Tannic acid/Fe3+ interlayer for preparation of high-permeability polyetherimide organic solvent nanofiltration membranes for organic solvent separation

doi:10.1016/j.cjche.2022.09.014

Abstract

Abstract: Organic solvent nanofiltration (OSN) membranes have a great application prospect in organic solvent separation, but the development of OSN membranes is mainly restricted by trade-off between permeability and rejection rate. In this work, a TA/Fe³⁺ polymer was introduced into polyetherimide (PEI) ultrafiltration membranes crosslinked with hexamethylene diamine as the intermediate layer, and OSN membranes with high separation performance and solvent permeability were obtained through interfacial polymerization and solvent activation. The interlayer with high surface hydrophilicity and a fixed pore structure controlled the adsorption/diffusion of the amine monomer during interfacial polymerization, forming a smooth (average surface roughness < 5.5 nm), ultra-thin (separation layer thickness reduced from 150 to 16 nm) and dense surface structure polyamide (PA) layer. The PA--HDA/PEI membrane retained more than 94% of methyl blue (BS) in 0.1 g·L^-1 BS ethanol solution at 0.6 MPa, and the ethanol permeation reached 28.56 L^-1·m^-2·h^-1. The average flux recovery ratio (FRR) of PA--HDA/PEI membrane was found to be 84%, which has better fouling resistance than PA-HDA/PEI membrane, and it was found to have better stability performance through different solvent immersion experiments and continuous operation in 0.1 g·L^-1 BS ethanol solution. Compared with thin-film composite nanofiltration membranes, the PA--HDA/PEI membrane can be manufactured from an economical and environment-friendly method and overcomes the trade-off between permeability and rejection rate, showing great application potential in organic solvent separation systems.

Key words: Nanofiltration membrane, Waste treatment, Surface, Filtration, Tannic acid, Interfacial polymerization

摘要： Organic solvent nanofiltration (OSN) membranes have a great application prospect in organic solvent separation, but the development of OSN membranes is mainly restricted by trade-off between permeability and rejection rate. In this work, a TA/Fe³⁺ polymer was introduced into polyetherimide (PEI) ultrafiltration membranes crosslinked with hexamethylene diamine as the intermediate layer, and OSN membranes with high separation performance and solvent permeability were obtained through interfacial polymerization and solvent activation. The interlayer with high surface hydrophilicity and a fixed pore structure controlled the adsorption/diffusion of the amine monomer during interfacial polymerization, forming a smooth (average surface roughness < 5.5 nm), ultra-thin (separation layer thickness reduced from 150 to 16 nm) and dense surface structure polyamide (PA) layer. The PA--HDA/PEI membrane retained more than 94% of methyl blue (BS) in 0.1 g·L^-1 BS ethanol solution at 0.6 MPa, and the ethanol permeation reached 28.56 L^-1·m^-2·h^-1. The average flux recovery ratio (FRR) of PA--HDA/PEI membrane was found to be 84%, which has better fouling resistance than PA-HDA/PEI membrane, and it was found to have better stability performance through different solvent immersion experiments and continuous operation in 0.1 g·L^-1 BS ethanol solution. Compared with thin-film composite nanofiltration membranes, the PA--HDA/PEI membrane can be manufactured from an economical and environment-friendly method and overcomes the trade-off between permeability and rejection rate, showing great application potential in organic solvent separation systems.

关键词: Nanofiltration membrane, Waste treatment, Surface, Filtration, Tannic acid, Interfacial polymerization

Haike Li, Xindong Li, Guozai Ouyang, Lang Li, Zhaohuang Zhong, Meng Cai, Wenhao Li, Wanfu Huang. Tannic acid/Fe³⁺ interlayer for preparation of high-permeability polyetherimide organic solvent nanofiltration membranes for organic solvent separation[J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 17-29.

