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A flame-retardant post-synthetically functionalized COF sponge as absorbent for spilled oil recovery

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Abstract

Frequent oil spills pose severe damages to the marine ecosystems and result in hazardous fires when the spilled oil is ignited. Developing high-performance, flame-retardant absorbent materials for large-scale water treatment is therefore urgently needed. Herein, we report an efficient post-synthetic silylation process to achieve a porous covalent-organic framework (COF), denoted as [CF3] − COF. The absorption capacity of oils and organic solvents in [CF3] − COF was explored by experimental measurements with the absorption mechanism illuminated by molecular simulations. The prepared [CF3] − COF powders were further loaded into melamine sponge to yield a highly hydrophobic absorbent denoted as [CF3] − COF@sponge, which was demonstrated to effectively remove oils/organic solvents with outstanding stability and excellent flame retardancy. Moreover, an oil-collecting apparatus was designed to continuously separate oils/organic solvents from water. The rapid recovery of oils/organic solvents from water using this device proves the great promise of [CF3] − COF@sponge in water treatment.

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References

  1. Diao S, Liu H, Chen S, Xu WL, Yu AR (2020) Oil adsorption performance of graphene aerogels. J Mater Sci 55:4578–4591. https://doi.org/10.1007/s10853-019-04292-z

    Article  CAS  Google Scholar 

  2. Maaz M, Elzein T, Dragoe D, Bejjani A, Jarroux N, Poulard C, Aubry-Barroca N, Nsouli B, Roger P (2019) Poly(4-vinylpyridine)-modified silica for efficient oil/water separation. J Mater Sci 54:1184–1196. https://doi.org/10.1007/s10853-018-2888-x

    Article  CAS  Google Scholar 

  3. Gu JC, Xiao P, Huang YJ, Zhang JW, Chen T (2015) Controlled functionalization of carbon nanotubes as superhydrophobic material for adjustable oil/water separation. J Mater Chem A 3:4124–4128

    Article  CAS  Google Scholar 

  4. Xue ZX, Cao YZ, Liu N, Feng L, Jiang L (2014) Special wettable materials for oil/water separation. J Mater Chem A 2:2445–2460

    Article  CAS  Google Scholar 

  5. Chen XM, Chen GH, Yue PL (2000) Separation of pollutants from restaurant wastewater by electrocoagulation. Sep Purif Technol 19:65–76

    Article  CAS  Google Scholar 

  6. Zhang L, Li HQ, Lai XJ, Su XJ, Liang T, Zeng XG (2017) Thiolated graphene-based superhydrophobic sponges for oil-water separation. Chem Eng J 316:736–743

    Article  CAS  Google Scholar 

  7. Zhang JP, Seeger S (2011) Polyester materials with superwetting silicone nanofilaments for oil/water separation and selective oil absorption. Adv Funct Mater 21:4699–4704

    Article  CAS  Google Scholar 

  8. Hayase G, Kanamori K, Fukuchi M, Kaji H, Nakanishi K (2013) Facile synthesis of marshmallow-like macroporous gels usable under harsh conditions for the separation of oil and water. Angew Chem Int Ed 52:1986–1989

    Article  CAS  Google Scholar 

  9. Yue XJ, Zhang T, Yang DY, Qiu FX, Rong J, Xu JC, Fang JS (2017) The synthesis of hierarchical porous Al2O3/acrylic resin composites as durable, efficient and recyclable absorbents for oil/water separation. Chem Eng J 309:522–531

    Article  CAS  Google Scholar 

  10. Mu XW, Zhou X, Wang W, Xiao YL, Liao C, Han LF, Kan YC, Song L (2021) Design of compressible flame retardant grafted porous organic polymer based separator with high fre safety and good electrochemical properties. Chem Eng J 405:126946

    Article  CAS  Google Scholar 

  11. Mu XW, Cai W, Xiao YL, He LX, Zhou X, Wang HJ, Guo WW, Xing WY, Song L (2020) A novel strategy to prepare COFs based BN co-doped carbon nanosheet for enhancing mechanical performance and fire safety to PVA nanocomposite. Compos Part B-Eng 198:108218

    Article  CAS  Google Scholar 

  12. Wang B, Liang WX, Guo ZG, Liu WM (2015) Biomimetic super-lyophobic and super-lyophilic materials applied for oil/water separation: a new strategy beyond nature. Chem Soc Rev 44:336–361

