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Coating sponge with multifunctional and porous metal-organic framework for oil spill remediation
Chemical Engineering Journal 370 (2019) 1181–1187
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Chemical Engineering Journal journal homepage: www.elsevier.com/locate/cej
Coating sponge with multifunctional and porous metal-organic framework for oil spill remediation ⁎
Zhouqing Xua, Jiwei Wanga, Huijun Lia, , Yan Wangb, a b
T
⁎
College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo, Henan 454000, China School of Safety Science and Engineering, Henan Polytechnic University, Jiaozuo 454000, China
H I GH L IG H T S
highly hydrophobic material was • Asynthesized by crystals and melamine
G R A P H I C A L A B S T R A C T
A highly hydrophobic and effective oil/water separation material was produced by a stable porous metal-organic framework (HPU-13) and melamine sponge as carrier.
sponge.
material exhibited excellent re• This cyclable absorption of oil and organic solvents.
oil adsorption capacity can reach • Its up to 13,000%. oil collecting device was conducted • An to collect oil continuously from water.
A R T I C LE I N FO
A B S T R A C T
Keywords: Oil spill Hydrophobic composite material Melamine sponge Oil collecting device
It is worth to synthesize high-efficient sorbents for oil spill on ocean or rivers due to its fatal influence on marine life as well as human beings. This article introduced a highly hydrophobic and oleophilic composite material (MS-CMC-HPU-13) consists of water-stable porous Metal-Organic Framework (MOF) crystals and melamine sponge (MS). This specified composite material exhibited excellent recoverable and recyclable absorption performance of oil and organic solvents. The oil adsorption capacity of MS-CMC-HPU-13 can reach up to 13,000%, proving its potential ability to clean up oil spill. Besides, an oil collecting device assembled by MS-CMC-HPU-13, pipe and self-suction pump is constructed, which can collect oil continuously from the water surface with high speed under harsh conditions.
1. Introduction Nowadays, due to the deadly effect on marine life as well as human beings from oil spills in ocean and rivers, the demand for low-cost and effective oil/water separation materials is increasingly urgent [1–3]. Generally speaking, the ideal oil/water separation material should meet the following criteria: a) can effectively recover the oil spill; b) environment-friendly; c) strong applicability under harsh sea conditions; ⁎
d) easy manipulation [4–7]. In this respect, hydrophobic and oleophilic porous sorbents have more advantages over general skimmers, booms, solidifiers, dispersants or in-situ combustion applied in removing oil spill [8–11]. As a kind of burgeoning materials, Metal-Organic Frameworks (MOFs) have gained enormous research attention in the past decade due to that their extraordinary features such as high porosity, functional tenability and easy synthesis process reward MOFs with potential candidates for a wide range of applications [12–15]. There are
Corresponding authors. E-mail addresses: [email protected] (H. Li), [email protected] (Y. Wang).
https://doi.org/10.1016/j.cej.2019.03.288 Received 14 December 2018; Received in revised form 29 March 2019; Accepted 30 March 2019 Available online 01 April 2019 1385-8947/ © 2019 Elsevier B.V. All rights reserved.
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large porous, highly hydrophobic and low-density MOFs participating in sewage treatment [16–21]. However, every bean has its black. MOFs often exhibit a few weak points such as poor physical strength and low processability [22,23]. Besides, the crystalline frameworks are brittle and typically exist as insoluble powders. Additionally, many researched MOFs are hydrolytically unstable, suffering from irreversible structural degradation after a few hours of exposure to humid air [24,25]. Under the unsatisfactory results, MOFs can be integrated onto or within various substrates to produce a cost-effective, shapeable and chemically inert product, which will expand their applications in practice [26,27]. This kind of composite material combining the advantages of carrier and modifiers, can effectively make up for the defects of single material so as to exhibit good oil/water separation performance. Melamine sponge (MS), made up of melamine formaldehyde, has the outstanding properties of cheap, light-weight, easy modification and commercially available, and is a good substrate for preparation of composite materials [28,29]. HPU-13 reported with oleophilic property and hierarchically engineered micropores showed high water-stability and remarkable adsorption toward Cr(VI) [30]. By taking advantage of its great benefits, HPU-13 may be an ideal oil/water separation material to be integrated onto substrate. However, there are not enough coordination functional groups on the pore surface of MS. We envision using carboxymethylcellulose sodium (CMC) to wrap the branches of sponge, providing a surface rich in hydroxy and carboxylic groups, and then cooperating with metal ions to make attachment of HPU-13 firmly. In addition, partial Cu(I) in HPU-13 could be oxidized to Cu(II) with higher coordination number and more diversified coordination configurations, which also can improve the coordination possibility of HPU-13 with carboxyl groups of MS-CMC. Herein, the hydrophobic composite MS-CMC-HPU-13, as convenient adsorbent, can rapidly adsorb oil from water with an oil adsorption capacity of up to 13,000%, showing an excellent oil/water separation performance. Moreover, MSCMC-HPU-13, pipe and self-suction pump assembled oil collecting device is also conducted to collect oil continuously from the water surface with high efficiency.
