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A One-step and Scalable Continuous-flow Nanoprecipitation for Catalytic Reduction of Organic Pollutants in Water Yuezhen He, Rodney D. Priestley, and Rui Liu Ind. Eng. Chem. Res., Just Accepted Manuscript • DOI: 10.1021/acs.iecr.6b02279 • Publication Date (Web): 25 Aug 2016 Downloaded from http://pubs.acs.org on August 29, 2016

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A

Industrial & Engineering Chemistry Research

One-step

and

Scalable

Continuous-flow

Nanoprecipitation for Catalytic Reduction of Organic Pollutants in Water Yuezhen He†‡, Rodney D Priestley§ and Rui Liu†* †Ministry of Education Key Laboratory of Advanced Civil Engineering Material, School of Materials Science and Engineering, and Institute for Advanced Study, Tongji University, Shanghai, China,201804; ‡Anhui Key Laboratory of Chemo-Biosensing and Ministry of Education Key Laboratory of Functional Molecular Solids, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, China, 241000; §Department of Chemical and Biological Engineering, and Princeton Institute for the Science and Technology of Materials, Princeton University, Princeton, New Jersey, USA, 08544

KEYWORDS: one-step, continuous-flow, nanoprecipitation, reduction, organic pollutants

ABSTRACT: Efficient treatment of organic pollutants in water with facile and green technique is a great challenge in environmental remediation. In this paper, we report a simple and low-energy strategy for catalytic reduction of organic pollutants in water by continuous-flow flash nanoprecipitation. The reported one-step processing technique integrates rapid supported catalyst nanoprecipitation and ACS Paragon Plus Environment

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catalytic reaction in a continuous-flow fashion. Such a concept is successfully demonstrated for simultaneous formation of Au@polymer nanospheres and catalytic reduction of organic pollutants (e.g. methylene blue or 4-nitrophenol) in water. Furthermore, the catalytic reaction rate can be easily tuned by varying the processing parameter (e.g. feeding concentration). The activity of the nanocatalyst was demonstrated 5 time recycles without any detectible loss. The characteristics of continuous-flow mode enables the one-step process scalable, making it a promising processing methodology for wastewater treatment.

1. INTRODUCTION Water pollution, a widespread problem throughout the world, has greatly threatened aqueous habitats and human's health[1-4].A wide range of pollutants are considered for remediation and many decontamination methods have gained considerable attention for wastewater treatment. Adsorption is one of widely used methods and many new adsorbents are emerging for contaminants removal[5-9].The newly developed nanomaterials and nanotechnology provide new alternative strategies for water purification as well as offer some other useful products[10-13]. Among all the current decontamination methods, catalytic reduction or degradation of organic pollutants in water with the presence of noble metal catalyst is considered one of the most effective, environmental friendly and economically methods for environmental remediation and recovery[14,15]. For example, catalytic reduction and fading of organic dyes (e.g. methylene blue, rhodamine B) contribute to the development of decontaminating procedures[16,17]. 4-nitrophenol, another prevalent organic pollutant in wastewater generated from industrial and agricultural sources, can be efficiently removed by catalytic reduction. At the same time, the reduction product 4-aminophenol is an important pharmaceutical precursor to make a variety of medicines[18, 19]. With the progressive size decrease, the metal catalysts exhibit distinct catalytic properties as compared to their bulk materials[20]. However, a suitable support is necessary to prevent the aggregation of metal nanoparticles (NPs) for their use both in the laboratory and industry ACS Paragon Plus Environment

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scales[21,22]. In some cases, supports also act actively in the reaction mechanism and are frequently designed to rationalize the catalytic activity[23]. Therefore, a ideal support should meet the following requirements: 1) environmental stable; 2) not alter or block the active site of catalyst; 3) the welldefined NPs with a narrow size evenly distribute on the support. Traditional synthesis of supported metal NPs is usually through a two- or multiple-step process. The first step is pre-synthesis of inorganic, organic or composite supports. Next, further coating step(s) are employed to deposit metal NPs on the surface of support. For example, electrostatic interaction or metal recognition layer have been utilized to assemble support and metal NPs together[24,25]. In-situ reduction and deposition of metal NPs from metal precursors represents another important technology for the preparation of supported nanocatalysts[26]. Currently, challenge for the synthesis of supported nanocomposites is the development of a one-step/pot strategy with facile, green and efficient features[27-30]. To achieve this goal for supported nanocatalysts, both of the precursors should simultaneously form support and metal NPs while the interaction between support and metal NPs should be designed to rationally direct support growth and metal deposition. Another major challenge in wastewater treatment is removal of organic pollutants from effluents with an economic fashion. The goal of efficient and green process can be realized through consolidation preparation and application of nanocatalysts together with minimum environmental impact. The development of novel synthetic and chemical processing techniques not only makes the large scale production of fine chemicals possible, but also provides versatile platforms to be able to combine the materials synthesis and applications into a one-step operation[31-34]. Herein, we consolidate of multiple preparation and application steps into one step and report a continuous-flow process that achieves simultaneous rapid supported-catalyst nanoprecipitation and catalytic reduction of organic compounds in water.

