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Unravelling the Mechanism of the Ru/C‐Catalysed Isohexide and Ether Isomerization by Hydrogen Isotope Exchange

Engel, Rebecca V. ; Niemeier, Johannes ; Fink, Anja ; Rose, Marcus (2023)
Unravelling the Mechanism of the Ru/C‐Catalysed Isohexide and Ether Isomerization by Hydrogen Isotope Exchange.
In: Advanced Synthesis & Catalysis, 2018, 360 (12)
doi: 10.26083/tuprints-00024536
Artikel, Zweitveröffentlichung, Postprint

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Kurzbeschreibung (Abstract)

In this article we show that the catalytic isomerization of isohexide sugar alcohols as well as their respective ethers can occur by a hydride-based mechanism rather than a dehydrogenation/re-hydrogenation. C−H bonds in α-position to hydroxy and ether groups are activated using Ru/C as solid catalyst at temperatures as high as 160 °C and above. Hydrogen isotope exchange experiments proved that a full hydride exchange and isomerization is possible for isohexides but unexpectedly also for their methyl ethers. This is of great importance as it proves the co-existence of the both mechanisms for reactions that were so far assumed to occur solely by a dehydrogenation/re-hydrogenation. Hence, this co-existence should be taken into account for kinetic investigations of such reaction systems especially in the conversion of biomass-based chemicals under hydrogenation conditions.

Typ des Eintrags: Artikel
Erschienen: 2023
Autor(en): Engel, Rebecca V. ; Niemeier, Johannes ; Fink, Anja ; Rose, Marcus
Art des Eintrags: Zweitveröffentlichung
Titel: Unravelling the Mechanism of the Ru/C‐Catalysed Isohexide and Ether Isomerization by Hydrogen Isotope Exchange
Sprache: Englisch
Publikationsjahr: 13 November 2023
Ort: Darmstadt
Publikationsdatum der Erstveröffentlichung: 2018
Ort der Erstveröffentlichung: Weinheim
Verlag: Wiley-VCH
Titel der Zeitschrift, Zeitung oder Schriftenreihe: Advanced Synthesis & Catalysis
Jahrgang/Volume einer Zeitschrift: 360
(Heft-)Nummer: 12
DOI: 10.26083/tuprints-00024536
URL / URN: https://tuprints.ulb.tu-darmstadt.de/24536
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Kurzbeschreibung (Abstract):

In this article we show that the catalytic isomerization of isohexide sugar alcohols as well as their respective ethers can occur by a hydride-based mechanism rather than a dehydrogenation/re-hydrogenation. C−H bonds in α-position to hydroxy and ether groups are activated using Ru/C as solid catalyst at temperatures as high as 160 °C and above. Hydrogen isotope exchange experiments proved that a full hydride exchange and isomerization is possible for isohexides but unexpectedly also for their methyl ethers. This is of great importance as it proves the co-existence of the both mechanisms for reactions that were so far assumed to occur solely by a dehydrogenation/re-hydrogenation. Hence, this co-existence should be taken into account for kinetic investigations of such reaction systems especially in the conversion of biomass-based chemicals under hydrogenation conditions.

Status: Postprint
URN: urn:nbn:de:tuda-tuprints-245363
Sachgruppe der Dewey Dezimalklassifikatin (DDC): 500 Naturwissenschaften und Mathematik > 540 Chemie
Fachbereich(e)/-gebiet(e): 07 Fachbereich Chemie
07 Fachbereich Chemie > Ernst-Berl-Institut > Fachgebiet Technische Chemie
07 Fachbereich Chemie > Ernst-Berl-Institut > Fachgebiet Technische Chemie > Technische Chemie II
Hinterlegungsdatum: 13 Nov 2023 15:43
Letzte Änderung: 06 Dez 2023 09:56
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