Iridium Catalyst for Fatty Acid Aromatization

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Solution Overview

Problem

Current processes for converting unsaturated fatty acids into bio-based fuels struggle to achieve the optimal aromatic content and naphthalene levels required for jet fuel, limiting the blending ratio with conventional fuels and affecting fuel properties.

Innovation Solution

The use of chloro-1,5-cyclooctadiene iridium (I) dimer as a catalyst for decarboxylation, isomerization, hydrogenation, dehydrogenation, and cyclization/aromatization of unsaturated fatty acids, resulting in products with at least 8% by volume aromatic content and less than 1% by volume naphthalenes, allowing for greater flexibility in fuel blending.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional decarboxylation processes are used on unsaturated fatty acids, then carbon dioxide is removed and alkene products are formed, but the aromatic content is insufficient (only about 6%) to meet jet fuel requirements

Engineering Contradiction:
Improvearomatic contentVSAvoidaromatic content control
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by modifying reaction conditions including temperature (200-400°C), pressure (1-50 atm), and catalyst composition (Ru3(CO)12 with Ir(COD)Cl2 in varying ratios) to optimize the decarboxylation process and achieve the desired aromatic content of 8-25% in the fuel product

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses composite catalyst systems combining ruthenium carbonyl clusters Ru3(CO)12 with iridium complexes Ir(COD)Cl2 in specific ratios (e.g., 95:5 to 50:50). This composite catalyst approach enables simultaneous decarboxylation and aromatic formation reactions that neither catalyst could achieve alone, resolving the contradiction between converting fatty acids and producing sufficient aromatic content

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If aromatic content is increased to meet minimum jet fuel requirements (8% by volume), then seal shrinkage and fuel density improve, but naphthalene content may exceed the 3% limit causing emissions problems

Engineering Contradiction:
Improvearomatic contentVSAvoidnaphthalene content
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The patent applies local quality by using selective catalysis where the Ru3(CO)12/Ir(COD)Cl2 catalyst system promotes specific reaction pathways that form desired aromatic hydrocarbons while suppressing naphthalene formation. The catalyst composition and reaction conditions are tuned to achieve local optimization of product distribution, ensuring aromatic content reaches 8-25% while keeping naphthalenes below 3%

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs feedback control by monitoring product composition (aromatic content and naphthalene levels) and adjusting catalyst ratios, temperature, and pressure to maintain product specifications. This allows real-time optimization to achieve the narrow target range of 8-25% aromatics with <3% naphthalenes

Inventive Principle:
Principle #23Feedback

3Adaptability or versatility

If bio-based fuel is blended with conventional jet fuel, then renewable energy content increases, but the blending ratio is limited (maximum 50%) due to insufficient aromatic content in the bio-based component

Engineering Contradiction:
Improvefuel blending flexibilityVSAvoidaromatic content
Core Design Contradiction:
Adaptability or versatilityVSQuantity of substance

Solution Approach 1:

The patent changes the key parameter of aromatic content in bio-based fuel from ~6% to 8-25% through optimized decarboxylation conditions, enabling the fuel to meet jet fuel specifications and expand blending flexibility from 50% to potentially 100% blending ratios

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent makes the bio-based fuel multi-functional by producing a product that simultaneously meets multiple jet fuel requirements: aromatic content (8-25%), naphthalene limitation (<3%), and overall composition specifications, allowing it to function as a direct jet fuel blendstock without blending restrictions

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 produces bio-based fuels with enhanced aromatic content, enabling them to be blended with conventional jet fuel in any proportion while avoiding excessive naphthalenes, thus improving fuel properties and reducing emissions.

Implementation Method 1

contacting a starting material which is an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride, in the presence of a catalyst at a temperature at which decarboxylation, isomerization, hydrogenation, dehydrogenation, and cyclization/aromatization occurs

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11186802B2Process for the decarboxylation, isomerization, hydrogenation, dehydrogenation and cyclization aromatization of fatty acids yielding products with significant aromatic content
Publication Date: 2021.11.30 THE GOVERNMENT OF THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY DEPARTMENT OF HEALTH & HUMAN SERVICES
  • US11186802B2 patent drawing
  • US11186802B2 patent drawing
  • US11186802B2 patent drawing

AI summary

Disclosed herein are processes for the decarboxylation, isomerization, hydrogenation, dehydrogenation, and cyclization/aromatization of fatty acids involving contacting a starting material which is an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride, in the presence of a catalyst at a temperature at which decarboxylation, isomerization, hydrogenation, dehydrogenation, and cyclization/aromatization occurs and recovering the unsaturated organic compound product; wherein the catalyst is chloro-1,5-cyclooctadiene iridium (I) dimer. The product may contain at least about 8% by volume aromatic content and less than about 25% by volume aromatic content, and wherein the product contains less than about 1% by volume of naphthalenes.