A Two-Step Oxidative Cleavage of 1,2-Diol Fatty Esters into Acids or Nitriles by a Dehydrogenation-Oxidative Cleavage Sequence.

Autor: Guicheret B; ICBMS-UMR 5246-Université Lyon 1, CNRS-INSA-ESCPE Bâtiment Lederer, 69622, Villeurbanne, France., Bertholo Y; ICBMS-UMR 5246-Université Lyon 1, CNRS-INSA-ESCPE Bâtiment Lederer, 69622, Villeurbanne, France., Blach P; Oleon, Avril Group, Rue les Rives de l'Oise, 60280, Compiègne, France., Raoul Y; Oleon, Avril Group, Rue les Rives de l'Oise, 60280, Compiègne, France., Métay E; ICBMS-UMR 5246-Université Lyon 1, CNRS-INSA-ESCPE Bâtiment Lederer, 69622, Villeurbanne, France., Lemaire M; ICBMS-UMR 5246-Université Lyon 1, CNRS-INSA-ESCPE Bâtiment Lederer, 69622, Villeurbanne, France.
Jazyk: angličtina
Zdroj: ChemSusChem [ChemSusChem] 2018 Oct 11; Vol. 11 (19), pp. 3431-3437. Date of Electronic Publication: 2018 Aug 23.
DOI: 10.1002/cssc.201801640
Abstrakt: Dehydrogenative oxidation of vicinal alcohols catalyzed by a commercially 64 wt.% Ni/SiO 2 catalyst leads to the formation of α-hydroxyketone. This first step was developed without additional solvent according to two protocols: "under vacuum" or "with an olefin scavenger". The synthesis of ketols was carried out with good conversions and selectivities. The recyclability of the supported nickel was also studied. Acyloin was then cleaved with oxidative reagent "formic acid/hydrogen peroxide", which is cheap and can be used on a large scale for industrial oxidation processes. The global yield of this sequential system was up to 80 % to pelargonic acid and azelaic acid monomethyl ester without intermediate purification. By treating the acyloin intermediate with hydroxylamine, nitriles were obtained with a good selectivity.
(© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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