    Article  Google Scholar 

  13. Fernandes SPS, Romero V, EspiÇa B, Salonen LM (2019) Tailoring covalent organic frameworks to capture water contaminants. Chem Eur J 25:6461–6473

    Article  CAS  Google Scholar 

  14. Liu FY, Nie CY, Dong QQ, Ma ZY, Liu W, Tong MP (2020) AgI modified covalent organic frameworks for effective bacterial disinfection and organic pollutant degradation under visible light irradiation. J Haz Mat 398:122865

    Article  CAS  Google Scholar 

  15. Ruan CP, Ai KL, Li XB, Lu LH (2014) A superhydrophobic sponge with excellent absorbency and flame retardancy. Angew Chem Int Ed 53:5556–5560

    Article  CAS  Google Scholar 

  16. Qi MH, Gao ML, Liu L, Han ZB (2018) Robust bifunctional core-shell MOF@ POP catalyst for one-pot tandem reaction. Inorg Chem 57:14467–14470

    Article  CAS  Google Scholar 

  17. Ding SY, Dong M, Wang YW, Chen YT, Wang HZ, Su CY, Wang W (2016) Thioether-based fluorescent covalent organic framework for selective detection and facile removal of mercury (II). J Am Chem Soc 138:3031–3037

    Article  CAS  Google Scholar 

  18. Sun Q, Aguila B, Perman JD, Earl L, Abney CW, Cheng YC, Wei H, Nguyen N, Wojtas L, Ma SQ (2017) Postsynthetically modified covalent organic frameworks for efficient and effective mercury removal. J Am Chem Soc 139:2786–2793

    Article  CAS  Google Scholar 

  19. Li Y, Yang CX, Yan XP (2017) Controllable preparation of core–shell magnetic covalent-organic framework nanospheres for efficient adsorption and removal of bisphenols in aqueous solution. Chem Commun 53:2511–2514

    Article  CAS  Google Scholar 

  20. Lin G, Gao CH, Zheng Q, Lei ZX, Geng HJ, Lin Z, Yang HH, Cai ZW (2017) Room-temperature synthesis of core–shell structured magnetic covalent organic frameworks for efficient enrichment of peptides and simultaneous exclusion of proteins. Chem Commun 53:3649–3652

    Article  CAS  Google Scholar 

  21. Ding SY, Wang W (2013) Covalent organic frameworks (COFs): from design to applications. Chem Soc Rev 42:548–568

    Article  CAS  Google Scholar 

  22. Segura J, Royuela S, Ramos M (2019) Post-synthetic modification of covalent organic frameworks. Chem Soc Rev 48:3903–3945

    Article  CAS  Google Scholar 

  23. Feng X, Ding XS, Jiang DL (2012) Covalent organic frameworks. Chem Soc Rev 41:6010–6022

    Article  CAS  Google Scholar 

  24. Pagliaro M, Ciriminna R (2005) New fluorinated functional materials. J Mater Chem 15:4981–4991

    Article  CAS  Google Scholar 

  25. Han N, Zhang ZX, Gao HK, Qian YQ, Tan LL, Yang C, Zhang HR, Cui ZY, Li W, Zhang XX (2019) Superhydrophobic covalent organic frameworks prepared via pore-surface modifications for functional coatings under harsh conditions. ACS Appl Mater Interfaces 12:2926–2934

    Article  Google Scholar 

  26. Sun Q, Aguila BA, Perman J, Butts T, Xiao FS, Ma SQ (2018) Integrating superwettability within covalent organic frameworks for functional coating. Chem 4:1726–1739

    Article  CAS  Google Scholar 

  27. Jiang YZ, Liu CY, Li YH, Huang AS (2019) Stainless-steel-net-supported superhydrophobic COF coating for oil/water separation. J Membr Sci 587:117177

    Article  CAS  Google Scholar 

  28. Zhu HG, Yang S, Chen DY, Li NJ, Xu QF, Li H, He JH, Lu JM (2016) A robust absorbent material based on light-responsive superhydrophobic melamine sponge for oil recovery. Adv Mater Interfaces 3:1500683

    Article  Google Scholar 

  29. Matsumoto MR, Dasari R, Ji W, Feriante CH, Parker TCR, Marder SR, Dichtel W (2017) Rapid, low temperature formation of imine-linked covalent organic frameworks catalyzed by metal triflates. J Am Chem Soc 139:4999–5002

