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Rapidly Degradable and Sustainable Polyhemiaminal Aerogels for Self-Driven Efficient Separation of Oil /Water Mixture Zhaoqian Li, Jia Qiu, Shen Yuan, Qingping Luo, and Chonghua Pei Ind. Eng. Chem. Res., Just Accepted Manuscript • Publication Date (Web): 16 May 2017 Downloaded from http://pubs.acs.org on May 19, 2017

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Industrial & Engineering Chemistry Research

Rapidly Degradable and Sustainable Polyhemiaminal Aerogels for Self-Driven Efficient Separation of Oil /Water Mixture Zhaoqian Li1*, Jia Qiu2, Shen Yuan1, Qingping Luo1, Chonghua Pei1* 1 State Key Laboratory Cultivation Base for Nonmetal Composites and Functional Materials, Southwest University of Science and Technology, Mianyang 621010, P. R. China. 2 School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, P. R. China

ABSTRACT: The separation of oil /water mixture by the use of selective absorption materials has been currently studied most wildly. However, the safe disposal of the absorbent waste is challenging. Here, Degradable polyhemiaminal (PHA) aerogel was fabricated by one-step precipitation-polymerization. The resulting PHA aerogels showed low density, hydrophobicity and high specific surface areas. This characteristic, together with the porous structure, imparted it with outstanding properties of oil/water separation. More interestingly, a device made of PHA aerogel can automatically collect gasoline on the water surface without external forces. Furthermore, PHA aerogel exhibited rapid degradation after use, and major raw material for synthesis of PHA aerogels is readily recoverable and further recycles. This work provides simple, environmentally friendly and sustainable materials for oil/water separation. KEYWORDS: Aerogels, Degradable, Polyhemiaminal, Oil/water separation, Self-driven 1. Introduction Separation of oil /water mixture has become a worldwide challenge because that water pollution resulting from the leakage of oils and organic solvents has caused serious environmental and ecological problems [1-2]. Filtration and absorption is two methods to selectively separate oil/water mixture at present. Filtration methods mainly adopt some filtration materials permitting only water or oil to pass through causing a selective separation [3-5]. 3-D porous materials (polymer aerogels/ sponges and carbon-based aerogels/ sponges) with high specific surface areas, highly efficient and recyclable

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absorption of organic solvents or oils have been developed to selectively separate oil/water mixture by absorption methods [6-17]. However, difficulties in in-situ removal for filtration materials and limited absorption capacity for porous absorbents restrict their wide practical applications. To solve these issues, self-driven oil/water separation method has been recently presented using some selective-wettability materials. For example, Song fabricated an oil container capped with superhydrophobic mesh[18]. The device can collect floating oil on water by surface-tension-driven and gravity-assisted. Wang et al. have designed a mini boat made from superhydrophobic fabric that can automatically dispose oil spill [19]. However, self-driven devices were fabricated from superhydrophobic materials easily fouled by oil, which resulted in a decrease in separation efficiency and its service life. Once they were abandoned after a limited recyclable absorption, they can easily result in secondary pollution to the environment. Therefore, it will be important to design environmentally friendly materials for oil/water separation [20-21]. Hence, aerogel sorbents derived from cellulose have been recently developed for oil-absorption. Cellulose aerogel made a hydrophobic surface treatment including chemical vapor deposition, atom layer deposition, sol−gel, and esterification have exhibited superior oil-absorption performance[22-29]. However, complex and energy-consuming hydrophobization process will be a challenge to the practical application. It’s also important to consider the degradability of hydrophobic cellulose after use. Herein, we used a simple approach to fabricate hemiaminal dynamic covalent networks polymer (Polyhemiaminal,

PHA)

aerogels

by

polymerization

of

paraformaldehyde

(POM)

and

4,4’-Diaminodiphenyl ether (ODA). PHA aerogels exhibited excellent absorption properties of oils and organic solvents; self-driven collection device made of PHA aerogel can effectively separate gasoline on water surface. Furthermore, the aerogel after use can be rapidly degradable and major raw material(ODA)


