Acidic Ionic Liquid Catalyst for Isomerization

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Solution Overview

Problem

Existing methods for isomerizing endo-tetrahydrodicyclopentadiene to exo-tetrahydrodicyclopentadiene result in significant waste production and equipment corrosion due to the use of strong acids or aluminum trichloride, leading to inefficient processes and environmental concerns.

Innovation Solution

The use of acidic ionic liquids, specifically chloroaluminate ionic liquids prepared with quaternary ammonium or phosphonium halides and aluminum trichloride, as catalysts for the isomerization of endo-tetrahydrodicyclopentadiene, with controlled mole ratios and temperatures between 25 and 120°C, to achieve high reaction conversion and selectivity while being environmentally friendly and recyclable.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If sulfuric acid is used as catalyst for isomerization, then reaction conversion is improved, but equipment corrosion and waste production worsen

Engineering Contradiction:
Improvereaction conversionVSAvoidequipment corrosion
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the catalyst system by replacing traditional strong mineral acids (sulfuric acid) with ionic liquids having controlled acidity. The ionic liquid catalyst system comprises specific cations (imidazolium, pyridinium, ammonium, or phosphonium) and anions (HSO4-, H2PO4-, or AlCl4-), where the acidity can be tuned by adjusting the molar ratio of components. This parameter change maintains high reaction conversion while eliminating equipment corrosion associated with traditional strong acids.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If aluminum trichloride is used as catalyst, then isomerization efficiency is improved, but sludge waste production worsens

Engineering Contradiction:
Improveisomerization efficiencyVSAvoidsludge waste
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent employs a composite ionic liquid catalyst system formed by combining organic cations with aluminum-based anions (HSO4-, H2PO4-, or AlCl4-). This composite material integrates the advantages of organic catalysts (low corrosion) and aluminum-based catalysts (high efficiency) while avoiding the formation of aluminum hydroxide sludge. The ionic liquid structure prevents precipitation of aluminum compounds that would otherwise form waste sludge during aqueous workup.

Inventive Principle:
Principle #40Composite materials

3Speed

If traditional acid catalysts are used, then reaction speed is improved, but environmental friendliness worsens

Engineering Contradiction:
Improvereaction speedVSAvoidenvironmental pollution
Core Design Contradiction:
SpeedVSObject-generated harmful factors

Solution Approach 1:

The ionic liquid catalyst system is designed to be self-contained and reusable. The catalyst can be recovered by simple extraction with non-polar solvents like dichloromethane or diethyl ether, and reused for multiple reaction cycles without significant loss of activity. This self-service capability eliminates the need for extensive neutralization and waste treatment steps required by traditional acid catalysts, making the process environmentally friendly while maintaining high reaction speed.

Inventive Principle:
Principle #25Self-service

4Manufacturing precision

If strong acids are used for isomerization, then selectivity is improved, but by-product formation worsens

Engineering Contradiction:
ImproveselectivityVSAvoidby-products
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The patent achieves high selectivity through the specific local chemical environment created by the ionic liquid catalyst. The unique structure of the ionic liquid, with its specific cation-anion pairing, creates a localized catalytic environment that favors the desired isomerization reaction while suppressing side reactions such as polymerization and degradation. This local quality control, achieved through careful selection of cation and anion types, maintains high selectivity without the harsh conditions that lead to by-product formation.

Inventive Principle:
Principle #3Local quality

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 achieves high reaction conversion and selectivity for exo-tetrahydrodicyclopentadiene production with minimal waste and equipment damage, ensuring an efficient and environmentally sustainable process.

Implementation Method 1

endo-tetrahydrodicyclopentadiene is processed with acidic ionic liquids to obtain exo-tetrahydrodicyclopentadiene through isomerization reaction

Methodology Applied
Scientific EffectAcid catalysis: Catalysis

Data Source

PatentUS7488860B2Method for producing exo-tetrahydrodicyclopentadiene using ionic liquid catalyst
Publication Date: 2009.02.10 PETROCHINA CO LTD
  • US7488860B2 patent drawing
  • US7488860B2 patent drawing
  • US7488860B2 patent drawing

AI summary

An exo-tetrahydrodicyclopentadiene is produced from endo-tetrahydrodicyclopentadiene through isomerization reaction. An acidic ionic liquid is used in the isomerization. The isomerization of endo-tetrahydrodicyclopentadiene gives a reaction conversion and a selectivity both higher than 99%. Besides, the ionic liquid used is environmental-friendly and recyclable.