In this study was used: iron (III) acetylacetonate (99%) from Sigma Aldrich (St. Louis, MO, USA), oleic acid (90%) from Panreac (Barcelona, Spain), benzyl ether (99%) from Sigma Aldrich (Madrid, Spain), 4-biphenylcarboxylic acid (99%) from Sigma Aldrich (Madrid, Spain), toluene (99.8%) from Panreac (Barcelona, Spain), hexane (99%) from Panreac (Barcelona, Spain), chloroform (99.9%) from Panreac (Barcelona, Spain), and nitrogen (99%) from Air Liquide (Paris, France). All solutions were made with distilled water.
Toluene
Manufactured by ITW Reagents
Sourced in Spain
Toluene is a colorless, flammable liquid chemical compound with a distinct aromatic odor. It is a widely used solvent in various industrial and laboratory applications. Toluene's core function is to serve as a solvent and diluent for a variety of materials, including paints, inks, adhesives, and cleaning agents.
Automatically generated - may contain errors
Lab products found in correlation
Hexane, by ITW Reagents (2 mentions)
Chloroform, by ITW Reagents (2 mentions)
Oleic acid, by Merck Group (2 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (2 mentions)
Benzyl ether, by Merck Group (1 mentions)
Oleic acid, by ITW Reagents (1 mentions)
Iron 3 acetylacetonate, by Merck Group (1 mentions)
Absolute ethanol, by ITW Reagents (1 mentions)
Octadecene, by Merck Group (1 mentions)
Dimercaptosuccinic acid, by Merck Group (1 mentions)
Sodium oleate, by Merck Group (1 mentions)
Acetic acid, by Merck Group (1 mentions)
Fecl3 6h2o, by Merck Group (1 mentions)
P toluenesulfonic acid monohydrate, by Merck Group (1 mentions)
Peg1k, by Merck Group (1 mentions)
3 mercaptopropionic acid, by Merck Group (1 mentions)
2 2 dimethoxy 2 phenylacetophenone dmpa, by Thermo Fisher Scientific (1 mentions)
Acetone, by Merck Group (1 mentions)
Methanol, by Merck Group (1 mentions)
Tetrahydrofuran, by Merck Group (1 mentions)
7 protocols using toluene
1
Synthesis of Monodisperse Nanoparticles
2
Synthesis of C60 Fullerene Nanoparticles
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3
Synthesis and Characterization of Iron Oxide Nanoparticles
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Sodium oleate 82%, FeCl3·6H2O 97%, oleic acid 90%, octadecene 90%, dimercaptosuccinic acid 98% (DMSA), dimethyl sulfoxide ≥99.9% (DMSO), acetic acid, and 12 kDa cellulose membrane were purchased from Sigma-Aldrich (Madrid, Spain). Absolute ethanol 99.5%, hexane 95% and toluene 99.5% were purchased from PanReac (Barcelona, Spain). All other chemicals (NaOH, HNO3 65%, HCl 37%, NaCl, MgCl2, etc.) were of the highest quality commercially available and used as received. Milli-Q water (resistivity 18.2 MΩ·cm at 25 °C) was used in all experiments. Type-I collagen powders extracted from rat tails (N_COL) were provided by NOVAICOS Srl (Novara, Italy, https://www.novaicos.com/ (accessed on 20 December 2021)).
4
Synthesis of Dendritic Building Blocks
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Reagents and solvents were purchased from commercial sources and used as received. The Pluronics L31, L35 and L61, PEG1k and PPG1k, and 3-mercaptopropionic acid and p-Toluenesulfonic acid monohydrate were purchased from Sigma Aldrich (St. Louis, MO, USA). 2,2-dimethoxy-2-phenylacetophenone (DMPA) was purchased from Acros Organics (Geel, Belgium). Toluene was purchased from PanReac (Barcelona, Spain). Chloroform was purchased from J.T. Baker (Phillipsburg, NJ, USA). Acetone, tetrahydrofuran, caffeic acid and methanol were purchased from Sigma Aldrich with the HPLC grade. Sulfuric acid was purchased from Hanssell (Madrid, Spain). Vinyl-decorated dendrimer Si-G1V8 (D1 ) and dendrons N3-G3V8 (D2 ) and HO-G3V8 (D3 ) were synthesized as previously reported [20 (link),21 (link)].
