Heteroatom Cyclic Dimer Production via Oligomer Recycling

Solution Overview

Problem

Current processes for preparing cyclic dimers of methionine hydroxy analogs have low yields, high capital costs, and generate large waste streams, necessitating improved methods for producing heteroatom-containing cyclic dimers.

Innovation Solution

A process involving the reaction of compounds of Formula (I) and (II) in a nonpolar solvent with an acid catalyst, followed by phase partitioning, extraction, and crystallization, with the option to recycle by-product oligomers back into the reaction, using a single nonpolar solvent throughout to enhance efficiency and reduce waste.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If current processes for preparing cyclic dimers of methionine hydroxy analogs are used, then production can be achieved, but yields are low and waste streams are large

Engineering Contradiction:

Improveproduction efficiencyVSAvoidwaste stream

Core Design Contradiction:

ProductivityVSLoss of substance

Solution Approach 1:

The patent recovers and recycles oligomeric by-products back into the reaction system. Instead of discarding the oligomeric by-products formed during cyclization, the process hydrolyzes them back to monomers and feeds them back into the reaction, thereby reducing waste and improving overall yield of the cyclic dimer product

Inventive Principle:

Principle #34Discarding and recovering

Solution Approach 2:

The patent implements a feedback loop where oligomeric by-products are converted back to starting monomers and recycled into the reaction system. This closed-loop approach continuously feeds valuable materials back into the production process, reducing loss and improving productivity

Inventive Principle:

Principle #23Feedback

2Productivity

If current processes for preparing cyclic dimers of methionine hydroxy analogs are used, then production can be achieved, but capital costs are high

Engineering Contradiction:

Improveproduction efficiencyVSAvoidcapital cost

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The patent recovers and recycles oligomeric by-products back into the reaction system. Instead of discarding the oligomeric by-products formed during cyclization, the process hydrolyzes them back to monomers and feeds them back into the reaction, thereby reducing waste and improving overall yield of the cyclic dimer product

Inventive Principle:

Principle #34Discarding and recovering

Solution Approach 2:

The patent implements a feedback loop where oligomeric by-products are converted back to starting monomers and recycled into the reaction system. This closed-loop approach continuously feeds valuable materials back into the production process, reducing loss and improving productivity

Inventive Principle:

Principle #23Feedback

3Manufacturing precision

If multiple solvents are used in the reaction and extraction steps, then separation efficiency may improve, but process complexity and waste increase

Engineering Contradiction:

Improveseparation efficiencyVSAvoidprocess complexity

Core Design Contradiction:

Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent employs a single nonpolar solvent that serves multiple functions throughout the process: as the reaction medium for cyclization, as the extraction solvent for isolating the cyclic dimer product, and as the medium for recycling oligomeric by-products. This multi-functional use of one solvent simplifies the overall process while maintaining separation efficiency

Inventive Principle:

Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent uses the same nonpolar solvent consistently across all reaction and extraction steps, creating a homogeneous process system. This consistency simplifies process design and operation compared to switching between multiple different solvents, while still achieving effective separation of the cyclic dimer from the aqueous phase

Inventive Principle:

Principle #33Homogeneity

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 increases production efficiency, reduces waste generation, and improves yield by converting oligomers into starting monomers, which are recycled back into the reaction, thereby optimizing the production of heteroatom-containing cyclic dimers.

Implementation Method 1

heating the reaction mixture in the presence of at least one acid catalyst under dehydration to form the compound of Formula (III)

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

extracting the aqueous phase with the nonpolar solvent to form another organic phase comprising the compound of Formula (III)

Methodology Applied

Scientific EffectLiquid-liquid extraction: Liquid-Liquid Extraction

Implementation Method 3

adding water to the reaction mixture after step (b) to form an aqueous phase and an organic phase comprising the compound of Formula (III)

Methodology Applied

Scientific EffectPhase separation: Phase Change

Data Source

PatentUS10266512B2Processes for preparing heteroatom containing cyclic dimers

Publication Date: 2019.04.23 NOVUS INTERNATIONAL INC

AI summary

Processes for preparing heteroatom containing cyclic dimers that result in increased production efficiency and reduced waste production.