Cyclic Ether Production via Hydrogenation of 2-Hydroxy Cyclic Ethers

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Conventional methods for producing cyclic ethers face challenges due to the unavailability of low-cost starting materials and low yields, with existing methods being complex and inefficient from an industrial perspective.

Innovation Solution

Reacting a readily available 2-hydroxy cyclic ether with hydrogen in the presence of a catalyst, specifically using a supported catalyst from groups 8 to 10 of the periodic table, under mild conditions to achieve high yields.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional methods using 2-alkoxytetrahydropyran are employed, then cyclic ether can be produced, but the starting material is not industrially available at low cost and the yield is insufficient

Engineering Contradiction:
Improveyield of cyclic etherVSAvoidavailability and cost of starting material
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The patent replaces expensive, industrially unavailable 2-alkoxytetrahydropyran with a cheap, readily available alternative: 2-hydroxycyclic ether. This substitution principle allows using a disposable, low-cost starting material that can be easily obtained, thereby resolving the contradiction between material availability and production yield.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the chemical parameter of the starting material from 2-alkoxytetrahydropyran to 2-hydroxycyclic ether. This parameter change (functional group substitution) enables the use of a more available, lower-cost material while achieving high yields through the specific hydrogenation reaction conditions described in the patent.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If two-step reaction method is used to synthesize cyclic ether from hydroxy cyclic ether, then the reaction can proceed, but the process is complex and yield is insufficient from industrial perspective

Engineering Contradiction:
Improveyield of cyclic etherVSAvoidnumber of reaction steps
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent merges two separate reaction steps (dehydration followed by hydrogenation) into a single hydrogenation step. By combining these operations, the process complexity is reduced while maintaining or improving the yield, directly addressing the contradiction between process simplicity and production efficiency.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent extracts and eliminates the intermediate dehydration step from the conventional two-step process. By removing this unnecessary intermediate step and proceeding directly to hydrogenation of the 2-hydroxycyclic ether, the method simplifies the overall process while achieving high yields.

Inventive Principle:
Principle #2Taking out (Extraction)

3Quantity of substance

If existing hydrogenation methods are employed, then cyclic ether can be synthesized, but high yield cannot be achieved

Engineering Contradiction:
Improveyield of cyclic etherVSAvoidconsistency of high yield
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent introduces a specific catalyst as an intermediary that mediates the hydrogenation reaction of 2-hydroxycyclic ether. This catalyst enables the reaction to proceed with high efficiency and consistency, achieving reliable high yields that were not attainable with conventional hydrogenation methods.

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

This method allows for the production of cyclic ethers with high yields using a cost-effective and industrially viable process, utilizing readily available compounds and optimizing reaction conditions such as pH, temperature, and catalyst loading.

Implementation Method 1

reacting a particular 2-hydroxy cyclic ether with hydrogen in the presence of a catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

reacting 2-alkoxytetrahydropyran with hydrogen in the presence of an acid and a catalyst to synthesize tetrahydropyran

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP3722287B1Method for producing cyclic ether
Publication Date: 2024.02.21 KURARAY CO LTD
  • EP3722287B1 patent drawing
  • EP3722287B1 patent drawing
  • EP3722287B1 patent drawing

AI summary

A method for producing a cyclic ether represented by formula (2) includes reacting a 2-hydroxy cyclic ether, represented by formula (1), with hydrogen in the presence of a catalyst.