Direct synthesis of asymmetric secondary amines from N-alkylation of nitriles with alcohols by heterogeneous catalysis

SEGOBIA DARIO; TRASARTI ANDRES; APESTEGUIA CARLOS

SAN DIEGO

Congreso; 17th International Congress On Catalysis (ICC); 2020

North American Catalysis Society

Asymmetric secondary amines (ASA) are widely used by the fine chemical industryas they are important building blocks for the synthesis of agrochemicals, bioactive compounds and pharmaceuticals. Different routes have been reported for the selective synthesis of secondary amines. Among them, the N-alkylation of primary amines with alcohols is an efficient and environmentally benign method to produce ASA because it affords only water as by-product and may proceed without adding hydrogen. As is well-known, primary amines are obtained at industrial level by selective hydrogenation of the corresponding nitriles. Thus, it becomes attractive to develop a one pot process to produce asymmetricsecondary amines via the direct amination of alcohols with nitriles,which avoids the synthesis, separation and purification of the primary aminesin a first step as shown in Fig. 1. The efficient synthesis of ASA fromamination of alcohols with nitriles requires the development of activeand selective metal-based catalysts that promote the reaction pathwayleading from reactants to ASA avoiding the formation of byproductsvia secondary reactions. In the present work we investigate the selectivesynthesis of ASA by N-alkylation of butyronitrile (BN) with primary (ethanol, n-propanol, isobutanol and n-octanol) and secondary (2-propanol, 2-butanol, 2-octanol) alcohols on silicasupported Co, Ni and Ru catalysts.