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is able to recover for recycling, which avoids the secondary pollution and ensures material sustainability. 2. Material and methods 2.1 Materials Paraformaldehyde (analytical reagent) and 4,4’-Diaminodiphenyl ether (98% purity) were provided by Aladdin Reagent (Shanghai) Co., Ltd. N-Methylpyrrolidone (NMP, analytical reagent) was purchased from ChengDu Kelong Chemical Reagent Company. All above-mentioned reagents and solvent were used as received. 2.2 Synthesis of PHA aerogel PHA was synthesized according to previous reports (Scheme 1) [30-32]. Different amounts ODA and POM (Table 1) was adequately dissolved in 30 mL NMP under nitrogen protection and the reactions were kept at 100 °C for 5 h. The white PHA gels were formed and were washed with NMP, acetone and ultrapure water in turn. Finally, PHA aerogels were obtained by a vacuum freeze-drying. N

O

O

+

NH2

H2N

O H

N H

N

N

N

O O

N

Scheme 1 Synthesis of PHA with ODA and POM Table 1 PHA aerogels with different monomer content Sample

ODA(g)

POM(g)

PHA-1.2

1.2

0.9



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PHA-1.6

1.6

1.2

PHA-2.0

2.0

1.5

2.3 Organic solvent or oil absorption PHA aerogel (~10 mg) were dipped into 10 mL of solvent or oil for 2 min. The oil absorption capacity was calculated as follows:

Cm = (m1 − m0 ) / m0 ×100% Where, m0 and m1 are the weight of PHA aerogel before and after sorption, respectively. 2.4 Degradation of PHA aerogels Sulfuric acid solution (1 mol/L) was dropwise added into PHA aerogels after absorption-drying process at room temperature and the degradation of PHA aerogels were recorded by a concealed camera. PHA aerogels were ground into powder, then added into a flask with 30 ml methanol/H2O (1:1, volume) solution including 3.0 g cation exchange resin. The system was immersed in a 80 °C oil bath. 2.5 Characterization Aerogel bulk density was determined according to ASTM D792-08. The specimen was weighed in air, and attached to the wire which attaches to the hook of the balance. Then the specimen and sinker were immersed in water at temperature of 23±2 °C. The mass of the suspended specimen, sinker and partially immersed wire were determined. Finally, weight the holder and sinker in water with immersion to same depth as used in the previous step and the bulk density of aerogels was calculated. The porosities were calculated using Porosity (%)=(1-ρaerogel/ρsolid) Where, ρaerogel and ρsolid are the densities of the aerogels and the densities of the solid, respectively. Contact angles measurements were carried out on a DSA-30 contact angle system (Kruss, Germany) at


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room temperature. Ultrapure water was used as test liquid. The morphology of cross-section of the aerogels was covered with Au and observed by Field-emission scanning electron microscopy (FE-SEM , Ultra 55, Carl zeiss SMT Pte Ltd). N2 adsorption and desorption at 77 k was carried on with apparatus and the specific surface area was determined by the Brunauer-Emmett-Teller (BET) model. Pore volume and pore size distribution of the aerogels was calculated by Barrett-Joyner-Halenda (BJH) method. Thermogravimetric analysis (TGA) of PHA aerogel was conducted by Q600 STD with heating rate of 10 K min-1 in air.

