The biocatalyst used was Novozym® 435, a commercial Candida antarctica lipase B (CalB), immobilized on a macroporous acrylic resin Lewatit VP OC 1600, which was kindly donated by Novozymes Spain S.A. Substrates 2-methylhexanoic acid (MHA, 99%) and 2-ethylhexanol (EH, 99.6%) were supplied by Sigma-Aldrich Co. (St. Louis, MO, USA) All other reagents and products were analytical-grade.
2 ethylhexanol
Manufactured by Merck Group
Sourced in United States
2-ethylhexanol is a colorless, oily liquid chemical compound with a characteristic odor. It is primarily used as an industrial solvent and an intermediate in the production of various chemical products. Its core function is to serve as a versatile building block in various chemical processes and formulations.
Automatically generated - may contain errors
Lab products found in correlation
Benzaldehyde, by Merck Group (2 mentions)
1 hexanol, by Merck Group (2 mentions)
Phenylethyl alcohol, by Merck Group (2 mentions)
Propylene glycol, by Merck Group (2 mentions)
Novozym 435, by Novozymes (1 mentions)
1 octen 3 ol, by Merck Group (1 mentions)
Benzyl acetate, by Merck Group (1 mentions)
Agilent 7890a gc, by Agilent Technologies (1 mentions)
Phenethyl acetate, by Merck Group (1 mentions)
3 octanol, by Merck Group (1 mentions)
Graphite powder, by Merck Group (1 mentions)
Quanta 250 feg, by Thermo Fisher Scientific (1 mentions)
Kerosene, by Merck Group (1 mentions)
X pert pro diffractometer, by Bruker (1 mentions)
Acetone, by Merck Group (1 mentions)
P toluenesulfonic acid ptsa, by Merck Group (1 mentions)
2 pentylfuran, by Merck Group (1 mentions)
1 butanol, by Merck Group (1 mentions)
Sodium chloride (nacl), by Merck Group (1 mentions)
Ethyl acetate, by Merck Group (1 mentions)
11 protocols using 2 ethylhexanol
1
Enzymatic Esterification of 2-Methylhexanoic Acid
2
GC-MS Analysis of Volatile Compounds
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The analysis
was performed using Agilent 7890 A GC with an HP-5MS capillary column
(0.25 mm × 30 m × 0.25 μm) and a quadrupole mass spectrometer
Agilent 5975 C (Agilent, Santa Clara, CA, USA) as the detector. The
temperature conditions of the column were referenced by Yang et al.34 (link) The MS detection proceeded in electron impact
mode, and the ionization energy was 70 eV. The mass-scan range was
29–350 m/z at 2.88 scans/s.
Helium was the carrier gas at 1 mL/min.
Volatile compound identifications
were carried out by matching standard compounds and mass spectral
libraries (Wiley6 and NIST 98). A total of 17 standard compounds,
including 1-hexanol, 1-octen-3-ol, 2-ethylhexanol, benzaldehyde, benzoic
acid, benzyl acetate, benzyl alcohol, ethyl benzoate, geraniol, hexyl
acetate, linalool, nonanal, phenethyl acetate, phenylethyl alcohol,
prenyl acetate, terpineol, and β-pinene, and the internal standard
3-octanol was purchased from Sigma-Aldrich (Shanghai) Trading Co.,
Ltd. (Shanghai, China). The retention index values were derived from
alkane series (C7–C30) (Sigma, St. Louis,
MO, USA). All volatile compounds were quantified as 3-octanol equivalents,
and the results were expressed in microgram standard equivalents per
kilogram fresh weight (μg/kg FW).
was performed using Agilent 7890 A GC with an HP-5MS capillary column
(0.25 mm × 30 m × 0.25 μm) and a quadrupole mass spectrometer
Agilent 5975 C (Agilent, Santa Clara, CA, USA) as the detector. The
temperature conditions of the column were referenced by Yang et al.34 (link) The MS detection proceeded in electron impact
mode, and the ionization energy was 70 eV. The mass-scan range was
29–350 m/z at 2.88 scans/s.
