Tetrahydrofuran Production via Amide Mediator

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

The continuous production of tetrahydrofuran (THF) from 1,4-butanediol is hindered by the deposition of by-product solids in reactors, leading to reduced productivity and increased costs due to catalyst deterioration and impurity issues, especially when using raw materials containing 2-(4-hydroxybutoxy)-tetrahydrofuran.

Innovation Solution

Incorporating a specified amount of amine or amide in the 1,4-butanediol to reduce the concentration of 2-(4-hydroxybutoxy)-tetrahydrofuran within the reactor, using an acid catalyst with a pKa value of not more than 4, and controlling the reaction conditions such as temperature and water content to inhibit by-product solid formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If 1,4-butanediol is used as raw material for continuous THF production, then productivity is improved, but by-product solid deposition occurs in the reactor

Engineering Contradiction:

ImproveTHF production efficiencyVSAvoidby-product solid deposition

Core Design Contradiction:

ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent introduces an intermediary substance (amine or amide) that mediates between the reactants and products. This intermediary selectively reacts with the by-product 2-(4-hydroxybutoxy)-tetrahydrofuran to prevent its polymerization and solid deposition, while allowing the main THF production reaction to proceed uninterrupted

Inventive Principle:

Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent converts the harmful by-product 2-(4-hydroxybutoxy)-tetrahydrofuran into a beneficial component by reacting it with the added amine or amide. This transformation turns the by-product that causes solid deposition into a soluble complex that remains in the liquid phase, eliminating the harmful deposition effect

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

2Productivity

If acid catalyst is used for dehydration cyclization reaction, then reaction efficiency is improved, but catalyst deterioration occurs under high-temperature conditions

Engineering Contradiction:

Improvereaction efficiencyVSAvoidcatalyst stability

Core Design Contradiction:

ProductivityVSReliability

Solution Approach 1:

The amine or amide acts as a protective intermediary that shields the acid catalyst from direct contact with harmful substances. This intermediary layer prevents catalyst deterioration under high-temperature conditions while maintaining the catalytic activity for the dehydration cyclization reaction

Inventive Principle:

Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent applies beforehand cushioning by introducing the amine or amide substance that preemptively protects the catalyst system from deterioration. This protective substance is present before the harmful effects can occur, cushioning the catalyst against temperature-induced degradation and extending its operational life

Inventive Principle:

Principle #11Beforehand cushioning (Prior cushioning)

3Duration of action of moving object

If raw material containing 2-(4-hydroxybutoxy)-tetrahydrofuran is used, then production continuity is maintained, but by-product solid formation is advanced

Engineering Contradiction:

Improveproduction continuityVSAvoidby-product solid formation

Core Design Contradiction:

Duration of action of moving objectVSObject-generated harmful factors

Solution Approach 1:

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The amine or amide serves as an intermediary that selectively interacts with the by-product 2-(4-hydroxybutoxy)-tetrahydrofuran. This intermediary substance prevents the by-product from forming solids by creating a soluble complex, allowing continuous production to proceed without solid deposition interruptions

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 effectively prevents by-product solid deposition, allowing for stable and high-productivity THF production by reducing the amount of 2-(4-hydroxybutoxy)-tetrahydrofuran, thereby reducing purification costs and maintaining reactor stability.

Implementation Method 1

a dehydration cyclization reaction of 1,4-butanediol by using an acid catalyst

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

carrying out a dehydration cyclization reaction of 1,4-butanediol in a presence of an acid catalyst

Methodology Applied

Scientific EffectDehydration cyclization:

Implementation Method 3

making a specified amount of at least one of an amine and an amide present in 1,4BG to be provided for the production of tetrahydrofuran, the amount of 2-(4-hydroxybutoxy)-tetrahydrofuran is reduced within a reactor

Methodology Applied

Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP2730566B1Method for producing tetrahydrofuran

Publication Date: 2017.09.06 MITSUBISHI CHEM CORP

AI summary

The present invention is concerned with a method for producing tetrahydrofuran including carrying out a dehydration cyclization reaction of 1,4-butanediol in the presence of an acid catalyst having a pKa value of not more than 4 within a reactor, wherein a raw material liquid containing 1,4-butanediol to be provided for the reaction contains from 0.01 to 0.35 % by weight of 2-(4-hydroxybutoxy)-tetrahydrofuran and 1 ppm by weight or more and not more than 1,000 ppm by weight of at least one of an amine and an amide in terms of a concentration as converted into a nitrogen atom.