Abstract
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.
Highlights
The production and use of fatty acid methyl esters (FAME) and fatty acid ethyl esters (FAEE) obtained from vegetable or animal fats and oils, usually known as biodiesel, has increased abruptly over the last decade due to the double threats of oil shortage and climate changes
The reactions were performed in an ionic liquid (IL)-based biphasic catalytic system; for comparison reasons, some reactions were performed in homogeneous media
The results shows that addition of the IFAME decreased by approximately 25% the fungus growth, which evidences the potential of using the modified biodiesel as antimicrobial additive
Summary
The production and use of fatty acid methyl esters (FAME) and fatty acid ethyl esters (FAEE) obtained from vegetable or animal fats and oils, usually known as biodiesel, has increased abruptly over the last decade due to the double threats of oil shortage and climate changes. Whilst the biodiesel production was 265 million gallons in 2001, in 2011 it increased to 5,651 million gallons.[1] Biodiesel is foremost used blended to conventional diesel. The addition of 7% of biodiesel in the commercialized diesel (B7 blend) is nowadays mandatory in Brazil and is the maximum percentage permitted in Europe. The use of even higher percentages is currently under discussion. The replacing of petroleum derivatives by biodiesel is ecologically advantageous because the biofuel gives rise to an equalized CO2-balance, besides proportionating lower emission of particulate matter into the atmosphere and no release of aromatic and sulfur-containing compounds.[2,3]
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