Knitted Microporous Polymers as Efficient Adsorbents for Wastewater Treatment: Effects of Skeleton Structure and Pore Distribution
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摘要
Hyper-cross-linked microporous organic polymers(MOP) with controlled skeleton structure and pore distribution were prepared by Friedel-Crafts alkylation reaction. The hyper-cross-linked polymers(HCPs) produced by knitting aromatic functional groups posses the typical micro-and meso-porous composite structure and specific surface areas of up to 957 m~2·g~(-1). The obtained materials were evaluated as adsorbents for methylene blue(MB) and subjected to several batch adsorption tests to investigate the effects of adsorbent dosage, concentration of MB, temperature, and pH on MB removal. The maximum adsorbed capacity(q_m) of KAPs-Ph(381 mg·g~(-1), knitted using benzene) exceeded those of less mesoporous KAPs-PhPh_3(310 mg·g~(-1) knitted using 1,3,5-triphenylbenzene) and chloromethyl polystyrene resin(58 mg·g~(-1)). Moreover, KAPs-Ph could be regenerated by Soxhlet extraction with ethanol and reused for up to 15 times with minimal loss of adsorption capacity. The results illustrate that adsorption performance can be improved by controlling the pore structure of the adsorbing materials, and KAPs-Ph has a potential application values for the industrial removal of organic dyes from wastewater.
Hyper-cross-linked microporous organic polymers(MOP) with controlled skeleton structure and pore distribution were prepared by Friedel-Crafts alkylation reaction. The hyper-cross-linked polymers(HCPs) produced by knitting aromatic functional groups posses the typical micro-and meso-porous composite structure and specific surface areas of up to 957 m~2·g~(-1). The obtained materials were evaluated as adsorbents for methylene blue(MB) and subjected to several batch adsorption tests to investigate the effects of adsorbent dosage, concentration of MB, temperature, and pH on MB removal. The maximum adsorbed capacity(q_m) of KAPs-Ph(381 mg·g~(-1), knitted using benzene) exceeded those of less mesoporous KAPs-PhPh_3(310 mg·g~(-1) knitted using 1,3,5-triphenylbenzene) and chloromethyl polystyrene resin(58 mg·g~(-1)). Moreover, KAPs-Ph could be regenerated by Soxhlet extraction with ethanol and reused for up to 15 times with minimal loss of adsorption capacity. The results illustrate that adsorption performance can be improved by controlling the pore structure of the adsorbing materials, and KAPs-Ph has a potential application values for the industrial removal of organic dyes from wastewater.
Hyper-cross-linked microporous organic polymers(MOP) with controlled skeleton structure and pore distribution were prepared by Friedel-Crafts alkylation reaction. The hyper-cross-linked polymers(HCPs) produced by knitting aromatic functional groups posses the typical micro-and meso-porous composite structure and specific surface areas of up to 957 m~2·g~(-1). The obtained materials were evaluated as adsorbents for methylene blue(MB) and subjected to several batch adsorption tests to investigate the effects of adsorbent dosage, concentration of MB, temperature, and pH on MB removal. The maximum adsorbed capacity(q_m) of KAPs-Ph(381 mg·g~(-1), knitted using benzene) exceeded those of less mesoporous KAPs-PhPh_3(310 mg·g~(-1) knitted using 1,3,5-triphenylbenzene) and chloromethyl polystyrene resin(58 mg·g~(-1)). Moreover, KAPs-Ph could be regenerated by Soxhlet extraction with ethanol and reused for up to 15 times with minimal loss of adsorption capacity. The results illustrate that adsorption performance can be improved by controlling the pore structure of the adsorbing materials, and KAPs-Ph has a potential application values for the industrial removal of organic dyes from wastewater.
引文
[1] WANG P, CAO M, WANG C, et al. Kinetics and thermodynamics of adsorption of methylene blue by a magnetic graphene-carbon nanotube composite[J]. Applied Surface Science, 2014, 290:116-124.
[2] LIN S, SONG Z, CHE G, et al. Adsorption behavior of metal-organic frameworks for methylene blue from aqueous solution[J]. Microporous Mesoporous Materials, 2014, 193: 27-34.