Helium was the carrier gas at 1 mL/min.
Volatile compound identifications
were carried out by matching standard compounds and mass spectral
libraries (Wiley6 and NIST 98). A total of 17 standard compounds,
including 1-hexanol, 1-octen-3-ol, 2-ethylhexanol, benzaldehyde, benzoic
acid, benzyl acetate, benzyl alcohol, ethyl benzoate, geraniol, hexyl
acetate, linalool, nonanal, phenethyl acetate, phenylethyl alcohol,
prenyl acetate, terpineol, and β-pinene, and the internal standard
3-octanol was purchased from Sigma-Aldrich (Shanghai) Trading Co.,
Ltd. (Shanghai, China). The retention index values were derived from
alkane series (C7–C30) (Sigma, St. Louis,
MO, USA). All volatile compounds were quantified as 3-octanol equivalents,
and the results were expressed in microgram standard equivalents per
kilogram fresh weight (μg/kg FW).
3
Poplar Genotypes for Biomass Feedstocks
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We employed eight different poplar genotypes as biomass feedstocks. Their genotype, origin, parentage, and hemicellulose, cellulose, and lignin content are shown in Table 1 . The selected genotypes were AF8, Bakan (Bak), Brandaris (Bra), Ellert (Ell), Grimminge (Gri), Hees (Hee), Skado (Ska), and Wolterson (Wol). The biomass samples were not pre-treated, except from shredding on a Retsch© SM 2000 mill equipped with a 4 mm sieve to decrease the grain size and thus increase the surface area. We purchased the solvent 2-Ethylhexanol and the catalyst 97% p-Toluenesulfonic acid (PTSA) from Sigma–Aldrich. Technical acetone for washing purposes was acquired locally.
4
Graphene Synthesis via Ball Milling
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Wet milling process was performed using a planetary ball mill (PM.100 CM, from Retsch, Haan, Germany), Hardened steel vial (500 cc), Hardened steel balls (5 mm in diameter). Graphite powders (Sigma Aldrich, <20 µm, Schnelldorf, Germany) were milled at which the weight of the milled Graphite powders was 10 g, and the weight of the milling balls was 500 g, then, the ball to powder ratio was 50:1 (i.e. B/P = 50). The milling speed was 400 rpm, and the milling time was 60 h. The Graphite powders were milled in the presence of both kerosene (commercially available, from ExxonMobil company, Cairo, Egypt), and 2-ethylhexanol (⩾99.6%, Sigma Aldrich, Saint Louis, MO, USA). The prepared samples were centrifuged at 5000 rpm for 20 min to be separated from the solvent. Heat treatment of the prepared samples was performed in a tube furnace under the flow of argon gas for 3 h at 600 °C. Structural characterizations were performed via X-ray diffraction (XRD- PANalytical’s X’Pert PRO diffractometer, Almelo, Netherlands), and Raman spectroscopy (Bruker Senterra instrument, Ettlingen, Germany, with a laser of 532 nm). On the other hand, Morphological characteristics of Graphite powders and the prepared graphene sheets were investigated by scanning electron microscopy (Quanta FEG 250 (FEI, Hillsboro, USA), and Transmission electron microscopy (TEM-JOEL-JEM-2100, Tokyo, Japan).
5
Liquefaction of Pine Biomass Fractions
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Several biomaterials were used as feedstock for the liquefaction process. Pinewood shavings (hereafter referred to as pinewood) were used as reference biomass. The Leiria National Park kindly supplied samples of slices of burned pinewood obtained from the fires of 2017. For liquefaction, five fractions were considered: bark, sapwood, heartwood, branches (Figure 1 ), and commercial pinewood shavings. The pine branches were collected from the forest ground.
