Alcohol to Olefin Conversion via Ester Intermediary

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Solution Overview

Problem

Current processes for converting light alcohols like isobutanol to olefins require high activity catalysts, severe processing conditions, and high recycle rates, and face challenges with bio-derived alcohols due to water presence and separation difficulties.

Innovation Solution

A process involving esterification of C2 to C5 alcohols with organic acids in the presence of an esterification catalyst, followed by catalytic or thermal degradation of the ester to produce olefins, using catalytic distillation reactor systems to simultaneously react and separate products, reducing the need for high catalyst activity and severe conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional dehydration catalysts are used to convert light alcohols to olefins, then conversion can be achieved, but high catalyst activity and severe processing conditions are required

Engineering Contradiction:

Improveconversion efficiencyVSAvoidprocessing conditions

Core Design Contradiction:

ReliabilityVSTemperature

Solution Approach 1:

The patent introduces an intermediary ester compound as a mediator between the alcohol reactant and the olefin product. The alcohol first reacts with a carboxylic acid to form an ester intermediate, which then decomposes to yield the olefin. This two-step pathway via ester formation avoids the need for severe dehydration conditions and high-activity catalysts required for direct alcohol-to-olefin conversion.

Inventive Principle:

Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction parameters by shifting from direct dehydration to esterification followed by ester decomposition. This parameter change allows the process to proceed under milder conditions, eliminating the need for high catalyst activity and severe temperature/pressure conditions while maintaining effective conversion.

Inventive Principle:

Principle #35Parameter changes

2Reliability

If high recycle rates are used to achieve acceptable conversion levels, then conversion can be improved, but process complexity and time loss increase

Engineering Contradiction:

Improveconversion levelVSAvoidrecycle time

Core Design Contradiction:

ReliabilityVSLoss of time

Solution Approach 1:

The patent enables continuous conversion by making the ester formation and decomposition steps proceed continuously through controlled reaction conditions. The ester intermediate is formed continuously from alcohol and carboxylic acid, then continuously decomposes to olefin, eliminating the need for high recycle rates to achieve acceptable conversion levels and reducing time loss.

Inventive Principle:

Principle #20Continuity of useful action

3Adaptability or versatility

If bio-derived alcohols with water are processed directly, then utilization of renewable feedstocks is achieved, but separation becomes difficult due to closer volatilities and azeotropes

Engineering Contradiction:

Improvefeedstock utilizationVSAvoidseparation process

Core Design Contradiction:

Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent uses ester formation as an intermediary step that separates the alcohol from water in the bio-derived feedstock. By converting the alcohol to an ester intermediate first, the water-alcohol azeotropic mixture is broken, allowing for easier separation of water from the organic phase. This simplifies the separation process while maintaining ability to process bio-derived feedstocks with water content.

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 approach effectively converts light alcohols to olefins with high purity, eliminating the need for high activity catalysts and severe processing conditions, and facilitates the use of bio-alcohols as renewable feedstocks for petrochemical production.

Implementation Method 1

contacting at least one C2 to C5 alcohol with an organic acid in the presence of an esterification catalyst to convert at least a portion of the at least one C2 to C5 alcohol and the organic acid to an ester

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

separating the water, ester, any unreacted organic acid, and any unreacted C2 to C5 alcohol

Methodology Applied

Scientific EffectDistillation: Distillation

Implementation Method 3

at least one of catalytically and thermally degrading the ester to form an organic acid and an olefin

Methodology Applied

Scientific EffectThermal degradation: Thermolysis

Data Source

PatentUS9272965B2Process for the conversion of alcohols to olefins

Publication Date: 2016.03.01 CATALYTIC DISTILLATION TECHNOLOGIES

AI summary

A process for the conversion of an alcohol to an olefin is disclosed. The process may include: contacting at least one C2 to C5 alcohol with an organic acid in the presence of an esterification catalyst to convert at least a portion of the at least one C2 to C5 alcohol and the organic acid to an ester; at least one of catalytically and thermally degrading the ester to form an organic acid and an olefin.