Retinal Dehydrogenation via Single-Step Oxidative Double Bond Introduction

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Solution Overview

Problem

Current methods for producing retinal are inefficient and require multiple steps to introduce double bonds, which can be costly and time-consuming under harsh conditions.

Innovation Solution

A new process using the compound of formula (I) with oxidative reactants like formula (IIIc) and additives in mild conditions introduces two double bonds in retinal (II) in a single step, employing solvents like benzene or toluene at moderate temperatures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If current methods are used to produce retinal, then multiple steps are required to introduce double bonds, but the process becomes costly and time-consuming under harsh conditions

Engineering Contradiction:
Improveproduction efficiencyVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent combines two separate dehydrogenation steps into a single reaction step by using a catalyst system that can simultaneously introduce both double bonds. This merging of operations reduces the overall process complexity and improves productivity by eliminating intermediate steps and harsh conditions that would otherwise be required.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention changes the reaction parameters by using a specific catalyst system and mild reaction conditions that enable simultaneous double bond formation. This parameter change allows the reaction to proceed under less harsh conditions while maintaining high efficiency, resolving the contradiction between productivity and process complexity.

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If multiple steps are used to introduce double bonds, then each step can be controlled separately, but the overall process time and cost increase

Engineering Contradiction:
Improvereaction controlVSAvoidprocess time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

By merging multiple dehydrogenation steps into one simultaneous reaction, the patent reduces total process time while maintaining manufacturing precision through the use of a carefully designed catalyst system that controls the reaction pathway and ensures proper double bond formation.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The catalyst system is pre-designed and prepared in advance to perform multiple dehydrogenation functions simultaneously. This preliminary preparation of the catalyst enables the reaction to proceed efficiently in a single step without requiring sequential control of multiple separate reactions.

Inventive Principle:
Principle #10Preliminary action

3Productivity

If harsh conditions are applied to introduce double bonds, then the reaction can proceed, but the process becomes less efficient and more costly

Engineering Contradiction:
Improvereaction efficiencyVSAvoidreaction conditions
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent changes the reaction parameters by introducing a catalyst system that enables the dehydrogenation reaction to proceed under mild temperature and pressure conditions. This parameter change improves productivity by allowing the reaction to occur efficiently without requiring harsh conditions that would increase costs and reduce overall process efficiency.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention replaces the need for harsh mechanical or thermal conditions with a chemical catalyst system that facilitates the reaction under milder conditions. This substitution maintains high reaction efficiency while avoiding the need for extreme temperatures and pressures.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 simplifies the production of retinal by integrating two double bonds in one step under mild conditions, enhancing efficiency and reducing the complexity of existing methods.

Implementation Method 1

dehydrogenation (DH) of the compound of formula (I) to the compound of formula (II) in the presence of at least one oxidative reactant of formula (III)

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS12258311B2Dehydrogenation process
Publication Date: 2025.03.25 DSM IP ASSETS BV
  • US12258311B2 patent drawing
  • US12258311B2 patent drawing
  • US12258311B2 patent drawing

AI summary

The present invention relates to a new compound and the dehydrogenation of that compound to produce retinal.