1-Butanol → Butanal

In U.S. Pat. No. 5,077,418 and U.S. Pat. No. 5,117,013 it is reported that the hydrogenation of vinyloxirane solutions over palladium-containing catalysts gives n-butyraldehyde as main product. For instance, hydrogenation of vinyloxirane together with tetrahydrofuran as solvent over a supported palladium catalyst (5% by weight of palladium on activated carbon) at a temperature of from 50 to 55° C. and a pressure of 3.5 bar gives after a reaction time of 3 h a hydrogenation effluent comprising 55% of n-butyraldehyde, only 27% of 1,2-butylene oxide and 9% of n-butanol. If the hydrogenation is carried out over alumina-supported palladium catalysts (5% of Pd/Al2O3), only traces of 1,2-butylene oxide are formed after 6 hours at from 25 to 55° C. and a pressure of 3.5 bar or after 4 hours at 100° C. and 20.7 bar. n-Butyraldehyde is formed as the main product with a selectivity of, respectively, 87% or 78% and quantitative conversion. The two U.S. applications also describe the hydrogenation of vinyloxirane over Raney nickel, when n-butanol is formed as the main product. The 1,2-butylene oxide yield is relatively low at 41%. The hydrogenation of vinyloxirane over a supported platinum catalyst (1% by weight of Pt/Al2O3) at 100° C. and 20.7 bar hydrogen pressure produces after 4.6 h and complete conversion only 40% of 1,2-butylene oxide and also 23% of n-butanol, 24% of butanols, 5% of crotonaldehyde and 3% of n-butyraldehyde. Other platinum catalysts give even lower 1,2-butylene oxide yields.

ORD record

ord-fbf126f71abe4921ab0aeab522d3da89

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05929261