    Article  CAS  Google Scholar 

  30. Chen R, Shi J, Ma Y, Lin GQ, Lang XJ, Wang C (2019) Designed synthesis of a 2D Porphyrin-Based sp2 carbon-conjugated covalent organic framework for heterogeneous photocatalysis. Angew Chem Int Ed 58:6430–6434

    Article  CAS  Google Scholar 

  31. Frenkel D, Smit B (2002) Understanding molecular simulation: From algorithms to applications. Academic Press, New York 1:1–638

    Google Scholar 

  32. Wang YG, Zhu YM, Yang C, Liu JH, Jiang W, Liang B (2018) Facile two-step strategy for the construction of a mechanically stable three-dimensional superhydrophobic structure for continuous oil-water separation. ACS Appl Mater Interfaces 10:24149–24156

    Article  CAS  Google Scholar 

  33. Liu SH, Xu QF, Latthe SB, Gurav A, Xing RM (2015) Superhydrophobic/superoleophilic magnetic polyurethane sponge for oil/water separation. Rsc Adv 5:68293–68298

    Article  CAS  Google Scholar 

  34. Jiang ZR, Ge J, Zhou YX, Wang ZYU, Chen DX, Yu SH, Jiang HL (2016) Coating sponge with a hydrophobic porous coordination polymer containing a low-energy CF3-decorated surface for continuous pumping recovery of an oil spill from water. NPG Asia Mater 8:e253

    Article  CAS  Google Scholar 

  35. Wu L, Li LX, Li BC, Zhang JP, Wang AQ (2015) Magnetic, durable, and superhydrophobic polyurethane@Fe3O4@SiO2@fluoropolymer sponges for selective oil absorption and oil/water separation. ACS Appl Mater Interfaces 7:4936–4946

    Article  CAS  Google Scholar 

  36. Karatum O, A. Steiner S, S. Griffin J, Shi W, L. Plata D, (2015) Flexible, mechanically durable aerogel composites for oil capture and recovery. ACS Appl Mater Interfaces 8:215–224

    Article  Google Scholar 

  37. Zhang Z, Sèbe G, Rentsch D, Zimmermann T, Tingaut P (2014) Ultralightweight and flexible silylated nanocellulose sponges for the selective removal of oil from water. Chem Mater 26:2659–2668

    Article  CAS  Google Scholar 

  38. Gui XC, Wei JQ, Wang KL, Cao AY, Zhu HW, Jia Y, Shu QK, Wu DH (2010) Carbon nanotube sponges. Adv Mater 22:617–621

    Article  CAS  Google Scholar 

  39. Moore S (1998) Silicone flame retardant boosts properties of polycarbonate. Mod Plast 75:35–36

    Google Scholar 

  40. Ohio Supercomputer Center (1987) Ohio Supercomputer Center. Columbus OH: Ohio Supercomputer Center. http://osc.edu/ark:/19495/f5s1ph73

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Acknowledgements

This work was supported by National Natural Science Foundation of China (51874331 and 51974345), Shandong Provincial Natural Science Foundation, China (ZR2017MEE028 and ZR2019MEM054), and The Fundamental Research Funds for the Central Universities (19CX05001A and 20CX06041A). The authors also thank the Ohio Supercomputer Center (OSC) for computational resources [40].

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Authors and Affiliations

  1. School of Materials Science and Engineering, China University of Petroleum (East China), Qingdao, 266580, Shandong, China

    Yanyan Liu, Qiang Lyu, Zhikun Wang, Yi Sun, Chunling Li, Shuangqing Sun & Songqing Hu

  2. William G. Lowrie Department of Chemical and Biomolecular Engineering, The Ohio State University, Columbus, OH, 43210, USA

    Qiang Lyu & Li-Chiang Lin

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  1. Yanyan Liu
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  2. Qiang Lyu
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Correspondence to Shuangqing Sun, Li-Chiang Lin or Songqing Hu.

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Liu, Y., Lyu, Q., Wang, Z. et al. A flame-retardant post-synthetically functionalized COF sponge as absorbent for spilled oil recovery. J Mater Sci 56, 13031–13042 (2021). https://doi.org/10.1007/s10853-021-06006-w

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