3. Results and discussion

Fig 1 a) FTIR of PHA aerogel. b) Photograph of PHA aerogel floated on water (dyed with writing ink). c) Water contact angle on PHA aerogel surface. PHA aerogel was prepared by the one-step precipitation-polymerization and FTIR spectra of PHA aerogel was shown in Fig 1a. The incorporation of methylene groups (2922, 2852 cm-1) into PHA structure indicated condensation of ODA and POM [30-32]. From Fig 1b, it can be seen that PHA aerogel floated on water, which reveals PHA aerogel possesses low density and light weight. The minimum bulk density of



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PHA aerogel was 82.5 mg/cm3 (Table2), which is comparable to that of polymer aerogels [33-34]. Meanwhile, the water contact angle of the PHA aerogel surface was 143.3° (Fig 1c), indicating that the PHA aerogel was hydrophobic. From Fig 2, it can be seen that aerogels exhibited a 3D interconnected, highly porous structures which were composed of randomly aggregated nanoparticles. The diameter of nanoparticles showed a gradual increase as the increase of concentrations of ODA. These phenomena have been observed in other precipitation-polymerization system, which might be attributed to the formation and growth rate of the nuclei particles [35-37]. In addition, there are many open pores of the size from nanometers to microns observed in the SEM micrographs, which would contribute to the adsorption of liquid.


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Fig 2 a,b). SEM images of PHA-1.2 aerogel. c,d) SEM images of PHA-1.6 aerogel. e,f) SEM images of PHA-2.0 aerogel. The porous property of PHA aerogels was examined by N2 adsorption-desorption analysis(Fig S1). As shown in Table 2, the BET surface areas of PHA-1.2, PHA-1.6 and PHA-2.0 aerogels are 167.16, 115.57 and 51.16 m2/g, respectively, and their corresponding total pore volumes are 0.575, 0.341 and 0.102 cm3/g. The mean pore sizes of PHA aerogels PHA-1.2, PHA-1.6 and PHA-2.0 aerogels are 13.7, 11.8 and 7.8 nm, respectively. PHA aerogel prepared at low concentration exhibits the highest porosity and its surface areas



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are greater than that of some polymer aerogels, which indicated that it has superior absorption properties in oil/water separation [14, 38]. The thermal stability and mechanical strength of PHA aerogel are essential to its application. The TGA for PHA aerogel demonstrated that it possessed 5% mass loss at ~180 °C(Fig S2). The mass loss was attributed mainly to the loss of water or NMP. PHA aerogel cylinder with 10 mm diameter can be subjected to a load of 100g, which assured mechanical strength enough in operation(Fig S3). Table 2 Physical parameters of PHA aerogels Sample

Bulk density

BET surface

Pore volume

Average pore

(g/cm3)

area (m2/g)

(cm3/g)

diameter(nm)

PHA-1.2

0.0825±0.0025

167.16

0.575

13.7

93.65

PHA-1.6

0.0953±0.0033

115.57

0.341

11.8

92.67

PHA-2.0

0.1041±0.0027

51.16

0.102

7.8

91.99

Porosity(%)

To simulate the removal oils from water, carbon tetrachloride was dropped at the bottom of water. When PHA aerogel was put into the water and contacted with carbon tetrachloride droplet, it selectively absorbed carbon tetrachloride from the water at once. The whole process of absorption happened within 1 second, indicating excellent organic solvents absorption from water (Fig 3a and Movies S1, Supporting Information). PHA aerogel could also quickly absorb mineral oil at the surface of water (Movies S2, Supporting Information). The adsorption kinetics of gasoline using the PHA aerogel is shown in Fig S4 (Supporting Information). It is found that aerogels need just 10 s to reach 90% of absorption equilibrium in gasoline. Such fast adsorption behaviors from water were assigned to the hydrophobic nature of PHA aerogel combining with features of high specific surface area.


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Fig 3 a) Absorption process of carbon tetrachloride (dyed with Sudan III) from water and b) Adsorption capacities of PHA aerogel (PHA-1.6) for various organic liquids. The absorption capability of PHA aerogels for several organic solvents and oils was determined by absorption experiments and is shown in Figure 3b. PHA aerogels can absorb up to 7-22 times of its own weight, determined by the densities of the liquids. The absorption capability of PHA aerogels is similar to the values reported for hydrophobic polymers[39]. Compared with some graphene-based aerogels, the absorption capability of PHA aerogels is lower, whereas its cost is low and its absorption-rate is quick,



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which should be considered for practical use [13-14]. Furthermore, we evaluated the adsorption cyclic performance of PHA aerogel via recovery cycles. The absorption capacities decreased with the number of cycles (Fig. S5), because the aerogel will contract during dry. If the aerogel was dried by supercritical fluid, the recycle of PHA aerogel will be fine due to its structural retention.

