Partial hydrogenation of a C18:3-rich FAME mixture over Pd/C

Quaranta, Eugenio; Cornacchia, Daniele

doi:10.1016/j.renene.2020.04.122

Cited by 17 publications

(9 citation statements)

References 37 publications

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“…All studies agree that an increase in temperature favors the isomerization of cis-monounsaturated FAMEs into trans [8,43,[45][46][47][48] because the formation of trans isomers is thermodynamically favored [8,39]. Moreover, it has often been reported that higher temperature leads to greater conversion to fully saturated FAMEs [43,46,48] and increases the reaction speed [45,46]. Hence, in order to achieve the best possible compromise between reaction speed and selectivity to cis-monounsaturated FAMEs, the preferred temperature is in the range of 80-120 • C, as shown in Table 1.…”

Section: Reaction Conditions In Heterogeneous Catalytic Systemssupporting

confidence: 57%

“…First, the parameter for which there are most reports is temperature. All studies agree that an increase in temperature favors the isomerization of cis-monounsaturated FAMEs into trans [8,43,[45][46][47][48] because the formation of trans isomers is thermodynamically favored [8,39]. Moreover, it has often been reported that higher temperature leads to greater conversion to fully saturated FAMEs [43,46,48] and increases the reaction speed [45,46].…”

Section: Reaction Conditions In Heterogeneous Catalytic Systemsmentioning

confidence: 54%

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Catalytic Upgrading of Biodiesel by Partial Hydrogenation of Its FAME Composition: A Systematic Review

Psalidas,

Emmanouilidou,

Kokkinos

2024

Energies

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Biodiesel is one of the most popular biofuels as it is a promising substitute for conventional diesel fuel, but for now, it cannot be used as a stand-alone fuel due to its low oxidative stability. For this reason, there have been efforts to upgrade biodiesel in the last few years through the partial hydrogenation of its fatty acid methyl esters (FAMEs). This procedure succeeds in resolving the problem of low oxidative stability, but in some cases, a new issue arises as non-selective hydrogenation deteriorates the fuel’s cold flow properties, which are crucial for vehicle’s operation without damaging the vehicle’s engine. More specifically, the problem of deteriorated cold flow properties is caused by the formation of trans-monounsaturated and fully saturated FAMEs during the hydrogenation reaction. Hydrogenated biodiesels are preferred to contain more cis-monounsaturated FAMEs because these are considered to have the best combination of high oxidative stability and good cold flow properties. As a result, various systems and methods have been tested to achieve selective partial hydrogenation of biodiesel FAMEs. In this review article, the catalytic systems and processes that stood out in various research studies are presented, and the factors that lead to the best possible outcome are investigated and discussed.

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Section: Reaction Conditions In Heterogeneous Catalytic Systemssupporting

confidence: 57%

Section: Reaction Conditions In Heterogeneous Catalytic Systemsmentioning

confidence: 54%

Catalytic Upgrading of Biodiesel by Partial Hydrogenation of Its FAME Composition: A Systematic Review

Psalidas,

Emmanouilidou,

Kokkinos

2024

Energies

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“…In addition, as conjugate dienes are easier to be hydrogenated than monoenes [41], As Pd-pol was more active than Ni-pol in the hydrogenation, it also hydrogenated the less sterically hampered C18:1 cis isomer faster than the trans one, leading to a cis-C18:1/trans-C18:1 molar ratio of less than 1 in the final mixture.…”

Section: Possible Explanation Of the Different Performances Of Pd-pol...mentioning

confidence: 99%

“…In addition, as conjugate dienes are easier to be hydrogenated than monoenes [41], the less active Ni-pol system was able to more rapidly hydrogenate methyl linoleate and methyl linolenate than methyl oleate, thus resulting in being selective towards the formation of C18:1 methyl ester.…”