Firstly, the biomass samples were cut into small cubes (Figure 1 c) and dried in an oven at 110 ± 3 °C for 24 h. The drying process was conducted to facilitate the characterisation since it has no impact on the liquefaction process. Afterwards, the cubes were shredded in a Retsch© SM 2000 mill equipped with a 4 mm sieve to increase the contact surface area between the solvent and the feedstock. The reagents were: 2-ethylhexanol, purity ≥ 99%, p-toluenesulfonic acid (PTSA), purity ≥ 99%, from Sigma-Aldrich, and acetone, technical grade, acquired from a local gross supplier.
Firstly, the biomass samples were cut into small cubes (
6
Comprehensive Analysis of Aroma Compounds
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The study used n-Alkane (C7-C30) standards and the available authentic standards, including ethyl acetate (≥99.5%), propyl acetate (≥99.5%), butyl acetate (99.7%), ethyl trans-2-butenoate, ethyl hexanoate (≥99%), ethyl heptanoate (≥99%), ethyl octanoate (≥99%), ethyl 3-hydroxybutyrate (≥ 98%), hexyl hexanoate (≥ 98%), hexanal (≥95%), (Z)-3-hexenal (50% in triacetin), (E)-2-hexenal (≥97%), nonanal (≥99.5%), benzaldehyde (≥99.5%), (E)-2-decenal (≥95%), citral (≥95%), 1-butanol (≥99.4%), 1-hexanol (≥99.9%), (E)-2-hexenol (96%), 1-octen-3-ol (≥98%), 1-heptanol (≥99.5%), 2-ethylhexanol (≥99%), 1-octanol (≥99%), 2-octen-1-ol (97%), (Z)-5-octen-1-ol (≥97%), (E)-5-decen-1-ol (≥97%), phenylethyl alcohol (≥99%), cinnamyl alcohol (≥96%), acetic acid (≥99.7%), hexanoic acid (≥98%), heptanoic acid (≥99%), octanoic acid (99%), nonanoic acid (≥99.5%), limonene (mixture of D- and L-form at ratio of 1:1, ≥95%), linalool (≥99%), citronellol (≥95%), nerol (≥97%), geraniol (≥98.5%), 2-octanone (≥99.5%), acetophenone (≥99.5%), 2-pentylfuran (≥97%), 2-octanol (≥97%), and sodium chloride (NaCl, ≥99%) which were all purchased from Sigma-Aldrich (St. Louis, MO, USA). Geranic acid (sum of isomers, 98%) was purchased from Alfa Aesar Corporation (Tianjin, China). Ultrapure water was prepared using a Milli-Q water purification system (Millipore Corporation, Bedford, MA, USA) with a 0.22 μm filter.
7
Synthesis and Characterization of Epoxy Composites
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Bisphenol A diglycidyl ether (DGEBA) epoxy oligomer (Epon resin 828), accelerator composed of 2,4,6-tris-dimethylaminomethyl phenol (Epikure Curing Agent 3253) were kindly provided by Hexion Inc (Pueblo, CO, USA). Hexahydro-4-methylphthalic anhydride (HP), ethylene glycol (EG), diethylene glycol (DG), propylene glycol (PG), 2-ethyl-hexanol (2EH), ethylene glycol monobutyl ether (EGMBE) and 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD), zinc acetylacetonate (Zn(Ac)2) and triphenylphosphine (PPh3) were purchased from Sigma-Aldrich (St. Louis, MO, USA) and used as received. Silicone mold releasing agent was purchased from Stoner (Quarryvile, PA, UAS). Sodium hydroxide (NaOH) was obtained from Avantor Performance Materials (Phillipsburg, NJ, USA).
