Tuned Bis-Layered Supported Ionic Liquid Catalyst (SILCA) for Competitive Activity in the Heck Reaction of Iodobenzene and Butyl Acrylate

• Published in: Catalysts Vol. 10; no. 9; p. 963
• Main Authors: Vucetic, Nemanja, Virtanen, Pasi, Nuri, Ayat, Shchukarev, Andrey, Mikkola, Jyri-Pekka, Salmi, Tapio
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 01.09.2020
• Subjects: catalyst screening; Catalysts; Chemical reactions; Chemical synthesis; Heck reaction; Ionic liquids; Ions; Ligands; Nanoparticles; NMR; Nuclear magnetic resonance; Optimization; Palladium; Pharmaceutical industry; Silicon dioxide; supported ionic liquid catalyst (SILCA); X ray photoelectron spectroscopy
• ISSN: 2073-4344; 2073-4344
• DOI: 10.3390/catal10090963

A thorough experimental optimization of supported ionic liquid catalyst (SILCA) was performed in order to obtain a stable and efficient catalyst for the Heck reaction. Out of fifteen proposed structures, propyl imidazolium bromide-tetramethylguanidinium pentanoate modified SiO2 loaded with PdCl2 appeared to be the most stable and to have a good activity in the reaction between butylacrylate and iodobezene, resulting in a complete conversion in 40 min at 100 °C, in four consecutive experiments. This study elucidated on the stability of the catalytic system with an ionic liquid layer during the catalyst synthesis but also under reaction conditions. In the bis-layered catalyst, the imidazolium moiety as a part of internal layer, brought rigidity to the structure, while in external layer pentanoic acid gave sufficiently acidic carboxylic group capable to coordinate 1,1,3,3-tetramethylguanidine (TMG) and thus, allow good dispersion of Pd nanoparticles. The catalyst was characterized by means of XPS, FT-IR, TEM, ICP-OES, ζ-potential, EDX, TGA, and 13C NMR. The release and catch mechanism was observed, whereas Pd re-deposition can be hindered by catalyst poisoning and eventual loss of palladium.