Fig. 1. PXRD patterns of different products and simulated HPU-13.
(MS) was divided into cubic objects with a side length of 1 cm and then was dipped into methanol and dried at 80 °C for 8 h to remove contaminants. After that, the cubic MS was immersed in the solution of CMC (0.01 g/mL) and kept at 40 °C for 12 h. The MS-CMC was obtained after washing with methanol and dried at 80 °C for 8 h. Preparation of MS-CMC-HPU-13. The loading of HPU-13 particles on the sponge can be prepared according to the following method. HPU-13 particles were dispersed in water/ethanol (v:v = 1:1) solution. Then, MS-CMC were immersed in the above HPU-13 emission, kept in an ultrasound environment and heated at 60 °C for 2 h. Finally, the product was separated and dried at 40 °C for 2 h. The resultant MSCMC-HPU-13 can be obtained by repeating the above steps for 4 cycles. 2.3. Oil removal tests
2. Experimental procedures
Herein, machine oil, gasoline, diesel oil, cyclohexane, n-hexane, trichloromethane, methylbenzene were used as models in the oil removal tests. The adsorption capacity of oil from water was calculated by measuring the mass of MS-CMC-HPU-13 before and after oil adsorption (Table S1). It is important to note that weight measurements should be performed as soon as possible to prevent organic solvent or oils evaporation. When MS-CMC-HPU-13 after oil adsorption was placed in air for half an hour, weight measurement was conducted again to obtain weight errors.
2.1. Materials and physical measurements All chemical reagents were available commercially and used for purchase. IR data were collected on a BRUKER TENSOR 27 spectrophotometer with KBr pellets in the region of 400–4500 cm−1. Powder X-ray diffraction (PXRD) patterns were examined by a PANalytical X’Pert PRO diffractometer with CuKα radiation. The field-emission scanning electron microscopy (SEM) (S-4800, Hitachi, Japan) was introduced to characterize the microstructures and morphologies of the materials. The surface elements of the materials were characterized by electron dispersive spectroscopy (EDS). Thermo Scientific ESCALAB 250Xi X-ray photoelectron spectrometer (XPS) system was employed to obtain XPS spectra (Al K X-ray source was used). An optical tensiometer (DSA100 Instruments) was used to measure the contact angles of water droplets on MOF-coated melamine foam.
3. Result and discussion As is dsscribed, HPU-13 shows a porous structural character with two different channels: hexagonal and triangular micropores along the c axis due to the existence of the skeletons of ligands. The hexagonal cage has large dimensions of 20.947 × 20.720 Å2. The triangular micropores have a pore size of 7.207 Å. The effective free voids of HPU-13 are occupied as 36.0% of the crystal volume calculated by PLATON analysis. The surface of the pores is packed with aromatic nucleus which gives rise to the hydrophobic property of HPU-13 (Fig. 2). The water contact angle of block HPU-13 is 122.2° which further confirms its hydrophobic property (Fig. S1). Moreover, porous HPU-13 with hydrophobic surface has been evidenced that it can retain its framework in water even for a long time. So we selected HPU-13 as an ideal candidate as the separation material for oil/water system. However, its powder form will restrict its practical application. Therefore, HPU-13 was coated on MS which is candidate for the fabrication of oil/water separation material due to its low density, easy modification, low cost and high porosity. Unfortunately, continuous phase of HPU-13 cannot be grown on the micropore surface of MS
2.2. Synthesis process Preparation of HPU-13. HPU-13 was synthesized according to the literature [30]. Briefly, a mixture of CuSO4 (24.9 mg) and HL (11 mg) in H2O and ethanol (8/2) was placed in a 15 mL bottle and heated for 72 h at 160 °C. The final solution was cooled to room temperature, and then yellow block crystals of HPU-13 were acquired, washed with acetone, and dried in air. Yield: 78%. PXRD pattern was recorded in Fig. 1, which showed that it was comparable to the simulated ones calculated from the single-crystal diffraction data, indicating a pure phase of sample. Preparation of MS-CMC. Commercially available melamine sponge 1182
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Fig. 2. View of a) the porous structure, b) triangular micro-pore, and c) hexagonal micro-pore of HPU-13.