8
Extraction and Purification of Precious Metals
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Commercial AuCl3 (Sigma-Aldrich, Poznan, Poland), palladium chloride PdCl2 (99%, Pol-Aura, Zabrze, Poland), PtCl4 (Pol-Aura, Zabrze, Poland), HNO3 (65%, Avantor Performance Materials Poland S.A., Gliwice, Poland), HCl (35%, Chempur, Piekary Slaskie, Poland), NH3aq (25%, Chempur, Piekary Slaskie, Poland), NH4SCN, and thiourea (both from Chempur, Piekary Slaskie, Poland) were used to prepare the initial solutions. Methylene chloride (Fluka, Busch, Switzerland), 2-ethylhexanol (99.6%, Sigma-Aldrich, Poznan, Poland), chloroform, and toluene (both from Chempur, Piekary Slaskie, Poland) were used as extractant’s diluents.
Ethylenodiamino-bis-acetylacetone (m.p. 110–111 °C) (Figure 2 ) was synthesized as a result of the condensation reaction of equimolar amounts of ethylenediamine with acetylacetone according to the procedure described in paper [38 (link)]. The structure has been confirmed in the nuclear magnetic resonance studies. The results are given in reference [38 (link)].
Ethylenodiamino-bis-acetylacetone (m.p. 110–111 °C) (
9
Antifungal Activity of Volatile Compounds against F. incarnatum
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To test the effect of dominant volatile compound participated in antifungal activity against F. incarnatum, the sealed plate method was conducted as shown in Section 2.3 . The compound phenylethyl alcohol (PEA) was purchased from Sigma-Aldrich (St. Louis, MO, USA). The effect of commercial PEA versus the other volatile antifungal compounds 2-ethylhexanol, 1-nonanol, 6-PP, and 2-methyl-1-butanol (Sigma-Aldrich, St. Louis, MO, USA) [6 (link)] was tested through the sealed plate method. PEA was dissolved in 95% ethanol and we adjusted the dilution to 10−1, 10−2, and 10−3. Each volatile compound was applied on a sterile cotton pad (20 µL) and subjected to the method of Wonglom et al. [6 (link)] Application of 95% ethanol served as a negative control. The tested plates were then incubated at 28 ± 2 °C for seven days. Each treatment was composed of five replicates and the experiment was repeated twice. Colony diameters of F. incarnatum were measured and the percentage inhibition was calculated as described in Section 2.2 .
10
Thermochemical Liquefaction of Pinewood and Stipa
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Pinewood shaves purchased from Versele-Laga (Deinze, Belgium), and Stipa tenacissima grass (referred to as Stipa throughout this paper), kindly provided by a Tunisian company, were used as raw materials for the thermochemical liquefaction process. The solvents 2-ethyl hexanol (2EH; ≥90 wt.%), propylene glycol (PG; ≥90 wt.%), 2-methyl tetrahydrofuran (2-MTHF; ≥99.5 wt.%) and deuterated chloroform (≥99.8 atom % D), as well as the catalyst p-toluenesulfonic acid (PTSA; ≥98 wt.%), were purchased from Sigma-Aldrich (Sigma-Aldrich Ltd., St. Louis, MO, USA). N,N-dimethylformamide (DMF; >99.5 wt.%) was obtained from Carlo Herba (Carlo Erba Reagents S.A.S., Val De Reuil, France). Desmodur® Eco N7300, a bio-based aliphatic 1,5-pentamethylene polyisocyanate, was obtained from Covestro (Covestro AG, Leverkusen, Germany). It has an NCO content of about 21.9%, a viscosity at 23 °C of ca. 9500 mPa.s, less than 0.3% of monomeric PDI and an equivalent weight (EW) of ca. 195. The 0.5 M and 0.1 M KOH solutions used in the determination of the polyols’ acid and hydroxyl values were purchased from Honeywell (Charlotte, NC, USA), and the solvent tetrahydrofuran (THF; 99.8 wt.%) was purchased from Fisher Scientific (Thermo Fisher Scientific Inc., Waltham, MA, USA). The DC01 carbon steel plates used were kindly provided by Voestalpine AG (Linz, Austria).
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