411:128514
38.
Liu Y, Fan X, Jia X, Zhang B, Zhang H, Zhang A, Zhang Q (2016) Hypercrosslinked polymers: controlled preparation and effective adsorption of aniline. J Mater Sci 51:8579–8592
39.
Zhou Q, Wang Y, Xiao J, Fan H (2016) Adsorption and removal of bisphenol A, α-naphthol and β-naphthol from aqueous solution by Fe3O4@polyaniline core–shell nanomaterials. Synthetic Met 212, 113–122.
40.
Chen B, Chen Z (2009) Sorption of naphthalene and 1-naphthol by biochars of orange peels with different pyrolytic temperatures. Chemosphere 76:127–133PubMed
41.
Sheng GD, Shao DD, Ren XM, Wang XQ, Li JX, Chen YX, Wang XK (2010) Kinetics and thermodynamics of adsorption of ionizable aromatic compounds from aqueous solutions by as-prepared and oxidized multiwalled carbon nanotubes. J Hazard Mater 178:505–516PubMed
42.
Yang Z, Zhang Y, Wang X, Tian Z, Yang W, Graham NJD (2020) Efficient adsorption of four phenolic compounds using a robust nanocomposite fabricated by confining 2D porous organic polymers in 3D anion exchangers. Chem Eng J 396:125296
43.
Peng H, Minic A, Banjerdteerakul K, Li K (2023) COF-300/PVDF adsorbents with aligned microchannels for fast removal of polycyclic aromatic hydrocarbons (PAHs). Chem Eng J 465:142901
44.
Liang L, Chen J, Chen X, Wang J, Qiu H (2022) In situ synthesis of a GO/COFs composite with enhanced adsorption performance for organic pollutants in water. Environ Sci-Nano 9:554–567
45.
Wang F, Haftka JJH, Sinnige TL, Hermens JLM, Chen W (2014) Adsorption of polar, nonpolar, and substituted aromatics to colloidal graphene oxide nanoparticles. Environ Pollut 186:226–233PubMed
46.
Zhao D, Zhao L, Zhu CS, Shen X, Zhang X, Sha B (2009) Comparative study of polymer containing β-cyclodextrin and –COOH for adsorption toward aniline, 1-naphthylamine and methylene blue. J Hazard Mater 171:241–246PubMed
47.
Wang J, Chen B (2015) Adsorption and coadsorption of organic pollutants and a heavy metal by graphene oxide and reduced graphene materials. Chem Eng J 281:379–388
48.
Zuo L, Yu S, Cheng L, Du E (2013) Adsorption of phenol and 1-naphthol onto XC-72 carbon. Korean J Chem Eng 30:714–723
49.
Anbia M, Moradi SE (2012) The examination of surface chemistry and porosity of carbon nanostructured adsorbents for 1-naphthol removal from petrochemical wastewater streams. Korean J Chem Eng 29:743–749
50.
Wang X, Chen C, Li J, Wang X (2015) Ozone degradation of 1-naphthol on multiwalled carbon nanotubes/iron oxides and recycling of the adsorbent. Chem Eng J 262:1303–1310
51.
52.
Xu W, Liu X, Cai J, Xue T, Tang K (2021) Synthesis of reusable cyclodextrin polymers for removal of naphthol and naphthylamine from water. Environ Sci Pollut R 29:22106–22121
53.
Kuang W, Liu YN, Huang J (2017) Phenol-modified hyper-cross-linked resins with almost all micro/mesopores and their adsorption to aniline. J Colloid Interf Sci 487:31–37
54.
Li G, Fang H, Jiang D, Zheng G (2018) Porous organic polymers based on melamine and 5,5′-bis(bromomethyl)-2,2′-bipyridine: functionalization with lanthanide ions for chemical sensing and highly efficient adsorption of methyl orange. New J Chem 42:19734–19739
Metadata
Title
Preparation of hyper-crosslinked polymers containing pyrene for adsorption of 1-naphthylamine and 1-naphthol
Authors
Liang Zhang
Xiaomeng Hu
Feng Zhang
Qiuxuan Zhou
Shiyuan Zhou
Peiyang Gu
Publication date
01-02-2025
Publisher
Springer Netherlands
Published in
Journal of Polymer Research / Issue 2/2025
Print ISSN: 1022-9760
Electronic ISSN: 1572-8935
DOI
https://doi.org/10.1007/s10965-025-04287-2

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