through the in-situ growth process. Because the synthesis of HPU-13 required high temperature, at which MS was not stable. Our previous report showed that the Cu(I) could be oxidized to Cu(II), which might afford higher coordination number and more diversified configurations of metal ions. However, there are not enough coordination sites on the micropore surface of MS ensuring the attachment. So we need versatile molecular linkers attaching HPU-13 onto the strut surface of sponge to ensure powerful attachment. CMC, with favorable adhesion and dispersion can form thin surface adherent on various materials primarily, and then serves as a platform for secondary expected modification. On the other hand, the presence of CMC on the sponge pore surface could offer many eCOOH and eOH groups as potential coordination sites [31]. Therefore, MS was firstly immersed into the solution of CMC to obtain CMC shrouded MS. XPS and IR were performed on MS-CMC (Figs. S2 and S3). XPS showed that the peaks of Na and O both proved the CMC modification on the MS. As shown in Fig. S3, the IR spectrum of MS-CMC shows the absorption band at 1128 cm−1 is due to CeO stretching of the ether group of the carboxymethylation of CMC [32,33]. Compared with the eC]O absorption band of CMC at 1640 cm−1, MS-CMC displays a slightly shift at 1630 cm−1. Besides, MS-CMC also shows the sharp triazine ring deformation vibration absorption at 810 cm−1, which is attributed the existence of MS. Moreover, it seems that the intensity of hydrogen bonding of CMC has been increased as a result of the polymerization of MS as indicated from the wide abroad absorption band starting at 3004 and end at 3692 cm−1. This may explain the formation of hydrogen bonding between the carboxylic groups themselves and the non-substituted hydroxyl groups of cellulose molecule. Therefore, CMC was successfully loaded on the surface of MS. Then, the loading of HPU-13 particles on MS-CMC was conducted by dipping MS-CMC into the water/ethanol suspension of HPU-13 by ultrasonication and keeping at 60 °C for 2 h. Under this condition, a small quantity of Cu(I) on the surface of HPU-13 reacted with oxidation material and changed to Cu(II) confirmed by XPS measurement. Cu(II) ions further coordinated with carboxyl groups of CMC enhancing the interaction between HPU-13 and MS-CMC. Powder X-ray diffraction (PXRD) analysis was carried out to verify the successful coating of HPU13 crystals on the sponge. From Fig. 1, MS-CMC-HPU-13 revealed crystalline diffraction peaks in accordance with the diffraction peaks of HPU-13, demonstrating the successful coating of HPU-13 on the sponge. Besides, the surface morphologies of MS, MS-CMC and MSCMC-HPU-13 were characterized by SEM (Figs. 3 and S4). The results
showed that the clean and smooth skeleton suface of the original sponge became very rough after coating HPU-13 for four cycles, which confirmed HPU-13 thin film was successfully prepared within the walls of sponge by the rapid in-situ growth method (Scheme 1). In order to explain the immobilization of HPU-13 on the surface of sponge, the chemical states of Cu in HPU-13 and MS-CMC-HPU-13 were analyzed by XPS. As shown in Fig. S5, there is only Cu(I) in HPU13. As for the product MS-CMC-HPU-13, the peaks deconvoluted into two doublets belongs to Cu 2p1/2 and Cu 2p3/2. The one made up of two peaks has the binding energies of 943.35 and 962.65 eV ascribed to Cu (II); the other with binding energies of 932.19 and 951.95 eV is corresponding to that of the Cu(I) suggesting the partial oxidation of Cu(I) to Cu(II) on the MS-CMC-HPU-13 occurred during the loading process. O 1 s analysis showed a shift of 0.5 eV for MS-CMC-HPU-13 (532.4 eV, O in MS-CMC is 531.9 eV), which is attributed to the interaction between HPU-13 and sponge via chemical bonding [16,34,35]. So the attachment of HPU-13 crystals to the surface of sponge was enhanced by the coordination of O to Cu(II) ions in HPU-13. Besides, the IR spectra of MS-CMC-HPU-13 indicated that the absorption peak of eCOOH at 1620 cm−1 showed a little shift compared with that of MS-CMC proving the coordination of CueO (Fig. S3). Then, we investigated the effect of HPU-13 coating on the sponge. We dipped one drop of water on MS-CMC-HPU-13 and found water could stand on the sponge. The water contact angle of MS-CMC-HPU-13 is in the range of 126.1–127.1° (Fig. 4). Comparatively, the water contact angle of MS was not obtained, which was attributed to the strong hydrophilic of MS. Besides, when both MS, MS-CMC and MSCMC-HPU-13 were immersed in water, only MS-CMC-HPU-13 could float on the surface without sinking, while MS and MS-CMC sank immediately after being immersed in water (Fig. S6). Even when MS-CMCHPU-13 was forced into water, it also could float back to the surface without absorbing water, proving its low density and hydrophobicity. However, MS-CMC-HPU-13 sank immediately in organic solvents confirming its lipophilicity (Fig. S6). In order to verify the potential application in water and oil separation system, we investigated the oil adsorption performance of MSCMC-HPU-13. As shown in Fig. 5, MS-CMC-HPU-13 could adsorb all oil on the surface of the mixture in several seconds. Even if heavy oil was used instead of light oil mixed with water, MS-CMC-HPU-13 also could adsorb the bottom oil immediately (video 1). Herein, different types of oils widely used in our daily life or industry were used as models to assess the adsorption characteristic of MS-CMC-HPU-13. As shown in 1183
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A
B
10 μm
10 μm
Fig. 3. SEM images of MS (A) and MS-CMC-HPU-13 after coating for four cycles (B). Inset: the photographs of MS and MS-CMC-HPU-13.
