Ruthenium Catalyst Isomerization Decarboxylation

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Solution Overview

Problem

Current methods for converting bio-based fatty acids and their derivatives into valuable industrial products like olefins or isomerized fatty compounds require high-cost catalysts and involve complex processes, necessitating the development of low-cost catalysts that can efficiently lower activation energy for isomerization and decarboxylation reactions without the need for additional reagents like carboxylic acid anhydride.

Innovation Solution

The use of ruthenium or osmium-based catalysts or catalyst precursors, which facilitate isomerization and decarboxylation of unsaturated fatty acids and their derivatives at reduced temperatures without the requirement for phosphine ligands or carboxylic acid anhydride, allowing for the production of isomerized and decarboxylated unsaturated organic compounds, including olefins, through processes that can be further subjected to oligomerization or polymerization reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If high-cost catalysts are used for isomerization and decarboxylation, then reaction efficiency is improved, but production cost increases

Engineering Contradiction:
Improvereaction efficiencyVSAvoidproduction cost
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent employs inexpensive metal catalysts such as ruthenium, osmium, and their precursors that can be used in small amounts and do not require expensive ligand systems. These catalysts achieve high turnover numbers and enable efficient isomerization and decarboxylation reactions without the need for costly phosphine ligands, thus resolving the contradiction between reaction efficiency and production cost

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the chemical parameters of the catalyst system by using simple metal salts and precursors (e.g., ruthenium chloride, osmium carbonyl) instead of complex organometallic catalysts. This parameter change maintains catalytic activity while dramatically reducing cost, achieving both high productivity and low manufacturing cost

Inventive Principle:
Principle #35Parameter changes

2Reliability

If complex processes with additional reagents like carboxylic acid anhydride are used, then reaction completeness is improved, but process complexity increases

Engineering Contradiction:
Improvereaction completenessVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent extracts and eliminates the need for additional reagents such as carboxylic acid anhydrides from the reaction system. The metal catalysts alone are sufficient to drive both isomerization and decarboxylation reactions to completion, simplifying the process while maintaining reaction completeness and reliability

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The metal catalysts exhibit multi-functionality by simultaneously catalyzing both isomerization and decarboxylation reactions without requiring different catalysts or additional reagents. This universal catalytic activity simplifies the overall process while ensuring complete conversion of feedstock to desired products

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

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 enables the cost-effective production of valuable isomerized and decarboxylated products with high turnover numbers, reducing the need for expensive catalysts and simplifying the reaction processes, while maintaining efficiency and product diversity, such as the conversion of unsaturated fatty acids to α-olefins and conjugated internal olefins.

Implementation Method 1

the use of a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, alkene, or an unsaturated triglyceride

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

the use of a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10457615B2Process for isomerization and decarboxylation of unsaturated organic compounds with a metal catalyst or catalyst precursor
Publication Date: 2019.10.29 THE GOVERNMENT OF THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY DEPARTMENT OF HEALTH & HUMAN SERVICES
  • US10457615B2 patent drawing
  • US10457615B2 patent drawing
  • US10457615B2 patent drawing

AI summary

Disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is the use of a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.