Aliphatic Dialkyl Ester Synthesis from Vegetable Oils
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Solution Overview
Problem
Existing processes for obtaining dicarboxylic acid derivatives from vegetable oils are inefficient due to high water consumption and complex, costly operations, and they often result in low yields and impurities that interfere with polymerization reactions.
Innovation Solution
A process involving the reaction of a triglycerides mixture containing saturated dicarboxylic acids with an aliphatic alcohol in the presence of catalysts capable of esterification and transesterification, followed by separation of aliphatic dialkyl esters, which allows for high-yield and high-purity dicarboxylic acid derivatives production, simplifying the separation of products and recovering glycerine effectively.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If hot water extraction is used to separate azelaic acid from glycerine and saturated monocarboxylic acids, then separation is achieved, but very large quantities of water are required and product recovery yield is reduced due to water solubility
Solution Approach 1:
The invention changes the separation parameter from water-based extraction to solvent-based extraction using hexane or heptane. These solvents have different solubility characteristics compared to water, allowing efficient separation of azelaic acid from glycerine and saturated monocarboxylic acids without the solubility losses encountered with water extraction.
Solution Approach 2:
The invention uses inexpensive aliphatic solvents (hexane or heptane) that can be easily removed by evaporation. These solvents serve their separation purpose and are then discarded through simple evaporation, avoiding the need for large quantities of water that would require extensive processing and recovery.
2Manufacturing precision
If thin film evaporation and distillation are used to separate azelaic acid from saturated monocarboxylic acids, then purification is achieved, but complex and costly operations are required
Solution Approach 1:
The invention introduces an intermediary substance (aliphatic solvent like hexane or heptane) that facilitates the separation process. The solvent selectively dissolves azelaic acid from the mixture, allowing simple filtration or decantation to separate it from glycerine and saturated monocarboxylic acids, avoiding complex distillation equipment.
Solution Approach 2:
The invention replaces the mechanical/thermal separation system (thin film evaporation and distillation columns) with a chemical separation system based on selective solubility. This substitution uses chemical properties rather than mechanical energy input, simplifying the equipment required while achieving the same purification goal.
3Productivity
If hydrolysis is used to obtain dicarboxylic acids from triglycerides, then acid release is achieved, but long chain saturated monocarboxylic acids are also released and interfere with polymerisation reactions
Solution Approach 1:
The invention extracts and removes the harmful long chain saturated monocarboxylic acids from the reaction mixture using water washing. These acids are more water-soluble than the desired dicarboxylic acid derivatives, allowing selective removal of the interfering substances while retaining the valuable polymerisation-grade product.
Solution Approach 2:
Instead of trying to prevent the formation of saturated monocarboxylic acids during hydrolysis, the invention inverts the approach by allowing their formation and then selectively removing them through water washing. This reverse strategy simplifies the process by accepting the by-products and eliminating them rather than preventing their formation.
4Productivity
If esterification and transesterification are performed to obtain dicarboxylic acid derivatives, then high yields are achieved, but complex separation from glycerine and long chain acid monoesters is required
Solution Approach 1:
The invention uses a simplified separation approach that copies the successful methodology from industrial oil refining processes. By using aliphatic solvents and simple washing operations similar to those already established in the industry, the complex separation problem is solved using proven, simple techniques rather than developing new complex separation systems.
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 (>60% by weight) of pure aliphatic dialkyl esters of dicarboxylic acids, simplifying product separation and enabling their direct use in polymerization reactions, while recovering glycerine in high concentrations.
Implementation Method 1
reacting a triglycerides mixture containing at least a triglyceride of at least one saturated dicarboxylic acid with an aliphatic alcohol in the presence of one or more catalysts capable of catalysing the esterification and transesterification reactions
Implementation Method 2
reacting a triglycerides mixture containing at least a triglyceride of at least one saturated dicarboxylic acid with an aliphatic alcohol in the presence of one or more catalysts capable of catalysing the esterification and transesterification reactions
Data Source
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AI summary
This invention relates to a process for obtaining highly pure aliphatic dialkyl esters of saturated dicarboxylic acids from vegetable oils, which can advantageously be used in polymerisation. The process comprises the steps of reacting with an aliphatic alcohol a triglycerides mixture containing at least one triglyceride of at least one saturated dicarboxylic acid in the presence of one or more catalysts capable of catalysing the esterification and transesterification reactions, and separating the dialkyl esters of saturated dicarboxylic acids from the reaction mixture thus obtained.