Scheme 1. Schematic of fabrication of HPU-13 coated melamine sponge.
lipophilicity of HPU-13 on the surface of sponge. The pore surface of HPU-13 packed with aromatic nucleus gives rise to the lipophilicity of the HPU-13, which repels water and makes MS-CMC-HPU-13 exhibit a superior adsorption capacity for diverse oils and organic solvents. More importantly, MS-CMC-HPU-13 can be recovered and reused simply by compressing the captured oil. However, the sumless times of adsorption-compressing operation make the purification of water so
Fig. 6 and Table S1, MS-CMC-HPU-13 has very high adsorption capacities for these oils, ranging from 6600 to 13,000%. Even when weight measurement were conducted half an hour later, MS-CMC-HPU-13 still has high adsorption capacities ranging from 4600 to 7600%. The excellent absorption capacity of MS-CMC-HPU-13 is higher than those of other MOFs-based composites [17,21] due to two aspects: i: the outstanding nature of melamine sponge as the composite template; ii: the
A
B
Fig. 4. A: The image of water on the surface of MS-CMC-HPU-13; B: contact angle measurements of MS-CMC-HPU-13. 1184
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Fig. 5. A) Light oil (dyed red) adsorption of MS-CMC-HPU-13 for oil spill cleanup from water; B) heavy oil (dyed red) adsorption of MS-CMC-HPU-13 for oil spill cleanup from water.
favourably confirming its ability to withstand harsh conditions. As we know, demulsification is also an important challenge for the oil/water separation. So the adsorption performance under emulsified conditions was also conducted (video 5). The results showed that emulsification almost did not affect oil adsorption. SEM showed that the crystals of HPU-13 were still attached on the walls of sponge without obvious defoliation or cracks after oil adsorption/desorption for several cycles, which should be attributed to the good affinity of HPU-13 with melamine sponge (Fig. 8).
tedious and boring that developing a simple method is necessary. Impaired that the introduction of pumping force will make the oil spill collection more continuously, in-situ pumping was applied to collect the oil and recycle the sorbents. First, we tried to connect MS-CMCHPU-13, tube, pump and the recycled vessel. When the device was conducted in water, only several air bubbles appeared in the collection vessel under the suction force of pump (video 2). For the oil/water mixed solution, the oil floating on the water surface was quickly adsorbed and transported continuously through the tube to the recycled vessel until all of the oil was collected (video 3). The complete process took only a few seconds, which suggested that this operation is very effective and time-saving (Fig. 7). In the real world, extreme weather conditions, such as strong winds or powerful waves often appeared in marine environment. In order to simulate the extreme environmental conditions at sea, the whole oil/water separation system was manually shaken. As shown in video 4, the separation system was also proceeded
4. Conclusions In summary, a highly hydrophobic and effective oil/water separation material was produced by a combination of stable porous metalorganic framework (HPU-13) and MS. The composite MS-CMC-HPU13, combining advantages of highly porosity of HPU-13 and portable
B
A
Fig. 6. The adsorption efficiency of MS-CMC-HPU-13 for diverse oils and organic solvents (A: weight measurements was performed as soon as possible to prevent organic solvent or oils evaporation; B: weight measurements was performed when MS-CMC-HPU-13 after oil adsorption was placed in air for half an hour). 1185
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i
ii
iii
Fig. 7. Photographs of continuously collecting methylbenzene (dyed red) in-situ from water surface with the apparatus (tube: the inner diameter is 2 mm, pump: 4.5 V).
Fig. 8. SEM and elemental mapping of MS-CMC-HPU-13 after adsorbing oil for four cycles.
substrate, could quickly adsorb oil from water and its oil adsorption capacity can reach up to 13,000% showing an excellent oil/water separation performance. Besides, consecutive collection of oil in-situ from water with a high speed was also realized by a self-assembly pump composed of MS-CMC-HPU-13 and pipes. On account of these data, we believe that this composite with good recoverability and recyclability would expand its potential ability of cleaning up oil spills.
