Ketoacid Dimerization via Ion Exchange Resin for Fuel Synthesis

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing methods for upgrading levulinic acid and other ketoacids to higher molecular weight compounds face challenges such as catalyst deactivation and low yields due to the formation of reactive intermediates, which can lead to undesired side reactions and reduced catalyst lifespan.

Innovation Solution

The method involves selective conversion of ketoacids to ketoacid dimers using an ion exchange resin catalyst, followed by C-C-coupling reactions at temperatures above 200 °C to increase molecular weight, thereby reducing catalyst deactivation and improving yield.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If direct upgrading routes using single reactors are used, then process economy is improved by reducing the number of process steps, but catalyst deactivation occurs due to formation of highly reactive intermediates with multiple functional groups

Engineering Contradiction:
Improveprocess economyVSAvoidcatalyst stability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The upgrading process is divided into two separate reaction steps performed in different reactors: first, conversion of levulinic acid to GVL and water, and second, C-C coupling of GVL to form higher molecular weight compounds. This segmentation prevents the formation of highly reactive intermediates with multiple functional groups that would otherwise cause catalyst deactivation in a single-reactor direct route.

Inventive Principle:
Principle #1Segmentation

2Reliability

If indirect upgrading routes using multiple reactors are used, then catalyst stability is improved by avoiding highly reactive intermediates, but process complexity increases due to additional process steps

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

Solution Approach 1:

The process is segmented into two reactors with distinct functions: the first reactor performs dehydration of levulinic acid to GVL using a solid acid catalyst, and the second reactor performs C-C coupling of GVL using a metal catalyst. This segmentation enables use of optimized catalysts for each specific reaction, improving overall catalyst stability and performance.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The first reactor system is designed to be universally applicable to different ketoacids (levulinic acid, itaconic acid, glutaric acid) by adjusting reaction conditions, while maintaining the same basic dehydration mechanism and catalyst type, thus reducing overall process complexity across different feedstocks.

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

3Reliability

If lower temperatures or dilute solutions are used to suppress side reactions, then catalyst deactivation is reduced, but product yield decreases

Engineering Contradiction:
Improvecatalyst stabilityVSAvoidproduct yield
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

By segmenting the reaction into two steps, each reactor can operate at optimal temperatures for its specific function without concern for side reactions from highly reactive intermediates. The first reactor operates at moderate temperatures for dehydration, while the second reactor can use higher temperatures to achieve high conversion and yield in the C-C coupling step, thus maintaining both catalyst stability and high product yield.

Inventive Principle:
Principle #1Segmentation

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, enhancing the production of higher molecular weight compounds suitable for fuel or base oil components while reducing processing costs and catalyst consumption.

Implementation Method 1

selective conversion of ketoacids to ketoacid dimers using an ion exchange resin catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

C-C-coupling reactions at temperatures above 200 °C to increase molecular weight

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentEP3050867B1Method for catalytic conversion of ketoacids via ketoacid dimer intermediate and hydrotreament to hydrocarbons
Publication Date: 2019.11.13 NESTE OYJ
  • EP3050867B1 patent drawingFigure 1~2
  • EP3050867B1 patent drawingFigure 3
  • EP3050867B1 patent drawingFigure 4

AI summary

The present invention relates to catalytic conversion of ketoacids, including methods for increasing the molecular weight of ketoacids, the method comprising the steps of providing in a reactor a raw material comprising at least one ketoacid. The raw material is then subjected to one or more C-C-coupling reaction(s) in the presence of an ion exchange resin catalyst to produce at least one ketocid dimer, the method further comprising providing steps of providing in a reactor a feedstock comprising the at least one ketoacid dimer and subjecting the feedstock to one or more C-C-coupling reaction(s) at a temperature of at least 200 °C.