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3 protocols using heptane

1

Synthesis and Characterization of Compounds

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Solvents used for synthesis (dichloromethane, ethyl acetate) were purchased from Lach-ner s.r.o. Tetrahydrofuran was dried with sodium and freshly distilled before use in the presence of benzophenone. Acetone was dried with calcium(II)chloride, distilled from phosphorus(V)oxide, and stored above molecular sieves. Chemicals used for synthesis were purchased from Merck KGaA (Darmstadt, Germany) and Fluorochem Ltd. (Hadfield, UK). Deuterated methanol (MeOD-d4, min. 99.8% D) for vibrational circular dichroism (VCD) analysis was purchased from ISOSAR GmbH (Saarbrücken, Germany) and methanol for electron circular dichroism (ECD) analysis with the purity of 99.8% from Sigma-Aldrich Inc. (St. Louis, MO, USA). Hexane, heptane, and propan-2-ol (2-PrOH) for liquid chromatography were purchased from Honeywell (Charlotte, NC, USA), ethanol (EtOH) was obtained from Fischer Scientific (Hampton, NY, USA), and diethylamine (DEA) from Merck KGaA (Darmstadt, Germany).
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2

Liquid Product Analysis of Biomass Conversion

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The analysis of the liquid products of the reaction necessitated the use of a number of high quality chemical reagents (detailed information regarding chemical grades can be found in ref. 42 (link)), i.e., linoleic acid, palmitic acid, oleic acid, stearic acid, tridecane, cyclohexanone, a mixture of 37 fatty acid methyl esters (all Sigma-Aldrich), heptane, dodecane, cyclohexane, chloroform (all Honeywell) and a calibration sample kit #2 for n-C8 to n-C18 alkanes (Agilent Technologies). The main components of the palm oil used as feed are presented in Table 1.
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3

Quantifying α-Tocopherol by NP-UHPLC-FLD

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α-Tocopherol consumption during the oxidation trial was analyzed
by the method from Aitta et al.29 (link) NP-UHPLC-FLD
with a Shimadzu Nexera XR LC-30 HPLC instrument equipped with an LC-20AD
XR pump, SIL-20AC autosampler, CTO-20AC prominence column oven, and
RF-20A prominence fluorescence detector (Shimadzu, Kyoto, Japan) was
used. Excitation and emission wavelengths were 292 and 325 nm, respectively.
A Restek Pinnacle DB Silica UHPLC column (1.9 μm, 100 ×
2.1 mm, Bellefonte, PA) was applied for an 8 min separation run at
30 °C. Tray cooler temperature was set to 4 °C. The mobile
phase (isocratic, 0.4 mL/min) consisted of 2% 1,4-dioxane (Sigma-Aldrich,
Steinheim, Germany) and 98% heptane (Honeywell/Riedel de Haën,
Seelze, Germany). Samples were transferred to heptane for analysis.
For quantification, the α-tocopherol standard curve was prepared
from the α-tocopherol stock solution. Limit of detection (LOD)
and limit of quantification (LOQ) for the method were 0.08 and 0.26
ng per column, respectively. Chromatographic data were processed by
LabSolutions 5.93 (Shimadzu Corporation, Kyoto, Japan).
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