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2. EXPERIMENTAL DETAILS 2.1 One-step continuous-flow nanoprecipitation for catalytic reduction A syringe containing 1 mL of 3 mg mL−1 polystyrene-b-poly(4-vinylpyridine) (PS793k-b-PVP35k, PDI = 1.08, Polymer Source Inc) in THF was placed at the inlet of Stream 1, and a syringe containing 1 mL of 0.45 mg mL−1 HAuCl4 in H2O was placed at the inlet of Stream 2. Subsequently, fluid was expressed manually from both syringes and merged into a mixing stream. The mixed exit stream was then inputted into a reservoir of 10 mL solution which contained 1 mg mL−1 of NaBH4 and 0.1 mg mL−1 of methylene blue (MB) or 0.02 mg mL−1 of 4-nitrophenol. The concentration of left HAuCl4 after reaction was spectrophotometrically determined by 3,3,5,5-tetramethylbenzidine (TMB) method[35]. After the nanoprecipitation process was completed, the catalyst was separated from the mixture by centrifuge, repeated wash and dried in a vacuum oven overnight for reuse in the next cycle. Effect of processing parameter on catalytic ability was studied by repeating the above procedure except the feeding HAuCl4 concentration at 0.15 mg mL−1. 2.2 Scalability of one-step continuous-flow process A two-stream CIJ mixer and a high-precision programmable syringe pump were employed to achieve a one-step continuous-flow nanoprecipitation for catalytic reduction of organic dye. In a typical experimental process, equal volumes (3.5 mL) of an organic stream (containing 3 mg mL−1 PS-b-PVP in THF) and a aqueous stream (containing 0.45 mg mL−1 HAuCl4) were admitted into the chamber of the mixer at controlled flow rate (~0.35mL s−1) using the syringe pump. After the syringe started, two streams mixed and flowed into the beaker containing 200 mL aqueous solution with 20 µg mL−1 MB and 0.1 mg mL−1 of NaBH4.

2.3 Characterization


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Transmission electron micrographs (TEM) were recorded on a JEOL JEM-2100F instrument at 200 kV equipped with a Gatan 894 Ultrascan 1k CCD camera (Japan). UV–vis absorption spectra were measured on Evolution 220 recording spectrophotometer (Thermofisher, America). 3. RESULTS AND DISCUSSION The basic concept of the proposed process is illustrated in Fig. 1 and employs the use of confined impinging jet (CIJ) mixer. The CIJ mixer, also termed Flash NanoPrecipitation (FNP), consists of three components (involving polymers, a solvent, and a non-solvent). The interior structure of CIJ mixer is T-shape mixer (Fig. S1), where syringe pumps are employed to drive two opposing liquid streams at high velocity and collide in the mixing chamber. The details of design and fabrication are described by Prud’homme[36] and Macosko[37]. During the FNP process, two high velocity linear jets of fluid mix in a small chamber [38-40]. In this manner, the block copolymer solution mixes with the non-solvent within a few milliseconds. The rapid mixing induces self-assembly of the block copolymers, which the water reservoir quenches into kinetically frozen NPs. The technique has been successfully used to make polymer NPs of uniform size within 30 nm to 800 nm, including pure polymer nanoparticles[41,42], hydrophobic molecules/particles entrapped biodegradable polymers[43,44],and metal supported polymer nanospheres[45]. The proposed use of CIJ mixer herein is based on a continuous confinedvolume flow system that enables simultaneous polymer self-assembly, metal formation and deposition, and catalytic reduction. In detail, two syringes were used: one containing PS-b-PVP dissolved in THF, and another containing HAuCl4 in H2O. Subsequently, two streams were expelled from both syringes through CIJ mixer at the same rate (~1 mL per second) and merged into a mixing stream. The mixed exit stream was then diluted into a water reservoir, which contained the reducing agent (e.g. NaBH4) and organic pollutants (e.g. methylene blue or 4-nitrophenol). The water reservoir quenched the precipitation of NPs while at the same time, the in-situ formed Au@PS-b-PVP NPs catalyzed the reduction reaction. Fig. 2A is photograph of the actual setup employed in the laboratory. The reduction of MB, a typical organic pollutant, was chosen as a model reaction. The reduction reaction did not proceed before flows ACS Paragon Plus Environment