References

[1] M. Paul, S.D. Jons, Chemistry and fabrication of polymeric nanofiltration membranes: A review, Polymer 103 (2016) 417–456.
[2] A.W. Mohammad, Y.H. Teow, W.L. Ang, Y.T. Chung, D.L. Oatley-Radcliffe, N. Hilal, Nanofiltration membranes review: Recent advances and future prospects, Desalination 356 (2015) 226–254.
[3] A. Koris, G. Vatai, Dry degumming of vegetable oils by membrane filtration, Desalination 148 (1–3) (2002) 149–153.
[4] J. Dreimann, F. Hoffmann, M. Skiborowski, A. Behr, A. Vorholt, Merging thermomorphic solvent systems and organic solvent nanofiltration for hybrid catalyst recovery in a hydroformylation process, Ind. \& Eng. Chem. Res. 56 (2017) 1354–1359.
[5] G. Abdi, A. Alizadeh, S. Zinadini, G. Moradi, Removal of dye and heavy metal ion using a novel synthetic polyethersulfone nanofiltration membrane modified by magnetic graphene oxide/metformin hybrid, J. Membr. Sci. 552 (2018) 326–335.
[6] H.R. Zhang, Q.M. He, J.Q. Luo, Y.H. Wan, S.B. Darling, Sharpening nanofiltration: Strategies for enhanced membrane selectivity, ACS Appl Mater Interfaces 12 (36) (2020) 39948–39966.
[7] M.A. Abdel-Fatah, Nanofiltration systems and applications in wastewater treatment: Review article, Ain Shams Eng. J. 9 (4) (2018) 3077–3092.
[8] P. Marchetti, M.F.J. Solomon, G. Szekely, A.G. Livingston, Molecular separation with organic solvent nanofiltration: A critical review, Chem Rev 114 (21) (2014) 10735–10806.
[9] G.M. Shi, Y.N. Feng, B.F. Li, H.M. Tham, J.Y. Lai, T.S. Chung, Recent progress of organic solvent nanofiltration membranes, Prog. Polym. Sci. 123 (2021) 101470.
[10] M.A. Abdulhamid, G. Szekely, Organic solvent nanofiltration membranes based on polymers of intrinsic microporosity, Curr. Opin. Chem. Eng. 36 (2022) 100804.
[11] K. Kimmerle, H. Strathmann, Analysis of the structure-determining process of phase inversion membranes, Desalination 79 (2–3) (1990) 283–302.
[12] R.B. Dai, J.Y. Li, Z.W. Wang, Constructing interlayer to tailor structure and performance of thin-film composite polyamide membranes: A review, Adv. Colloid Interface Sci. 282 (2020) 102204.
[13] C.H. Ji, Z. Zhai, C. Jiang, P. Hu, S.Z. Zhao, S.M. Xue, Z. Yang, T. He, Q.J. Niu, Recent advances in high-performance TFC membranes: A review of the functional interlayers, Desalination 500 (2021) 114869.
[14] S. Karan, Z. Jiang, A.G. Livingston, Sub–10 nm polyamide nanofilms with ultrafast solvent transport for molecular separation, Science (American Association for the Advancement of Science), 348(6241) (2015)1347-1351.
[15] Y.Z. Liang, C. Li, S.X. Li, B.W. Su, M.Z. Hu, X.L. Gao, C.J. Gao, Graphene quantum dots (GQDs)-polyethyleneimine as interlayer for the fabrication of high performance organic solvent nanofiltration (OSN) membranes, Chemical Engineering Journal , 380(2020)122462.
[16] M.Y. Wu, J.Q. Yuan, H. Wu, Y.L. Su, H. Yang, X.D. You, R.N. Zhang, X.Y. He, N.A. Khan, R. Kasher, Z.Y. Jiang, Ultrathin nanofiltration membrane with polydopamine-covalent organic framework interlayer for enhanced permeability and structural stability, J. Membr. Sci. 576 (2019) 131–141.
