Cyclic Diester Production via Alkaline-Earth Salt Pyrolysis

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

The classical production process of Polylactic Acid (PLA) from Lactic Acid is inefficient due to high energy requirements, large waste production, and racemization issues during depolymerization, leading to high production costs and impurity levels, which are not adequately addressed by existing technologies.

Innovation Solution

A process involving the direct conversion of alkalino-earth salts of alpha-hydroxyacids, such as Calcium or Magnesium Lactate, into cyclic diesters through evaporation-crystallization and pyrolysis, eliminating waste and reducing energy consumption by using mild temperatures and water vapor, thereby producing high-purity PLA without racemization.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If the classical production process uses multiple evaporation and purification steps to produce high-purity cyclic diester, then the product purity is improved, but the energy consumption and production cost increase significantly

Engineering Contradiction:
Improveproduct purityVSAvoidenergy consumption
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The invention changes the physical-chemical parameters of the system by using alkaline earth metal salts (Ca, Sr, Ba) instead of traditional catalysts, and by controlling the water activity and temperature parameters during fermentation. This allows the system to achieve high purity cyclic diester through a simplified process with fewer evaporation steps, thereby reducing energy consumption while maintaining product purity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention extracts and removes the problematic racemization step and multiple purification steps from the classical process. By using alkaline earth metal salts that form stable complexes and by controlling the fermentation conditions to directly produce cyclic diester, the process eliminates the need for complex downstream purification, reducing both energy consumption and production time

Inventive Principle:
Principle #2Taking out (Extraction)

2Adaptability or versatility

If the classical process uses depolymerization to produce cyclic diester, then the production flexibility is improved, but racemization occurs leading to loss of enantiomeric purity

Engineering Contradiction:
Improveproduction flexibilityVSAvoidenantiomeric purity
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The invention performs the cyclization reaction during the fermentation process itself, before any polymerization or depolymerization steps. By using alkaline earth metal salts as catalysts during fermentation and controlling the water activity, the cyclic diester is formed in situ, eliminating the need for subsequent depolymerization steps that cause racemization

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

Alkaline earth metal salts (Ca, Sr, Ba) serve as intermediary catalysts that enable direct cyclization during fermentation. These salts form stable complexes with the hydroxyacid intermediates, facilitating cyclic diester formation without requiring high-temperature depolymerization, thus preserving enantiomeric purity while maintaining production flexibility

Inventive Principle:
Principle #24Intermediary (Mediator)

3Manufacturing precision

If the classical process produces PLA from Lactic Acid through multiple steps, then the product quality is maintained, but the production cost increases due to large waste production and recycle requirements

Engineering Contradiction:
Improveproduct qualityVSAvoidproduction cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention eliminates the need for large recycle flows by designing a process where alkaline earth metal salts are used in controlled amounts and can be easily separated. The process discards the need for extensive purification and recycle operations, as the direct fermentation approach produces high-purity cyclic diester with minimal impurities, thereby reducing production cost while maintaining product quality

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

By changing the catalyst system to alkaline earth metal salts and controlling fermentation parameters (water activity, temperature, pH), the process achieves high conversion efficiency and product purity in a single step. This eliminates the need for multiple purification steps and large recycle flows, reducing production cost while maintaining PLA quality

Inventive Principle:
Principle #35Parameter changes

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 process significantly reduces production costs and energy consumption, minimizes waste, and maintains high enantiomeric purity of PLA by eliminating racemization, making PLA production more economically viable and environmentally friendly.

Implementation Method 1

the mixture is treated by evaporation-crystallization, so that a hydrate of the alkalino-earth salt of the linear dimer of the corresponding alpha-hydroxyacid precipitates

Methodology Applied
Scientific EffectEvaporation-crystallization: Crystallisation

Implementation Method 2

the hydrated salt is dehydrated to give the corresponding anhydrous salt

Methodology Applied
Scientific EffectDehydration: Evaporation

Implementation Method 3

the anhydrous salt is pyrolyzed (preferably in the presence of water vapor or an inert carrier), releasing the cyclic diester of the corresponding alpha-hydroxyacid and leaving the alkalino-earth hydroxide as solid residue

Methodology Applied
Scientific EffectPyrolysis: Pyrolysis

Data Source

PatentUS8383835B2Process for the production of cyclic diesters of alpha-hydroxyacids
Publication Date: 2013.02.26 KTANTON LTD
  • US8383835B2 patent drawing

AI summary

Process for the synthesis of a cyclic diester of an alpha-hydroxyacid, comprising the following steps:an alkalino-earth salt of the corresponding alpha-hydroxyacid is mixed with said alpha-hydroxyacid and water;the mixture is treated by evaporation-crystallization, so that a hydrate of the alkalino-earth salt of the linear dimer of the corresponding alpha-hydroxyacid precipitates;the hydrated salt is dehydrated to give the corresponding anhydrous salt; andthe anhydrous salt is pyrolyzed, releasing the cyclic diester of the corresponding alpha-hydroxyacid and leaving the alkalino-earth hydroxide as solid residue.