Hydrogenation of biomass-derived substrates
View Patent ↗The α,β-unsaturated ketone moiety of a substrate representative of non-food based biomass was hydrogenated to the corresponding saturated alcohol moiety using a composition including (1) a copper salt; (2) a phosphine; (3) a polar aprotic solvent such as acetonitrile, and (4) a compound suitable for providing hydrogen for the hydrogenation, such as a suitable silane material or a suitable siloxane material.
1. A process for hydrogenation of an α,β-unsaturated ketone moiety of a furan-containing substrate, the process comprising:
preparing a composition by combining a copper salt, a phosphine, a polar aprotic solvent, and a material suitable for providing hydrogen for the hydrogenation, the suitable material selected from the group consisting of a silane material and a siloxane material; and
adding the composition to the furan-containing substrate having the α,β-unsaturated keton moiety under conditions effective for hydrogenation of both an olefin moiety and a ketone moiety of the α,β-unsaturated ketone moiety, whereby a furan-containing alcohol is produced.
2. The process of claim 1 , wherein the phosphine is selected from the group consisting of bis(diethylphosphino)ethane, 1,3-bis(diisopropylphosphino)propane, and combinations thereof.
3. The process of claim 1 , wherein the copper salt includes copper(II) fluoride.
4. The process of claim 1 , wherein the copper salt is copper(I) chloride and the composition further includes a material that reacts with copper(I) chloride to provide a composition effective for hydrogenation of both the olefin moiety and the ketone moiety of the α,β-unsaturated ketone moiety of the furan-containing substrate.
5. The process of claim 1 , wherein the polar aprotic solvent includes acetonitrile.
6. The process of claim 1 , wherein the hydrogen-providing material includes phenyl silane or polymethylhydrosiloxane.