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6 protocols using 1 methylnaphthalene

1

Wash Oil Characterization for GC Analysis

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Wash oil, the feed of this study, was provided by OCI Company Ltd. (Seoul, Korea). Naphthalene (NA, 99% purity), QU (98% purity), IN (≥99% purity), 2-methylNaphthalene (2MNA, 97% purity), 1-methylNaphthalene (1MNA, ≥95% purity), and biphenyl (BP, ≥99.5% purity), which were used GC identification or quantification of the constitutive components presenting in the wash oil, were purchased from Sigma Aldrich, Seoul, Korea. Methanol (≥99.5% purity) and n-hexane (≥99% purity), used as the solvent of each operation in this study, were also purchased from Sigma-Aldrich, Seoul, Korea. In this study, the above-mentioned eight kinds of commercial reagents were used without further purification.
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2

Composition of Pyrolysis Liquid Mixture

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n-Octane (99+%), n-hexadecane (99%) and 1-hexene (97%) were received from Acros (Belgium). Cumene, 1-methylnaphthalene and toluene (99.5%) were received from Sigma Aldrich. N-heptane was received from Alfa Aesar. Pyrolysis liquids were kindly supplied by Urbaser, Spain. All chemicals were used as received. Table 2 shows the composition of the model mixture used in this study, whereas the chemical composition of the real pyrolysis mixture is given in Table 3.
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3

Polymer Fractionation and Crude Oil Analysis

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Commercially available Torlon® 4000T-LV and Matrimid®5218 were purchased from Solvay Advanced Polymers (Alpharetta, GA) and Huntsman, respectively. SBAD-1, DUCKY-9, and DUCKY-10 polymers were synthesized from literature procedures detailed in two previous publications4 ,5 (link). Two real crude oils (Permian and Arabian light crude oils) were provided from ExxonMobil Technology and Engineering Company. The experimental results of the two fractionations were published previously4 ,5 (link). All other chemicals (p-xylylene diamine, lithium nitrate, chloroform, tetrahydrofuran, 1-methylpyrroldone, ethanol, methanol, hexane, toluene, toluene, Tert-butyl benzene, 1,3,5-triisopropyl benzene, n-Octane, iso-Octane, iso-cetane, methylcyclohexane, decalin, 1-methylnaphthalene, o-xylene, propyl benzene, mesitylene, n-butylcyclohexane, tetralin, bi-phenyl, dodecylbenzene, 1,3,5-triphenylbenzene, 1,3,5-Tris[(3-methylphenyl) phenylamino]benzene), methanol, and guaiacol were purchased from Sigma Aldrich, Alfa Aesar, or TCI and used as received.
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4

Chemical Reagent Acquisition and Purification

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Dichloromethane and anhydrous sodium sulfate were purchased from VWR (Darmstadt, Germany). All chemicals were at least of analytical grade. To improve its purity, DCM was freshly distilled prior to use. Acetic acid, benzaldehyde, sec-butylbenzene, 1-butanol, (E)-2-butenal, butyl acrylate, decanal, ethenylbenzene (styrene), 2-ethylhexyl acrylate, methyl octanoate, 1-methylnaphthalene, 2-methylnaphthalene, naphthalene, octanal and propylbenzene were obtained from Sigma-Aldrich (Steinheim, Germany). Butyl acetate, ethylbenzene, (propan-2-yl)benzene (cumene) and 3-phenyl-1-propene (allylbenzene), were purchased from TCI Europe (Zwijndrecht, Belgium). 1,2-Dimethylnaphthalene, 1,7-dimethylnaphthalene and 3-methyl-4-heptanone were obtained from abcr (Karlsruhe, Germany), and 2-acetyl-1-pyrroline from aromaLAB (Planegg, Germany).
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5

Deuterated Compound Synthesis and NMR Analysis

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d-(+)-Xylose (>99%), D2O (99.9% atom D), toluene-d8 (99% atom D), 3-(trimethylsilyl)propionic-2,2,3,3-d4 acid sodium salt (TMSP, 98% atom D), 1-methylnaphthalene (98%), sodium sulfate (99%), sulfolane (99%) were purchased from Sigma-Aldrich, while phenylboronic acid (PBA, 99%), dioxane (99%) and tetramethylsilane (TMS) were obtained from Alfa Aesar.
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6

Analytical Evaluation of Naphthalene Derivatives

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Ammonium acetate and methanol (LC/MS grade; Fisher Scientific, Fair Lawn, NJ, USA), and compressed CO2 gas (grade 4.5; Praxair Canada, Mississauga, ON, Canada) were used. Analogs of postulated structures 5‐(2‐thienyl)pentanoic acid, thiochroman‐4‐one, 1‐methylnaphthalene, 1‐ethylnaphthalene, 2‐n‐propylnaphthalene and 2,6‐diisopropylnaphthalene were obtained from Sigma‐Aldrich (Oakville, ON, Canada).
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