5
Synthesis of Bis-Aldehydes and PAM
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All chemicals used in the synthesis of bis-aldehydes and PAM were purchased from commercial suppliers and were of high purity. Hydroquinone (m.p. = 172–175 °C), resorcinol (m.p. = 110 °C), pyrocatechol (m.p. = 100–103 °C), 4-fluorobenzaldehyde (98%), 44′-dihydroxybiphenyl (97%, m.p. = 284–285 °C), bisphenol A (m.p. = 158–159 °C), (111,333-hexafluoro)–bisphenol propane (m.p. = 160–163 °C) were obtained from Sigma Aldrich. The chemicals K2CO3 anhydrous (Fluka), 14-phenylenediamine (m.p. = 138–143 °C, Sigma Aldrich), 44′-diaminodiphenyl ether (97%, m.p. = 188–192 °C, Sigma Aldrich), p-toluene sulfonic acid monohydrate (PTSA) were purchased from Fluka (Switzerland). The solvents n-hexane, dimethylsulfoxide, and diethyl ether were procured from Merck (Germany) whereas chloroform, ethylacetate, and toluene were purchased from Panreac (Spain). The ethanol, methanol, and N,N-dimethylformamide were obtained from Deijing (Korea) while hydrochloric acid, and sulfuric acid were procured from Riedel-de-Haen (Germany). The solvents used in this work were dried where necessary with standard procedures.[22 ]
6
Synthesis and Characterization of Dipyrrolylmeten Complexes
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The compounds bis(1,2,3,7,8-pentamethyl-2,2′-dipyrrolylmeten-9-yl)methane bis(difluoroborate) (1 ), (1,2,3,7,9-pentamethyl-2,2’-dipyrrolylmeten-8-yl)-(1,2,3,7,8-pentamethyl-2,2’-dipyrrolylmeten-9-yl)methane bis(difluoroborate) (2 ), and bis(1,2,3,7,9-pentamethyl-2,2′-dipyrrolylmeten-8-yl)methane bis(difluoroborate) (3 ) were synthesized according to proven technology [21 (link)]. The synthesis techniques and the results of the identification of 1–3 are presented in SI. Spectrophotometric-grade benzene, heptane, cyclohexane, toluene, ethanol, 1-propanol, DMF, DMSO, and acetone (for analysis, Panreac, Barcelona) were used without further purification. Solvent parameters (DN, SB, and ε) were taken from [32 (link)] and are listed in Table S2 .
7
Crude Oil Wettability Restoration Protocol
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The polymer employed was a commercial partially HPAM provided by
SNF Floerger (Andrézieux, France) with molecular weight and
degree of hydrolysis of 6–8 MDa and 30%, respectively. Commercial
SiO2 nanoparticles were purchased from Sigma-Aldrich (St.
Louis, MO, USA). Oleic acid (≥99%), sodium hydroxide pellets
(97%), and ethanol (99.5%) were obtained from Sigma-Aldrich (St. Louis,
MO, USA) and were employed for the synthesis of the sodium oleate
surfactant. Potassium bromide (PIKE Technologies, Inc., USA) was used
for FTIR analysis. An extra heavy crude oil of 7° API was used
for wettability restoration of the cores to an oil-wet state. Colombian
crude oil of 20° API was used for the contact angle measurements
and coreflooding tests. For the displacement tests, clean silica sand
(Ottawa sand, US sieves 50/60 mesh) was used for the preparation of
the porous medium and was purchased from Minercol S.A. (Colombia).
Additionally, deionized water was used as a solvent for preparing
different solutions used in this research. Toluene (99.8%), methanol
(99.8%), and HCl (37%) were obtained from Panreac (Barcelona, Spain)
and were employed for porous media cleaning.
SNF Floerger (Andrézieux, France) with molecular weight and
degree of hydrolysis of 6–8 MDa and 30%, respectively. Commercial
SiO2 nanoparticles were purchased from Sigma-Aldrich (St.
Louis, MO, USA). Oleic acid (≥99%), sodium hydroxide pellets
(97%), and ethanol (99.5%) were obtained from Sigma-Aldrich (St. Louis,
MO, USA) and were employed for the synthesis of the sodium oleate
surfactant. Potassium bromide (PIKE Technologies, Inc., USA) was used
for FTIR analysis. An extra heavy crude oil of 7° API was used
for wettability restoration of the cores to an oil-wet state. Colombian
crude oil of 20° API was used for the contact angle measurements
and coreflooding tests. For the displacement tests, clean silica sand
(Ottawa sand, US sieves 50/60 mesh) was used for the preparation of
the porous medium and was purchased from Minercol S.A. (Colombia).
Additionally, deionized water was used as a solvent for preparing
different solutions used in this research. Toluene (99.8%), methanol
(99.8%), and HCl (37%) were obtained from Panreac (Barcelona, Spain)
and were employed for porous media cleaning.
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