[17] M. Vera, B.F. Urbano, Tannin polymerization: An overview, Polymer Chemistry, 12(3) (2021) 4272-4429.
[18] A.K. Koopmann, C.Schuster, J. Torres-Rodríguez, S. Kain, H. Pertl-Obermeyer, A. Petutschnigg, N. Hüsing, Tannin-based hybrid materials and their applications: A review, Molecules 25 (21) (2020) E4910.
[19] Q.S. Yao, S.X. Li, R.R. Zhang, L.H. Han, B.W. Su, High-throughput thin-film composite membrane via interfacial polymerization using monomers of ultra-low concentration on tannic acid - Copper interlayer for organic solvent nanofiltration, Sep. Purif. Technol. 258 (2021) 118027.
[20] H.K. Li, X.D. Li, G.Z. Ouyang, L. Li, W.H. Li, W.F. Huang, Preparation and properties of HKUST-1 doped polyetherimide mixed matrix membrane, Fine Chemicals, 39(05) (2022)8.
[21] A.S. Gorzalski, C. Donley, O. Coronell, Elemental composition of membrane foulant layers using EDS, XPS, and RBS, J. Membr. Sci. 522 (2017) 31–44.
[22] M.Y. Wu, T.Y. Ma, Y.L. Su, H. Wu, X.D. You, Z.Y. Jiang, R. Kasher, Fabrication of composite nanofiltration membrane by incorporating attapulgite nanorods during interfacial polymerization for high water flux and antifouling property, J. Membr. Sci. 544 (2017) 79–87.
[23] X. Zhang, Y. Lv, H.C. Yang, Y. Du, Z.K. Xu, Polyphenol coating as an interlayer for thin-film composite membranes with enhanced nanofiltration performance, ACS Appl Mater Interfaces 8 (47) (2016) 32512–32519.
[24] Y. Zhang, M. Zhong, B.B. Luo, J.D. Li, Q.P. Yuan, X.J. Yang, The performance of integrally skinned polyetherimide asymmetric nanofiltration membranes with organic solvents, J. Membr. Sci. 544 (2017) 119–125.
[25] W. Albrecht, B. Seifert, T. Weigel, M. Schossig, A. Holländer, T. Groth, R. Hilke, Amination of poly(ether imide) membranes using di- and multivalent amines, Macromol. Chem. Phys. 204 (3) (2003) 510–521.
[26] A. Shakeri, H. Mighani, N. Salari, H. Salehi, Surface modification of forward osmosis membrane using polyoxometalate based open frameworks for hydrophilicity and water flux improvement, J. Water Process. Eng. 29 (2019) 100762.
[27] Y. Zhang, Y.L. Su, J.M. Peng, X.T. Zhao, J.Z. Liu, J.J. Zhao, Z.Y. Jiang, Composite nanofiltration membranes prepared by interfacial polymerization with natural material tannic acid and trimesoyl chloride, J. Membr. Sci. 429 (2013) 235–242.
[28] K. Vanherck, P. Vandezande, S.O. Aldea, I.F.J. Vankelecom, Cross-linked polyimide membranes for solvent resistant nanofiltration in aprotic solvents, J. Membr. Sci. 320 (1–2) (2008) 468–476.
[29] W.R. Bowen, S.Y. Cheng, T.A. Doneva, D.L. Oatley, Manufacture and characterisation of polyetherimide/sulfonated poly(ether ether ketone) blend membranes, J. Membr. Sci. 250 (1–2) (2005) 1–10.
[30] X.F. Fang, J.S. Li, X. Li, S.L. Pan, X.Y. Sun, J.Y. Shen, W.Q. Han, L.J. Wang, B. van der Bruggen, Iron-tannin-framework complex modified PES ultrafiltration membranes with enhanced filtration performance and fouling resistance, J Colloid Interface Sci 505 (2017) 642–652.