Section: Possible Explanation Of the Different Performances Of Pd-pol...mentioning

confidence: 99%

Partial Hydrogenation of Soybean and Waste Cooking Oil Biodiesel over Recyclable-Polymer-Supported Pd and Ni Nanoparticles

et al. 2022

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Biodiesel obtained through the transesterification in methanol of vegetable oils, such as soybean oil (SO) and waste cooking oil (WCO), cannot be used as a biofuel for automotive applications due to the presence of polyunsaturated fatty esters, which have a detrimental effect on oxidation stability (OS). A method of upgrading this material is the catalytic partial hydrogenation of the fatty acid methyl ester (FAME) mixture. The target molecule of the partial hydrogenation reaction is monounsaturated methyl oleate (C18:1), which represents a good compromise between OS and the cold filter plugging point (CFPP) value, which becomes too high if the biodiesel consists of unsaturated fatty esters only. In the present work, polymer-supported palladium (Pd-pol) and nickel (Ni-pol) nanoparticles were separately tested as catalysts for upgrading SO and WCO biodiesels under mild conditions (room temperature for Pd-pol and T = 100 °C for Ni-pol) using dihydrogen (p = 10 bar) as the reductant. Both catalysts were obtained through co-polymerization of the metal containing monomer M(AAEMA)2 (M = Pd, Ni; AEEMA− = deprotonated form of 2-(acetoacetoxy)ethyl methacrylate)) with co-monomers (ethyl methacrylate for Pd and N,N-dimethylacrilamide for Ni) and cross-linkers (ethylene glycol dimethacrylate for Pd and N,N’-methylene bis-acrylamide for Ni), followed by reduction. The Pd-pol system became very active in the hydrogenation of C=C double bonds, but poorly selective towards the desirable C18:1 product. The Ni-pol catalyst was less active than Pd-pol, but very selective towards the mono-unsaturated product. Recyclability tests demonstrated that the Ni-based system retained its activity and selectivity with both the SO and WCO substrates for at least five subsequent runs, thus representing an opportunity for waste biomass valorization.

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“…Vegetable oil-derived compounds such as castor oil-based ricinoleic acid (12-hydroxy-9-octadecenoic acid) have been considered to be an important alternative to diesel fuel. − Methyl undecenoate, which comes from methyl ricinoleate pyrolysis, is also an interesting substrate because its carbon chain length is suitable for jet fuels . The CC hydrogenation of oleochemicals, one of the most encountered chemical transformations for these compounds, involves metal heterogeneous catalysts in most of the cases. − For non-noble-metal-based hydrogenation catalysts, nickel and copper appear to be good candidates. − Supported catalysts containing noble metals, for example, rhodium, palladium, − ruthenium, − and platinum , have also been investigated. According to our literature survey, the reaction conditions with supported metal catalysts are generally harsh in terms of temperature.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Hydrogenation of Derived Vegetable Oils Using Ion-Exchange Resin-Supported Ruthenium Nanoparticles: Scope and Limitations

Madureira

Noël

Léger

et al. 2022

ACS Sustainable Chem. Eng.

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The hydrogenation of vegetable oil-derived compounds using ion-exchange resin-supported ruthenium nanoparticles is reported for the first time. These supported metal catalysts (Ru_DOWEX 2 -X) were prepared by a simple two-step procedure using commercial and cheap materials, affording high efficiency with a low metal loading. They were characterized by several physicochemical techniques and showed well-dispersed ruthenium nanoparticles into robust beads of the strong cation-exchange resin DOWEX 2 -X. Their catalytic activity was evaluated for the hydrogenation of methyl undecenoate in heptane under mild experimental conditions (30 °C, 10 bar of H 2 ), and the high activities of the metal solid catalysts deeply depended on the amount of water inside the pores. In terms of recyclability, several physicochemical analyses after successive catalytic runs showed the robustness of the immobilized ruthenium nanoparticles, for which very low metal leaching and no particle aggregation were observed. The decrease in the catalytic activity could be explained by progressive water loss contained in the resin pores, which was illustrated by a decrease in the bead diameter. The immobilized ruthenium nanoparticles were also evaluated in the catalytic hydrogenation of vegetable oils and their corresponding methyl esters and showed a remarkably high activity compared to other catalytic systems tested under similar mild reaction conditions.

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Partial hydrogenation of a C18:3-rich FAME mixture over Pd/C

Cited by 17 publications

References 37 publications

Catalytic Upgrading of Biodiesel by Partial Hydrogenation of Its FAME Composition: A Systematic Review

Catalytic Upgrading of Biodiesel by Partial Hydrogenation of Its FAME Composition: A Systematic Review

Partial Hydrogenation of Soybean and Waste Cooking Oil Biodiesel over Recyclable-Polymer-Supported Pd and Ni Nanoparticles

Catalytic Hydrogenation of Derived Vegetable Oils Using Ion-Exchange Resin-Supported Ruthenium Nanoparticles: Scope and Limitations

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