[3] CHEN B, LIN Y, CHEN S, et al. Nitrogen-rich core/shell magnetic nanostructures for selective adsorption and separation of anionic dyes from aqueous solution[J]. Environmental Science: Nano, 2016, 3(3): 670- 681.
[4] ZHONG N B, CHEN M, LUO Y H, et al. A novel photocatalytic optical hollow-fiber with high photocatalytic activity for enhancement of 4-chlorophenol degradation[J]. Chemical Engineering Journal, 2019, 355: 731-739.
[5] ZHANG T, LIN W. Metal-organic frameworks for artificial photosynthesis and photocatalysis[J]. Chemical Society Reviews, 2014, 43(16): 5982-5993.
[6] LIN J, YE W, ZENG H, et al. Fractionation of direct dyes and salts in aqueous solution using loose nanofiltration membranes[J]. Journal Membrane Science, 2015, 477: 183-193.
[7] PEREZ J F, LLANOS J, SAEZ C, et al. Development of an innovative approach for low-impact wastewater treatment: a microfluidic flow-through electrochemical reactor[J]. Chemical Engineering Journal, 2018, 351: 766-772.
[8] WU J, WANG J, LI H, et al. Designed synthesis of hematite-based nanosorbents for dye removal[J]. Journal of Materials Chemistry A, 2013, 1(34): 9837-9847.
[9] BEDIN K C, MARTINS A C, CAZETTA A L, et al. KOH-activated carbon prepared from sucrose spherical carbon: adsorption equilibrium, kinetic and thermodynamic studies for methylene blue removal[J]. Chemical Engineering Journal, 2016, 286: 476-484.
[10] FU H, LI X, WANG J, et al. Activated carbon adsorption of quinolone antibiotics in water: Performance, mechanism, and modeling[J]. Journal of Environmental Sciences, 2017, 56(6): 145-152.
[11] HOLMES A B, GU F X. Emerging nanomaterials for the application of selenium removal for wastewater treatment[J]. Environmental Science: Nano, 2016, 3: 982-996.
[12] HOU Y, SUN J, ZHANG D, et al. Porphyrin-alkaline earth MOFs with the highest adsorption capacity for methylene blue[J]. Chemistry A European Journal, 2016, 22(18): 6345- 6352.
[13] KOZLOVA E A, PANCHENKO V N, HASAN Z, et al. Photoreactivity of metal-organic frameworks in the decolorization of methylene blue in aqueous solution[J]. Catalysis Today, 2016, 266: 136-143.
[14] CHEN L, LI Y, DU Q, et al. High performance agar/graphene oxide composite aerogel for methylene blue removal[J]. Carbohydrate Polymers, 2017, 155: 345-353.
[15] WAN W, ZHANG R, LI W, et al. Graphene-carbon nanotube aerogel as an ultra-light, compressible and recyclable highly efficient absorbent for oil and dyes[J]. Environmental Science: Nano, 2016, 3(1): 107-113.
[16] ZHENG D, ZHANG M, DING L, et al. Facile synthesis of magnetic resorcinol-formaldehyde(RF) coated carbon nanotubes for methylene blue removal[J]. RSC Advances, 2016, 6(15): 11973-11979.
[17] SHAO Y, ZHOU L, BAO C, et al. Magnetic responsive metal-organic frameworks nanosphere with core-shell structure for highly efficient removal of methylene blue[J]. Chemical Engineering Journal, 2016, 283: 1127-1136.
[18] CHENG T, ZHIJUAN Z, YUFANG F, et al. Highly dispersed DPPF locked in knitting hyper crosslinked polymers as efficient and recyclable catalyst[J]. Chemistry Select, 2018, 3(21): 5987-5992.
[19] YANG R X, WANG T T and DENG W Q. Extraordinary capability for water treatment achieved by a perfluorous conjugated microporous polymer[J]. Scientific Reports, 2015, 5: 10155.
[20] WANG J, WANG G, WANG W, et al. Hydrophobic conjugated microporous polymer as a novel adsorbent for removal of volatile organic compounds[J]. Journal of Materials Chemistry A, 2014, 2(34): 14028-14037.
