Production of additives with antimicrobial activity via tandem hydroformylation-amine condensation of soybean fame using an ionic liquid-based biphasic catalytic system

• Autor(a) principal: Ramalho, Hugo de Farias
• Data de Publicação: 2016
• Outros Autores: Ferreira, Karlla M. C., Machado, Paula M. A., Silva, Tamyris B., Rangel, Ellen T., Prauchner, Marcos Juliano, Suarez, Paulo Anselmo Ziani
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional da UnB
• Texto Completo: http://repositorio.unb.br/handle/10482/30222; http://dx.doi.org/10.5935/0103-5053.20150250
• topic: Biodiesel; Líquidos - íons; Aditivos

A biphasic catalytic system based in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate was employed for tandem hydroformylation-amine condensation reactions of soybean FAME using HRhCO(PPh3)3 as the catalyst precursor and n-butylamine. Using a tenfold excess of the ligand PPh3, the presence of the ionic liquid increased the selectivity for imine if compared to the reaction carried out under similar conditions, but in homogeneous media.The yield for imine reached 75% after 24 h. On the other hand, in the absence of a PPh3 excess, the effect of using the ionic liquid was opposite and the selectivity for imine decreased. This supposedly occurred due to the generation ofN-heterocyclics carbenes, which would coordinate to Rh to form species active for parallel and/or consecutive reactions. When an excess PPh3 is used, it suppress the carbenes coordination, maintaining the Rh complex in a form active for hydroformylation.The obtained imine products presented remarkable antimicrobial activity towards a set of fungi and bacteria commonly present in fuel storage tanks.