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Acknowledgements This work was supported by the Science and technology research project of Henan province (182102311085), National Natural Science Foundation of China (No. 21601050), NSFC – Henan region mutual funds (U1604124), the key scientific research project of Henan higher education (16A150010), and Henan basic and frontier technology research project (162300410219). Appendix A. Supplementary data Supplementary data to this article can be found online at https:// doi.org/10.1016/j.cej.2019.03.288. References [1] L.R. Shi, K. Chen, R. Du, A. Bachmatiuk, M.H. Rümmeli, K.W. Xie, Y.Y. Huang, Y.F. Zhang, Z.F. Liu, Scalable Seashell-based chemical vapor deposition growth of three-dimensional graphene foams for oil-water separation, J. Am. Chem. Soc. 138 (2016) 6360–6393.
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Chemical Engineering Journal journal homepage: www.elsevier.com/locate/cej
Coating sponge with multifunctional and porous metal-organic framework for oil spill remediation ⁎
Zhouqing Xua, Jiwei Wanga, Huijun Lia, , Yan Wangb, a b
T
⁎
College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo, Henan 454000, China School of Safety Science and Engineering, Henan Polytechnic University, Jiaozuo 454000, China
H I GH L IG H T S
highly hydrophobic material was • Asynthesized by crystals and melamine
G R A P H I C A L A B S T R A C T
A highly hydrophobic and effective oil/water separation material was produced by a stable porous metal-organic framework (HPU-13) and melamine sponge as carrier.
sponge.
material exhibited excellent re• This cyclable absorption of oil and organic solvents.
oil adsorption capacity can reach • Its up to 13,000%. oil collecting device was conducted • An to collect oil continuously from water.
A R T I C LE I N FO
A B S T R A C T
Keywords: Oil spill Hydrophobic composite material Melamine sponge Oil collecting device
It is worth to synthesize high-efficient sorbents for oil spill on ocean or rivers due to its fatal influence on marine life as well as human beings. This article introduced a highly hydrophobic and oleophilic composite material (MS-CMC-HPU-13) consists of water-stable porous Metal-Organic Framework (MOF) crystals and melamine sponge (MS). This specified composite material exhibited excellent recoverable and recyclable absorption performance of oil and organic solvents. The oil adsorption capacity of MS-CMC-HPU-13 can reach up to 13,000%, proving its potential ability to clean up oil spill. Besides, an oil collecting device assembled by MS-CMC-HPU-13, pipe and self-suction pump is constructed, which can collect oil continuously from the water surface with high speed under harsh conditions.
1. Introduction Nowadays, due to the deadly effect on marine life as well as human beings from oil spills in ocean and rivers, the demand for low-cost and effective oil/water separation materials is increasingly urgent [1–3]. Generally speaking, the ideal oil/water separation material should meet the following criteria: a) can effectively recover the oil spill; b) environment-friendly; c) strong applicability under harsh sea conditions; ⁎
d) easy manipulation [4–7]. In this respect, hydrophobic and oleophilic porous sorbents have more advantages over general skimmers, booms, solidifiers, dispersants or in-situ combustion applied in removing oil spill [8–11]. As a kind of burgeoning materials, Metal-Organic Frameworks (MOFs) have gained enormous research attention in the past decade due to that their extraordinary features such as high porosity, functional tenability and easy synthesis process reward MOFs with potential candidates for a wide range of applications [12–15]. There are
Corresponding authors. E-mail addresses: [email protected] (H. Li), [email protected] (Y. Wang).
https://doi.org/10.1016/j.cej.2019.03.288 Received 14 December 2018; Received in revised form 29 March 2019; Accepted 30 March 2019 Available online 01 April 2019 1385-8947/ © 2019 Elsevier B.V. All rights reserved.
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large porous, highly hydrophobic and low-density MOFs participating in sewage treatment [16–21]. However, every bean has its black. MOFs often exhibit a few weak points such as poor physical strength and low processability [22,23]. Besides, the crystalline frameworks are brittle and typically exist as insoluble powders. Additionally, many researched MOFs are hydrolytically unstable, suffering from irreversible structural degradation after a few hours of exposure to humid air [24,25]. Under the unsatisfactory results, MOFs can be integrated onto or within various substrates to produce a cost-effective, shapeable and chemically inert product, which will expand their applications in practice [26,27]. This kind of composite material combining the advantages of carrier and modifiers, can effectively make up for the defects of single material so as to exhibit good oil/water separation performance. Melamine sponge (MS), made up of melamine formaldehyde, has the outstanding properties of cheap, light-weight, easy modification and commercially available, and is a good substrate for preparation of composite materials [28,29]. HPU-13 reported with oleophilic property and hierarchically engineered micropores showed high water-stability and remarkable adsorption toward Cr(VI) [30]. By taking advantage of its great benefits, HPU-13 may be an ideal oil/water separation material to be integrated onto substrate. However, there are not enough coordination functional groups on the pore surface of MS. We envision using carboxymethylcellulose sodium (CMC) to wrap the branches of sponge, providing a surface rich in hydroxy and carboxylic groups, and then cooperating with metal ions to make attachment of HPU-13 firmly. In addition, partial Cu(I) in HPU-13 could be oxidized to Cu(II) with higher coordination number and more diversified coordination configurations, which also can improve the coordination possibility of HPU-13 with carboxyl groups of MS-CMC. Herein, the hydrophobic composite MS-CMC-HPU-13, as convenient adsorbent, can rapidly adsorb oil from water with an oil adsorption capacity of up to 13,000%, showing an excellent oil/water separation performance. Moreover, MSCMC-HPU-13, pipe and self-suction pump assembled oil collecting device is also conducted to collect oil continuously from the water surface with high efficiency.