[21] FENG L J, CHEN Q, ZHU J H, et al. Adsorption performance and catalytic activity of porous conjugated polyporphyrins via carbazole-based oxidative coupling polymerization[J]. Polymer Chemistry, 2014, 5: 3081-3088.
[22] TAN L, TAN B. Hypercrosslinked porous polymer materials: design, synthesis, and applications[J]. Chemical Society Reviews, 2017, 46(11): 3322-3356.
[23] XU S, SONG K, LI T, et al. Palladium catalyst coordinated in knitting N-heterocyclic carbene porous polymers for efficient Suzuki-Miyaura coupling reactions[J]. Journal of Materials Chemistry A, 2015, 3(3): 1272-1278.
[24] LI Q, ZHAN Z, JIN S, et al. Wettable magnetic hypercrosslinked microporous nanoparticle as an efficient adsorbent for water treatment[J]. Chemical Engineering Journal, 2017, 326: 109-116.
[25] SONG K, ZOU Z, WANG D, et al. Microporous organic polymers derived microporous carbon supported Pd catalysts for oxygen reduction reaction: impact of framework and heteroatom[J]. the Journal of Physical Chemistry C, 2016, 120(4): 2187-2197.
[26] SONG K, LIU P, WANG J, et al. Controlled synthesis of uniform palladium nanoparticles on novel micro-porous carbon as a recyclable heterogeneous catalyst for the Heck reaction[J]. Dalton Transactions, 2015, 44(31): 13906-13913.
[27] FU Y F, SONG K P, ZOU Z J, et al. External cross-linked sulfonate-functionalized N-heterocyclic carbenes: an efficient and recyclable catalyst for Suzuki-Miyaura reactions in water[J]. Transition Metal Chemistry, 2018, 43(8): 665-672.
[28] MARION N, NOLAN S P. Well-defined N-heterocyclic carbenes palladium(II) precatalysts for cross-coupling reactions[J]. Accounts of Chemical Research, 2008, 41(11): 1440-1449.
[29] HASSAN A F, ABDEL-MOHSEN A M, FOUDA M M G. Comparative study of calcium alginate, activated carbon, and their composite beads on methylene blue adsorption[J]. Carbohydrate Polymers, 2014, 102: 192-198.
[30] ZHANG X, ZHANG L, LI Z, et al. Rational design of antifouling polymeric nanocomposite for sustainable fluoride removal from NOM-rich water[J]. Environmental Science Technology, 2017, 51(22): 13363-13371.
[31] GONTE R, BALASUBRAMIAN K. Heavy and toxic metal uptake by mesoporous hypercrosslinked SMA beads: Isotherms and kinetics[J]. Journal of Saudi Chemical Society, 2016, 20: S579-S590.
[32] BALARAK D, JAAFARI J, HASSANI G, et al. The use of low-cost adsorbent(Canola residues) for the adsorption of methylene blue from aqueous solution: Isotherm, kinetic and thermodynamic studies[J]. Colloids and Interface Science Communications, 2015, 7: 16-19.
[33] WANG Y, ZHANG W, QIN M, et al. Green one-pot preparation of α-Fe2O3@carboxyl-functionalized yeast composite with high adsorption and catalysis properties for removal of methylene blue[J]. Surface and Interface Analysis, 2018, 50(5): 311-320.
[34] ZHANG S, ZENG M, LI J, et al. Porous magnetic carbon sheets from biomass as an adsorbent for the fast removal of organic pollutants from aqueous solution[J]. Journal of Materials Chemistry A, 2014, 2(12): 4391- 4397.
[35] HAN J, DU Z, ZOU W, et al. In-situ improved phenol adsorption at ions-enrichment interface of porous adsorbent for simultaneous removal of copper ions and phenol[J]. Chemical Engineering Journal, 2015, 262: 571-578.
[36] NEKOUEI F, NEKOUEI S, TYAGI I, et al. Kinetic, thermodynamic and isotherm studies for acid blue 129 removal from liquids using copper oxide nanoparticle-modified activated carbon as a novel adsorbent[J]. Journal of Molecular Liquids, 2015, 201: 124-133.