[31] Y.Z. Song, X. Kong, X. Yin, Y. Zhang, C.C. Sun, J.J. Yuan, B.K. Zhu, L.P. Zhu, Tannin-inspired superhydrophilic and underwater superoleophobic polypropylene membrane for effective oil/water emulsions separation, Colloids Surf. A Physicochem. Eng. Aspects 522 (2017) 585–592.
[32] Z.H. Guo, W.S. Xie, J.S. Lu, X.X. Guo, J.Z. Xu, W.L. Xu, Y.J. Chi, N. Takuya, H. Wu, L.Y. Zhao, Tannic acid-based metal phenolic networks for bio-applications: A review, J Mater Chem B 9 (20) (2021) 4098–4110.
[33] W.T. Yan, M.Q. Shi, C.X. Dong, L.F. Liu, C.J. Gao, Applications of tannic acid in membrane technologies: A review, Adv Colloid Interface Sci 284 (2020) 102267.
[34] F. Lin, Y.Y. Ma, Y.L. Su, R.N. Zhang, Y.N. Liu, Q. Zhang, Z.Y. Jiang, Green coating by coordination of tannic acid and iron ions for antioxidant nanofiltration membranes, RSC Advances, 2015,5(130): 107777-107784.
[35] Z.W. Song, J.M. Zhu, L.Y. Jiang, Novel polysiloxaneimide/polyetherimide/non-woven fabric composite membranes for organophilic pervaporation, J. Membr. Sci. 472 (2014) 77–90.
[36] G.H. Gong, P. Wang, Z.Y. Zhou, Y.X. Hu, New insights into the role of an interlayer for the fabrication of highly selective and permeable thin-film composite nanofiltration membrane, ACS Appl Mater Interfaces 11 (7) (2019) 7349–7356.
[37] K.S. Goh, J.Y. Chong, Y.F. Chen, W.X. Fang, T.H. Bae, R. Wang, Thin-film composite hollow fibre membrane for low pressure organic solvent nanofiltration, J. Membr. Sci. 597 (2020) 117760.
[38] K. Chen, P. Li, H.Y. Zhang, H.X. Sun, X.J. Yang, D.H. Yao, X.J. Pang, X.L. Han, Q.J. Niu, Organic solvent nanofiltration membrane with improved permeability by in situ growth of metal-organic frameworks interlayer on the surface of polyimide substrate, Sep. Purif. Technol. 251 (2020) 117387.
[39] M.Q. Shi, W.T. Yan, Y. Zhou, Z. Wang, L.F. Liu, S. Zhao, Y.L. Ji, J.X. Wang, C.J. Gao, P. Zhang, X.Z. Cao, Combining tannic acid-modified support and a green co-solvent for high performance reverse osmosis membranes, J. Membr. Sci. 595 (2020) 117474.
[40] J. Geens, B.V. der Bruggen, C. Vandecasteele, Characterisation of the solvent stability of polymeric nanofiltration membranes by measurement of contact angles and swelling, Chem. Eng. Sci. 59 (5) (2004) 1161–1164.
[41] E.J. Kappert, M.J.T. Raaijmakers, K. Tempelman, F.P. Cuperus, W. Ogieglo, N.E. Benes, Swelling of 9 polymers commonly employed for solvent-resistant nanofiltration membranes: A comprehensive dataset, J. Membr. Sci. 569 (2019) 177–199.
[42] Y. Li, Z. Guo, S. Li, B. van der Bruggen, Interfacially polymerized thin-film composite membranes for organic solvent nanofiltration, Adv. Mater. Interfaces 8 (3) (2021) 2001671.
[43] A. Asadi Tashvigh, T.S. Chung, Facile fabrication of solvent resistant thin film composite membranes by interfacial crosslinking reaction between polyethylenimine and dibromo-p-xylene on polybenzimidazole substrates, J. Membr. Sci. 560 (2018) 115–124.
[44] Z.F. Gao, G.M. Shi, Y. Cui, T.S. Chung, Organic solvent nanofiltration (OSN) membranes made from plasma grafting of polyethylene glycol on cross-linked polyimide ultrafiltration substrates, J. Membr. Sci. 565 (2018) 169–178.
