Ketoacid Conversion via Segmented Catalyst Beds

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Solution Overview

Problem

Current methods for upgrading levulinic acid and other ketoacids to higher molecular weight compounds face challenges such as high reactivity of intermediates leading to unwanted oligomerization and coking, resulting in low yields and reactor plugging, especially when using single reactors.

Innovation Solution

A method involving C—C-coupling reactions in the presence of a dual function catalyst system with both hydrogenation and C—C-coupling activity, conducted in a single reactor with a feedstock containing at least one ketoacid, where the catalyst system includes a mixture of metal oxide and noble or transition metal catalysts, suppressing coking tendencies and enhancing molecular weight production.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Device complexity

If a single reactor is used for upgrading levulinic acid, then the number of process steps is reduced, but the yield of desired product decreases due to unwanted oligomerization and coking reactions

Engineering Contradiction:
Improvenumber of process stepsVSAvoidyield of desired product
Core Design Contradiction:
Device complexityVSProductivity

Solution Approach 1:

The single reactor is divided into multiple catalyst beds with different functions: first bed contains acid catalyst for C-C coupling, second bed contains base catalyst for ketonization, and third bed contains metal catalyst for hydrogenation. This segmentation allows each catalyst to perform its specific function optimally while preventing unwanted side reactions that would occur if all catalysts were mixed together.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Different regions (catalyst beds) within the reactor are assigned different catalytic properties tailored to specific reaction needs. The acid catalyst bed promotes C-C coupling, the base catalyst bed promotes ketonization, and the metal catalyst bed promotes hydrogenation. This local differentiation of catalytic quality enables selective product formation while minimizing unwanted oligomerization and coking.

Inventive Principle:
Principle #3Local quality

2Productivity

If multiple reactors are used for upgrading levulinic acid, then the yield of desired product is improved through better control of reactions, but the number of process steps increases

Engineering Contradiction:
Improveyield of desired productVSAvoidnumber of process steps
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

Multiple reactor systems are merged into a single reactor by arranging multiple catalyst beds in series within the same reaction vessel. This allows the benefits of multi-stage reaction control (improved selectivity and yield) to be achieved while avoiding the complexity of multiple separate reactors, including multiple feed systems, heating zones, and product withdrawal systems.

Inventive Principle:
Principle #5Merging (Combining)

3Temperature

If strong acidic heterogenous catalyst is used for dimerization, then the reaction proceeds at lower temperature and pressure, but highly reactive intermediates form that lead to unwanted oligomerization and coking

Engineering Contradiction:
Improvereaction temperatureVSAvoidunwanted oligomerization and coking
Core Design Contradiction:
TemperatureVSObject-generated harmful factors

Solution Approach 1:

The harmful function of the acid catalyst (promoting oligomerization and coking) is extracted and separated from the useful function (C-C coupling). By placing the acid catalyst in the first bed followed by base and metal catalyst beds, the harmful side reactions are suppressed in subsequent beds, effectively removing the harmful effect while retaining the beneficial C-C coupling reaction.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The highly reactive intermediates that would normally lead to unwanted oligomerization and coking are converted into beneficial products through subsequent ketonization and hydrogenation reactions in the following catalyst beds. The reactive intermediates are not allowed to accumulate or undergo unwanted side reactions but are instead directed toward desired product formation.

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

4Device complexity

If direct upgrading route is used in a single reactor, then the process is simplified, but the catalyst lifetime decreases due to coking and reactor plugging

Engineering Contradiction:
Improveprocess simplificationVSAvoidcatalyst lifetime
Core Design Contradiction:
Device complexityVSDuration of action of stationary object

Solution Approach 1:

The base catalyst and metal catalyst act as intermediaries that protect the acid catalyst from deactivation. The base catalyst neutralizes acidic byproducts that would otherwise accumulate and cause coking, while the metal catalyst hydrogenates reactive intermediates before they can polymerize. This intermediary action extends catalyst lifetime while maintaining process simplicity.

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 increases the molecular weight of ketoacids, improving yield and reducing processing costs by controlling coking reactions and promoting the formation of higher molecular weight compounds suitable for fuel or heavy oil components.

Implementation Method 1

subjecting the feedstock to one or more C—C-coupling reaction(s) wherein the C—C-coupling reaction(s) are conducted in the presence of hydrogen and in the presence of a dual function catalyst system having both hydrogenation activity and C—C-coupling activity

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

a dual function catalyst system having both hydrogenation activity and C—C-coupling activity

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS10550062B2Method for catalytic conversion of ketoacids and hydrotreament to hydrocarbons
Publication Date: 2020.02.04 NESTE OYJ
  • US10550062B2 patent drawing
  • US10550062B2 patent drawing
  • US10550062B2 patent drawing

AI summary

A method for the catalytic conversion of ketoacids, including methods for increasing the molecular weight of ketoacids, the method comprising the steps of providing in a reactor a feedstock comprising at least one ketoacid. The feedstock is then subjected to one or more C—C coupling reaction(s) in the presence of hydrogen, and in the presence of a catalyst system having both hydrogenation activity and C—C coupling activity.