[37] ZHANG L, LIU Y, WANG S, et al. Selective removal of cationic dyes from aqueous solutions by an activated carbon-based multicarboxyl adsorbent[J]. RSC Advances, 2015, 5(121): 99618-99626.
[38] LALLEY J, HAN C, LI X, et al. Phosphate adsorption using modified iron oxide-based sorbents in lake water: kinetics, equilibrium, and column tests[J]. Chemical Engineering Journal, 2016, 284: 1386-1396.
[39] WAN X, ZHAN Y, LONG Z, et al. Core@double-shell structured magnetic halloysite nanotube nano-hybrid as efficient recyclable adsorbent for methylene blue removal[J]. Chemical Engineering Journal, 2017, 330: 491-504.
[40] PEYDAYESH M, RAHBAR-KELISHAMI A. Adsorption of methylene blue onto Platanus orientalis leaf powder: kinetic, equilibrium and thermodynamic studies[J]. Journal of Industrial and Engineering Chemistry, 2015, 21: 1014-1019.
[41] GHAEDI M, HAJJATI S, MAHMUDI Z, et al. Modeling of competitive ultrasonic assisted removal of the dyes-Methylene blue and Safranin-O using Fe3O4 nanoparticles[J]. Chemical Engineering Journal, 2015, 268: 28-37.
[42] SHOKOOHI R, TORKSHAVAND Z, MAHMOUDI M M, et al. Effective removal of Azo dye reactive blue 222 from aqueous solutions using modified magnetic nanoparticles with sodium alginate/hydrogen peroxide[J]. Environmental Progress & Sustainable Energy, 2018. DOI: 10.1002/ep.12971.
[43] WANG D, YU H, FAN X, et al. High aspect ratio carboxylated cellulose nanofibers cross-linked to robust aerogels for superabsorption-flocculants: paving way from nanoscale to macroscale[J]. ACS Applied Materials Interfaces, 2018, 10(24): 20755-20766.
[2] LIN S, SONG Z, CHE G, et al. Adsorption behavior of metal-organic frameworks for methylene blue from aqueous solution[J]. Microporous Mesoporous Materials, 2014, 193: 27-34.
[3] CHEN B, LIN Y, CHEN S, et al. Nitrogen-rich core/shell magnetic nanostructures for selective adsorption and separation of anionic dyes from aqueous solution[J]. Environmental Science: Nano, 2016, 3(3): 670- 681.
[4] ZHONG N B, CHEN M, LUO Y H, et al. A novel photocatalytic optical hollow-fiber with high photocatalytic activity for enhancement of 4-chlorophenol degradation[J]. Chemical Engineering Journal, 2019, 355: 731-739.
[5] ZHANG T, LIN W. Metal-organic frameworks for artificial photosynthesis and photocatalysis[J]. Chemical Society Reviews, 2014, 43(16): 5982-5993.
[6] LIN J, YE W, ZENG H, et al. Fractionation of direct dyes and salts in aqueous solution using loose nanofiltration membranes[J]. Journal Membrane Science, 2015, 477: 183-193.
[7] PEREZ J F, LLANOS J, SAEZ C, et al. Development of an innovative approach for low-impact wastewater treatment: a microfluidic flow-through electrochemical reactor[J]. Chemical Engineering Journal, 2018, 351: 766-772.
[8] WU J, WANG J, LI H, et al. Designed synthesis of hematite-based nanosorbents for dye removal[J]. Journal of Materials Chemistry A, 2013, 1(34): 9837-9847.
[9] BEDIN K C, MARTINS A C, CAZETTA A L, et al. KOH-activated carbon prepared from sucrose spherical carbon: adsorption equilibrium, kinetic and thermodynamic studies for methylene blue removal[J]. Chemical Engineering Journal, 2016, 286: 476-484.
[10] FU H, LI X, WANG J, et al. Activated carbon adsorption of quinolone antibiotics in water: Performance, mechanism, and modeling[J]. Journal of Environmental Sciences, 2017, 56(6): 145-152.
