Water-selective hybrid membranes with improved interfacial compatibility from mussel-inspired dopamine-modified alginate and covalent organic frameworks

doi:10.1016/j.cjche.2019.03.007

Chinese Journal of Chemical Engineering ›› 2020, Vol. 28 ›› Issue (1): 90-97.DOI: 10.1016/j.cjche.2019.03.007

• Separation Science and Engineering • Previous Articles Next Articles

Water-selective hybrid membranes with improved interfacial compatibility from mussel-inspired dopamine-modified alginate and covalent organic frameworks

Hao Yang^1,2, Hong Wu^1,2,3, Fusheng Pan^1,2,4, Meidi Wang^1,2, Zhongyi Jiang^1,2, Qifan Cheng^1,2, Cheng Huang^1,2

1 Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2 Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300072, China;
3 Tianjin Key Laboratory of Membrane Science and Desalination Technology, Tianjin University, Tianjin 300072, China;
4 State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China

Received:2019-02-14 Revised:2019-03-13 Online:2020-03-31 Published:2020-01-28
Contact: Zhongyi Jiang
Supported by:
Supported by the National Natural Science Foundation of China (21621004, 21490583, 21878215, 21878216), the Program of Introducing Talents of Discipline to Universities (B06006) and the State Key Laboratory of Organic-Inorganic Composites (oic-201801003).

Water-selective hybrid membranes with improved interfacial compatibility from mussel-inspired dopamine-modified alginate and covalent organic frameworks

Hao Yang^1,2, Hong Wu^1,2,3, Fusheng Pan^1,2,4, Meidi Wang^1,2, Zhongyi Jiang^1,2, Qifan Cheng^1,2, Cheng Huang^1,2

1 Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2 Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300072, China;
3 Tianjin Key Laboratory of Membrane Science and Desalination Technology, Tianjin University, Tianjin 300072, China;
4 State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China

通讯作者: Zhongyi Jiang
基金资助:
Supported by the National Natural Science Foundation of China (21621004, 21490583, 21878215, 21878216), the Program of Introducing Talents of Discipline to Universities (B06006) and the State Key Laboratory of Organic-Inorganic Composites (oic-201801003).

Abstract

Abstract: Hybrid membranes combining the merits of both polymer matrices and fillers have drawn extensive attention. The rational design of polymer-filler interface in hybrid membranes is vitally important for reducing the occurrence of void defects. Herein, imine-type covalent organic frameworks (COFs) were selected as the fillers due to their totally organic nature and multi-functionalities. Mussel-inspired dopamine-modified sodium alginate (AlgDA) was synthesized as the polymer matrix. The dopamine modification significantly improves the AlgDA-COF compatibility, which enhances the COF content up to 50 wt% in the hybrid membranes. The improved interfacial compatibility enhances the membrane separation selectivity. Accordingly, when utilized for dehydration of ethanol/water mixed solution (water concentration of 10 wt%), the hybrid membrane reveals high water concentration of ~98.7 wt% in permeate, and stable permeation flux larger than 1500 g·m^-2·h^-1. This work might afford useful insights for fabricating hybrid membranes with high separation selectivity by optimizing the polymer-filler interface. Keywords:Alginate Dopamine Covalent organic framework Membrane

Key words: Alginate, Dopamine, Covalent organic framework, Membrane, Pervaporation, Interface

摘要： Hybrid membranes combining the merits of both polymer matrices and fillers have drawn extensive attention. The rational design of polymer-filler interface in hybrid membranes is vitally important for reducing the occurrence of void defects. Herein, imine-type covalent organic frameworks (COFs) were selected as the fillers due to their totally organic nature and multi-functionalities. Mussel-inspired dopamine-modified sodium alginate (AlgDA) was synthesized as the polymer matrix. The dopamine modification significantly improves the AlgDA-COF compatibility, which enhances the COF content up to 50 wt% in the hybrid membranes. The improved interfacial compatibility enhances the membrane separation selectivity. Accordingly, when utilized for dehydration of ethanol/water mixed solution (water concentration of 10 wt%), the hybrid membrane reveals high water concentration of ~98.7 wt% in permeate, and stable permeation flux larger than 1500 g·m^-2·h^-1. This work might afford useful insights for fabricating hybrid membranes with high separation selectivity by optimizing the polymer-filler interface. Keywords:Alginate Dopamine Covalent organic framework Membrane

关键词: Alginate, Dopamine, Covalent organic framework, Membrane, Pervaporation, Interface

Hao Yang, Hong Wu, Fusheng Pan, Meidi Wang, Zhongyi Jiang, Qifan Cheng, Cheng Huang. Water-selective hybrid membranes with improved interfacial compatibility from mussel-inspired dopamine-modified alginate and covalent organic frameworks[J]. Chinese Journal of Chemical Engineering, 2020, 28(1): 90-97.

