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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 (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
Article, Secondary publication, Postprint

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Item Type: Article
Type of entry: Secondary publication
Title: Modulating Catalytic Selectivity by Base Addition in Aqueous Reductive Amination of 1,6-Hexanediol Using Ru/C
Language: English
Date: 2 October 2023
Place of Publication: Darmstadt
Year of primary publication: 2022
Publisher: American Chemical Society
Journal or Publication Title: ACS Sustainable Chemistry & Engineering
Volume of the journal: 10
Issue Number: 44
DOI: 10.26083/tuprints-00024545
Corresponding Links:
Origin: Secondary publication service
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.

Uncontrolled Keywords: amination, 1,6-hexanediol, Ru-supported carbon, base effect, aqueous-phase reaction
Status: Postprint
URN: urn:nbn:de:tuda-tuprints-245453
Classification DDC: 500 Science and mathematics > 540 Chemistry
Divisions: 07 Department of Chemistry > Ernst-Berl-Institut > Fachgebiet Technische Chemie
Date Deposited: 02 Oct 2023 09:29
Last Modified: 25 Oct 2023 13:38
URI: https://tuprints.ulb.tu-darmstadt.de/id/eprint/24545
PPN: 51269138X
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