[11] HOLMES A B, GU F X. Emerging nanomaterials for the application of selenium removal for wastewater treatment[J]. Environmental Science: Nano, 2016, 3: 982-996.
[12] HOU Y, SUN J, ZHANG D, et al. Porphyrin-alkaline earth MOFs with the highest adsorption capacity for methylene blue[J]. Chemistry A European Journal, 2016, 22(18): 6345- 6352.
[13] KOZLOVA E A, PANCHENKO V N, HASAN Z, et al. Photoreactivity of metal-organic frameworks in the decolorization of methylene blue in aqueous solution[J]. Catalysis Today, 2016, 266: 136-143.
[14] CHEN L, LI Y, DU Q, et al. High performance agar/graphene oxide composite aerogel for methylene blue removal[J]. Carbohydrate Polymers, 2017, 155: 345-353.
[15] WAN W, ZHANG R, LI W, et al. Graphene-carbon nanotube aerogel as an ultra-light, compressible and recyclable highly efficient absorbent for oil and dyes[J]. Environmental Science: Nano, 2016, 3(1): 107-113.
[16] ZHENG D, ZHANG M, DING L, et al. Facile synthesis of magnetic resorcinol-formaldehyde(RF) coated carbon nanotubes for methylene blue removal[J]. RSC Advances, 2016, 6(15): 11973-11979.
[17] SHAO Y, ZHOU L, BAO C, et al. Magnetic responsive metal-organic frameworks nanosphere with core-shell structure for highly efficient removal of methylene blue[J]. Chemical Engineering Journal, 2016, 283: 1127-1136.
[18] CHENG T, ZHIJUAN Z, YUFANG F, et al. Highly dispersed DPPF locked in knitting hyper crosslinked polymers as efficient and recyclable catalyst[J]. Chemistry Select, 2018, 3(21): 5987-5992.
[19] YANG R X, WANG T T and DENG W Q. Extraordinary capability for water treatment achieved by a perfluorous conjugated microporous polymer[J]. Scientific Reports, 2015, 5: 10155.
[20] WANG J, WANG G, WANG W, et al. Hydrophobic conjugated microporous polymer as a novel adsorbent for removal of volatile organic compounds[J]. Journal of Materials Chemistry A, 2014, 2(34): 14028-14037.
[21] FENG L J, CHEN Q, ZHU J H, et al. Adsorption performance and catalytic activity of porous conjugated polyporphyrins via carbazole-based oxidative coupling polymerization[J]. Polymer Chemistry, 2014, 5: 3081-3088.
[22] TAN L, TAN B. Hypercrosslinked porous polymer materials: design, synthesis, and applications[J]. Chemical Society Reviews, 2017, 46(11): 3322-3356.
[23] XU S, SONG K, LI T, et al. Palladium catalyst coordinated in knitting N-heterocyclic carbene porous polymers for efficient Suzuki-Miyaura coupling reactions[J]. Journal of Materials Chemistry A, 2015, 3(3): 1272-1278.
[24] LI Q, ZHAN Z, JIN S, et al. Wettable magnetic hypercrosslinked microporous nanoparticle as an efficient adsorbent for water treatment[J]. Chemical Engineering Journal, 2017, 326: 109-116.
[25] SONG K, ZOU Z, WANG D, et al. Microporous organic polymers derived microporous carbon supported Pd catalysts for oxygen reduction reaction: impact of framework and heteroatom[J]. the Journal of Physical Chemistry C, 2016, 120(4): 2187-2197.
[26] SONG K, LIU P, WANG J, et al. Controlled synthesis of uniform palladium nanoparticles on novel micro-porous carbon as a recyclable heterogeneous catalyst for the Heck reaction[J]. Dalton Transactions, 2015, 44(31): 13906-13913.
[27] FU Y F, SONG K P, ZOU Z J, et al. External cross-linked sulfonate-functionalized N-heterocyclic carbenes: an efficient and recyclable catalyst for Suzuki-Miyaura reactions in water[J]. Transition Metal Chemistry, 2018, 43(8): 665-672.
[28] MARION N, NOLAN S P. Well-defined N-heterocyclic carbenes palladium(II) precatalysts for cross-coupling reactions[J]. Accounts of Chemical Research, 2008, 41(11): 1440-1449.
