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22 protocols using 1 3 propanesultone

1

Synthesis of Bisphenol E Cyanate Ester

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Ammonium hydroxide solution (25% of NH3, TatChemProduct, Kazan, Russia), tetraethylorthosilicate (TEOS, >99.9%, ALDRICH Chemistry, Saint Louis, MI, USA), tetrabutylammonium hydroxide solution (40% in water, Fluka Analytical, Saint Louis, MI, USA), 1,3-propanesultone (98%, ALDRICH Chemistry, Saint Louis, MI, USA), bisphenol E (>98%, TCI, Zwijndrecht, Belgium), phosphorus pentoxide (99%, Vecton, Saint Petersburg, Russia), n-hexane (>98%, EKOS-1, Moscow, Russia), toluene (99.5%, EKOS-1, Moscow, Russia), and tetrahydrofuran (THF, >98%, ChemMed, Kazan, Russia) were purchased and used without additional purification. Bisphenol E cyanate ester of purity 99.5% was synthesized according to the previously described synthetic procedure (Figure 1) [32 (link),33 (link)]. The purity of synthesized monomer was no less than 99.5% according to high-performance liquid chromatography (HPLC). Absolute ethanol was obtained by consecutive distillations of 96% ethanol over CaO and CaH2. Deionized water (18.2 MΩ) was obtained by Arium mini instrument (Sartorius, Goettingen, Germany).
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2

Synthesis and Characterization of EASB-1a and EASB-1b

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Example 1

Materials

Glycolic acid ethoxylate lauryl ether (average Mn ˜360, 98%, sigma), glycolic acid ethoxylate lauryl ether (average Mn ˜690, sigma), 3-(dimethylamino)-1-propylamine (Aldrich, 99%), sodium fluoride (ACS reagent, ≥99%), 1,3-propanesultone (98%, Aldrich), aluminum oxide (puriss., ≥98% Al2O3 basis) were used for the synthesis of EASB-1a and EASB-1b. Solvents were distilled for the synthesis and purification of EASB-1a and EASB-1b. Salts for the preparation of formation water (FW) and sea water (SW) including NaHCO3, NaCl, CaCl2, Na2SO4, and MgCl2 were purchased from Sigma-Aldrich. Table 1 summarizes the amount of each ion in FW and SW.

TABLE 1
Composition of simulated oilfield water
Formation waterSea water
Ions(g/L)(g/L)
Na59.518.3
Ca19.10.7
Mg2.52.1
SO42−0.44.3
Cl132.132.2
HCO30.40.1
Total21457.7

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3

Synthesis and Characterization of Surfactant-based Crude Oil Emulsions

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Curcumin (CRC) (≥99.5%), 1,3-propanesultone (≥99%), potassium tertiary butoxide (t-BuOK) (≥98%), glycidyl 4-nonylphenyl ether (GNE), ethanolamine (EA) (≥98%), diethylene glycol (DEG) (99%), bis (2-chloroethyl) ether (BCE) (≥99%), ethanol absolute (≥99.8%), xylene, dimethylformamide (DMF), and dioxane were purchased from Sigma-Aldrich Co (Missouri, MO, USA). The crude oil was obtained from Aramco Co. Saudi Arabia, and its specifications were fully reported in our previous work [17 (link)]. The brine solution (35 g/L) was prepared in the laboratory using sodium chloride and distilled water.
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4

Zwitterionic Polyethersulfone Membrane Synthesis

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Polyethersulfone (PES) in pellet form (Solvay Specialty Polymers), N-Methyl-2-pyrrolidone (purity >99.5%, RCl-Labscan) and polyvinylpyrrolidone (PVP K30, Sigma-Aldrich) as additive were used for fabrication of membrane substrate. 1,3-phenylenediamine (MPD) and trimesoyl chloride (TMC) purchased from Sigma Aldrich were used to form a PA layer on top of the PES substrate. To synthesize zwitterion properties polymer, 2-(dimethylamino)ethyl methacrylate (DMAEMA, 95%), 2-bromoisobutyrate bromide, diisobutylaluminium hydride (1.0 M in toluene), ethyl 2-bromoisobutyrate (EBiB, 98%), 1,3-propanesultone (99%), dipyridyl (Bpy, AR), 2-bromoisobutyryl bromide (98%), copper(I) bromide (CuBr, 99%) and 1-hexyl-3-methylimidazolium chloride (HMImCl) were purchased from Sigma Aldrich. Diethyl ether was purchased from RCl-Labscan. Sodium chloride (NaCl, Merck) was used as test solute for membrane flux and rejection determination. The feed solution containing the respective test solute was prepared by dissolving the solute in deionized (DI) water.
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5

Cationic Surfactant Synthesis Protocol

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N,N′-Dimethyl-1,6-hexanediamine, alkyl bromide and 1,3-propanesultone were purchased from Sigma–Aldrich. Potassium carbonate and acetone were obtained from Chempur; acetonitrile was purchased from POCh SA. All compounds were AR quality and they were used without further purification.
All the surfactants solutions were prepared with the use of water from the PURELAB Classic, Elga with resistivity 18.2 MΩ cm.
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6

