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5 protocols using 3 dimethylamino 1 propylamine

1

Synthesis of Amino Acid Derivatives

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1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), NaCl, NaBr, NaI, benzylamine, 33 wt% methylamine in absolute ethanol, 66.0–72.0% ethylamine in H2O, 3-(Dimethylamino)-1-propylamine, latex beads (polystyrene, 0.1 µm mean particle size), 4-morpholineethanesulfonic acid (MES) buffer were all purchased from Sigma–Aldrich. The precursor N-Boc-L-aspartic acid 1 and N-Boc-L-glutamic acid 3 were purchased from Alfa Aesar and TCI, respectively. All chemicals were used without any further purification. The precursor 2-hexen-1-yl-succinic acid 2 was synthesized by treating the corresponding anhydride with two (mass)-equivalents of MQ water, stirred overnight at room temperature, and then lyophilized41 (link). The product was stored at −20 °C until further use. The anhydride of N-Boc-L-aspartic acid was synthesized according to a previously published procedure, treating the diacid with the carbodiimide coupling agent DCC and recrystallization from an acetone/hexane mixture30 . HPLC grade acetonitrile was purchased from VWR. Milli-Q water was used provided from a Millipore water purifier system.
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2

Synthesis and Characterization of Viscoelastic Surfactants

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Stearic
acid (reagent grade, 95%, Sigma Aldrich), 1,3-propanesultone (≥99%,
Sigma Aldrich), 3-(dimethylamino)-1-propylamine (99%, Sigma Aldrich),
1,4-butane sultone (≥99%, Sigma Aldrich), piperazine (99%,
Sigma Aldrich), CaCl2 (anhydrous, powder, 99.99%, Sigma
Aldrich), acetone (≥99.8%, Honeywell), ethyl acetate (≥99.5%,
Honeywell), diethyl ether (≥99.5%, Honeywell), methanol-d4 (99 atom % D, Sigma Aldrich), D2O (99.9 atom % D, Sigma Aldrich), and CDCl3 (99.8 atom
% D, Sigma Aldrich) were purchased and used as received. Before each
experiment, the fresh stock solutions of anhydrous CaCl2 (10–30%) were prepared in deionized water. The final products
of VES molecules and the intermediates were characterized by 1H-NMR and 13C-NMR on a 400 MHz Bruker spectrometer
(AVANCE III) using TMS as an internal solvent by dissolving samples
in deuterated solvents. The functional groups were ascertained by
an FT-IR spectrophotometer (Perkin Elmer 16F PC, Perkin Elmer Inc.
USA). The apparent viscosities of different VES formulations were
determined using a Brookfield Rheometer DV3T linked with thermosel
through a programmable temperature controller (Ametek, USA). Thermogravimetric
analysis (TGA) was performed to assess the thermal stability of the
final products using an SDT Q600 (V20.9 Build 20) thermal analyzer.
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3

Chiral Column Synthesis and Evaluation

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CF6, C36H60O30, m.w. 972, was obtained from AZYP (Arlington, TX). Daiso silica gel particles SP-100-5-P with 5 μm spherical diameter (10 nm pore diameter, 1.1 mL/g pore volume, 440 m2/g surface area and 1.25 particle size distribution as d40/d90) was obtained from Daiso Fine Chemical USA, Inc. (Torrance, CA). The derivatized silica particles were slurry packed into 25 cm × 0.46 cm (i.d) stainless steel columns at 84 MPa (12,000 psi). Anhydrous toluene, anhydrous pyridine, anhydrous dimethylformamide (DMF), ethyl acetate, acetic acid (AA), triethylamine (TEA), trifluoroacetic acid (TFA), ammonium acetate, 3-(triethoxysilyl) propyl isocyanate, 1,1′-carbonyl diimidazole (CDI), 1-(3-aminopropyl) imidazole, 2-(aminomethyl) benzimidazole dihydrochloride, 3-(dimethylamino)-1-propylamine, 4-(dimethylamino) phenyl isocyanate and 3-pyridyl isothiocyanate were purchased from Sigma-Aldrich (St. Louis, MO). All of 34 racemic analytes tested in this study were purchased from Sigma–Aldrich and Anichem (North Brunswick, NJ, USA). Acetonitrile (ACN), methanol (MeOH), n-heptane (Hep), isopropyl alcohol (IPA) of HPLC grade were obtained from VWR (Sugarland, TX). Water was purified by a Milli-Q-water purification system (Millipore, Billerica, MA).
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4

Synthesis of Polyketones and Novel Compounds

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3-(Dimethylamino)-1-propylamine (DMP), 1-bromododecane and 2,5-hexanodione (Sigma-Aldrich) were purchased and used as received. Aliphatic polyketones made of ethylene, propylene, and carbon monoxide were synthesized according to a reported procedure yielding a polyketone with 30 mol% ethylene and 70 mol% propylene (PK) (Mw 2930).21 DPS12 was synthesized as previously reported,22 (link) whereas DPS11 (ref. 23 (link)) was prepared by means of an unprecedented synthetic pathway, as described below (Fig. 9).
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5

Carbonate Reservoir Wettability Alteration

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The following materials were purchased from Sigma Aldrich: aluminium oxide (Al2O3), 1,12-dibromododecane (99%), NaF (99%), 3-dimethylamino-1-propylamine (99%), glycolic acid ethoxylate lauryl ether (average mn   ~ 690). NaCl, CaCl2, Na2SO4, MgCl2, and NaHCO3, were all used for formulating the brine compositions and obtained from Panreac. Indiana limestone carbonate core samples were used.
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