[29] HASSAN A F, ABDEL-MOHSEN A M, FOUDA M M G. Comparative study of calcium alginate, activated carbon, and their composite beads on methylene blue adsorption[J]. Carbohydrate Polymers, 2014, 102: 192-198.
[30] ZHANG X, ZHANG L, LI Z, et al. Rational design of antifouling polymeric nanocomposite for sustainable fluoride removal from NOM-rich water[J]. Environmental Science Technology, 2017, 51(22): 13363-13371.
[31] GONTE R, BALASUBRAMIAN K. Heavy and toxic metal uptake by mesoporous hypercrosslinked SMA beads: Isotherms and kinetics[J]. Journal of Saudi Chemical Society, 2016, 20: S579-S590.
[32] BALARAK D, JAAFARI J, HASSANI G, et al. The use of low-cost adsorbent(Canola residues) for the adsorption of methylene blue from aqueous solution: Isotherm, kinetic and thermodynamic studies[J]. Colloids and Interface Science Communications, 2015, 7: 16-19.
[33] WANG Y, ZHANG W, QIN M, et al. Green one-pot preparation of α-Fe2O3@carboxyl-functionalized yeast composite with high adsorption and catalysis properties for removal of methylene blue[J]. Surface and Interface Analysis, 2018, 50(5): 311-320.
[34] ZHANG S, ZENG M, LI J, et al. Porous magnetic carbon sheets from biomass as an adsorbent for the fast removal of organic pollutants from aqueous solution[J]. Journal of Materials Chemistry A, 2014, 2(12): 4391- 4397.
[35] HAN J, DU Z, ZOU W, et al. In-situ improved phenol adsorption at ions-enrichment interface of porous adsorbent for simultaneous removal of copper ions and phenol[J]. Chemical Engineering Journal, 2015, 262: 571-578.
[36] NEKOUEI F, NEKOUEI S, TYAGI I, et al. Kinetic, thermodynamic and isotherm studies for acid blue 129 removal from liquids using copper oxide nanoparticle-modified activated carbon as a novel adsorbent[J]. Journal of Molecular Liquids, 2015, 201: 124-133.
[37] ZHANG L, LIU Y, WANG S, et al. Selective removal of cationic dyes from aqueous solutions by an activated carbon-based multicarboxyl adsorbent[J]. RSC Advances, 2015, 5(121): 99618-99626.
[38] LALLEY J, HAN C, LI X, et al. Phosphate adsorption using modified iron oxide-based sorbents in lake water: kinetics, equilibrium, and column tests[J]. Chemical Engineering Journal, 2016, 284: 1386-1396.
[39] WAN X, ZHAN Y, LONG Z, et al. Core@double-shell structured magnetic halloysite nanotube nano-hybrid as efficient recyclable adsorbent for methylene blue removal[J]. Chemical Engineering Journal, 2017, 330: 491-504.
[40] PEYDAYESH M, RAHBAR-KELISHAMI A. Adsorption of methylene blue onto Platanus orientalis leaf powder: kinetic, equilibrium and thermodynamic studies[J]. Journal of Industrial and Engineering Chemistry, 2015, 21: 1014-1019.
[41] GHAEDI M, HAJJATI S, MAHMUDI Z, et al. Modeling of competitive ultrasonic assisted removal of the dyes-Methylene blue and Safranin-O using Fe3O4 nanoparticles[J]. Chemical Engineering Journal, 2015, 268: 28-37.
[42] SHOKOOHI R, TORKSHAVAND Z, MAHMOUDI M M, et al. Effective removal of Azo dye reactive blue 222 from aqueous solutions using modified magnetic nanoparticles with sodium alginate/hydrogen peroxide[J]. Environmental Progress & Sustainable Energy, 2018. DOI: 10.1002/ep.12971.
[43] WANG D, YU H, FAN X, et al. High aspect ratio carboxylated cellulose nanofibers cross-linked to robust aerogels for superabsorption-flocculants: paving way from nanoscale to macroscale[J]. ACS Applied Materials Interfaces, 2018, 10(24): 20755-20766.