Mixed Metal Oxide Catalysts for Fusel Oil Upgrading

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Solution Overview

Problem

Current methods for producing ketones and isoprene from fusel oils are inefficient, requiring complex multi-step processes and relying on petroleum-derived materials, with low yields and high costs, while existing catalysts for dehydration of aldehydes have stability and selectivity issues, making commercial-scale production unfeasible.

Innovation Solution

A process using mixed metal oxide catalysts, specifically Zn/Mg/Cu/Mn/Zr, to convert fusel oil mixtures into high-value chemicals like methyl isobutyl ketone, di-isobutyl ketone, isoprene, and isoamylene, with controlled reaction conditions to achieve high yields and selectivity, and zeolite catalysts for dehydrogenation to produce bio-based aldehydes and olefins.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If conventional multi-step processes are used to convert fusel oils to ketones and isoprene, then product diversity is achieved, but process complexity and production cost increase significantly

Engineering Contradiction:
Improveproduct diversityVSAvoidprocess complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent combines multiple reaction steps (dehydration, dehydrogenation, isomerization) into a single catalytic process using mixed metal oxide catalysts. The catalyst system simultaneously performs functions that previously required separate process stages, thereby reducing overall process complexity while maintaining the ability to produce diverse products including ketones, isoprene, and other valuable chemicals from fusel oil feedstocks.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The mixed metal oxide catalyst system exhibits multi-functionality by catalyzing multiple reaction pathways concurrently. A single catalyst formulation can promote dehydration to aldehydes, dehydrogenation to ketones, and isomerization reactions, allowing one catalytic system to replace multiple specialized catalysts and process units, thus simplifying the overall production process while achieving product diversity.

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

2Productivity

If existing catalysts are used for dehydration of aldehydes, then reaction proceeds, but catalyst stability and selectivity are insufficient for commercial-scale production

Engineering Contradiction:
Improvereaction throughputVSAvoidcatalyst stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent employs composite mixed metal oxide catalysts comprising multiple metal components (e.g., Mo, V, Nb, W, Bi, Sb) combined in specific ratios. These composite catalysts exhibit enhanced stability and selectivity compared to single-metal catalysts. The synergistic interaction between different metal oxides in the composite structure improves resistance to deactivation, maintains consistent activity over extended operation periods, and achieves high selectivity for desired products, making the process suitable for commercial-scale production.

Inventive Principle:
Principle #40Composite materials

3Ease of manufacture

If petroleum-derived materials are used as feedstock, then production cost is reduced, but renewable chemical production is not achieved

Engineering Contradiction:
Improveproduction costVSAvoidrenewable chemical production
Core Design Contradiction:
Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The patent converts fusel oil, which is traditionally considered a waste byproduct of ethanol fermentation and often discarded or used as low-value fuel, into high-value renewable chemicals. By developing catalytic processes that efficiently transform this waste stream into ketones, isoprene, and other valuable products, the invention turns a harmful economic burden (waste disposal costs) into a beneficial revenue source, achieving both cost-effectiveness and renewable chemical production.

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

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 high yields and selectivity for bio-based ketones, aldehydes, and olefins, providing cost-competitive renewable chemicals and enabling the production of isoprene from bio-based sources, addressing the inefficiencies and cost issues of existing methods.

Implementation Method 1

dehydration of fusel oil mixtures provides predominately 3-methyl-1-butene, 1-methyl-2-butene, and 2-methyl-2-butene

Methodology Applied
Scientific EffectDehydration:

Implementation Method 2

dehydrogenation of the crude fusel oil alcohol mixture, consisting primarily of 3-methyl-1-butanol and 2-methyl-1-butanol, provides access to the corresponding bio-based C5 aldehydes in excellent yields

Methodology Applied
Scientific EffectDehydrogenation:

Implementation Method 3

which upon in-situ isomerization results in high yields to cost competitive bio-based isoamylene

Methodology Applied
Scientific EffectIsomerization:

Implementation Method 4

converted in high yield to crude liquid product mixes consisting of industrially relevant symmetrical and asymmetrical C2-C9 ketones

Methodology Applied
Scientific EffectCondensation: Condensation

Data Source

PatentEP3735401B1Upgrading fusel oil mixtures over heterogeneous catalysts to higher value renewable chemicals
Publication Date: 2023.04.26 GEVO INC

AI summary

This present disclosure relates to catalytic processes for upgrading crude and/or refined fusel oil mixtures to higher value renewable chemicals, via mixed metal oxide or zeolite catalysts. Disclosed herein are processes passing a vaporized stream of crude and/or refined fusel oils over various mixed metal oxide catalysts, metal doped zeolites, or non-metal doped zeolites and/or metal oxides providing options to valorize fusel oil mixtures to higher value products. Renewable chemicals formed, via these upgrading catalyst platforms, are comprised of, but not limited to, methyl isobutyl ketone (MIBK), di-isobutyl ketone (DIBK), isoamylene, and isoprene.