Fig. 1. PXRD patterns of different products and simulated HPU-13.
(MS) was divided into cubic objects with a side length of 1 cm and then was dipped into methanol and dried at 80 °C for 8 h to remove contaminants. After that, the cubic MS was immersed in the solution of CMC (0.01 g/mL) and kept at 40 °C for 12 h. The MS-CMC was obtained after washing with methanol and dried at 80 °C for 8 h. Preparation of MS-CMC-HPU-13. The loading of HPU-13 particles on the sponge can be prepared according to the following method. HPU-13 particles were dispersed in water/ethanol (v:v = 1:1) solution. Then, MS-CMC were immersed in the above HPU-13 emission, kept in an ultrasound environment and heated at 60 °C for 2 h. Finally, the product was separated and dried at 40 °C for 2 h. The resultant MSCMC-HPU-13 can be obtained by repeating the above steps for 4 cycles. 2.3. Oil removal tests
2. Experimental procedures
Herein, machine oil, gasoline, diesel oil, cyclohexane, n-hexane, trichloromethane, methylbenzene were used as models in the oil removal tests. The adsorption capacity of oil from water was calculated by measuring the mass of MS-CMC-HPU-13 before and after oil adsorption (Table S1). It is important to note that weight measurements should be performed as soon as possible to prevent organic solvent or oils evaporation. When MS-CMC-HPU-13 after oil adsorption was placed in air for half an hour, weight measurement was conducted again to obtain weight errors.
2.1. Materials and physical measurements All chemical reagents were available commercially and used for purchase. IR data were collected on a BRUKER TENSOR 27 spectrophotometer with KBr pellets in the region of 400–4500 cm−1. Powder X-ray diffraction (PXRD) patterns were examined by a PANalytical X’Pert PRO diffractometer with CuKα radiation. The field-emission scanning electron microscopy (SEM) (S-4800, Hitachi, Japan) was introduced to characterize the microstructures and morphologies of the materials. The surface elements of the materials were characterized by electron dispersive spectroscopy (EDS). Thermo Scientific ESCALAB 250Xi X-ray photoelectron spectrometer (XPS) system was employed to obtain XPS spectra (Al K X-ray source was used). An optical tensiometer (DSA100 Instruments) was used to measure the contact angles of water droplets on MOF-coated melamine foam.
3. Result and discussion As is dsscribed, HPU-13 shows a porous structural character with two different channels: hexagonal and triangular micropores along the c axis due to the existence of the skeletons of ligands. The hexagonal cage has large dimensions of 20.947 × 20.720 Å2. The triangular micropores have a pore size of 7.207 Å. The effective free voids of HPU-13 are occupied as 36.0% of the crystal volume calculated by PLATON analysis. The surface of the pores is packed with aromatic nucleus which gives rise to the hydrophobic property of HPU-13 (Fig. 2). The water contact angle of block HPU-13 is 122.2° which further confirms its hydrophobic property (Fig. S1). Moreover, porous HPU-13 with hydrophobic surface has been evidenced that it can retain its framework in water even for a long time. So we selected HPU-13 as an ideal candidate as the separation material for oil/water system. However, its powder form will restrict its practical application. Therefore, HPU-13 was coated on MS which is candidate for the fabrication of oil/water separation material due to its low density, easy modification, low cost and high porosity. Unfortunately, continuous phase of HPU-13 cannot be grown on the micropore surface of MS
2.2. Synthesis process Preparation of HPU-13. HPU-13 was synthesized according to the literature [30]. Briefly, a mixture of CuSO4 (24.9 mg) and HL (11 mg) in H2O and ethanol (8/2) was placed in a 15 mL bottle and heated for 72 h at 160 °C. The final solution was cooled to room temperature, and then yellow block crystals of HPU-13 were acquired, washed with acetone, and dried in air. Yield: 78%. PXRD pattern was recorded in Fig. 1, which showed that it was comparable to the simulated ones calculated from the single-crystal diffraction data, indicating a pure phase of sample. Preparation of MS-CMC. Commercially available melamine sponge 1182
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Fig. 2. View of a) the porous structure, b) triangular micro-pore, and c) hexagonal micro-pore of HPU-13.
