Liquid-phase hydrogenation of 2-acetyl-5-methylfuran
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In the hydrogenation of 2-acetyl-5-methylfuran over Pt-C and Pd-C in the liquid phase at 100° with an initial hydrogen pressure of 100 atm the furan ring is not hydrogenated into the tetrahydrofuran ring, but its hydrogenolysis at the C-O bond adjacent to the carbonyl group occurs. This results in the formation of 2,6-heptanedione, which suffers further transformations in two directions: 1) cyclization into the corresponding homologs of cyclohexanone and cyclohexanol (20–30%), and 2) hydrogenation into 2,6-heptanediol, which is partially cyclized into tetrahydro-2,6-dimethylpyran (total yield of the two: 50–60%).
Over a skeletal Pd-Al catalyst at 180° in the 2-acetyl-5-methylfuran molecule first the carbonyl group is reduced to CH2 and then the furan ring is hydrogenated to a tetrahydrofuran ring. As a result of these reactions 2ethyl-tetrahydro-5-methylfuran is formed (about 60%).
Over a skeletal Ni-Al catalyst at 150° in the liquid phase 2-acetyl-5-methylfuran is converted into the corresponding tetrahydrofurfuryl alcohol (about 90%) as a result of the hydrogenation of the carbonyl group into an alcohol group and the furan ring into the tetrahydrofuran ring.
KeywordsLiquid Phase Carbonyl Group Furan Tetrahydrofuran Total Yield
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