Iodinated Fatty Acid Ethyl Ester via Phosphoric Acid Protonation

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Solution Overview

Problem

Existing methods for preparing iodinated fatty acid ethyl esters are time-consuming due to slow reaction rates, making them inefficient for meeting the increasing demand for cost-effective radio-opaque contrast agents.

Innovation Solution

A process involving a protonation reaction of a fatty acid ester with phosphoric acid followed by an iodination reaction with an alkali metal iodide, enhancing the reaction rate and efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional iodination methods using hydrogen iodide gas or hydroiodic acid are used, then the reaction can proceed, but the reaction rate is slow and the process is time-consuming

Engineering Contradiction:
Improvereaction rateVSAvoidreaction time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent introduces phosphoric acid as an intermediary catalyst in the iodination reaction. The phosphoric acid facilitates the reaction between fatty acid ethyl ester and iodine by forming a more reactive intermediate complex, thereby significantly accelerating the reaction rate without being consumed in the process. This mediator enables the reaction to proceed much faster than conventional direct iodination methods.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction parameters by using phosphoric acid to modify the chemical environment and intermediate states. By altering the reaction mechanism through catalysis and forming reactive intermediates, the reaction proceeds through different kinetic pathways with lower activation energy, resulting in dramatically improved reaction rates and reduced reaction times.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If Lipiodol is used as a radio-opaque contrast agent, then diagnostic imaging can be performed, but the cost is relatively high

Engineering Contradiction:
Improvecontrast agent effectivenessVSAvoidproduction cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent replaces the expensive proprietary Lipiodol product with a cost-effective alternative synthesized from readily available edible oils. By using common agricultural products as raw materials and a simplified catalytic iodination process, the method produces a functional substitute that achieves the same radio-opaque contrast effect at significantly lower production cost, making the contrast agent more accessible and economically viable.

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

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

The process significantly increases the iodine content and reaction rate, producing iodinated fatty acid ethyl esters with properties similar to Lipiodol, addressing the inefficiencies of prior art methods.

Implementation Method 1

subjecting a fatty acid ester selected from the group consisting of a fatty acid ethyl ester and a triglyceride to a protonation reaction with phosphoric acid to form a protonated fatty acid ester

Methodology Applied
Scientific EffectProtonation:

Implementation Method 2

subjecting the protonated fatty acid ester to an iodination reaction with an alkali metal iodide to obtain an iodinated fatty acid ester

Methodology Applied
Scientific EffectIodination reaction:

Data Source

PatentEP3428256B1Process for preparing an iodinated fatty acid ethyl ester
Publication Date: 2021.09.01 FOOD IND RES & DEV INST
  • EP3428256B1 patent drawingFigure 1
  • EP3428256B1 patent drawingFigure 2
  • EP3428256B1 patent drawingFigure 3

AI summary

A process for preparing an iodinated fatty acid ethyl ester includes steps of subjecting a fatty acid ester to a protonation reaction with phosphoric acid to form a protonated fatty acid ester, and subjecting the protonated fatty acid ester to an iodination reaction with an alkali metal iodide to obtain an iodinated fatty acid ester.