Fig 4 a) Photograph of PHA aerogel boat (PHA-1.6). b -e) Process of collection gasoline from water surface with PHA aerogel boat. f) Photograph of the self-driven separation of oil/water equipment. To improve absorption capability of PHA aerogels, we made a boat of PHA aerogel and carried on an experiment that simulated the self-driven collection oil on the water surface, as shown in Fig 4. The boat of PHA aerogel can float on water covered with gasoline, and gasoline can easily be quickly absorbed by PHA aerogel boat and penetrated into the boat with the aid of hydrostatic pressure and capillary force(benefit of the high porosity and surface areas). Meanwhile, water was not transmitted through the boat and excluded outside the boat, which may have been due to the hydrophobic nature of PHA aerogel (Fig 4b-e). The gasoline in the boat can be collected by the collection device utilizing siphonage (Fig 4f,


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Movies S3, Supporting Information). The process can be sustained until almost all gasoline existed on water was collected, even though more gasoline were further added to this system. About 12 mL gasoline was collected, which takes as long as 30 min. Boat/gasoline contact area may have implications for gasoline permeation into aerogel boat. The whole process requires no additional energy and is self-driven, which makes the collection of oil-spill easier. We made 3 time tries of recycling of PHA aerogel boat and found the separation properties of PHA aerogel boat were almost constant.

Fig 5 Rapid degradation of PHA aerogel (PHA-1.6) after use in H2SO4 solution. The rapid degradation of PHA aerogel after it was used is one salient point of our PHA aerogels, considering most absorbents could cause more pollution problems. As shown in Fig 5 (Screenshot of Movies S4, Supporting Information), PHA aerogel (After a cycle of absorption and release of carbon tetrachloride) quickly collapsed and was split into little pieces when sulfuric acid solution was dropped onto it. The little pieces further hydrolyzed and became the monomer dissolved into acid solution within a minute (Movies S4, Supporting Information). Depolymerization mechanism of PHA aerogel under H+ was shown in Scheme 2.



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N

O

O

H H2O H2N

N N

+

NH2

O H

H

N

N

O O

N

Scheme 2 Degradation of PHA aerogels. Based on it, we keep trying to hydrolyze the PHA aerogel using strongly acidic styrene type cation exchange resin which is environment-friendly in place of sulfuric acid. As shown in Fig 6, white turbid solution became clear after 15 min at 80 °C, which indicated PHA aerogel can be fractured and decomposed.

Fig 6 Degradation of PHA aerogel in cation exchange resin solution. a) before hydrolysis. b) after hydrolysis. In addition, major raw material(ODA) is able to recycle when saturated Na2CO3 solution was added to the solution, which caused plenty of bubbles formation and a precipitate to form finally (Movies S5, Supporting Information); the monomer ODA could be recovered through solution filter and has been corroborated by FTIR (Fig S6). Thus, the recovery and reuse of absorbents may mitigate the waste of


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resources and to prohibit the secondary pollution. Meanwhile, PHA aerogel exhibited its chemical stability towards pH>2 acidic solution, which assured its application under normal circumstances (Table S1).