References

[1] D.L. Gin, R.D. Noble, Designing the next generation of chemical separation membranes, Science 332(2011) 674-676.
[2] W.J. Koros, C. Zhang, Materials for next-generation molecularly selective synthetic membranes, Nat. Mater. 16(2017) 289-297.
[3] P. Marchetti, M.F.J. Solomon, G. Szekely, A.G. Livingston, Molecular separation with organic solvent nanofiltration:A critical review, Chem. Rev. 114(2014) 10735-10806.
[4] Y. Li, G. He, S. Wang, S. Yu, F. Pan, H. Wu, Z. Jiang, Recent advances in the fabrication of advanced composite membranes, J. Mater. Chem. A 1(2013) 10058-10077.
[5] Y.D. Cheng, Y.P. Ying, S. Japip, S.D. Jiang, T.S. Chung, S. Zhang, D. Zhao, Advanced porous materials in mixed matrix membranes, Adv. Mater. 30(2018) 1802401.
[6] C.Y. Chuah, K. Goh, Y.Q. Yang, H.Q. Gong, W. Li, H.E. Karahan, M.D. Guiver, R. Wang, T.H. Bae, Harnessing filler materials for enhancing biogas separation membranes, Chem. Rev. 118(2018) 8655-8769.
[7] N. Huang, P. Wang, D.L. Jiang, Covalent organic frameworks:A materials platform for structural and functional designs, Nat. Rev. Mater. 1(2016) 16068.
[8] P.J. Bereciartua, A. Cantin, A. Corma, J.L. Jorda, M. Palomino, F. Rey, S. Valencia, E.W. Corcoran, P. Kortunov, P.I. Ravikovitch, A. Burton, C. Yoon, Y. Wang, C. Paur, J. Guzman, A.R. Bishop, G.L. Casty, Control of zeolite framework flexibility and pore topology for separation of ethane and ethylene, Science 358(2017) 1068-1071.
[9] M.X. Shan, B. Seoane, E. Andres-Garcia, F. Kapteijn, J. Gascon, Mixed-matrix membranes containing an azine-linked covalent organic framework:Influence of the polymeric matrix on post-combustion CO₂-capture, J. Membr. Sci. 549(2018) 377-384.
[10] C.C. Zou, Q.Q. Li, Y.Y. Hua, B.H. Zhou, J.G. Duan, W.Q. Jin, Mechanical synthesis of COF nanosheet cluster and its mixed matrix membrane for efficient CO₂ removal, ACS Appl. Mater. Interfaces 9(2017) 29093-29100.
[11] H. Yang, H. Wu, F.S. Pan, Z. Li, H. Ding, G.H. Liu, Z.Y. Jiang, P. Zhang, X.Z. Cao, B.Y. Wang, Highly water-permeable and stable hybrid membrane with asymmetric covalent organic framework distribution, J. Membr. Sci. 520(2016) 583-595.
[12] H.L. Zhou, J.Q. Zhang, Y.H. Wan, W.Q. Jin, Fabrication of high silicalite-1 content filled PDMS thin composite pervaporation membrane for the separation of ethanol from aqueous solutions, J. Membr. Sci. 524(2017) 1-11.
[13] Y.D. Cheng, Z.H. Wang, D. Zhao, Mixed matrix membranes for natural gas upgrading:Current status and opportunities, Ind. Eng. Chem. Res. 57(2018) 4139-4169.
[14] B.A. Al-Maythalony, A.M. Alloush, M. Faizan, H. Dafallah, M.A.A. Elgzoly, A.A.A. Seliman, A. Al-Ahmed, Z.H. Yamani, M.A.M. Habib, K.E. Cordova, O.M. Yaghi, Tuning the interplay between selectivity and permeability of ZIF-7 mixed matrix membranes, ACS Appl. Mater. Interfaces 9(2017) 33401-33407.
[15] H.L. Wang, S.F. He, X.D. Qin, C.E. Li, T. Li, Interfacial engineering in metal-organic framework-based mixed matrix membranes using covalently grafted polyimide brushes, J. Am. Chem. Soc. 140(2018) 17203-17210.
[16] Z.G. Wang, D. Wang, S.X. Zhang, L. Hu, J. Jin, Interfacial design of mixed matrix membranes for improved gas separation performance, Adv. Mater. 28(2016) 3399-3405.
[17] H. Lee, S.M. Dellatore, W.M. Miller, P.B. Messersmith, Mussel-inspired surface chemistry for multifunctional coatings, Science 318(2007) 426-430.
