Solvents from Biorenewable Sources: Ionic Liquids Based on Fructose
Scott T. Handy*, Maurice Okello and Gary Dickenson
*Department of Chemistry, Middle Tennessee State University, Murfreesboro,
Tennessee 37132, Email: shandy
mtsu.edu
S. T. Handy, M. Okello, G. Dickenson, Org. Lett., 2003, 5, 2513-2515.
DOI: 10.1021/ol034778b
Abstract
Novel room-temperature ionic liquids (RTILs) have been prepared from fructose which are comparable to conventional imidazole-based RTILs. A system for Heck reactions was developed. Recycling of RTIL/catalyst was possible without significant loss of activity.
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Details
Researchers from the State University of New York at Binghamton have developed a new class of room-temperature ionic liquids (RTILs) derived from fructose. These RTILs exhibit tunable solvent properties similar to conventional imidazole-based RTILs and have been successfully used as recyclable solvents for the Heck reaction of aryl iodides. The study highlights the environmental benefits of using biorenewable resources over petroleum-based solvents. The synthesis involves converting fructose into hydroxymethyleneimidazole, followed by alkylation to form imidazolium cations. The resulting RTILs, with various anions, show different viscosities and solubility properties. The triflimide and dicyanimide salts were found to be the least viscous and displayed complementary solubility characteristics. The fructose-derived RTILs were effective in catalyzing the Heck reaction, with the catalyst and solvent being recyclable up to five times. However, they were less effective with aryl bromides. The study also explored the kinetics of the Heck reaction in different RTILs, finding that the fructose-derived RTILs had a slower reaction rate compared to conventional [bmim] salts. The research suggests that these new RTILs could be used for other transition metal-catalyzed reactions, offering a greener alternative to traditional solvents.
Key Words
Ionic Liquids, biorenewable, green chemistry, Heck Reaction
ID: J54-Y2003-010
