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7 protocols using nitrobenzene

1

Synthesis and Characterization of Aromatic Compounds

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Nitrobenzene (+99%), 1,4-diNitrobenzene (+98%), 4-chloroaniline (+98%) and naphthalene (+99%) were purchased from Acros Organics Co.; 3-Nitroaniline (+98%) was purchased from Sigma-Aldrich Chemistry Co.; 2-Chlorophenol (+99%), 4-chlorophenol (+99%), 2-chloroaniline (+98%), 2-nitroaniline (+99%) and 4-methylaniline (+99.7%) were purchased from Aladdin Reagent Co.; 4-MethylNitrobenzene (+99.5%), 4-chlosroNitrobenzene (+98%), phenanthrene (+98%) and pyrene (+97%) were purchased from Fluka Chemistry Co.; 1,2-DiNitrobenzene (+98%), 1,3-dinitro benzene (+99%) and 1,3,5-triNitrobenzene (wetted with 40% water) were purchased from Tokyo Chemical Industry Co.; 2,4-Dichlorophenol (+99.5%), 4-methylphenol (+98%), 2-nitrophenol (+99%), 3-nitrophenol (+99%), 4-nitrophenol (+99.5%) and 4-nitroaniline (+99.5%) were purchased from Sinopharm Chemical Reagent Co.; Aniline (+99.5%) was purchased from Shanghai Reagent Co.; and phenol (+99.7%) was purchased from Hangzhou Shuanglin Chemical Co. All these aromatic chemicals were used as received. The selected properties including water solubility (Sw), octanol-water partitioning coefficients (logKow), molecular weight, maximum absorption wavelength (λmax), dissociated constant (pKa) of the 25 investigated aromatic chemicals are listed in Table S3.
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2

Synthesis of Cobalt and Nickel Ferrite Catalysts

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The cobalt ferrite and nickel ferrite catalyst supports were synthetized from the following precursors: cobalt(II) nitrate hexahydrate, Co(NO3)2∙6H2O, MW: 291.03 g/mol (Sigma-Aldrich, Saint Louis, MO 63103, USA); nickel(II) nitrate hexahydrate, Ni(NO3)2∙6H2O, MW: 290.79 g/mol (Thermo Fisher GmbH, D-76870 Kandel, Germany); iron(III) nitrate nonahydrate, Fe(NO3)3∙9H2O (VWR International, Leuven, Belgium); ethylene glycol, HOCH2CH2OH, (VWR Int. Ltd., F-94126 Fontenay-sous-Bois, France); monoethanolamine, NH2CH2CH2OH (Merck KGaA, D-64271 Darmstadt, Germany); and sodium acetate, CH3COONa (ThermoFisher GmbH, D-76870 Kandel, Germany). Palladium(II) nitrate dihydrate, Pd(NO3)2·2H2O (Alfa Aesar Ltd., Ward Hill, MA 01835, USA) was used to deposit Pd onto the ferrite catalyst supports. Nitrogen (purity 4.0, Messer) and hydrogen (purity 4.0, Messer) were used during the experiments. Nitrobenzene (NB, Acros Organics, Morris Plains, NJ 07950, USA) was used as reactant during the catalytic hydrogenation tests. The analytical standards applied (azobenzene, nitrosobenzene, N-methylaniline) were purchased from Sigma-Aldrich Co. (St. Louis, MO 63118, USA).
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3

Palladium-Catalyzed Carbon Foam Hydrogenation

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For the preparation of the carbon-based foam, 4-nitroaniline (Alfa Aesar GmbH, 76185 Karlsruhe, Germany) and sulfuric acid (95 wt%, VWR Intern. S.A.S, F-94126 Fontanay-sous-Bois, France) were used. Carbon dioxide was used to activate the prepared foam (Gourmet, Messer). Palladium(II) nitrate dihydrate (Pd(NO3)2*2H2O, Alfa Aesar Ltd., Ward Hill, 01835 MA, USA) was applied to deposit Pd onto the carbon foil support. Nitrogen (purity 4.0, Messer) and hydrogen (purity 4.0, Messer) were used during the experiments. Nitrobenzene (NB, Acros Organics, Fair Lawn, 07950 NJ, USA) was used as reactant during the catalytic hydrogenation tests. The applied analytical standards (azobenzene, nitrosobenzene, N-methylaniline) were purchased from Sigma-Aldrich Co. (St. Louis, 63118 MO, USA).
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4

