10576-04-2Relevant articles and documents
Dehydrogenation of amines to nitriles in aqueous micelles
Biondini, Daniele,Brinchi, Lucia,Germani, Raimondo,Goracci, Laura,Savelli, Gianfranco
, p. 3060 - 3063 (2005)
An aqueous reaction medium, based on a surfactant solution of dimethyldodecylamine N-oxide (DDAO) has been developed for the oxidative dehydrogenation of primary amines using NiSO4 as catalyst and K 2S2O8 as oxidant. This reaction medium enhances the rate of the reaction relative to other media previously reported in the literature, which are also toxic. The reactions of various aliphatic and cyclic amines have been investigated and gave nitriles with yields of >90% in mild conditions. The aqueous surfactant solution and reagents were recycled for future use. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Preparation of nitrogen-doped carbon supported cobalt catalysts and its application in the reductive amination
Yuan, Ziliang,Liu, Bing,Zhou, Peng,Zhang, Zehui,Chi, Quan
, p. 347 - 356 (2019/01/24)
The use of non-noble metal catalysts with high activity is of great importance for organic transformations. Herein, nitrogen-doped carbon supported cobalt catalysts with high surface area up to 981.2 m2/g were prepared via the simple pyrolysis of cobalt coordinated organic polymers with silica as the hard template. The pyrolysis temperature showed a great effect on the structure and properties of the as-prepared catalysts. The Co@NC-800 catalyst with the pyrolysis temperature of 800 °C demonstrated a high activity for the selective reductive amination of carbonyl compounds to primary amines with ammonia and hydrogen. Structurally-diverse primary amines with yields in the range from 81.8% to 100% were attained under the optimal conditions. The Co@NC-800 catalyst could be reused without the loss of its activity. The Co@NC-800 catalyst demonstrated comparable activity as the reported heterogeneous noble metal catalysts.
Catalytic Hydrogen Production by Ruthenium Complexes from the Conversion of Primary Amines to Nitriles: Potential Application as a Liquid Organic Hydrogen Carrier
Ventura-Espinosa, David,Marzá-Beltrán, Aida,Mata, Jose A.
, p. 17758 - 17766 (2016/11/28)
The potential application of the primary amine/nitrile pair as a liquid organic hydrogen carrier (LOHC) has been evaluated. Ruthenium complexes of formula [(p-cym)Ru(NHC)Cl2] (NHC=N-heterocyclic carbene) catalyze the acceptorless dehydrogenation of primary amines to nitriles with the formation of molecular hydrogen. Notably, the reaction proceeds without any external additive, under air, and under mild reaction conditions. The catalytic properties of a ruthenium complex supported on the surface of graphene have been explored for reutilization purposes. The ruthenium-supported catalyst is active for at least 10 runs without any apparent loss of activity. The results obtained in terms of catalytic activity, stability, and recyclability are encouraging for the potential application of the amine/nitrile pair as a LOHC. The main challenge in the dehydrogenation of benzylamines is the selectivity control, such as avoiding the formation of imine byproducts due to transamination reactions. Herein, selectivity has been achieved by using long-chain primary amines such as dodecylamine. Mechanistic studies have been performed to rationalize the key factors involved in the activity and selectivity of the catalysts in the dehydrogenation of amines. The experimental results suggest that the catalyst resting state contains a coordinated amine.
