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9 protocols using 1 3 5 benzenetricarbonyl trichloride

1

Synthesis of Organic Benzene Derivatives

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1,3,5-Benzenetricarbonyl trichloride,
5-aminoisopthalic acid, and terephthaloyl chloride were bought from
Sigma-Aldrich. 4-Dimethylaminopyridine and methylene blue were bought
from Sisco Research Laboratories (SRL). Congo red was bought from
Alfa Aesar, and all the metal salts and solvents were bought from
Central Drug House (CDH) and utilized without further purification.
The solvents N,N-dimethylformamide
and N,N-dimethylacetamide (DMA)
were used without further distillation.
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2

Synthesis of PA Membranes with TiO2 NPs

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m-phenylenediamine (MPD, ≥99%) and 1,3,5-benzenetricarbonyl trichloride (TMC, 98%) were purchased from Sigma-Aldrich and used as reacting monomers for the synthesis of the PA films. Sodium dodecyl sulfate (SDS), camphorsulfonic acid (CSA), and triethylamine (TEA) were obtained from Fisher Scientific and utilized as the chemical additives in MPD-aqueous solution70 (link). Titanium (IV) isopropoxide (98%, density of 0.96 g/ml and molar mass of 284.215 g/mol), oleic acid (OA, ≥99%) and heptane (≥99%) were purchased from Sigma-Aldrich and employed for the synthesis of the TiO2 NPs. All chemicals were used as obtained without further purification. Polyethersulfone (PES) microfiltration sheets with average pore size of 100 nm were obtained from Sterlitech Co. (WA, USA) and applied as a supporting layer for the fabrication of the composite membranes.
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3

Synthesis and Characterization of Polymer Membranes

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N-methyl-2-pyrrolodinone (NMP, ≥99.5%), bovine serum albumin (BSA, ≥96%), polyethylene glycol 400 (PEG, Mn = 400g/mol), m-phenylene diamine (MPD, ≥99%), fluorescein isothiocyanate conjugated bovine serum albumin (BSA-FITC) and 1,3,5-benzenetricarbonyl trichloride (TMC, ≥99.9%) were purchased from Sigma-Aldrich (Shanghai, China). Sodium alginate (SA, C6H7NaO6, ≥96%), sodium sulfate (Na2SO4, ≥96%), sodium dodecyl benzene sulfonate (SDBS, ≥96%), N-hexane (≥96%) and sodium chloride (NaCl, ≥96%) were provided by Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China). Polyether sulfone (PES) was provided by BASF Co., Ltd. (Shanghai, China). Edible oil was purchased from Guo Brothers Grain Oil Co., Ltd. (Malaysia, Singapore). Yeast was purchased from Angel Yeast Co., Ltd. (Shanghai, China). Carbon fiber paper was obtained from Ce-Tech Co., Ltd. (Wuhan, China). All solutions were prepared with deionized water (DI-H2O) supplied by a Milli-Q Direct 8 purification system (Millipore, Burlington, MA, USA).
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4

Fabrication of Polysulfone Membranes with Cadmium Chloride Hydrate

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Cadmium chloride hydrate (99.998%, CdCl2·xH2O, x ≈ 2.5; Alfa Aesar), ethanolamine (>98%; Sigma-Aldrich), MPD (99%; Sigma-Aldrich), 1,3,5-benzenetricarbonyl trichloride (also known as TMC; 98%, Sigma-Aldrich), molecular sieves (3 Å, 1- to 2-mm beads; Alfa Aesar), hydrochloric acid (36.5 to 38.0%, HCl; Macron), polysulfone film (PS35, Sepro Corporation), potassium hydroxide (KOH), hexanes (99.9%; Fisher Chemical), isopropyl alcohol (IPA), and methanol (99.9%; Fisher Chemical for synthesis, and high-performance liquid chromatography (HPLC) grade, Fisher for permeance test) were used as received. Approximately 225-g molecular sieves were baked at 110°C in a glass jar for 1 day and then stored with hexane (1 liter). Water used in this study is nanopure water processed by a Milli-Q Advantage A10 system (18.2 megohm·cm at 25°C). All glassware was cleaned with a base bath (saturated KOH in IPA), followed by an acid bath (1 M HCl), thoroughly rinsed with water, and dried with nitrogen gas. Cadmium chloride hydrate, MPD, and TMC were carefully stored in a desiccator to prevent exposure to moisture, which is important for reproducible membrane synthesis.
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5