through the in-situ growth process. Because the synthesis of HPU-13 required high temperature, at which MS was not stable. Our previous report showed that the Cu(I) could be oxidized to Cu(II), which might afford higher coordination number and more diversified configurations of metal ions. However, there are not enough coordination sites on the micropore surface of MS ensuring the attachment. So we need versatile molecular linkers attaching HPU-13 onto the strut surface of sponge to ensure powerful attachment. CMC, with favorable adhesion and dispersion can form thin surface adherent on various materials primarily, and then serves as a platform for secondary expected modification. On the other hand, the presence of CMC on the sponge pore surface could offer many eCOOH and eOH groups as potential coordination sites [31]. Therefore, MS was firstly immersed into the solution of CMC to obtain CMC shrouded MS. XPS and IR were performed on MS-CMC (Figs. S2 and S3). XPS showed that the peaks of Na and O both proved the CMC modification on the MS. As shown in Fig. S3, the IR spectrum of MS-CMC shows the absorption band at 1128 cm−1 is due to CeO stretching of the ether group of the carboxymethylation of CMC [32,33]. Compared with the eC]O absorption band of CMC at 1640 cm−1, MS-CMC displays a slightly shift at 1630 cm−1. Besides, MS-CMC also shows the sharp triazine ring deformation vibration absorption at 810 cm−1, which is attributed the existence of MS. Moreover, it seems that the intensity of hydrogen bonding of CMC has been increased as a result of the polymerization of MS as indicated from the wide abroad absorption band starting at 3004 and end at 3692 cm−1. This may explain the formation of hydrogen bonding between the carboxylic groups themselves and the non-substituted hydroxyl groups of cellulose molecule. Therefore, CMC was successfully loaded on the surface of MS. Then, the loading of HPU-13 particles on MS-CMC was conducted by dipping MS-CMC into the water/ethanol suspension of HPU-13 by ultrasonication and keeping at 60 °C for 2 h. Under this condition, a small quantity of Cu(I) on the surface of HPU-13 reacted with oxidation material and changed to Cu(II) confirmed by XPS measurement. Cu(II) ions further coordinated with carboxyl groups of CMC enhancing the interaction between HPU-13 and MS-CMC. Powder X-ray diffraction (PXRD) analysis was carried out to verify the successful coating of HPU13 crystals on the sponge. From Fig. 1, MS-CMC-HPU-13 revealed crystalline diffraction peaks in accordance with the diffraction peaks of HPU-13, demonstrating the successful coating of HPU-13 on the sponge. Besides, the surface morphologies of MS, MS-CMC and MSCMC-HPU-13 were characterized by SEM (Figs. 3 and S4). The results
showed that the clean and smooth skeleton suface of the original sponge became very rough after coating HPU-13 for four cycles, which confirmed HPU-13 thin film was successfully prepared within the walls of sponge by the rapid in-situ growth method (Scheme 1). In order to explain the immobilization of HPU-13 on the surface of sponge, the chemical states of Cu in HPU-13 and MS-CMC-HPU-13 were analyzed by XPS. As shown in Fig. S5, there is only Cu(I) in HPU13. As for the product MS-CMC-HPU-13, the peaks deconvoluted into two doublets belongs to Cu 2p1/2 and Cu 2p3/2. The one made up of two peaks has the binding energies of 943.35 and 962.65 eV ascribed to Cu (II); the other with binding energies of 932.19 and 951.95 eV is corresponding to that of the Cu(I) suggesting the partial oxidation of Cu(I) to Cu(II) on the MS-CMC-HPU-13 occurred during the loading process. O 1 s analysis showed a shift of 0.5 eV for MS-CMC-HPU-13 (532.4 eV, O in MS-CMC is 531.9 eV), which is attributed to the interaction between HPU-13 and sponge via chemical bonding [16,34,35]. So the attachment of HPU-13 crystals to the surface of sponge was enhanced by the coordination of O to Cu(II) ions in HPU-13. Besides, the IR spectra of MS-CMC-HPU-13 indicated that the absorption peak of eCOOH at 1620 cm−1 showed a little shift compared with that of MS-CMC proving the coordination of CueO (Fig. S3). Then, we investigated the effect of HPU-13 coating on the sponge. We dipped one drop of water on MS-CMC-HPU-13 and found water could stand on the sponge. The water contact angle of MS-CMC-HPU-13 is in the range of 126.1–127.1° (Fig. 4). Comparatively, the water contact angle of MS was not obtained, which was attributed to the strong hydrophilic of MS. Besides, when both MS, MS-CMC and MSCMC-HPU-13 were immersed in water, only MS-CMC-HPU-13 could float on the surface without sinking, while MS and MS-CMC sank immediately after being immersed in water (Fig. S6). Even when MS-CMCHPU-13 was forced into water, it also could float back to the surface without absorbing water, proving its low density and hydrophobicity. However, MS-CMC-HPU-13 sank immediately in organic solvents confirming its lipophilicity (Fig. S6). In order to verify the potential application in water and oil separation system, we investigated the oil adsorption performance of MSCMC-HPU-13. As shown in Fig. 5, MS-CMC-HPU-13 could adsorb all oil on the surface of the mixture in several seconds. Even if heavy oil was used instead of light oil mixed with water, MS-CMC-HPU-13 also could adsorb the bottom oil immediately (video 1). Herein, different types of oils widely used in our daily life or industry were used as models to assess the adsorption characteristic of MS-CMC-HPU-13. As shown in 1183
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A
B
10 μm
10 μm
Fig. 3. SEM images of MS (A) and MS-CMC-HPU-13 after coating for four cycles (B). Inset: the photographs of MS and MS-CMC-HPU-13.
