Tertiary Ether Production via Catalytic Distillation

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Solution Overview

Problem

Existing etherification processes for producing tertiary alkyl ethers are hindered by catalyst deactivation due to nitrile impurities like acetonitrile and propionitrile, which require complex and costly processes to minimize contact between nitriles and catalysts, leading to inefficiencies and increased capital and operating costs.

Innovation Solution

A catalytic distillation reactor system is used to separate nitriles from hydrocarbons and alcohols, maintaining a selected alcohol concentration profile that limits propionitrile contact with the catalyst to less than 25%, allowing for effective etherification of C4 to C6 isoolefins with minimal catalyst deactivation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional etherification processes are used with feedstocks containing nitrile impurities, then ether production can proceed, but catalyst deactivation occurs leading to reduced catalyst life and increased operating costs

Engineering Contradiction:
Improveether production efficiencyVSAvoidcatalyst life
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The process separates the etherification reaction from the feedstock containing nitriles by using a guard bed as a distinct segment that protects the main catalyst. This segmentation allows the reaction to proceed while isolating the catalyst from deactivating impurities.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

A guard bed acts as an intermediary component between the nitrile-containing feedstock and the etherification catalyst. This intermediary selectively removes or neutralizes nitrile impurities before they reach the main catalyst, preventing deactivation while allowing the desired reaction to occur.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If guard beds are added to protect the catalyst from nitriles, then catalyst life is extended, but process complexity and capital costs increase

Engineering Contradiction:
Improvecatalyst lifeVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The guard bed is designed to perform multiple functions: removing nitrile impurities, preventing catalyst deactivation, and potentially serving as a pre-reaction zone. This multi-functionality reduces the need for separate units and simplifies the overall process.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The guard bed functionality is merged with the existing etherification process flow, combining impurity removal and catalytic reaction in an integrated system rather than separate sequential units, thereby reducing capital complexity.

Inventive Principle:
Principle #5Merging (Combining)

3Reliability

If nitriles are removed from the feedstock before etherification, then catalyst deactivation is minimized, but process costs and complexity increase

Engineering Contradiction:
Improvecatalyst stabilityVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The guard bed performs preliminary removal of nitrile impurities before the feedstock enters the main etherification catalyst zone. This preliminary action protects the catalyst without requiring complete upstream removal of nitriles, simplifying the overall process.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The guard bed selectively extracts or removes nitrile impurities from the feedstock stream before it contacts the main catalyst, taking out only the harmful components while allowing the desired reactants to proceed to the etherification reaction.

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 approach extends catalyst life, reduces process complexity and costs, and enables efficient production of tertiary ethers with reduced capital and operating expenses by minimizing nitrile-catalyst interaction.

Implementation Method 1

A catalytic distillation reactor system is used to separate nitriles from hydrocarbons and alcohols

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 2

The etherification process typically uses strongly acidic ion exchange resins as etherification catalysts

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

Etherification reactions are the reaction of olefins, such as isobutylene and isoamylenes, or other olefinic compounds, with an alcohol to form the corresponding ether

Methodology Applied
Scientific EffectEtherification reaction: Chemical Bonding

Data Source

PatentEP2197825B1Method of producing tertiary amyl ethyl ether
Publication Date: 2015.11.04 CATALYTIC DISTILLATION TECHNOLOGIES
  • EP2197825B1 patent drawingFigure 1
  • EP2197825B1 patent drawingFigure 2
  • EP2197825B1 patent drawingFigure 3~4

AI summary

A process for the production of tertiary ethers, including: feeding a hydrocarbon stream comprising isoolefins and propionitrile to a distillation column reactor system containing at least one etherification reaction zone; feeding a C2 to C6 monoalcohol or mixture thereof to the distillation column reactor; concurrently in the distillation column reactor system: reacting a portion of the isoolefins with a portion of the alcohols to form a tertiary ether; and separating the tertiary ether from unreacted isoolefins; withdrawing the tertiary ether and propionitrile from the distillation column reactor system as a bottoms; withdrawing the unreacted isoolefins from the distillation column reactor system as an overheads; and operating the distillation column reactor system such that the etherification reaction zone is substantially free of propionitrile.