Gupta, Navneet Kumar ; Palenicek, Phillip ; Nortmeyer, Lucas ; Meyer, Gregor Maurice ; Schäfer, Timo ; Hellmann, Tim ; Hofmann, Jan P. ; Rose, Marcus (2023)
Modulating Catalytic Selectivity by Base Addition in Aqueous Reductive Amination of 1,6-Hexanediol Using Ru/C.
In: ACS Sustainable Chemistry & Engineering, 2022, 10 (44)
doi: 10.26083/tuprints-00024545
Artikel, Zweitveröffentlichung, Postprint
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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: | 2023 |
| Autor(en): | Gupta, Navneet Kumar ; Palenicek, Phillip ; Nortmeyer, Lucas ; Meyer, Gregor Maurice ; Schäfer, Timo ; Hellmann, Tim ; Hofmann, Jan P. ; Rose, Marcus |
| Art des Eintrags: | Zweitveröffentlichung |
| Titel: | Modulating Catalytic Selectivity by Base Addition in Aqueous Reductive Amination of 1,6-Hexanediol Using Ru/C |
| Sprache: | Englisch |
| Publikationsjahr: | 2 Oktober 2023 |
| Ort: | Darmstadt |
| Publikationsdatum der Erstveröffentlichung: | 2022 |
| Verlag: | American Chemical Society |
| Titel der Zeitschrift, Zeitung oder Schriftenreihe: | ACS Sustainable Chemistry & Engineering |
| Jahrgang/Volume einer Zeitschrift: | 10 |
| (Heft-)Nummer: | 44 |
| DOI: | 10.26083/tuprints-00024545 |
| URL / URN: | https://tuprints.ulb.tu-darmstadt.de/24545 |
| Zugehörige Links: | |
| Herkunft: | Zweitveröffentlichungsservice |
| 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. |
| Freie Schlagworte: | amination, 1,6-hexanediol, Ru-supported carbon, base effect, aqueous-phase reaction |
| Status: | Postprint |
| URN: | urn:nbn:de:tuda-tuprints-245453 |
| Sachgruppe der Dewey Dezimalklassifikatin (DDC): | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Fachbereich(e)/-gebiet(e): | 07 Fachbereich Chemie 07 Fachbereich Chemie > Ernst-Berl-Institut 07 Fachbereich Chemie > Ernst-Berl-Institut > Fachgebiet Technische Chemie |
| Hinterlegungsdatum: | 02 Okt 2023 09:29 |
| Letzte Änderung: | 19 Feb 2024 09:15 |
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| Suche nach Titel in: | TUfind oder in Google |
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- Modulating Catalytic Selectivity by Base Addition in Aqueous Reductive Amination of 1,6-Hexanediol Using Ru/C. (deposited 02 Okt 2023 09:29) [Gegenwärtig angezeigt]
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