Keto-Intermediate Furan Synthesis from Glucose Feedstocks
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
The production of furan compounds like 5-hydroxymethylfurfural is hindered by low yield and high cost, and they are not stable for isolation, while existing methods rely on fructose as an intermediate, which is not as common as glucose, and glucose does not form furanose tautomers efficiently.
Innovation Solution
A method is developed to convert glucose into keto-intermediates such as 2-keto-3-deoxygluconic acid, which forms keto-furanose tautomers, allowing for efficient dehydration into furan derivatives, such as 5-hydroxymethylfurfural, which are then oxidized into furandicarboxylic acid derivatives.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If fructose is used as an intermediate to produce 5-hydroxymethylfurfural, then the synthesis pathway is established, but fructose is not as common and cheaper than glucose, increasing raw material cost
Solution Approach 1:
The invention changes the chemical parameters of glucose by using enzymatic oxidation to convert it into 2-keto-3-deoxygluconic acid, which has keto-furanose tautomers similar to fructose. This parameter change allows glucose to follow a dehydration pathway analogous to fructose, enabling furan synthesis from the more abundant and cheaper glucose原料
Solution Approach 2:
The invention introduces 2-keto-3-deoxygluconic acid as an intermediary substance that bridges glucose and furan derivatives. This intermediary has the key structural feature (keto-furanose tautomers) needed for furan formation, allowing the conversion of glucose into furan products through a two-step process that overcomes glucose's inability to directly form furanose structures
2Ease of operation
If 5-hydroxymethylfurfural is isolated as an intermediate, then the synthesis pathway can be controlled, but 5-hydroxymethylfurfural is unstable and difficult to isolate
Solution Approach 1:
The invention performs preliminary oxidation of glucose to 2-keto-3-deoxygluconic acid before the dehydration step. This preliminary action creates a more stable intermediate that can be handled and processed more easily than 5-hydroxymethylfurfural, while still maintaining the ability to proceed to furan derivatives through controlled dehydration
Solution Approach 2:
The invention uses 2-keto-3-deoxygluconic acid as a stable intermediary that replaces unstable 5-hydroxymethylfurfural in the synthesis pathway. This intermediary maintains the essential keto-furanose tautomer structure needed for furan formation while being more stable and easier to handle during the synthesis process
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This method enables the production of furan derivatives like 5-hydroxymethyl-2-furoic acid and furandicarboxylic acid in high yield and high yield, bypassing the stability and isolation challenges, using glucose as a starting material, and provides a starting material for furan derivatives.
Implementation Method 1
dehydrating gluconic acid to provide 2-keto-3-deoxygluconic acid
Implementation Method 2
dehydrating 2-keto-3-deoxygluconic acid to provide 5-hydroxymethyl-2-furoic acid
Implementation Method 3
oxidizing the furan derivative to provide furandicarboxylic acid or a furandicarboxylic acid derivative
Data Source
Figure 1
Figure 2
Figure 3
AI summary
The present invention provides a method of preparing a furan derivative comprising the steps of (a) converting a monosaccharide to provide a keto-intermediate product; and (b) dehydrating the keto-intermediate product to provide a furan derivative; wherein the keto- intermediate product is pre-disposed to forming keto-furanose tautomers in solution. The method may further comprising a step of oxidizing the furan derivative to provide a furandicarboxylic acid or a furandicarboxylic acid derivative.