Macrocyclic Lactone Synthesis via Polyester Cyclo-Depolymerization

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

The existing methods for producing macrocyclic lactones, such as AMBRETTOLIDE, are costly and inefficient due to dependence on natural sources, which are climatically and socio-economically vulnerable, leading to a need for scalable and cost-effective industrial processes for their synthesis and purification.

Innovation Solution

A process involving the cyclo-depolymerization of olefin-containing random polyesters, where the polyesters are depolymerized to form fragments capable of intramolecular cyclization, resulting in the formation and separation of macrocyclic lactones, using diene ester monomers and metathesis reactions with suitable catalysts like Molybdenum or Tungsten-based catalysts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If macrocyclic lactones are produced from natural sources, then the desired musk odour and quality are achieved, but the production cost increases and scalability is limited due to climatic and socio-economic vulnerabilities

Engineering Contradiction:

Improvequality consistencyVSAvoidproduction scalability

Core Design Contradiction:

ReliabilityVSProductivity

Solution Approach 1:

The invention changes the source material from natural extracts to synthetically produced olefin-containing polyesters, transforming the production parameters from agricultural dependency to controlled chemical synthesis. This allows scalable industrial production while maintaining product quality through controlled reaction conditions

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention uses readily available, inexpensive olefin-containing polyesters as starting materials that can be synthesized on demand, replacing expensive and scarce natural sources. These polymer materials serve as disposable feedstocks that can be continuously produced and converted to macrocyclic lactones

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

2Reliability

If macrocyclic lactones are produced from natural sources, then the desired musk odour is achieved, but the production cost increases due to extraction costs from natural sources

Engineering Contradiction:

Improveodour qualityVSAvoidproduction cost

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The invention replaces expensive natural extracts with inexpensive synthetic olefin-containing polyesters as starting materials. These polymer feedstocks are commercially available at low cost and can be continuously produced, eliminating the need for expensive extraction processes from natural sources

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The invention changes the manufacturing approach from extraction of natural products to synthesis from readily available chemical feedstocks. This parameter change transforms the cost structure by using inexpensive, easily manufactured starting materials that undergo controlled conversion to the desired macrocyclic lactones

Inventive Principle:

Principle #35Parameter changes

3Productivity

If conventional synthesis methods are used for macrocyclic lactones, then production is possible, but the process efficiency and yield are reduced due to multiple steps and purification requirements

Engineering Contradiction:

Improveprocess efficiencyVSAvoidsynthesis steps

Core Design Contradiction:

ProductivityVSDevice complexity

Solution Approach 1:

The invention combines multiple synthetic steps into a single integrated process. The olefin-containing polyester undergoes simultaneous depolymerization, cyclization, and product formation in one reaction vessel, eliminating the need for separate isolation and purification steps that complicate conventional methods

Inventive Principle:

Principle #5Merging (Combining)

Solution Approach 2:

The invention segments the reaction process into distinct functional phases within a single operation: depolymerization of the polyester chain, intramolecular cyclization of fragments, and formation of macrocyclic lactone products. This segmentation allows each transformation to occur optimally without requiring separate processing equipment

Inventive Principle:

Principle #1Segmentation

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 enables the efficient and cost-effective production of macrocyclic lactones, such as AMBRETTOLIDE, by converting olefin-containing random polyesters into desired macrocyclic lactones with high yield and purity, addressing the limitations of natural source dependence and scalability.

Implementation Method 1

depolymerizing the olefin-containing random polyester in a reaction mixture to form fragments capable of intramolecular cyclization

Methodology Applied

Scientific EffectDepolymerization:

Implementation Method 2

the intramolecular cyclization of said fragments to form a desired macrocyclic lactone

Methodology Applied

Scientific EffectIntramolecular cyclization:

Implementation Method 3

cyclo-depolymerization of olefin-containing random polyesters, where the polyesters are depolymerized to form fragments capable of intramolecular cyclization

Methodology Applied

Scientific EffectMetathesis reaction: Catalysis

Data Source

PatentUS10633359B2Preparation of macrocyclic lactones

Publication Date: 2020.04.28 GIVAUDAN SA

AI summary

A process for preparing a macrocyclic lactone comprising 14 to 17 ring carbon atoms, the process comprising the steps of i) subjecting a reaction mixture comprising an olefin-containing random polyester, formed by metathesis to a cyclo-depolymerization reaction to form the macrocyclic lactone, and ii) concomitant removal of the macrocyclic lactone from the reaction mixture.