Fabrication of Superhydrophobic PVDF Membrane

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A flat sheet PVDF film (average thickness of 50 μm, pore size of 45 μm), silica nanoparticles (SiNPs, 10–20 nm), and 1,3,5-Benzenetricarbonyl trichloride (TMC, 98%) were purchased from Sigma-Aldrich, St. Louis, MO, USA. 1H,1H,2H,2H-Perfluorooctyltriethoxysilane (POTS, 98%) was acquired from Gelest, Morrisville, PA, USA. Sodium hydroxide, hexane was acquired from Daejung, Siheung-si, Korea. Copper tape, copper conductor, and Kapton tape were purchased from the local market.
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6

Synthesis and Characterization of Chlorine-Resistant Membranes

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PES was supplied by BASF Co., Germany. Polyvinylpyrrolidone (PVP), hexane, and 1,3,5-benzenetricarbonyl trichloride (TMC) with a purity of > 98% dispersed in hexane (98%; Aldrich, China) were supplied by Aladdin Co., China. N, N-dimethylacetamide (DMA) and 1,3-phenylenediamine were obtained from Sigma Co., China (MPD; 99%). HA was purchased from (Sigma-Aldrich Co., USA), and DA hydrochloride was obtained from Sigma-Aldrich Co., USA (International Laboratory, USA; 99%). Researchers have employed graphite (Sigma-Aldrich, USA), NaNO3 (Beijing Chemical Factory, China), H2O2, H2SO4 (Beijing Chemical Factory, China), and KMnO4 (Sigma-Aldrich, USA) to produce GO nanosheets (GONs), after which sodium hypochlorite was employed to assess the chlorine resistance of the membrane (Sigma Co., Egypt). For the FO experiment, sodium chloride (NaCl) was dissolved in deionized water (DI), which was prepared by a Milli-Q system (ACS reagent, Beijing Chemical Factory, China) (Millipore, USA). Sodium alginate, (KH2PO4), magnesium chloride (MgCl2), sodium hydrogen carbonate (NaHCO3), calcium chloride (CaCl2), and ammonium chloride (NH4Cl) (Chemical Supply Pty Ltd, China) were employed for the membrane fouling tests.
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7

Polysulfone-based Nanofiltration Membrane Fabrication

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Polysulfone (PSf) with an average molecular weight of 22 000 g mol−1 was purchased from Solvay (China). N,N-Dimethylformamide (DMF) (analytical purity of 99.5%), 1,3,5-benzenetricarbonyl trichloride (TMC, 98%), m-phenylenediamine (MPD, 99%), l-lysine (98%), hexane (anhydrous, 99%) and colloidal silica (with a particle size of 7–40 nm and specific surface area (BET) of 300 m2 g−1) were purchased from Aldrich (China).
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8

Synthesis of NIPAAm Hydrogels

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N-isopropylacrylamide (NIPAAm) (97%) was purchased from Sigma (Taufkirchen, Germany). Tetramethylethylenediamine (TEMED), ammonium persulfate (APS), N,N′-methylenebisacrylamide (MBA), 1,3,5-benzenetricarbonyltrichloride (TMC, 98%), n-hexane, p-phenylenediamine (PPD, 99%), triethylamine (TEA, 99.5%), polyethylene glycol (PEG-600), benzophenone, sodium chloride (NaCl,) propanol, and ethanol were obtained from Merck (Steinheim am Albuch, Germany).
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9

Polymeric Membranes for Water Purification

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Polysulfone (PSf, Udel® P-1700, MW = 67,000 g mol−1, Solvay) and polyethersulfone (PES, 3000 P, MW = 58,000 g mol−1, Merck) were dried overnight in an oven at 80 °C. N-methyl-2-pyrrolidone (NMP, ≥99.5%, MW = 99.13 g mol−1), polyethylene glycol 600 (PEG 600, MW = 570 g mol−1), 1,4-phenylenediamine (PPD, ≥99%, MW = 108.14 g mol−1), 1,3,5-benzenetricarbonyl trichloride (TMC, 98%, MW = 265.47 g mol−1), n-hexane (ACS grade, ≥96%, MW = 86.18 g mol−1) were all purchased from Merck & Co., Darmstadt, Germany. The sodium chloride (NaCl, MW = 58.44 g mol−1) was purchased from Hamburg Chemicals, Hamburg, Germany.
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