Catalytic process for producing furan derivatives in a biphasic reactor
AssigneeWisconsin Alumni Research Foundation
InventorsJames A. Dumesic, Yuriy Rom{acute over (α)}n-Leshkov, Juben N. Chheda
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Abstract
Described is a catalytic process for converting sugars to furan derivatives (e.g. 5-hydroxymethylfurfural, furfural, dimethylfuran, etc.) using a biphasic reactor containing a reactive aqueous phase and an organic extracting phase. The process provides a cost-effective route for producing di-substituted furan derivatives. The furan derivatives are useful as value-added intermediates to produce polymers, as precursors to diesel fuel, and as fuel additives.
Claims27
A process to make furan derivative compounds, the process comprising:
- dehydrating a feedstock solution comprising a carbohydrate, in the presence of an acid catalyst, in a reaction vessel containing a biphasic reaction medium comprising an aqueous reaction solution and a substantially immiscible organic extraction solution;
- wherein the aqueous reaction solution, the organic extraction solution, or both the aqueous reaction solution and the organic extraction solution contain at least one modifier to improve selectivity of the process to yield furan derivative compounds, wherein the modifier is selected from the group of consisting of dimethylsulfoxide (DMSO), dimethylformamide, N-methylpyrrolidinone (NMP), acetonitrile, butyrolactone, dioxane, pyrrolidinone, and poly(1-vinyl-2-pyrrolidinone);
- and
- wherein the carbohydrate is dehydrated in the aqueous reaction solution to yield a furan derivative, and the furan derivative is extracted into the organic extraction solution.
A method of making a compound of Formula I:
- wherein each R is independently selected from the group consisting of hydrogen, C1—C6-alkyl, hydroxy-C1—C6-alkyl, acyl-C1—C6-alkyl, C1—C6-alkylcarbonyl-C1—C6-alkyl, and carboxy-C1—C6-alkyl, and provided the both R's are not simultaneously hydrogen, comprising:
- dehydrating a feedstock solution comprising a carbohydrate, in the presence of an acid catalyst, in a reaction vessel containing a biphasic reaction medium comprising:
- (i) an aqueous reaction solution comprising water, a salt, and a modifier selected from the group of consisting of dimethylsulfoxide (DMSO), dimethylformamide, N-methylpyrrolidinone (NMP), acetonitrile, butyrolactone, dioxane, pyrrolidinone and poly(1-vinyl-2-pyrrolidinone);
- and
- (ii) a substantially immiscible organic extraction solution;
- and
- wherein the carbohydrate is dehydrated in the aqueous reaction solution to yield a furan derivative, and the furan derivative is extracted into the organic extraction solution.
Dependencies are inferred from the claim text.