[18] J. Zhao, C.H. Fang, Y.W. Zhu, G.W. He, F.S. Pan, Z.Y. Jiang, P. Zhang, X.Z. Cao, B.Y. Wang, Manipulating the interfacial interactions of composite membranes via a mussel-inspired approach for enhanced separation selectivity, J. Mater. Chem. A 3(2015) 19980-19988.
[19] T. Lee, E.K. Jeon, B.S. Kim, Mussel-inspired nitrogen-doped graphene nanosheet supported manganese oxide nanowires as highly efficient electrocatalysts for oxygen reduction reaction, J. Mater. Chem. A 2(2014) 6167-6173.
[20] K.H. Oh, M.J. Choo, H. Lee, K.H. Park, J.K. Park, J.W. Choi, Mussel-inspired polydopamine-treated composite electrolytes for long-term operations of polymer electrolyte membrane fuel cells, J. Mater. Chem. A 1(2013) 14484-14490.
[21] G.M. Shi, T.S. Chung, Thin film composite membranes on ceramic for pervaporation dehydration of isopropanol, J. Membr. Sci. 448(2013) 34-43.
[22] Z. Yang, X.Y. Huang, J.Q. Wang, C.Y.Y. Tang, Novel polyethyleneimine/TMC-based nanofiltration membrane prepared on a polydopamine coated substrate, Front. Chem. Sci. Eng. 12(2018) 273-282.
[23] X.L. Wang, Z.Y. Jiang, J.F. Shi, Y.P. Liang, C.H. Zhang, H. Wu, Metal-organic coordination-enabled layer-by-layer self-assembly to prepare hybrid microcapsules for efficient enzyme immobilization, ACS Appl. Mater. Interfaces 4(2012) 3476-3483.
[24] B.P. Biswal, S. Kandambeth, S. Chandra, D.B. Shinde, S. Bera, S. Karak, B. Garai, U.K. Kharul, R. Banerjee, Pore surface engineering in porous, chemically stable covalent organic frameworks for water adsorption, J. Mater. Chem. A 3(2015) 23664-23669.
[25] X.X. Cheng, F.S. Pan, M.R. Wang, W.D. Li, Y.M. Song, G.H. Liu, H. Yang, B.X. Gao, H. Wu, Z.Y. Jiang, Hybrid membranes for pervaporation separations, J. Membr. Sci. 541(2017) 329-346.
[26] Y.K. Ong, G.M. Shi, N.L. Le, Y.P. Tang, J. Zuo, S.P. Nunes, T.S. Chung, Recent membrane development for pervaporation processes, Prog. Polym. Sci. 57(2016) 1-31.
[27] C.X. Yang, C. Liu, Y.M. Cao, X.P. Yan, Facile room-temperature solution-phase synthesis of a spherical covalent organic framework for high-resolution chromatographic separation, Chem. Commun. 51(2015) 12254-12257.
[28] B.P. Biswal, S. Chandra, S. Kandambeth, B. Lukose, T. Heine, R. Banerjeet, Mechanochemical synthesis of chemically stable isoreticular covalent organic frameworks, J. Am. Chem. Soc. 135(2013) 5328-5331.
[29] K. Cao, Z. Jiang, X. Zhang, Y. Zhang, J. Zhao, R. Xing, S. Yang, C. Gao, F. Pan, Highly water-selective hybrid membrane by incorporating g-C₃N₄ nanosheets into polymer matrix, J. Membr. Sci. 490(2015) 72-83.
[30] H. Yang, H. Wu, Z. Yao, B. Shi, Z. Xu, X. Cheng, F. Pan, G. Liu, Z. Jiang, X. Cao, Functionally graded membranes from nanoporous covalent organic frameworks for highly selective water permeation, J. Mater. Chem. A 6(2018) 583-591.
[31] S.N. Yu, Z.Y. Jiang, S. Yang, H. Ding, B.F. Zhou, K. Gu, D. Yang, F.S. Pan, B.Y. Wang, S. Wang, X.Z. Cao, Highly swelling resistant membranes for model gasoline desulfurization, J. Membr. Sci. 514(2016) 440-449.
[32] X. Cheng, Z. Jiang, X. Cheng, S. Guo, L. Tang, H. Yang, H. Wu, F. Pan, P. Zhang, X. Cao, B. Wang, Bimetallic metal-organic frameworks nanocages as multi-functional fillers for water-selective membranes, J. Membr. Sci. 545(2018) 19-28.
[33] H.W. Fan, J.H. Gu, H. Meng, A. Knebel, J. Caro, High-flux membranes based on the covalent organic framework COF-LZU1 for selective dye separation by nanofiltration, Angew. Chem. Int. Ed. 57(2018) 4083-4087.
