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Symposium Year: 2013
Student(s): Erin Nicole Benton, Matthew Christopher Ellison
Faculty Mentor(s): Dr. Benjamin Norris
This research was conducted to produce a reusable non-petroleum based solvent from mixtures of choline chloride and hydrogen bond donors. Examples include choline chloride and urea in a 1:2 mixture, choline chloride and glycerol in a 1:1 mixture, and choline chloride and isosorbide in a 1:3 mixture. These solvents where then used to perform l-proline-catalyzed aldol reactions between benzaldehyde and 3-pentanone. Overall these attempts yielded no positive results. The components of the solvent mixtures interfered with the reactions in all experiments. Due to the lack of success with the aldol reaction, an electrophilic aromatic substitution reaction was attempted between 1,4-dimethoxybenzene and tert-butanol. This reaction normally occurs in acetic acid and sulfuric acid at 0°C, and has a high rate of reaction. The reaction was altered to eliminate the need for the sulfuric acid in the reaction. To compensate, the temperature at which the reaction takes place was increased to around 80°C, and allowed to heat and stir for one week. Even with a different reaction the same problem was occurring, the solvent was interacting with the reactants causing an undesired product to be obtained.
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