[45] J.H. Kim, S.J. Moon, S.H. Park, M. Cook, A.G. Livingston, Y.M. Lee, A robust thin film composite membrane incorporating thermally rearranged polymer support for organic solvent nanofiltration and pressure retarded osmosis, J. Membr. Sci. 550 (2018) 322–331.
[46] A. A. Tashvigh, Y. Feng, M. Weber, C. Maletzko, T. S. Chung, 110th anniversary: Selection of cross-linkers and cross-linking procedures for the fabrication of solvent-resistant nanofiltration membranes: A review, Ind. Eng. Chem. Res. 58 (2019) 10678-10691.
[47] Y.C. Xu, F.J. You, H.G. Sun, L. Shao, Realizing mussel-inspired polydopamine selective layer with strong solvent resistance in nanofiltration toward sustainable reclamation, ACS Sustain. Chem. \& Eng. 5 (2017) 5520–5528.
[48] J. Aburabie, K.V. Peinemann, Crosslinked poly(ether block amide) composite membranes for organic solvent nanofiltration applications, J. Membr. Sci. 523 (2017) 264–272.
[49] S.X. Li, C. Li, X.J. Song, B.W. Su, B. Mandal, B. Prasad, X.L. Gao, C.J. Gao, Graphene quantum dots-doped thin film nanocomposite polyimide membranes with enhanced solvent resistance for solvent-resistant nanofiltration, ACS Appl Mater Interfaces 11 (6) (2019) 6527–6540.
[50] C. Li, S.X. Li, L. Lv, B.W. Su, M.Z. Hu, High solvent-resistant and integrally crosslinked polyimide-based composite membranes for organic solvent nanofiltration, J. Membr. Sci. 564 (2018) 10–21.
[51] H. Mariën, I.F.J. Vankelecom, Transformation of cross-linked polyimide UF membranes into highly permeable SRNF membranes via solvent annealing, J. Membr. Sci. 541 (2017) 205–213.
[52] D.Y. Xing, S.Y. Chan, T.S. Chung, The ionic liquid [EMIM]OAc as a solvent to fabricate stable polybenzimidazole membranes for organic solvent nanofiltration, Green Chemistry 16 (3) (2014) 1383–1392.
[53] D.J. Chen, S.S. Yu, M. Yang, D.D. Li, X.F. Li, Solvent resistant nanofiltration membranes based on crosslinked polybenzimidazole, RSC Advances 6(21) (2016) 16925-16932.
[54] D. Fritsch, P. Merten, K. Heinrich, M. Lazar, M. Priske, High performance organic solvent nanofiltration membranes: Development and thorough testing of thin film composite membranes made of polymers of intrinsic microporosity (PIMs), J. Membr. Sci. 401-402 (2012) 222–231.
[55] M.H. Davood Abadi Farahani, D. Hua, T.S. Chung, Cross-linked mixed matrix membranes consisting of carboxyl-functionalized multi-walled carbon nanotubes and P84 polyimide for organic solvent nanofiltration (OSN), Sep. Purif. Technol. 186 (2017) 243–254.
[56] I. Strużyńska-Piron, J. Loccufier, L. Vanmaele, I.F. Vankelecom, Synthesis of solvent stable polymeric membranes via UV depth-curing, Chem Commun (Camb) 49 (98) (2013) 11494–11496.

Tannic acid/Fe³⁺ interlayer for preparation of high-permeability polyetherimide organic solvent nanofiltration membranes for organic solvent separation

Tannic acid/Fe³⁺ interlayer for preparation of high-permeability polyetherimide organic solvent nanofiltration membranes for organic solvent separation

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