Comprehensive Solvent Characterization for Research

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A total of 23 solvents
were used in this study: n-heptane (99.0% purity),
toluene (100.0% purity), chloroform
(99.99% purity), tetrahydrofuran (THF) (99.0% purity), ethanol (99.5%
purity), and dimethyl sulfoxide (DMSO) (99.8% purity) were purchased
from Echo Chemical Co. Ltd. (Taiwan R.O.C.). Xylene (98.5% purity)
and 1,4-dioxane (98.0% purity) were purchased from Avantor Performance
Materials Co. Ltd. (PA, USA). p-Xylene (99.0% purity),
ethyl acetate (99.5% purity), methyl tert-butyl ether
(MTBE) (99.9% purity), benzene (99.0% purity), methyl ethyl ketone
(MEK) (99.6% purity), acetone (99.5% purity), n-butyl
alcohol (99.4% purity), isopropyl alcohol (IPA) (99.8% purity), benzyl
alcohol (99.8% purity), acetonitrile (99.96% purity), dimethylformamide
(DMF) (99.8% purity), and methanol (99.9% purity) were purchased from
TEDIA (USA). N,N-dimethylaniline
(DMA) (99.0% purity) and nitrobenzene (99.0% purity) were purchased
from Acros Organics (NJ, USA). Water was clarified by reverse osmosis
(RO) through a water purification system (model Milli-RO Plus) bought
from Millipore (Billerica, MA, USA).
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5

Titanium Sheet Synthesis Using Solvothermal Method

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A 20 × 10 mm2, 2 mm thick titanium sheet (99.6%, Strem Chemicals) was prepared as a Ti source. Ethylene glycol (EG, ≥99.5%), ammonia fluoride (NH4F, AR), and nitrobenzene (C6H5NO2, AR) were bought from Acros Organics and used as received. Deionized (DI) water (Millipore, 18.2 MU cm resistivity) was used throughout the study.
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6

Chitosan-Based Nanomaterial Synthesis

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In the present research, chitosan powders supplied by Sigma-Aldrich (Saint Louis, MO, USA) (molecular weights M1 = 210 kg/mol, M2 = 1300 kg/mol; degrees of deacetylation DD1 = 80%, DD2 = 70% [35 (link)]), high purity carbon dioxide (99.995%, Moscow Gas Refinely Plant, Moscow, Russia), specially purified and deionized water (Millipore Milli-Q, MilliporeSigma, Burlington, NJ, USA), copper sulfate (cat. No. 451657, Sigma-Aldrich, Saint Louis, MO, USA), sodium borohydride (cat. No. 16940-66-2, Acros organics, Geel, Belgium), nitrobenzene (cat. No 98-95-3, Sigma-Aldrich, Saint Louis, MO, USA), hydrogen (99.99%, Gazprodukt, Moscow, Russia), and helium (99.995%, Gazprodukt, Moscow, Russia) were used.
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7

Characterizing Organic Solvent Purity

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n-Heptane (99% purity; Lot,
EA8351), toluene (≥99.5% purity; Lot, ETA140403), chloroform
(99.99% purity; Lot, E554180), THF (99% purity; Lot, E704198), ethanol
(99.5% purity; Lot, 262611), acetone (99.5% purity; Lot, EHAD105),
and DMSO (99.8% purity; Lot, EA3M741) were purchased from Echo Chemical
Co. Ltd. (Taiwan). Xylene (98.5% purity; Lot, E03B34) and 1,4-dioxane
(98% purity; Lot, SP-34332R) were purchased from Avantor Performance
Materials Co. Ltd. p-Xylene (99% purity, Lot, 802551),
ethyl acetate (99.5% purity; Lot, 711912), MTBE (99.9% purity; Lot,
1005355), benzene (99% purity; Lot, 310008), MEK (99.6% purity; Lot,
SMEI40421), n-butyl alcohol (99.4% purity; Lot, 205027),
IPA (99.8% purity; Lot, 14030108), benzyl alcohol (99.8% purity; Lot,
70950), acetonitrile (99.96% purity; Lot, 14050419), DMF (99.8% purity;
Lot, 912313), and methanol (99.9% purity; Lot, 14050368) were purchased
from TEDIA company. DMA (99% purity; Lot, A0213203001), and nitrobenzene
(99% purity; Lot, A0282673) were purchased from Acros Organics company.
Reversible osmosis water was clarified by a water purification system
(model Milli-RO Plus) bought from Millipore (Billerica, MA).
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