Catalysts for hydrodeoxygenation of oxygenated hydrocarbons
AssigneeVirent, Inc.
InventorsBrian Blank, Randy Cortright, Taylor Beck, Elizabeth Woods, Mike Jehring
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Abstract
The present invention provides catalysts, methods, and reactor systems for converting oxygenated hydrocarbons to oxygenated compounds. The invention includes methods for producing cyclic ethers, monooxygenates, dioxygenates, ketones, aldehydes, carboxylic acids, and alcohols from oxygenated hydrocarbons, such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like, using catalysts containing palladium, molybdenum, tin, and tungsten. The oxygenated compounds produced are useful in the production of liquid fuels, chemicals, and other products.
Claims28
A method for converting oxygenated hydrocarbons to lower molecular weight oxygenated compounds, the method comprising the step of reacting an aqueous feedstock solution with hydrogen, at a temperature of between about 100° C. and about 300° C., in the presence of a heterogeneous catalyst, to produce a reaction product comprising a cyclic ether and one or more oxygenated compounds selected from the group consisting of a polyol, a ketone, an aldehyde, a carboxylic acid, and an alcohol, wherein the aqueous feedstock solution comprises water and one or more oxygenated hydrocarbons selected from the group consisting of a starch, a polysaccharide, an oligosaccharide, a trisaccharide, a disaccharide, a monosaccharide, a polyhydric alcohol, a sugar, a sugar alcohol, a sugar degradation product, and combinations thereof, wherein the heterogeneous catalyst comprises palladium, molybdenum, tin, and tungsten, wherein the oxygenated compound has a lower molecular weight than the oxygenated hydrocarbon, and wherein the cyclic ether is a monooxygenate cyclic ether and the monooxygenate cyclic ether is greater than or equal to 17 wt % and less than 26 wt % of the aqueous feedstock carbon.
A method of generating cyclic oxygenated compounds from oxygenated hydrocarbons, the method comprising:
- a. Providing a feedstock comprising a solvent and at least one soluble oxygenated hydrocarbon;
- b. Catalytically reacting the oxygenated hydrocarbon with hydrogen in the presence of a heterogeneous catalyst comprising palladium, molybdenum, tin, and tungsten, at a reaction temperature and a reaction pressure to produce a reaction product comprising cyclic ethers and cyclic ketones, wherein the cyclic ethers comprise monooxygenate cyclic ethers and the monooxygenate cyclic ethers are greater than or equal to 17 wt % and less than 26 wt % of the feedstock carbon.
A method of generating cyclic ethers, the method comprising:
- a. providing a heterogeneous catalyst comprising:
- i. a support;
- and
- ii. a catalytic composition adhered to the support, the catalytic composition comprising palladium, molybdenum, tin, and tungsten;
- b. contacting the heterogeneous catalyst with hydrogen and an aqueous feedstock, the aqueous feedstock comprising:
- i. a solvent;
- and
- ii. one or more oxygenated hydrocarbons selected from the group consisting of polysaccharides, oligosaccharides, trisaccharides, disaccharides, starches, sugars, sugar alcohols, sugar degradation products, and mixtures thereof, at:
- 1. a temperature between about 100° C. to about 300° C.;
- 2. a weight hourly space velocity of greater than 0.01 gram of oxygenated hydrocarbon per gram of heterogeneous catalyst per hour;
- and
- 3. a pressure between about 70 psig to about 2000 psig;
- c. producing a reaction product comprising cyclic ethers, wherein the cyclic ethers comprise monooxygenate cyclic ethers and the monooxygenate cyclic ethers are greater than or equal to 17 wt % and less than 26 wt % of the aqueous feedstock carbon.
Dependencies are inferred from the claim text.