[34] S.D. Bhat, N.N. Mallikarjuna, T.M. Aminabhavi, Microporous alumino-phosphate (AlPO₄-5) molecular sieve-loaded novel sodium alginate composite membranes for pervaporation dehydration of aqueous-organic mixtures near their azeotropic compositions, J. Membr. Sci. 282(2006) 473-483.
[35] S. Panahian, A. Raisi, A. Aroujalian, Multilayer mixed matrix membranes containing modified-MWCNTs for dehydration of alcohol by pervaporation process, Desalination 355(2015) 45-55.
[36] C.H. Kang, Y.F. Lin, Y.S. Huang, K.L. Tung, K.S. Chang, J.T. Chen, W.S. Hung, K.R. Lee, J. Y. Lai, Synthesis of ZIF-7/chitosan mixed-matrix membranes with improved separation performance of water/ethanol mixtures, J. Membr. Sci. 438(2013) 105-111.
[37] Z. Huang, Y. Shi, R. Wen, Y.H. Guo, J.F. Su, T. Matsuura, Multilayer poly(vinyl alcohol)-zeolite 4A composite membranes for ethanol dehydration by means of pervaporation, Sep. Purif. Technol. 51(2006) 126-136.
[38] S. Qiu, L. Wu, G. Shi, L. Zhang, H. Chen, C. Gao, Preparation and pervaporation property of chitosan membrane with functionalized multiwalled carbon nanotubes, Ind. Eng. Chem. Res. 49(2010) 11667-11675.
[39] A. Kudasheva, S. Sorribas, B. Zornoza, C. Tellez, J. Coronas, Pervaporation of water/ethanol mixtures through polyimide based mixed matrix membranes containing ZIF-8, ordered mesoporous silica and ZIF-8-silica core-shell spheres, J. Chem. Technol. Biotechnol. 90(2015) 669-677.
[40] J. Zhao, Y.W. Zhu, F.S. Pan, G.W. He, C.H. Fang, K.T. Cao, R.S. Xing, Z.Y. Jiang, Fabricating graphene oxide-based ultrathin hybrid membrane for pervaporation dehydration via layer-by-layer self-assembly driven by multiple interactions, J. Membr. Sci. 487(2015) 162-172.
[41] R.S. Xing, H. Wu, C.H. Zhao, H. Gomaa, J. Zhao, F.S. Pan, Z.Y. Jiang, Fabrication of chitosan membranes with high flux by magnetic alignment of in situ generated Fe₃O₄, Chem. Eng. Technol. 39(2016) 969-978.
[42] S. Sorribas, A. Kudasheva, E. Almendro, B. Zornoza, O. de la Iglesia, C. Tellez, J. Coronas, Pervaporation and membrane reactor performance of polyimide based mixed matrix membranes containing MOF HKUST-1, Chem. Eng. Sci. 124(2015) 37-44.
[43] G. Liu, Z. Jiang, C. Chen, L. Hou, B. Gao, H. Yang, H. Wu, F. Pan, P. Zhang, X. Cao, Preparation of ultrathin, robust membranes through reactive layer-by-layer (LbL) assembly for pervaporation dehydration, J. Membr. Sci. 537(2017) 229-238.
[44] S.V. Kononova, E.V. Kruchinina, V.A. Petrova, Y.G. Baklagina, V.V. Klechkovskaya, A.S. Orekhov, E.N. Vlasova, E.N. Popova, G.N. Gubanova, Y.A. Skorik, Pervaporation membranes of a simplex type with polyelectrolyte layers of chitosan and sodium hyaluronate, Carbohydr. Polym. 209(2019) 10-19.
[45] S.V. Kononova, A.V. Volod'ko, V.A. Petrova, E.V. Kruchinina, Y.G. Baklagina, E.A. Chusovitin, Y.A. Skorik, Pervaporation multilayer membranes based on a polyelectrolyte complex of lambda-carrageenan and chitosan, Carbohydr. Polym. 181(2018) 86-92.
[46] S.V. Kononova, E.V. Kruchinina, V.A. Petrova, Y.G. Baklagina, K.A. Romashkova, A.S. Orekhov, V.V. Klechkovskaya, Y.A. Skorik, Two-ply composite membranes with separation layers from chitosan and sulfoethylcellulose on a microporous support based on poly(diphenylsulfone-N-phenylphthalimide), Molecules 22(2017) 2227.

