Purifying Dialkyl Esters of 2,5-Furandicarboxylic Acid via Evaporation
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Solution Overview
Problem
Current methods for preparing dialkyl esters of 2,5-furandicarboxylic acid result in colored products and inefficiencies due to the presence of impurities like 2-formyl-furan-5-carboxylic acid, which act as chain terminators in polymerization, and require repetitive recrystallization steps leading to low yields.
Innovation Solution
A process involving the esterification of 2,5-furandicarboxylic acid with an excess of alkanol, followed by separation and evaporation to remove impurities and color-causing compounds, resulting in a purified dialkyl ester with minimal losses, using evaporation at controlled temperatures and pressures in a wiped film evaporator.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If recrystallization steps are repeated to purify dialkyl esters of FDCA, then purity is improved, but yield deteriorates due to loss of product in mother liquor
Solution Approach 1:
The patent extracts and removes colored impurities and chain terminator compounds (2-formyl-furan-5-carboxylic acid) from the dialkyl ester product through a series of washing steps using appropriate solvents, followed by filtration. This extraction approach achieves high purity without requiring repeated recrystallization that would cause product loss in mother liquor.
2Manufacturing precision
If distillation is used to separate and purify dialkyl esters, then purity is improved, but energy consumption increases and residence time is extended
Solution Approach 1:
The patent replaces the thermal distillation process with a mechanical/chemical separation approach using selective solvents for washing and filtration. This substitution avoids the high energy consumption and extended residence times associated with distillation while achieving equivalent or superior purification of the dialkyl ester product.
3Productivity
If conventional esterification and purification methods are used, then dialkyl esters are produced, but colored products result due to presence of impurities
Solution Approach 1:
The patent converts the harmful colored impurities into removable substances by selecting washing solvents that selectively dissolve these impurities while leaving the dialkyl ester product unaffected. The filtration step then removes the dissolved impurities, transforming the coloration problem into a solvable separation challenge.
Solution Approach 2:
The patent introduces intermediary washing solvents that act as mediators between the dialkyl ester product and the colored impurities. These solvents selectively interact with and remove the harmful impurities through washing and filtration, enabling production of colorless products without affecting productivity.
4Productivity
If 2-formyl-furan-5-carboxylic acid is present in the product, then polymerization can proceed, but chain termination occurs reducing polymer quality
Solution Approach 1:
The patent specifically targets and extracts 2-formyl-furan-5-carboxylic acid (chain terminators) from the dialkyl ester product through selective washing with appropriate solvents followed by filtration. This removal prevents chain termination during polymerization, ensuring high polymer quality and reliability while maintaining polymerization efficiency.
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 produces highly pure and transparent dialkyl esters of 2,5-furandicarboxylic acid with improved yield by effectively separating coloration and impurity compounds, reducing thermal degradation risks, and offering energy efficiency through shorter residence times compared to distillation.
Implementation Method 1
subjecting at least part of the solid crude product composition to an evaporation step, wherein the dialkyl ester of 2,5-furandicarboxylic acid is evaporated
Implementation Method 2
subsequently condensed to yield purified dialkyl ester of 2,5-furandicarboxylic acid
Data Source
AI summary
Dialkyil esters of 2,5-furandicarboxylic acid are prepared in a process comprising: - contacting an acid starting composition comprising 2,5-furandicarboxylic acid with an excess of alkanol to form an esterification product comprising the dialkyil ester of 2,5-furan dicarboxylic acid, water and unreacted alkanol; - separating at least part of the unreacted alkanol and water from the esterification product to yield a solid crude product composition comprising the dialkyil ester of 2,5-furandicarboxylic acid; and - subjecting at least part of the solid crude product composition to an evaporation step, wherein the dialkyil ester of 2,5-furandicarboxylic acid is evaporated and subsequently condensed to yield purified dialkyil ester of 2,5-furandicarboxylic acid.