Scheme 1. Schematic of fabrication of HPU-13 coated melamine sponge.
lipophilicity of HPU-13 on the surface of sponge. The pore surface of HPU-13 packed with aromatic nucleus gives rise to the lipophilicity of the HPU-13, which repels water and makes MS-CMC-HPU-13 exhibit a superior adsorption capacity for diverse oils and organic solvents. More importantly, MS-CMC-HPU-13 can be recovered and reused simply by compressing the captured oil. However, the sumless times of adsorption-compressing operation make the purification of water so
Fig. 6 and Table S1, MS-CMC-HPU-13 has very high adsorption capacities for these oils, ranging from 6600 to 13,000%. Even when weight measurement were conducted half an hour later, MS-CMC-HPU-13 still has high adsorption capacities ranging from 4600 to 7600%. The excellent absorption capacity of MS-CMC-HPU-13 is higher than those of other MOFs-based composites [17,21] due to two aspects: i: the outstanding nature of melamine sponge as the composite template; ii: the
A
B
Fig. 4. A: The image of water on the surface of MS-CMC-HPU-13; B: contact angle measurements of MS-CMC-HPU-13. 1184
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Fig. 5. A) Light oil (dyed red) adsorption of MS-CMC-HPU-13 for oil spill cleanup from water; B) heavy oil (dyed red) adsorption of MS-CMC-HPU-13 for oil spill cleanup from water.
favourably confirming its ability to withstand harsh conditions. As we know, demulsification is also an important challenge for the oil/water separation. So the adsorption performance under emulsified conditions was also conducted (video 5). The results showed that emulsification almost did not affect oil adsorption. SEM showed that the crystals of HPU-13 were still attached on the walls of sponge without obvious defoliation or cracks after oil adsorption/desorption for several cycles, which should be attributed to the good affinity of HPU-13 with melamine sponge (Fig. 8).
tedious and boring that developing a simple method is necessary. Impaired that the introduction of pumping force will make the oil spill collection more continuously, in-situ pumping was applied to collect the oil and recycle the sorbents. First, we tried to connect MS-CMCHPU-13, tube, pump and the recycled vessel. When the device was conducted in water, only several air bubbles appeared in the collection vessel under the suction force of pump (video 2). For the oil/water mixed solution, the oil floating on the water surface was quickly adsorbed and transported continuously through the tube to the recycled vessel until all of the oil was collected (video 3). The complete process took only a few seconds, which suggested that this operation is very effective and time-saving (Fig. 7). In the real world, extreme weather conditions, such as strong winds or powerful waves often appeared in marine environment. In order to simulate the extreme environmental conditions at sea, the whole oil/water separation system was manually shaken. As shown in video 4, the separation system was also proceeded
4. Conclusions In summary, a highly hydrophobic and effective oil/water separation material was produced by a combination of stable porous metalorganic framework (HPU-13) and MS. The composite MS-CMC-HPU13, combining advantages of highly porosity of HPU-13 and portable
B
A
Fig. 6. The adsorption efficiency of MS-CMC-HPU-13 for diverse oils and organic solvents (A: weight measurements was performed as soon as possible to prevent organic solvent or oils evaporation; B: weight measurements was performed when MS-CMC-HPU-13 after oil adsorption was placed in air for half an hour). 1185
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ii
iii
Fig. 7. Photographs of continuously collecting methylbenzene (dyed red) in-situ from water surface with the apparatus (tube: the inner diameter is 2 mm, pump: 4.5 V).
Fig. 8. SEM and elemental mapping of MS-CMC-HPU-13 after adsorbing oil for four cycles.
substrate, could quickly adsorb oil from water and its oil adsorption capacity can reach up to 13,000% showing an excellent oil/water separation performance. Besides, consecutive collection of oil in-situ from water with a high speed was also realized by a self-assembly pump composed of MS-CMC-HPU-13 and pipes. On account of these data, we believe that this composite with good recoverability and recyclability would expand its potential ability of cleaning up oil spills.
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