Synthesis of furan derivatives via cascade-type reactions catalyzed by solid acids

Chávez-Sifontes, Marvin; Dómine, Marcelo E.; Valencia, Susana

doi:10.1016/j.cattod.2015.04.018

Cited by 7 publications

(7 citation statements)

References 33 publications

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“…Ethanol is miscible with water and 2-methylfuran and is thus a suitable solvent for the process. In experiments carried out by Chavez-Sifontes et al., a 2-MF/solvent ratio of 50/50 (wt %) was used. In our experiments, we tried decreasing the amount of ethanol.…”

Section: Experimental Results and Discussionmentioning

confidence: 99%

“…In addition, other catalysts were studied, and the results were similar: adding water to the reaction mixture increases the yield of trimers and decreases the conversion . The trimer selectivity can also be enhanced by conducting the reaction in an ethanol–water solvent …”

Section: Carbon Chain Increase Reactionsmentioning

confidence: 93%

“…As early as the 1960s, it was shown that 2-methylfuran forms 5,5-bis(5-methyl-2-furyl)pentan-2-one (trimer) through a condensation reaction in the presence of sulfuric acid . The reaction proceeds via the hydrolytic ring opening of one 2-methylfuran molecule to an aldehyde (4-oxopentanal), followed by hydroxyalkylation/alkylation of the formed aldehyde with two molecules of 2-methylfuran. ,, This trimerization can be done in aqueous sulfuric acid (50–12–38 (wt %) 2-MF–H 2 SO 4 –H 2 O) at 75% yield and a high-purity (96%) trimer can be achieved after distillation …”

Section: Carbon Chain Increase Reactionsmentioning

confidence: 99%

See 2 more Smart Citations

Carbon Chain Length Increase Reactions of Platform Molecules Derived from C5 and C6 Sugars

Käldström

Lindblad

Lamminpää

et al. 2017

Ind. Eng. Chem. Res.

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The production of liquid fuels from lignocellulose-derived platform molecules has attracted much interest in recent years. Platform molecules mostly have a shorter carbon chain length, compared to liquid fuels, which have a typical chain length varying between 4 and 25 carbon atoms, whereas aviation and especially diesel fuel have a carbon chain length exceeding 10 carbon atoms. For this reason, some carbon chain length increase reactions are required. In this article, carbon chain length increase reactions are compared for typical lignocellulose-derived platform molecules. The focus is placed on the ability of the molecules to participate in self-condensation reactions in a controlled manner. Hydrogen plays a key role when producing fuels from platform molecules. Hydrotreatment is applied not only when converting the products from a carbon chain length increase reaction into hydrocarbons but also for modifying the functional groups of the model compounds and, thereby, their reactivity.

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Section: Experimental Results and Discussionmentioning

confidence: 99%

Section: Carbon Chain Increase Reactionsmentioning

confidence: 93%

Section: Carbon Chain Increase Reactionsmentioning

confidence: 99%

See 1 more Smart Citation

Carbon Chain Length Increase Reactions of Platform Molecules Derived from C5 and C6 Sugars

Käldström

Lindblad

Lamminpää

et al. 2017

Ind. Eng. Chem. Res.

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“…Hence, hexose is completely deoxygenated to butene which is then oligomerized. [8][9][10][11] Aldol condensation reactions [12,13] and hydroalkylations/alkylations [14][15][16][17][18][19] have also been employed to build up fuel precursors from small molecules. Thereby, it can be seen that the latter transformations can proceed with a high degree of selectivity (with respect to the carbon atom number), and it has been proposed to carry out the carbon-carbon bond formations with moderately oxygenated molecules.…”

Section: Introductionmentioning

confidence: 99%

Direct conversion of carboxylic acids (C n ) to alkenes (C 2n−1 ) over titanium oxide in absence of noble metals

Oliver-Tomas

Renz

Corma

2016

Journal of Molecular Catalysis A: Chemical

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Carbon-carbon bond formations and deoxygenation reactions are important for biomass up-grading. The classical ketonic decarboxylation of carboxylic acids provides symmetrical ketones with 2n+1 carbon atoms and eliminates three oxygen atoms.Herein, this reaction is carried out with titanium oxide at 400 ºC, and an olefin with 2n+1 carbon atoms is obtained instead of the ketone. For olefin formation hydrogen transfer reactions are required from suitable precursors to form aromatics and coke.Additional aldol condensation reactions increase further molecular weight in the product mixture. Hence, a combination of titanium oxide with a hydrodeoxygenation bed provides double amount of diesel fuel as the combination with zirconium oxide when reacting hexose-derived pentanoic acid.

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“…11 Aldol condensations of FF/HMF and/or their derivatives with carbonyl groups like acetone, [12][13][14][15][16] hydroxyacetone, 17 butaldehyde, 18 2-butanone, 19 methyl isobutyl ketone, 20 levulinic acid 11,21,22 and angelica lactone 23 have commonly been conducted to obtain the C 9 -C 16 fuel precursors, but these carbonyl compounds originate from fossil resources or are produced from biomass by multi-step reactions, leading to low efficiency and high cost for the entire synthesis. As an alternative, hydroxyalkylation-alkylation of FF and 2-methylfuran obtained by hydrodeoxygenation of FF was reported to produce C 15 fuel precursors with a branched carbon framework.…”

Section: -4mentioning

confidence: 99%

Production of renewable long-chained cycloalkanes from biomass-derived furfurals and cyclic ketones

et al. 2018

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a Developing renewable long-chain cycloalkanes from lignocellulosic biomass is of significance because it offers huge resource storage, wide applications in aviation/diesel fuels and mitigation of CO 2 emissions.In this paper, cycloalkanes with carbon chain lengths of 13-18 were produced from biomass-derived furfural species (furfural and 5-hydroxymethylfurfural) and cyclic ketones (cyclopentanone and cyclohexanone) via aldol condensation, followed by hydrogenation to saturate the C]C and C]O bonds, and hydrodeoxygenation to remove oxygen atoms. The aldol condensation of the furfural species with cyclic ketones was catalyzed by NaOH and the target condensation intermediates were obtained in yields of more than 90% at room temperature (30 C) with a short reaction time (40 min). By using amorphous zirconium phosphate combined with Pd/C as the catalyst, liquid cycloalkanes were produced at the optimal conditions with a yield of 76%. When the combined solid catalyst was reused, the target products reduced after the second run but the initial yield could be largely recovered by recalcination of the spent zirconium phosphate. Considering that cyclopentanone and cyclohexanone can be easily produced from furfural (originating from hemicellulose) and phenol (originating from lignin), respectively, this condensation has the potential to achieve the integrated conversion of biomassderived cellulose, hemicellulose and lignin to jet fuel and/or diesel additives.

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Synthesis of furan derivatives via cascade-type reactions catalyzed by solid acids

Cited by 7 publications

References 33 publications

Carbon Chain Length Increase Reactions of Platform Molecules Derived from C5 and C6 Sugars

Carbon Chain Length Increase Reactions of Platform Molecules Derived from C5 and C6 Sugars

Direct conversion of carboxylic acids (C n ) to alkenes (C 2n−1 ) over titanium oxide in absence of noble metals

Production of renewable long-chained cycloalkanes from biomass-derived furfurals and cyclic ketones

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