Olefin Etherification Catalyst Extraction for Yield

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Solution Overview

Problem

The commercial viability of olefin etherification processes is limited by low conversion of olefins to desired ethers due to the instability of ethers under reaction conditions and the tendency of olefins to isomerize, requiring large excesses of reactants for marginal yields.

Innovation Solution

A process involving contacting olefins and alcohols with a heterogeneous etherification catalyst in a reaction zone, followed by removing unconsumed reactants and products to a catalyst-free zone, where the reaction is repeated until a desired amount of ether accumulates, allowing for higher yields without prolonged contact that leads to equilibrium-driven conversion back to starting materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If the ether product remains in contact with the catalyst for extended periods to achieve high conversion, then the conversion efficiency improves, but the ether undergoes equilibrium-driven reverse conversion back to starting materials, reducing yield

Engineering Contradiction:
Improveconversion efficiencyVSAvoidproduct yield
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent extracts the ether product from the reaction zone at predetermined time intervals, removing it from contact with the catalyst. This prevents the reverse reaction while maintaining high conversion efficiency by periodically separating the product from the catalytic environment that causes equilibrium-driven decomposition.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent implements periodic removal of the ether product at predetermined time intervals during the reaction process. This periodic action allows the reaction to proceed to high conversion while intermittently preventing reverse conversion, resolving the contradiction between maintaining catalytic activity and preventing product degradation.

Inventive Principle:
Principle #19Periodic action

2Reliability

If large excesses of reactants are used to compensate for low conversion, then the desired ether yield is achieved, but the raw material consumption increases significantly, raising costs

Engineering Contradiction:
Improveether yieldVSAvoidraw material consumption
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The patent employs continuous recycling of unreacted olefin and alcohol from the separation zone back to the reaction zone. This continuous action ensures that reactants are repeatedly exposed to the catalyst over extended periods, achieving high conversion and yield without requiring large initial excesses of reactants, thereby reducing raw material consumption and costs.

Inventive Principle:
Principle #20Continuity of useful action

3Productivity

If the reaction is allowed to proceed to completion with prolonged catalyst contact, then high conversion is achieved, but olefin isomerization increases, reducing reactivity and etherification efficiency

Engineering Contradiction:
Improveolefin conversionVSAvoidolefin isomerization
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent extracts the ether product at predetermined time intervals before complete reaction, removing it from the catalytic environment. This prevents prolonged catalyst contact that would cause olefin isomerization, while still achieving high conversion by maintaining continuous reaction cycles with periodic product removal.

Inventive Principle:
Principle #2Taking out (Extraction)

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 achieves higher conversion and yield of ether products with reduced raw material usage, decreasing costs and mitigating the need for large excesses of starting materials, while maintaining the ether product out of contact with the catalyst to prevent reverse conversion.

Implementation Method 1

contacting an olefin and an alcohol with a heterogeneous etherification catalyst in a reaction zone under etherification conditions to form an ether compound

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2623488B1Process for olefin etherification
Publication Date: 2014.08.20 DOW GLOBAL TECHNOLOGIES LLC
  • EP2623488B1 patent drawingFigure 1
  • EP2623488B1 patent drawingFigure 2
  • EP2623488B1 patent drawingFigure 3

AI summary

A process for preparing an ether compound, the process comprising: (a) contacting an olefin with an alcohol in the presence of an etherification catalyst, under etherification conditions, to form an ether compound; (b) recovering the ether compound, unreacted alcohol and unconsumed olefin; and (c) using at least a portion of the unconsumed olefin of step (b) in an etherification process conducted according to step (a), wherein the alcohol is linear or branched alcohol alkyl containing one or two alcohol groups, and further substituted with 1, 2, or 3 activating groups independently selected from CN, NO2, F, Cl, Br, I, C1-C6 alkoxy, and -C(O)O-alkyl.