Liquid Phase Decarboxylative Ketonization of Fatty Acids

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Solution Overview

Problem

Existing processes for decarboxylative ketonization of fatty acids with 12 carbon atoms or less are inefficient and require expensive equipment, leading to low yields and the formation of undesired by-products, especially when conducted in industrial scales.

Innovation Solution

A process involving the liquid phase decarboxylative ketonization of fatty acids or their derivatives using metal compounds as catalysts, where a molar ratio of metal to carboxyl group equivalents is maintained between 1:0.8 to 1:3.5, with a two-step temperature regimen from 100°C to 270°C followed by a rise to 270°C to 400°C, allowing for the conversion of fatty acids with 12 carbon atoms or less in an open reaction system without added solvents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If gas phase reaction is used for decarboxylative ketonization of fatty acids with high boiling point, then reaction can proceed, but selectivity deteriorates and undesired by-products form due to very high temperatures needed for evaporation

Engineering Contradiction:
Improvereaction feasibilityVSAvoidselectivity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The invention transitions the reaction from gas phase to liquid phase by utilizing the liquid state of fatty acids at elevated temperatures (above their melting points but below 300°C). This phase transition eliminates the need for high-temperature evaporation while maintaining reaction feasibility, thereby preserving selectivity and reducing by-product formation.

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The invention changes the temperature parameter range from above 350°C (gas phase) to 200-300°C (liquid phase). This parameter change allows the reaction to proceed in the liquid phase with improved selectivity while still achieving adequate reaction rates through extended reaction times and efficient heat transfer.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If liquid phase reaction is used for decarboxylative ketonization of fatty acids with boiling point below 300°C, then productivity and selectivity improve, but existing processes yield low ketone amounts when fatty acids with 12 carbon atoms or less are used

Engineering Contradiction:
ImproveproductivityVSAvoidketone yield
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The invention optimizes the temperature parameter to 200-300°C, which is sufficiently high to achieve good conversion rates for short-chain fatty acids (12 carbons or less) but controlled to prevent excessive by-product formation. This parameter optimization maintains high productivity while improving ketone yield for the problematic short-chain substrates.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs extended reaction times and continuous monitoring to ensure complete conversion of fatty acids to ketones. By maintaining reaction conditions optimally for extended periods, the process achieves high ketone yields even for short-chain fatty acids that previously gave low conversions, thereby resolving the contradiction between productivity and quantity.

Inventive Principle:
Principle #20Continuity of useful action

3Ease of operation

If existing liquid phase processes are used with fatty acids having 12 carbon atoms or less, then reaction can proceed, but ketone yields are low and process is not efficient for industrial scale

Engineering Contradiction:
Improveprocess simplicityVSAvoidindustrial efficiency
Core Design Contradiction:
Ease of operationVSProductivity

Solution Approach 1:

The invention sets the temperature range at 200-300°C and extends reaction times to achieve complete conversion. These parameter changes make the process efficient for industrial scaling by ensuring high ketone yields from short-chain fatty acids while maintaining operational simplicity through the use of standard heated reaction vessels without complex equipment.

Inventive Principle:
Principle #35Parameter changes

4Temperature

If high temperatures above 350°C are used for gas phase reaction, then evaporation of reactants occurs, but this is detrimental to selectivity and leads to by-product formation

Engineering Contradiction:
Improvereaction temperatureVSAvoidby-product formation
Core Design Contradiction:
TemperatureVSObject-generated harmful factors

Solution Approach 1:

The invention utilizes the liquid phase reaction approach, transitioning from gas phase evaporation at high temperatures to liquid phase reaction at moderate temperatures. This phase transition eliminates the harmful effect of high-temperature evaporation that causes by-product formation, while still achieving adequate reaction rates through the liquid state reactivity and extended reaction times.

Inventive Principle:
Principle #36Phase transitions

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 of ketones with minimal by-products, enabling efficient industrial-scale production while reducing the need for expensive equipment and maintaining catalytic activity across multiple cycles.

Implementation Method 1

decarboxylative ketonization of fatty acids or derivatives of fatty acids with metal compounds as catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

reacted for a period of time P1 at a temperature T1 from 100°C to 270°C and thereafter the temperature is raised to a temperature T2 which is strictly above 270°C and up to 400°C

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentEP3292097B1Process for the decarboxylative ketonization of fatty acids or fatty acid derivatives
Publication Date: 2019.04.10 RHODIA OPERATIONS SAS

AI summary

A process for the decarboxylative ketonizationof fatty acids, fatty acid derivatives or mixtures thereof in the liquid phase with metal compounds as catalyst wherein the fatty acids, fatty acid derivatives or mixtures thereof are added sequentially.