Nitrogen Monoxide Cis/Trans Isomerization Catalyst
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Solution Overview
Problem
There is a need for an efficient process to isomerize unsaturated compounds such as ketones, ketals, aldehydes, acetals, carboxylic acids, esters, amides, and alcohols, which have isolated carbon-carbon double bonds, as existing methods are ineffective in converting undesired isomers to desired forms, especially in mixtures.
Innovation Solution
The process involves adding nitrogen monoxide to the unsaturated compounds and heating them to a temperature between 10°C and their boiling point, leading to a mixture of cis/trans isomers, with nitrogen monoxide acting as a catalyst to efficiently convert the undesired isomers into the desired form.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional isomerization methods are used on unsaturated compounds with isolated double bonds, then the process works for polyconjugated compounds, but the isomerization efficiency is poor and conversion is incomplete
Solution Approach 1:
The patent changes the chemical parameter of the catalyst system by introducing nitrogen monoxide (NO) as a novel catalyst for isomerization. This parameter change enables complete conversion of unsaturated compounds with isolated double bonds, resolving the contradiction between isomerization efficiency and conversion completeness that plagues conventional methods.
2Manufacturing precision
If nitrogen monoxide is used as catalyst, then essentially all undesired isomers are transformed into desired isomers, but the process requires heating to temperatures between 10°C and boiling point
Solution Approach 1:
The patent utilizes temperature as a controllable parameter within the range of 10°C to boiling point to activate the nitrogen monoxide catalysis. By optimizing this temperature parameter, the process achieves high isomer purity through complete conversion while maintaining operationally simple heating conditions.
3Adaptability or versatility
If existing isomerization processes are applied, then they can handle polyconjugated compounds, but they are ineffective for compounds with isolated double bonds such as unsaturated ketones, aldehydes, and carboxylic acids
Solution Approach 1:
The patent establishes nitrogen monoxide as a universal catalyst that functions across diverse substrate types including unsaturated ketones, ketals, aldehydes, acetals, carboxylic acids, esters, amides, and alcohols with isolated double bonds. This universal applicability resolves the contradiction between broad substrate scope and effective isomerization rate.
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 method effectively transforms essentially all undesired isomers into the desired isomer, both in pure and mixed forms, achieving a high yield and purity of the desired isomer, particularly useful for compounds like citral and geranial, where the trans isomer has distinct properties.
Implementation Method 1
nitrogen monoxide acting as a catalyst to efficiently convert the undesired isomers into the desired form
Implementation Method 2
heating the mixture of nitrogen monoxide and cis or trans isomer of the unsaturated compound A to a temperature of between 10° C. and the boiling point of the unsaturated compound A
Data Source
AI summary
The present invention relates to a process of a cis/trans isomerization of an unsaturated compound A being selected from the group consisting of unsaturated ketones, unsaturated ketals, unsaturated aldehydes, unsaturated acetals, unsaturated carboxylic acids, esters of an unsaturated carboxylic acid and amides of an unsaturated carboxylic acid using nitrogen monoxide as cis/trans isomerization catalyst. It has been observed that the isomerization is very efficient and fast.