Synthesis and Purification of Zwitterionic Monomer

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Styrene (Sty, 99%, Sigma) was passed through a column filled with basic alumina to remove inhibitors and then stored at −20 °C before use. The zwitterion sulfobetaine monomer (SB) was synthesized according to our previously reported procedure using N-(4-vinyl benzyl)-N,N-dimethylamine (90%) which was purchased from ACROS and 1,3-propane sultone (99%, Sigma) in dichloromethane at 50 °C for 24 h.38 (link) The initiator potassium persulfate (K2S2O8, KPS, 99.9%, Sigma) was used without further purification. Other solvents and reagents were of analytical grade and purchased from Merck, VWR and Fisher Scientific. The dialysis tubing (Spectra/Por®) regenerated cellulose membrane with a molecular weight cutoff (MWCO) of 12k–14k Da were purchased from Spectrum Laboratories. Deionized water (DI water) was purified using a Millipore water purification system and filtered by 0.45 μm filter before use. The silicon wafers and the glass substrate were supplied by Latech, Singapore. The silicon wafer and the glass substrate were cleaned using hexane, soap-solution and ethanol followed by drying under nitrogen flow and then kept in the oven at 50 °C before use.
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7

Synthesis of Nafion-Graphite-Ceria Composite

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The Nafion solution (5 wt%) in aqueous alcohol and graphite powder used were commercial products of DuPont (Wilmington, DE, USA), with the trade name of D521, and Asbury Carbons with the trade name of 3775, respectively. Ceria, with a particle size of 25 nm or less, was purchased from Sigma-Aldrich (St. Louis, MO, USA). Sodium nitrate (NaNO3, ≥99%), potassium permanganate (KMnO4, ≥99%), sodium hydride (NaH, 90%), 1,3-propane sultone (98%), N,N-dimethylacetamide (DMAc, ≥99.5%), and iron(II) chloride tetrahydrate (FeCl2•4H2O, ≥99%) were also purchased from Sigma-Aldrich (St. Louis, MO, USA). Sulfuric acid (H2SO4, 95%), hydrochloric acid (HCl, 35%), tetrahydrofuran anhydrous (THF, 99%), and hydrogen peroxide (H2O2, 30%) were purchased from Daejung Chemicals (Siheung, Gyeonggi, Korea). All reagents were used as received without further purifications.
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8

Quantification of Phenolic Acids via CEC

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Standards of salicylic acid (1), cinnamic acid (2), syringic acid (3), rosmarinic acid (4), caffeic acid (5) and chlorogenic acid (6) were purchased from Sigma Aldrich (St. Louis, MO, USA); their purity was ≥98%. All solvents (acetonitrile, methanol) and chemicals (ammonium acetate and ammonia) required for CEC analysis had p.A. quality and were bought from Merck Eurolab (Vienna, Austria). Ultrapure water was prepared using a Sartorius arium purification system (Göttingen, Germany).
Chemicals for preparation of the monolith, i.e. 1,4 butanedione, 1-propanol, 2,2-diphenyl-1-picryl-hydrazyl, 3-(trimethoxysilyl) propyl methacrylate, dimethylformamide, allylimidazole, 1,3-propanesultone, dimethylformamide, 2,2-dimethoxy-2-phenylacetophenone and ethyleneglycol dimethacrylate were also obtained from Sigma Aldrich.
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9

Synthesis of NIPAM-based Polymers

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Azobisisobutyronitrile (AIBN, Merck, 98%) and N-isopropylacrylamide (NIPAM, Acros, 99%) purification was performed via re-crystallization from methanol and n-hexane respectively. 4-Vinylpyridine (4-VP, Sigma-Aldrich, 95%) was refined through vacuum distillation. 2-(Dodecylthiocarbonothioylthio)-2-methylpropionic acid (DDMAT, Sigma-Aldrich, 98% HPLC) make dried under vacuum, preliminary to use. 1,4-Dioxane (Fluka, 99.5%) dried initially using CaCl2 and then by refluxing in the presence of sodium wire. 1,3-Propanesultone (Sigma-Aldrich, 98%) was used as obtained.
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10

Immobilization of Lipase from Candida antarctica

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Lipase from Candida Antarctica B (CALB) (powder), imidazole, KOH, K2CO3, MgSO4, FeCl3.6H2O, FeCl2.4H2O, NaOH, n-alkylbromide *, 1,3-propane sultone, (3-aminopropyl)triethoxysilane and glutaraldehyde were obtained from Sigma-Aldrich (Saint Louis, Missouri, MO, USA). The solvent solutions (acetonitrile, ethyl acetate, acetone, hexane, dichloromethane, chloroform, methanol, toluene) were purchased from Synth (Diadema, São Paulo, Brazil) and used without previous purification. * Corresponding to n = 4, 10 and 18.
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