Browsing by Author "Lee, Roland"
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- ItemConversion of lignin pyrolysis oil to cyclohexyl methyl ethers as a promising biomass-derived solvent(2021) Haseeb, Sohaib; Vanderveen, Jesse R.; Elamaldeniya, Devni; Harris, Jesse; Boniface, Kyle J.; Lee, Roland; Champagne, Pascale; Jessop, Philip G.A mixture of cyclohexyl methyl ethers was prepared from Kraft lignin pyrolysis oil for use as a biomass-derived aliphatic solvent. Using Kamlet–Taft solvatochromic parameters, it was determined that the solvent mixture is somewhat more basic and polar than cyclopentyl methyl ether. Neither the biomass-derived solvent nor pure cyclohexyl methyl ether formed any detectable peroxides in 12 weeks of exposure to air, even though THF formed peroxides rapidly under such conditions. This mixture can be used as a biomass-derived aliphatic ether solvent and as a potential replacement for THF, dioxane, ethyl acetate, acetone and 2-butanone.
- ItemSodium methyl carbonate as an effective C1 synthon. Synthesis of carboxylic acids, benzophenones, and unsymmetrical ketones(2019) Hurst, Timothy E.; Deichert, Julie A.; Kapeniak, Lucas; Lee, Roland; Harris, Jesse; Jessop, Philip G.; Snieckus, VictorReported is the synthesis of carboxylic acids, symmetrical ketones, and unsymmetrical ketones with selectivity achieved by exploiting the differential reactivity of sodium methyl carbonate with Grignard and organolithium reagents.
- ItemTransesterification of soybean oil using a switchable-hydrophilicity solvent, 2-(dibutylamino)ethanol(2019) Viner, Kelsey J.; Roy, Hannah M.; Lee, Roland; He, Ouwen; Champagne, Pascale; Jessop, Philip G.Renewable and environmentally friendly biodiesel has been studied extensively as a replacement for petroleum-derived diesel fuel. Biodiesel contains long chain fatty acid methyl esters (FAMEs) prepared from triglycerides and methanol with basic catalysts such as sodium or potassium hydroxides. The recovery of the basic catalysts is plagued by high water solubility and unwanted soap formation, such that neutralization of the bases with strong acid, rather than recovery, is usually practiced. As an alternative base, switchable-hydrophilicity solvents (SHS) are proposed because they can be readily recovered and reused thanks to their ability to reversibly switch from being hydrophobic to hydrophilic under atmospheric CO2. This novel approach has been tested with 2-(dibutylamino)ethanol (2-DBAE), an SHS, as both solvent and recoverable base catalyst for the transesterification of soybean oil. Carbonated water extracts the SHS from the product FAMEs, while removal of the CO2 from the aqueous stream triggers the separation of the SHS from the water. The FAME yield was approximately 80–85% and the recovery of 2-DBAE was roughly 92%.
- ItemUse of a switchable-hydrophilicity solvent as both a solvent and a catalyst in aldol condensation(2019) Poole, Hailey; Gauthier, Jeremy; Vanderveen, Jesse R.; Jessop, Philip G.; Lee, RolandA switchable-hydrophilicity solvent, N,N-dimethylcyclohexylamine, was used as a recyclable catalyst and solvent for aldol condensation, giving >97% pure product in 94% isolated yield without the need for purification or additional solvents. CO2-triggered separation produced yields greater than conventional workup and allowed facile recycling of the amine.