Polylactide Depolymerization via Catalyst System for Lactide Yield

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Solution Overview

Problem

Current depolymerization processes for polylactide (PLA) are inefficient in selectively producing D-lactide and meso-lactide, focusing more on purity rather than racemization, and are slow, with existing methods struggling to achieve high yields of these cyclic esters.

Innovation Solution

A process involving heating polylactide in the presence of a catalyst system at specific temperatures (200-290°C) under reduced pressure to form a vapor product stream, which is then distilled to recover increased amounts of D-lactide and meso-lactide, using a catalyst system comprising metals and co-catalysts like Sn octanoate, triphenylphosphine, and organic acids to enhance the production of these esters.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional depolymerization processes are used to recover lactide from polylactide, then the purity of L-lactide is maintained, but the production of D-lactide and meso-lactide is insufficient and the process is slow

Engineering Contradiction:
Improveproduction rate of D-lactide and meso-lactideVSAvoidselectivity of lactide enantiomers
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by optimizing the catalyst system composition (specific ratios of tin octanoate, triphenylphosphine, and organic acids), temperature (180-250°C range), and pressure conditions to simultaneously achieve high productivity of D-lactide and meso-lactide while maintaining manufacturing precision through controlled racemization. This resolves the contradiction by finding optimal parameter settings that satisfy both requirements.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses a specific catalyst system comprising tin octanoate, triphenylphosphine, and organic acids as intermediaries to mediate the depolymerization process. These catalysts facilitate controlled racemization and enable the simultaneous production of multiple lactide enantiomers, resolving the contradiction between productivity and selectivity by providing a mechanism that can be tuned to achieve both goals.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If depolymerization is focused on purity of lactide recovery, then L-lactide purity is maintained, but racemization to produce D-lactide and meso-lactide is insufficient

Engineering Contradiction:
Improvepurity of lactide enantiomersVSAvoidyield of D-lactide and meso-lactide
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent changes process parameters including temperature (180-250°C), pressure, and catalyst composition to control the degree of racemization. By adjusting these parameters, the process can achieve both high purity of individual enantiomers and high overall yield of D-lactide and meso-lactide, resolving the contradiction between manufacturing precision and productivity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces dynamic control of the depolymerization process through adjustable catalyst system composition and reaction conditions. The catalyst system can be tuned to achieve different levels of racemization, allowing the process to dynamically adapt between prioritizing purity or maximizing yield of specific enantiomers, thus resolving the contradiction.

Inventive Principle:
Principle #15Dynamics

3Productivity

If thermal depolymerization is performed without optimized catalyst system, then process simplicity is maintained, but the yield and selectivity of cyclic esters are low

Engineering Contradiction:
Improveyield of cyclic estersVSAvoidcatalyst system composition
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent optimizes specific parameters of the catalyst system (compositions, ratios, concentrations) to achieve high yield of cyclic esters. By carefully controlling these parameters, the process achieves high productivity without requiring overly complex equipment or procedures, thus resolving the contradiction between productivity and device complexity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a specifically designed catalyst system as an intermediary that enhances the depolymerization efficiency. The catalyst components (tin octanoate, triphenylphosphine, organic acids) work together to improve yield and selectivity, justifying the increased complexity by delivering significant productivity improvements that would not be achievable through simple thermal depolymerization alone.

Inventive Principle:
Principle #24Intermediary (Mediator)

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

The process achieves a higher yield of D-lactide and meso-lactide, up to 35% by weight, even when starting with polylactide having a low D-enantiomer content, and allows for the production of copolymers with balanced L and D units, improving the efficiency and selectivity of the depolymerization process.

Implementation Method 1

heating the polylactide in the presence of a catalyst system in a reaction zone at temperature and pressure at which the polylactide is molten

Methodology Applied
Scientific EffectThermal decomposition: Pyrolysis

Implementation Method 2

forming a vapor product stream from the reaction zone

Methodology Applied
Scientific EffectEvaporation: Evaporation

Implementation Method 3

heating polylactide in the presence of a catalyst system at specific temperatures (200-290°C) under reduced pressure

Methodology Applied
Scientific EffectVacuum: Vacuum

Implementation Method 4

which is then distilled to recover increased amounts of D-lactide and meso-lactide

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS10227322B2Production of meso-lactide, D-lactide and L-lactide by back biting of polylactide
Publication Date: 2019.03.12 FUTERRO SA
  • US10227322B2 patent drawing

AI summary

Process for increasingly producing D-Lactide and meso lactide by depolymerizing by back biting polylactide (PLA) said process which comprises:(i) Depolymerizing polylactide into its corresponding dimeric cyclic esters by heating the polylactide in the presence of a catalyst system comprising a catalyst and a co-catalyst in a reaction zone at temperature and pressure at which the polylactide is molten;(ii) Forming a vapor product stream from the reaction zone;(iii) Removing the vapor product stream and optionally condense it;(iv) Recovering, either together or separately meso-lactide, D-lactide and L-lactide.