Butyric Acid Ester Production via Selective Liquid-Liquid Extraction
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Solution Overview
Problem
Producing esters of butyric acid from natural butyric acid is challenging due to its dilute form in fermentation liquor, contamination by salt and other carboxylic acids, and impurities like acetic and lactic acids, as well as fermentation by-products.
Innovation Solution
A method involving an aqueous carboxylic acid mixture with at least 30% free butyric acid, contacted with a liquid extractant of low Hildebrand solubility parameter, followed by separation and reaction with alkanol in the presence of an acid catalyst to form esters, while removing water and impurities.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If natural butyric acid from fermentation liquor is used directly for ester production, then the process is simple, but the product purity is low due to contamination by salts, other carboxylic acids, and fermentation by-products
Solution Approach 1:
The patent applies liquid-liquid extraction to separate butyric acid from fermentation liquor. An organic solvent is used to extract butyric acid from the aqueous fermentation broth, effectively removing it from contaminants such as salts, proteins, and other carboxylic acids. This extraction step isolates the target compound while leaving impurities in the aqueous phase, thereby resolving the contradiction between process simplicity and product purity.
Solution Approach 2:
The patent adjusts pH parameters to control the distribution of butyric acid between aqueous and organic phases. By adjusting the pH to below the pKa of butyric acid, the acid is protonated and preferentially partitions into the organic phase during extraction. This parameter change enables selective separation of butyric acid from other components, achieving high purity while maintaining operational simplicity.
2Productivity
If fermentation liquor containing multiple carboxylic acids is used, then the raw material utilization is high, but the ester product is contaminated by other carboxylic acid esters
Solution Approach 1:
The patent uses selective liquid-liquid extraction to isolate butyric acid from a mixture of carboxylic acids in fermentation liquor. The organic solvent selectively extracts butyric acid while leaving other carboxylic acids (such as acetic and lactic acid) in the aqueous phase. This selective removal enables high raw material utilization from the fermentation broth while preventing contamination of the ester product by other carboxylic acid esters.
Solution Approach 2:
The patent creates different local environments in the extraction system. The organic phase provides a local environment favorable for butyric acid extraction, while the aqueous phase retains other carboxylic acids. This spatial separation of different carboxylic acids based on their distribution coefficients enables selective recovery of butyric acid, achieving both high productivity and product purity.
3Ease of manufacture
If dilute fermentation liquor is used as feedstock, then the production cost is reduced, but the concentration of butyric acid is low requiring larger processing volumes
Solution Approach 1:
The patent introduces an organic solvent as an intermediary substance to facilitate the transfer of butyric acid from dilute fermentation liquor to a concentrated form in the organic phase. This intermediary enables efficient mass transfer and concentration of butyric acid without requiring large volumes of processing, thereby reducing production costs while achieving high concentration in the extracted product.
Solution Approach 2:
The patent exploits phase transition during liquid-liquid extraction. Butyric acid transitions from the aqueous phase to the organic phase, achieving concentration in the organic extract. This phase transition mechanism enables efficient concentration of butyric acid from dilute fermentation liquor, reducing the volume of material that needs to be processed and thereby lowering production costs.
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 effectively produces high-purity esters of butyric acid by separating and refining the butyric acid extract, reducing contamination and impurities, and achieving high yields of esters like tributyrin glycerol.
Implementation Method 1
contacting in an extractor said acid mixture with a liquid extractant having a Hildebrand solubility parameter of less than 25 MPa(1/2), whereby a butyric acid-comprising extract and a residual aqueous phase are formed
Implementation Method 2
contacting in a reactor said separated butyric acid-comprising extract with said alkanol in the presence of an acid catalyst, whereby a product comprising an ester of butyric acid with said alkanol and optionally water are formed in said reactor
Data Source
AI summary
Provided is a method for producing an ester of butyric acid from an acid mixture, comprising contacting an aqueous carboxylic acid mixture comprising butyric acid and at least one additional carboxylic acid selected from the group consisting of formic acid, acetic acid, propionic acid, lactic acid, hydroxybutyric acid and combinations thereof, wherein at least 30% of the total amount of acids in the aqueous carboxylic acid mixture are in free acid form, with a liquid extractant having a Hildebrand solubility parameter of less than 25 MPa(1/2); separating a resultant butyric acid-comprising extract from a residual aqueous phase; contacting a resultant separated butyric acid-comprising extract with an alkanol in the presence of an acid catalyst, to form a product comprising an ester of butyric acid and alkanol and optionally water; wherein when water is formed, separating water to provide a separated product comprising an ester of butyric acid.