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started, as evidenced by a constant blue color and constant absorption peak at 663 nm. When both streams started to flow, merged and then were introduced into the solution containing MB and NaBH4, the absorption at 663 nm quickly decreased (see Fig. 2B). The reaction was completed in 2 min, also demonstrated by the complete decoloration of MB from blue to clear (see Fig. 2A). The rate constant k, determined by a linear plot of ln(C0/Ct) and reaction time t, is 1.43 min−1 . The reaction rate is faster than that of the reported Au entrapped mesoporous silica[46] and core–shell Fe3O4@PolydopamineAg[47]. The fast reaction kinetics is believed to come from the direct and fast contact of reactant with the well-defined Au NPs with a narrow size deposited on the polymer support. A transmission electron microscopic (TEM) image in Fig. 3A of NPs collected after catalytic reaction shows that the obtained NPs with a regular spherical morphology have a uniform diameter about ~120 nm. It is clearly observed that the NP consists of a PS-b-PVP nanosphere, and Au NPs with a diameter of ~3 nm evenly distributed on the surface of polymer nanospheres. Lattice spacing of 0.259 nm corresponding to the (111) plane of face-centred cubic (fcc) structure of Au NPs is visually confirmed (Fig. 3A inset). No Au3+ was detected in the solution after the reaction, indicating 100% conversion of Au3+ to Au NPs and gold loading of 0.44 mmol g−1 in Au@PS-b-PVP. The turnover frequencies reaches 1.18 min-1 for one-step MB reduction. Noted that our previous report has prepared Au@PS-b-PVP composites through one-step FNP process[45]: mixing induced self-assembly of block polymer and complexation with AuCl4-, then complex dispersed into a water reservoir containing NaBH4 to reduce and form Au@PS-b-PVP. A control experiment was carried out by using DMF solution of poly(4-vinyl pyridine) (PVP, Mw of 60 000, Sigma-Aldrich) in Stream 1. As shown in Fig. S2B, only free Au NPs are formed while no polymeric nanospheres are observed, which may be due to the ionic and hydrophilic property of PVP units. On the other hand, both pure polystyrene nanospheres and free Au NPs are formed when feeding polystyrene solution in stream1[45]. The above comparison strongly indicate that the use of amphiphilic block copolymer PS-b-PVP is the key for the formation of polymer particle supported Au NPs. In current setup, the extension of catalytic application into one-step continuous flow mode was successfully demonstrated by the introduction of MB in the quenched solution with excess NaBH4. The ACS Paragon Plus Environment

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quenched nanocatalyst composites effectively catalyze the reduction of MB in the collection solution. The whole process simply integrates physical self-assembly, metal deposition and catalytic reduction into one continuous-flow nanoprecipitation process. The stability of supported nanocatalyst was investigated by repeating the same reduction reaction with the same catalyst after one-step reduction reaction. The catalyst retained the conversion close to 100% within 2 min of reaction time after 5 successive recycles (see Fig. 2B, inset). TEM images in Fig.3B clearly indicate that Au NPs are still well-dispersed on the surface of polymer support after 5 reaction cycles. Clearly, the polymer supports are stable enough to effectively prevent the coalescence of catalytic NPs, making the supported catalyst robust for repeated reaction cycles. A control experiment was carried out to exclude the possibility of MB adsorption by the pre-formed Au@PS-b-PVP[45]. No noticeable decrease of UV-vis absorption was observed after adding catalysts for 30 min with the absence of NaBH4 (see Fig. S3), indicating that adsorption is negligible for the initial MB reduction. The effect of processing parameter on the catalytic performance was studied by varying gold salt feeding concentration. Fig. 2C shows the UV-vis curve when decreasing the feeding HAuCl4 concentrations to 0.15 mg mL-1. The reduction reaction was completed in 5 min and the rate constant k was 0.71 min−1. Compared to the catalytic performance at HAuCl4 feeding concentrations of 0.45 mg mL-1, the reaction rate was decreased. TEM in Fig.S4 shows that low feeding concentration leads to the formation of Au NPs with sparser distribution on the surface of polymer nanospheres. The different catalytic behavior can be ascribed to the different coating density of gold due to the difference in the concentration of feeding stream, which demonstrates the tunable catalytic performance of the technique reported here. The simple process can be conveniently applied for other catalytic reduction reactions. Fig.4 shows the UV-vis curve of catalytic performance for 4-nitrophenol reduction. The absorption of 4-nitrophenol at 400nm quickly decreased and the absorption at 295 nm of the product 4-aminophenol increased when both streams started to flow. The whole reduction reaction was completed in 3 min and the rate constant ACS Paragon Plus Environment

