Journal
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
Volume 54, Issue 28, Pages 7059-7066Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.iecr.5b00766
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Fructose has been hydrodeoxygenated to 2,5-dimethyltetrahydrofuran using a sulfided Pt/C catalyst. The reaction was carried out in a stirred reactor at 10.3 MPa H-2 and 175 degrees C which allowed a 10% fructose solution to be converted in 2 h. The selectivity was greatly enhanced by using ethanol as solvent with 95% ethanol giving 50% DMTHF versus 9% in water. The only intermediate found along the reaction pathway was 2,5-hexanedione. This is presumed to be hydrogenated to 2,5-hexanediol which then ring closes to DMTHF. Molecular simulation at the B3LYP/6-311++G(2df,2p) level was used to propose a reaction pathway from fructose to 2,5-hexanedione and then to explain the preference for the cis isomer of DMTHF.
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