4. Conclusions Degradable and hydrophobic PHA aerogels were fabricated by facile precipitation-polymerization. The resulting PHA aerogels showed low density, excellent absorption capacity of organic solvents and oils. Furthermore, self-driven oil collection can be achieved by a collection device made of PHA aerogels. More importantly, PHA aerogels also exhibited superior degradability after use and recovery of raw material for synthesis of PHA aerogel can be further recycled. These results demonstrate PHA aerogels are wonderful candidates for oil adsorption to settle oil spill or oil/water separation in the sight of further environmental protection and sustainable use of natural resources. Supporting Information Supporting material includes Nitrogen adsorption-desorption isothermal curves of PHA aerogel, TG curve of PHA aerogel, PHA aerogel supports a load of 100g, Adsorption kinetics of gasoline using PHA aerogel, Absorption recyclability of PHA aerogels, FTIR spectra of recovered ODA and Stability of PHA aerogel with different pH value (PDF); Remove of carbon tetrachloride with PHA aerogel from the bottom of water (wmv); Remove of mineral oil with PHA aerogel from water surface (wmv); Self-driven separation of oil/water mixture (wmv); Rapid degradation of PHA aerogel after use with sulfuric acid solution(wmv); Recovery process of ODA (wmv). Corresponding Author *Email: [email protected]; [email protected] Acknowledgements



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This work is supported by the doctoral research foundation of Southwest University of Science and Technology (No. 10zx7115) and the innovation team foundation of Education Department of Sichuan Province (No. 15TD0014). References (1) Whitfield, J. How to clean a beach, Nature 2003,422, 464-466. (2) Bove, F. J.;Fulcomer, M. C.;Klotz, J. B.;Esmart, J.;Dufficy, E. M.;Savrin, J. E. Public Drinking Water Contamination and Birth Outcomes, Am. J. Epidemiol. 1995,141, 850-862. (3) Kota, A. K.;Kwon, G.;Choi, W.;Mabry, J. M.;Tuteja, A. Hygro-responsive membranes for effective oil–water separation, Nat. Commun. 2012,3, 1025. (4) Gao, X.;Xu, L.-P.;Xue, Z.;Feng, L.;Peng, J.;Wen, Y.;Wang, S.;Zhang, X. Dual-Scaled Porous Nitrocellulose Membranes with Underwater Superoleophobicity for Highly Efficient Oil/Water Separation, Adv. Mater. 2014,26, 1771-1775. (5) Xue, Z.;Wang, S.;Lin, L.;Chen, L.;Liu, M.;Feng, L.;Jiang, L. A Novel Superhydrophilic and Underwater Superoleophobic Hydrogel-Coated Mesh for Oil/Water Separation, Adv. Mater. 2011,23, 4270-4273. (6) Gui, X.;Wei, J.;Wang, K.;Cao, A.;Zhu, H.;Jia, Y.;Shu, Q.;Wu, D. Carbon Nanotube Sponges, Adv. Mater. 2010,22, 617-621. (7) Qiu, S.;Jiang, B.;Zheng, X.;Zheng, J. T.;Zhu, C. S.;Wu, M. B. Hydrophobic and fire-resistant carbon monolith from melamine sponge: A recyclable sorbent for oil-water separation, Carbon 2015,84, 551-559. (8) Calcagnile, P.;Fragouli, D.;Bayer, I. S.;Anyfantis, G. C.;Martiradonna, L.;Cozzoli, P. D.;Cingolani, R.;Athanassiou, A. Magnetically Driven Floating Foams for the Removal of Oil Contaminants from Water, ACS Nano 2012,6, 5413-5419. (9) Wang, H.;Wang, E.;Liu, Z.;Gao, D.;Yuan, R.;Sun, L.;Zhu, Y. A novel carbon nanotubes reinforced superhydrophobic and superoleophilic polyurethane sponge for selective oil-water separation through a chemical fabrication, J. Mater. Chem. A 2015,3, 266-273. (10) Zhang, L.;Wu, J. T.;Zhang, X. M.;Gong, G. M.;Liu, J. G.;Guo, L. Multifunctional, marvelous polyimide aerogels as highly efficient and recyclable sorbents, Rsc Adv. 2015,5, 12592-12596. (11) Lee, P.;Rogers, M. A. Phase-Selective Sorbent Xerogels as Reclamation Agents for Oil Spills, Langmuir 2013,29, 5617-5621. (12) Yang,

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TOC 35x26mm (600 x 600 DPI)


Rapidly Degradable and Sustainable ... - ACS Publications

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