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Cellulose-derived platform chemicals offer viable substitutes for most petroleumbased polymers and also enable the development of novel functional materials. In the focus of this work are thermophysical and thermochemical studies of dihydro-levoglucosenone (Cyrene) and levoglucosenone, which are considered as potential "green" replacements for industrial polar aprotic solvents. The densities, viscosities, absolute vapor pressures, and combustion energies of cyrene and levoglucosenone were measured in this work. The thermodynamic properties of levoglucosan derivatives are reliable for thermochemical calculations and used to calculate reaction enthalpies of valorization of the cellulose component of biomass. These enthalpies of reaction are useful in the further optimization and development of sustainable syntheses of commodity chemicals and fuels from biomass. The data provided in this work will aid researchers and engineers as the use of these new solvents grows.

Conversion of epichlorohydrin to glycidyl ethers creates versatile precursors that can be transformed into a variety of molecular species with glycerol skeletons, enabling the design of molecules with highly tailored functionalities. The synthesis of 2,2,2-trifluoroethyl glycidyl ether (TFGE, IUPAC name: 2-[(2,2,2-trifluoroethoxy) methyl]oxirane, CAS# 1535-91-7) was optimized to provide high yield/selectivity and good "green metrics." TFGE was then used as a platform molecule in the synthesis of asymmetric glycerol 1,3-diether-2-alcohol derivatives, which were subsequently transformed to 1,2,3-triethers or 1,3-diether-2-ketones. The density, viscosity, and CO 2 solubility of each molecule were measured and compared with those of other glycerol-derived compounds as well as compounds with similar functional groups. Furthermore, quantum chemical calculations were performed to understand the structure-property-performance relationships of these molecules for CO 2 absorption. Based on the results in this work, we foresee that TFGE (and similar glycidyl ethers) would offer great flexibility in molecular design of green solvents and precursors to more complex compounds.

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