Esterification of Beta-Hydroxyalkanoate Bottoms to Recover Unsaturated Esters

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Solution Overview

Problem

The production of beta-hydroxycarboxylic acids results in significant yield loss and waste due to the purging of less-volatile components containing oligomers and saccharide esters during purification, leading to increased disposal costs and reduced efficiency in the fermentation process.

Innovation Solution

A method involving the combination of beta-hydroxy carboxylic acid recovery bottoms with C1 to C6 mono-alcohols, followed by heating, distillation, and optional catalyst use to produce esters of alpha-beta unsaturated carboxylic acids, enhancing recovery and yield while minimizing waste.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If beta-hydroxycarboxylic acid is evaporated or distilled from less-volatile components during purification, then the beta-hydroxycarboxylic acid can be recovered, but significant yield loss occurs and solid waste disposal costs increase

Engineering Contradiction:
Improvepurification effectivenessVSAvoidbeta-hydroxycarboxylic acid yield
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The invention converts the harmful waste stream (less-volatile components purged during distillation) into a beneficial resource by processing it through esterification and dehydration reactions to produce valuable alpha-beta unsaturated carboxylic acid esters. This transforms the waste disposal problem into a profit-generating opportunity while recovering beta-hydroxycarboxylic acid at over 95% yield

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The invention changes the chemical parameters of the waste stream by adding alcohol and catalyst to enable esterification, then applying heat and vacuum to promote dehydration. These parameter changes (temperature, pressure, chemical composition) convert the unwanted oligomers and saccharide esters into desirable unsaturated ester products with high market value

Inventive Principle:
Principle #35Parameter changes

2Reliability

If less-volatile components are purged out as waste during purification, then purification is achieved, but solid waste disposal costs increase significantly

Engineering Contradiction:
Improvepurification qualityVSAvoidwaste disposal costs
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention transforms the harmful waste stream into a beneficial product stream by processing the less-volatile components through chemical reactions (esterification and dehydration) to produce valuable alpha-beta unsaturated carboxylic acid esters. This eliminates waste disposal costs entirely while creating a new revenue stream from what was previously considered waste material

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Manufacturing precision

If conventional distillation is used to separate beta-hydroxycarboxylic acid, then purification is achieved, but process efficiency is reduced due to yield loss

Engineering Contradiction:
Improvepurification separationVSAvoidoverall process efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention merges the waste treatment step with a value-added product generation step. Instead of separately disposing of waste and then processing fresh feedstock, the invention combines both functions by converting the waste stream into additional product, thereby increasing overall productivity without compromising purification quality

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention recovers beta-hydroxycarboxylic acid from the waste stream at over 95% yield through esterification and dehydration, then uses the resulting unsaturated esters as the final product. This recovery process transforms what would have been discarded material into a valuable commodity, significantly improving overall process efficiency

Inventive Principle:
Principle #34Discarding and recovering

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 achieves high recovery and yield of alpha-beta unsaturated carboxylic acid esters, reducing waste and disposal costs by effectively converting beta-hydroxyalkanoate equivalents into valuable products, with percent recovery and yield exceeding 95% in many instances.

Implementation Method 1

combining beta-hydroxy carboxylic acid recovery bottoms with C1 to C6 mono-alcohols, followed by heating, distillation, and optional catalyst use to produce esters of alpha-beta unsaturated carboxylic acids

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Implementation Method 2

combining beta-hydroxy carboxylic acid recovery bottoms with C1 to C6 mono-alcohols, followed by heating, distillation, and optional catalyst use to produce esters of alpha-beta unsaturated carboxylic acids

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS10774026B2Methods for producing an ester of an alpha, beta-unsaturated carboxylic acid
Publication Date: 2020.09.15 CARGILL INC

AI summary

A method for producing esters of an alpha, beta-unsaturated carboxylic acid are disclosed, the method includes reacting a three or four carbon beta-hydroxyalkanoate composition or mixtures thereof with a mono-alcohol under heating conditions to form a reaction product and distilling the reaction product to recover a composition containing at least fifty percent by weight of the ester of the alpha, beta-unsaturated carboxylic acid.