The reaction of primary aromatic amines with alkylene carbonates for the selective synthesis of bis-N-(2-hydroxy)alkylanilines: the catalytic effect of phosphonium-based ionic liquids

• Published in: Organic & biomolecular chemistry Vol. 8; no. 22; pp. 5187 - 5198
• Main Authors: Selva, Maurizio, Fabris, Massimo, Lucchini, Vittorio, Perosa, Alvise, Noè, Marco
• Format: Journal Article
• Language: English
• Published: England 21.11.2010
• Subjects: Alkylation; Amines - chemistry; Aniline Compounds - chemical synthesis; Aniline Compounds - chemistry; Catalysis; Dioxolanes - chemistry; Hydrocarbons, Aromatic - chemistry; Ionic Liquids - chemistry; Kinetics; Organophosphorus Compounds - chemistry; Phosphines - chemistry; Propane - analogs & derivatives; Propane - chemistry; Temperature; Zeolites - chemistry

At T≥ 140 °C, different primary aromatic amines (pX-C(6)H(4)NH(2); X = H, OCH(3), CH(3), Cl) react with both ethylene- and propylene-carbonates to yield a chemoselective N-alkylation process: bis-N-(2-hydroxyalkyl)anilines [pX-C(6)H(4)N(CH(2)CH(R)OH)(2); R = H, CH(3)] are the major products and the...