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k was 0.62 min−1 at feeding HAuCl4 concentration of 0.45 mg mL-1(Fig.4A), while the catalytic reaction rate decreased when the feeding HAuCl4 reduced as shown in Fig. 4B,. The nanocatalysts also exhibited good reusability for 4-nitrophenol reduction without any detectible loss in activity after 5 times re-use (Fig.4A, inset). The characteristics of continuous-flow makes the one-step process scalable. As shown in Fig. 5A, twostream CIJ mixer and a high-precision programmable syringe pump were employed to scale up the whole process. Briefly, equal volumes 3.5 mL of block copolymer stream in THF and an aqueous stream were admitted into CIJ mixer at controlled flow rate using the syringe pump. After the pump started, two streams mixed and flowed into the beaker of 200 mL solution containing 20 µg mL-1of MB and 0.1 mg mL-1 of NaBH4.The solution of MB was quickly changed to colorless solution with a continuousflow fashion (see Fig.5B and Video S1).

4. CONCLUSIONS We have demonstrated a new methodology for one-step continuous-flow catalytic reduction of methylene blue or 4-nitrophenol in water. The whole process includes simultaneous rapid nanocatalyst preparation and catalytic reaction, which is believed to reduce the complexity and increase the efficiency of water purification. Control over the reaction rate and scalability of the process have been easily achieved. The nanocatalysts also exhibited good reusability. The one-step process presented here is therefore a simple, effective and versatile approach towards wastewater treatment. Meanwhile, the feature of continuous-flow makes possible the scalable treatment of polluted water from most industrial fields.


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Figure 1.Schematic process of one-step continuous-flow nanoprecipitation for catalytic reduction of organic pollutant in water

Figure 2.(a) Laboratory setup of one-step process for methylene blue reduction; (b) UV-vis absorption spectra of methylene blue reduction at feeding HAuCl4 concentration of 0.45 mg mL-1. Insets: graphic illustration of the reduction of methylene blue after 2 min versus the number of catalyst recycles; (c) UV-vis absorption spectra of methylene blue reduction at feeding HAuCl4 concentration of 0.15 mg mL1

Insets: the relationship between ln(C0/Ct) and reaction time at feeding HAuCl4 concentration of 0.45

mg mL-1 (black) and 0.15 mg mL-1 (red)


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Figure 3.(a) TEM image of supported nanocatalysts collected after catalytic reaction; (b) TEM image of supported nanocatalysts after 5 times re-uses


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Figure 4.(a) UV-vis absorption spectra of 4-nitrophenol reduction at feeding HAuCl4 concentration of 0.45 mg mL-1. Insets: graphic illustration of the reduction of 4-nitrophenol reduction after 3min versus the number of catalyst recycles; (b) UV-vis absorption spectra of 4-nitrophenol reduction solution at feeding HAuCl4 concentration of 0.15 mg mL-1 Insets: the relationship between ln(C0/Ct) and reaction time at feeding HAuCl4 concentration of 0.45 mg mL-1 (black) and 0.15 mg mL-1 (red)


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Figure 5.Scalable process of one-step continuous-flow nanoprecipitation for catalytic reduction (a) before flows started and (b)after flows ended

ASSOCIATED CONTENT Supporting Information is available free of charge on the ACS Publications website. Experimental procedures and characterizations (PDF) Video S1(AVI)

AUTHOR INFORMATION Corresponding Author * E-mail : [email protected] Notes The authors declare no competing financial interest.

ACKNOWLEDGMENT R.L. acknowledges the start-up funding from Tongji University and the Young Thousand Talented Program. Y.H. acknowledges support of the National Younger Natural Science Foundation of China ACS Paragon Plus Environment

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A One-Step and Scalable Continuous-Flow ... - ACS Publications

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