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Efficient C-C coupling of bio-based furanics and carbonyl compounds to liquid hydrocarbon precursors over lignosulfonate derived acidic carbocatalysts
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry. Laboratory of Industrial Chemistry and Reaction Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, Turku, Finland .
2018 (English)In: Catalysis Science & Technology, ISSN 2044-4753, E-ISSN 2044-4761, Vol. 8, no 9, p. 2449-2459Article in journal (Refereed) Published
Abstract [en]

This paper demonstrates the catalytic potential of novel Na-lignosulfonate (LS) derived meso/macroporous solid protonic acids upon C–C coupling of bio-based furanics and carbonyl compounds. The materials demonstrated catalytic activity for solventless hydroxyalkylation/alkylation (HAA) of 2-methylfuran with furfural, acetone, butanal, cyclohexanone, levulinic acid and α-angelica lactone under mild reaction conditions (50–60 °C) producing branched-chain C12–C16 hydrocarbon precursors in yields approaching 96%. Moreover, the carbon materials exhibiting high total acidity (6–6.4 mmol g−1) outperformed sulfonic acid resins (Amberlyst®70, Amberlite®IR120 and LS resin), zeolites and liquid acids (p-toluenesulfonic acid, acetic acid and phenol). In fact, the most active carbocatalyst (60LS40PS350H+) exhibited the same turnover frequency as p-toluenesulfonic acid (186 h−1) upon furfural conversion but with an improved HAA product yield (up to 88%) and reusability, maintaining 98% of its original activity up to seven reaction cycles. The observed catalytic activity and operational stability of the LS derived acidic carbocatalysts were attributed to the strongly Brønsted acidic –SO3H groups covalently incorporated into their structural carbon framework and the promotional effects of hydrophilic surface functional groups (–COOH and –OH) favoring adsorption of oxygenated reactant molecules.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2018. Vol. 8, no 9, p. 2449-2459
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-146304DOI: 10.1039/C7CY02601CISI: 000433163900021OAI: oai:DiVA.org:umu-146304DiVA, id: diva2:1195202
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Bio4EnergyAvailable from: 2018-04-04 Created: 2018-04-04 Last updated: 2019-08-29Bibliographically approved

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Konwar, Lakhya JyotiSamikannu, AjaikumarMikkola, Jyri-Pekka

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