Herein, we report an approach to produce levoglucosenone (LGO) from cellulose in yields up to 51% under mild reaction conditions (170–230 °C; 5–20 mM H2SO4) using polar, aprotic solvents such as tetrahydrofuran (THF).
Herein, we elucidate the reaction network for catalytic hydrogenation of the biomass-derived intermediate levoglucosenone into several different renewable chemicals.
The low temperature hydrogenation of pyrolytic lignin over Ru/TiO2 was studied and characterized with quantitative 13C and 2D 1H–13C HSQC NMR to determine the changes in carbon functionality.
The reaction pathway and products of cellulose supercritical methanol depolymerization and hydrodeoxygenation (SCM-DHDO) were investigated. Monoalcohols, diols, alcohol ethers, and methyl esters were produced from cellulose at 300 °C with a CuMgAl mixed metal-oxide catalyst. Timecourse experiments show that cellulose is rapidly solubilized and depolymerized within 1 h with C 2 −C 4 diols being intermediates. Experiments with glucose-13 C 6 show that methanol is incorporated in all liquid products accounting for approximately 30−40% of the carbon in these products. Experiments with model compounds (dihydroxyacetone, isosorbide, and 5-hydroxymethylfurfural) indicate that the reaction pathway for cellulose occurs primarily through retroaldol condensation of solubilized cellulose followed by recondensation with methanol. Methanol produces H 2 , CO, and CO 2 through reformation with 30% of the generated H 2 being incorporated into the liquid products. Analysis of the liquid products with Fourier transform ion cyclotron resonance MS (FT-ICR MS) measured C 7 −C 12 partially oxygenated species with 2−6 double bond equivalence which could not be detected via gas chromatography (GC). We conclude that the reaction pathway occurs through rapid solubilization and depolymerization of cellulose followed by retro-aldol condensation to C 2 −C 4 oxygenates. Retro-aldol condensation products undergo hydrodeoxygenation and extensive carbon−carbon coupling to produce C 2 −C 7 alcohols or other oxygenates.
In this work we present an alternate method for the conversion of tetrahydropyran-2-methanol (THP2M), a cellulose-derived renewable building block, to 1,6-hexanediol (1,6-HDO).
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