Water-selective hybrid membranes with improved interfacial compatibility from mussel-inspired dopamine-modified alginate and covalent organic frameworks

Water-selective hybrid membranes with improved interfacial compatibility from mussel-inspired dopamine-modified alginate and covalent organic frameworks

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xinxin Li, Hongwei Shao, Shichao Zhang, Yong Li, Jingjing Gu, Qiang Huang, Jin Ran. Two dimensional MoS₂ finding its way towards constructing high-performance alkaline recovery membranes [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 155-164.
[2]	Wenwen Zhang, Zhigang Xue, Liyun Cui, Haoliang Gao, Di Zhao, Rongfei Zhou, Weihong Xing. Synthesis of an IMF zeolite membrane for the separation of xylene isomer [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 205-211.
[3]	Hammad Saulat, Jianhua Yang, Tao Yan, Waseem Raza, Wensen Song, Gaohong He. Tungsten incorporated mobil-type eleven zeolite membranes: Facile synthesis and tuneable wettability for highly efficient separation of oil/water mixtures [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 242-252.
[4]	Sinu Poolachira, Sivasubramanian Velmurugan. Graphene oxide/hydrotalcite modified polyethersulfone nanohybrid membrane for the treatment of lead ion from battery industrial effluent [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 253-261.
[5]	Yong Xu, Qingbai Chen, Yang Gao, Jianyou Wang, Huiqing Fan, Fei Zhao. Performance comparison of lithium fractionation from magnesium via continuous selective nanofiltration/electrodialysis [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 42-50.
[6]	Meihua Zhu, Xingguo An, Tian Gui, Ting Wu, Yuqin Li, Xiangshu Chen. Effects of ion-exchange on the pervaporation performance and microstructure of NaY zeolite membrane [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 176-181.
[7]	Yafei Su, Xuke Zhang, Hui Li, Donglai Peng, Yatao Zhang. In-situ incorporation of halloysite nanotubes with 2D zeolitic imidazolate framework-L based membrane for dye/salt separation [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 103-111.
[8]	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.
[9]	Jiajun Wang, Wenbin Yang, Jiangtao Geng, Zhigang Shao, Wei Song. Experimental investigation on degradation mechanism of membrane electrode assembly at different humidity under automotive protocol [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 70-79.
[10]	Xingzhong Li, Kunlin Yu, Zibo He, Bo Liu, Rongfei Zhou, Weihong Xing. Improved SSZ-13 thin membranes fabricated by seeded-gel approach for efficient CO₂ capture [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 273-280.
[11]	Wufeng Wu, Xilu Hong, Jiang Fan, Yanying Wei, Haihui Wang. Research progress on the substrate for metal–organic framework (MOF) membrane growth for separation [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 299-313.
[12]	Yingxiang Ni, Can Yuan, Shilong Li, Jian Lu, Lei Yan, Wei Gu, Weihong Xing, Wenheng Jing. Temperature-induced hydrophobicity transition of MXene membrane for directly preparing W/O emulsions [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 59-62.
[13]	Taoyan Mao, Runhui Xiao, Peng Liu, Jiale Chen, Junqiang Luo, Su Luo, Fengwei Xie, Cheng Zheng. Facile fabrication of durable superhydrophobic fabrics by silicon polyurethane membrane for oil/water separation [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 73-83.
[14]	Qi Han, Xin-Yuan Zhang, Hai-Bo Wu, Xian-Tai Zhou, Hong-Bing Ji. Different efficiency toward the biomimetic aerobic oxidation of benzyl alcohol in microchannel and bubble column reactors: Hydrodynamic characteristics and gas–liquid mass transfer [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 84-92.
[15]	Zhengchi Yin, Xiaoke Wu, Yanwei Yang, Huayu Zhang, Wangtao Li, Ruimin Zhu, Qiancheng Zheng, Zhengbao Wang. Fabrication of ZIF-8 membranes on dual-layer ZnO-PES/PES organic hollow fibers by in-situ crystallization [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 101-110.