Oxidative Cleavage of Vegetable Oils for Saturated Acids
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Solution Overview
Problem
Existing processes for producing saturated carboxylic acids and triglycerides with multiple acid functions require preliminary modifications like transesterification and large quantities of water, leading to industrial inefficiencies and environmental challenges.
Innovation Solution
A process that directly converts non-modified vegetable oils containing unsaturated fatty acids into saturated monocarboxylic acids and triglycerides with multiple acid functions through oxidative cleavage, using hydrogen peroxide and specific catalysts without the need for solvents or excessive water, allowing for efficient separation and reuse of catalysts.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of operation
If transesterification is performed as a preliminary step to reduce viscosity, then the reaction intermediate becomes less viscous and easier to handle, but toxic solvents like methyl alcohol must be used requiring safety measures and additional economic costs
Solution Approach 1:
The invention extracts and eliminates the harmful transesterification step from the process. By directly oxidizing triglycerides without preliminary modification, the process removes the need for toxic methyl alcohol solvent while still achieving manageable viscosity through the oxidation reaction itself.
Solution Approach 2:
The invention converts the harmful high viscosity of triglycerides directly into a benefit by performing oxidation in situ. The oxidation reaction transforms the triglyceride structure, reducing viscosity and creating the desired dicarboxylic acid products simultaneously, eliminating the need for separate transesterification.
2Ease of manufacture
If large quantities of water are added to perform oxidative cleavage of high viscosity intermediates, then the reaction can proceed, but large-volume reactors are required and catalyst recovery becomes burdensome
Solution Approach 1:
The invention performs the oxidation action preliminarily on the triglyceride before cleavage. By oxidizing the double bonds in situ while the triglyceride is still in its original form, the process creates a more reactive intermediate that requires minimal water for the subsequent cleavage step, eliminating the need for large water quantities.
Solution Approach 2:
The invention changes the chemical parameters of the triglyceride through oxidation, transforming it into a more reactive state with modified physical properties. This parameter change enables the cleavage reaction to proceed with minimal water, as the oxidized triglyceride is inherently more reactive toward cleavage.
3Manufacturing precision
If multiple processing steps including transesterification and purification are used, then product purity is achieved, but process complexity and economic costs increase
Solution Approach 1:
The invention merges multiple separate processing steps into a single integrated oxidation-cleavage process. By combining the oxidation of double bonds with the subsequent cleavage in one continuous operation starting from triglycerides, the process reduces the number of steps while maintaining product purity through the specific reaction conditions and catalyst system.
Solution Approach 2:
The oxidation step serves multiple functions simultaneously: it activates the triglyceride for cleavage, modifies the molecular structure to reduce viscosity, and creates the reactive intermediates needed for dicarboxylic acid formation. This multi-functionality eliminates the need for separate transesterification and purification steps.
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 reduces industrial costs and environmental impact by eliminating the need for preliminary modifications and large water usage, achieving high yields of desired products like azelaic acid and allowing for their use in polymer production and pharmaceutical applications.
Implementation Method 1
reacting the triglycerides of unsaturated fatty acids with hydrogen peroxide in the presence of a catalyst for the oxidation reaction of the olefinic double bond of the unsaturated fatty acid, and obtaining a vicinal diol as an intermediate product
Implementation Method 2
reacting said intermediate product obtained from step (a) with oxygen or a compound containing oxygen, in the presence of a catalyst for the oxidation reaction of the two hydroxyl groups of the vicinal diol to carboxylic groups
Data Source
AI summary
Process for the production of saturated monocarboxylic acids and triglycerides of saturated carboxylic acids having more than one acid function starting from non-modified vegetable oils containing triglycerides of unsaturated fatty acids, comprising the oxidative cleavage of the unsaturated fatty acids.