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Modulating catalytic selectivity by base addition in aqueous reductive amination of 1,6-hexanediol using Ru/C

Gupta, Navneet Kumar ; Palenicek, Phillip ; Nortmeyer, Lucas ; Meyer, Gregor Maurice ; Schäfer, Timo ; Hellmann, Tim ; Hofmann, Jan P. ; Rose, Marcus (2022)
Modulating catalytic selectivity by base addition in aqueous reductive amination of 1,6-hexanediol using Ru/C.
In: ACS Sustainable Chemistry & Engineering, 10 (44)
doi: 10.1021/acssuschemeng.2c04301
Artikel, Bibliographie

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Kurzbeschreibung (Abstract)

Efficient base-modulated product selectivity in the aqueous-phase Ru/C-catalyzed reductive amination of 1,6-hexanediol (HDO) was reported by performing the reaction at mild conditions (463 K, 25 bar H2). High selectivity of amines could be controlled by the addition of different bases; for example, Cs2CO3 addition gave a high yield of 6-amino-1-hexanol (AH, 26%). However, the addition of Ba(OH)2 resulted in the formation of high yield of secondary amination products, hexamethylenediamine (HMDA, 34%) and azepane (26%). The hydroxide base, especially Ba(OH)2, aids in the initial conversion of HDO to AH by significantly decreasing the apparent activation energy from 68 to 48 kJ mol–1. A closer analysis of the formation of secondary products (azepane and HMDA) revealed a faster reaction between NH3 and the carbonyl-containing intermediate by the addition of Ba(OH)2 into the reaction solution.

Typ des Eintrags: Artikel
Erschienen: 2022
Autor(en): Gupta, Navneet Kumar ; Palenicek, Phillip ; Nortmeyer, Lucas ; Meyer, Gregor Maurice ; Schäfer, Timo ; Hellmann, Tim ; Hofmann, Jan P. ; Rose, Marcus
Art des Eintrags: Bibliographie
Titel: Modulating catalytic selectivity by base addition in aqueous reductive amination of 1,6-hexanediol using Ru/C
Sprache: Englisch
Publikationsjahr: 2022
Ort: Washington
Verlag: ACS Publications
Titel der Zeitschrift, Zeitung oder Schriftenreihe: ACS Sustainable Chemistry & Engineering
Jahrgang/Volume einer Zeitschrift: 10
(Heft-)Nummer: 44
DOI: 10.1021/acssuschemeng.2c04301
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Kurzbeschreibung (Abstract):

Efficient base-modulated product selectivity in the aqueous-phase Ru/C-catalyzed reductive amination of 1,6-hexanediol (HDO) was reported by performing the reaction at mild conditions (463 K, 25 bar H2). High selectivity of amines could be controlled by the addition of different bases; for example, Cs2CO3 addition gave a high yield of 6-amino-1-hexanol (AH, 26%). However, the addition of Ba(OH)2 resulted in the formation of high yield of secondary amination products, hexamethylenediamine (HMDA, 34%) and azepane (26%). The hydroxide base, especially Ba(OH)2, aids in the initial conversion of HDO to AH by significantly decreasing the apparent activation energy from 68 to 48 kJ mol–1. A closer analysis of the formation of secondary products (azepane and HMDA) revealed a faster reaction between NH3 and the carbonyl-containing intermediate by the addition of Ba(OH)2 into the reaction solution.

Fachbereich(e)/-gebiet(e): 07 Fachbereich Chemie
07 Fachbereich Chemie > Ernst-Berl-Institut
07 Fachbereich Chemie > Ernst-Berl-Institut > Fachgebiet Technische Chemie
07 Fachbereich Chemie > Ernst-Berl-Institut > Fachgebiet Technische Chemie > Technische Chemie II
Hinterlegungsdatum: 12 Mai 2023 12:17
Letzte Änderung: 19 Feb 2024 09:15
PPN: 507762584
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