Selective Synthesis of Primary Amines from Nitriles under Hydrogenation Conditions

• Published in: Advanced synthesis & catalysis Vol. 360; no. 8; pp. 1726 - 1732
• Main Authors: Yoshimura, Masatoshi, Komatsu, Akira, Niimura, Masaru, Takagi, Yukio, Takahashi, Tohru, Ueda, Shun, Ichikawa, Tomohiro, Kobayashi, Yutaka, Okami, Hiroki, Hattori, Tomohiro, Sawama, Yoshinari, Monguchi, Yasunari, Sajiki, Hironao
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 17.04.2018; Wiley Subscription Services, Inc
• Subjects: Acetic acid; Aliphatic compounds; Aluminum oxide; Amines; Catalysis; Catalysts; Chemistry; Chemistry, Applied; Chemistry, Organic; chemoselectivity; gold; heterogeneous catalysis; Hydrogen storage; Hydrogenation; Nitriles; palladium; Physical Sciences; Science & Technology; Selectivity; Surface structure; Synthesis; chemoselectivity; heterogeneous catalysis; MECHANISM; CONVERSION; CATALYTIC-HYDROGENATION; amines; BUTYRONITRILE; hydrogenation; N-BUTYLAMINE; gold; LIQUID-PHASE; nitriles; REDUCTION; palladium; VINYL-ACETATE SYNTHESIS; INSIGHTS
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201800102

The hydrogenation of aliphatic nitriles over Pd/C, Pd/Al2O3, and Pd−Au/Al2O3 catalysts were evaluated for the selective hydrogenation of aliphatic nitriles to the corresponding primary amines. The highest selectivity (>99%) toward primary amines was achieved when the reaction was carried out in acetic acid using 10 mol% of 25% Pd‐5% Au/Al2O3 under relatively low hydrogen pressure (0.8 MPa). Characterization of the catalysts by XRD, CO adsorption experiments, and EXAFS revealed that the excellent selectivity of 25% Pd‐5% Au/Al2O3 toward the synthesis of primary amines is determined by the electronic properties and/or the surface structure resulting from alloying Pd with Au.