Reduction of HMF ethers with metal catalyst
AssigneeArcher Daniels Midland Company
InventorsPaul D. Bloom, Alexandra Sanborn
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Abstract
Methods of making reduced derivatives of hydroxymethyl furfural using metal catalysts are described. The derivatives may have tetrahydrofuran or furan nucleus with alkoxymethyl ether or ester moieties on the 5′ carbon and methanol on the 2′ carbon. Suitable metal catalyst include Raney nickel, a nickel catalyst with a zirconium promoter, a chromite catalyst with a barium, a palladium catalyst, such as palladium on carbon, or a ruthenium catalyst. Also provided are a new class of compounds, which are n-alkoxy hexane diols (i.e., 1,2 or 1,5 hexane diol ethers) and methods of making the same by reduction of furan or tetrahydrofuran derivatives.
Claims11
A method of making at least one desired compound selected from the group consisting of a (5-alkoxymethyl)-tetrahydrofuran-2-methanol compound of the formula:
- and a (5-alkoxymethyl)-furan-2-methanol compound of the formula:
- wherein R is an alkyl group of 1 to 5 carbons, comprising contacting a source of R-5′ alkoxy methylfurfural ether with hydrogen and a catalyst selected from the group consisting of:
- a nickel catalyst, a nickel catalyst with a zirconium promoter, a copper chromite catalyst with a barium promoter, a ruthenium catalyst, and a palladium catalyst, at a temperature and a pressure and for a time selected to convert at least 80% of the R-5′ alkoxy methylfurfural to at least one desired compound in a single step.
A method of making a derivative compound, comprising, obtaining at least one starting compound selected from the group consisting of (5-alkoxymethyl)-tetrahydrofuran-2-methanol of the formula:
- and a (5-alkoxymethyl)-furan-2-methanol compound of the formula:
- and making the derivative compound from the starting compound, wherein the derivative compound is selected from the group consisting of an n-alkoxy hexane diol, an acrylate of the starting compound, an acrylamide of the starting compound, an amidate of the starting compound and an ester of the starting compound.
Dependencies are inferred from the claim text.