Flow Reaction Deodorization for Aldehyde Production

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Solution Overview

Problem

Current methods for producing aldehyde or ketone compounds through oxidation reactions, such as Swern and Corey-Kim oxidations, generate malodorous by-products like dimethyl sulfide, which are difficult to remove efficiently and cost-effectively, limiting their industrial application due to environmental and health concerns.

Innovation Solution

A method involving a flow reaction in a flow passage for deodorization, using a sulfur-atom-containing organic compound like dialkyl sulfoxide and acid anhydride or halide, with an oxidizing agent like hypochlorous acid, to oxidize malodorous materials generated during the reaction, effectively removing them while producing the desired aldehyde or ketone compounds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If conventional deodorization methods (cleaning, adsorption, combustion) are used to remove malodorous materials, then the malodorous materials can be removed, but the manufacturing equipment must be enlarged, costs increase, and environmental burden increases

Engineering Contradiction:
Improvemalodorous material removalVSAvoidequipment size and cost
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent combines the oxidation reaction and deodorization steps into a single integrated process. The oxidizing agent serves dual purposes: it oxidizes the alcohol compound to produce the aldehyde/ketone product while simultaneously oxidizing the malodorous sulfide by-products to non-malodorous sulfone/sulfonate compounds. This eliminates the need for separate deodorization equipment and reduces overall system complexity.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent converts the harmful malodorous sulfide by-products into beneficial non-malodorous sulfone or sulfonate compounds through oxidation. The same oxidizing agent that performs the useful oxidation of alcohol also eliminates the harmful odor, transforming a waste removal problem into a value-added function of the main reaction.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

2Object-affected harmful factors

If multiple deodorization methods are combined to remove malodorous materials, then removal efficiency improves, but manufacturing costs and environmental burden increase

Engineering Contradiction:
Improvemalodorous material removal efficiencyVSAvoidprocessing cost
Core Design Contradiction:
Object-affected harmful factorsVSQuantity of substance

Solution Approach 1:

The oxidizing agent performs multiple functions simultaneously: (1) oxidizing the alcohol substrate to produce the desired aldehyde or ketone product, (2) oxidizing the malodorous sulfide by-products to eliminate odor, and (3) serving as the sole reagent for both synthesis and deodorization. This multi-functionality eliminates the need for multiple separate treatment methods and reduces overall processing costs.

Inventive Principle:
Principle #6Universality (Multi-functionality)

3Object-affected harmful factors

If a closed system is implemented to prevent malodorous material diffusion, then odor control improves, but equipment cost increases

Engineering Contradiction:
Improveodor diffusion preventionVSAvoidequipment cost
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent applies preliminary action by adding the oxidizing agent at the beginning of the reaction process, so that malodorous sulfide by-products are oxidized to non-malodorous compounds as they are formed during the reaction. This proactive approach prevents odor generation rather than requiring closed systems to contain and control odor after it is produced.

Inventive Principle:
Principle #10Preliminary action

4Productivity

If Swern or Corey-Kim oxidation is used for aldehyde or ketone production, then synthesis effectiveness improves, but malodorous by-products are generated that are difficult and costly to remove

Engineering Contradiction:
Improveoxidation reaction efficiencyVSAvoidmalodorous by-product generation
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the reaction system by selecting a specific oxidizing agent (such as sodium hypochlorite, calcium hypochlorite, or peracetic acid) that produces different by-products compared to traditional Swern or Corey-Kim oxidations. This parameter change transforms the malodorous sulfide by-products into non-malodorous sulfone or sulfonate compounds, maintaining high oxidation efficiency while eliminating the odor problem.

Inventive Principle:
Principle #35Parameter changes

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 approach allows for the easy and inexpensive removal of malodorous materials, reducing environmental burden and maintaining the integrity of the aldehyde or ketone compounds, making the process more viable for industrial use.

Implementation Method 1

a deodorization step using a flow reaction in a flow passage, wherein a malodorous material generated or remaining in a reaction step is removed from a reaction liquid... the reaction step is an oxidation reaction... the deodorization step is an oxidation reaction of the malodorous material

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP3357898B1Method for producing organic compound
Publication Date: 2020.11.25 FUJIFILM WAKO PURE CHEMICAL CORP
  • EP3357898B1 patent drawingFigure 1
  • EP3357898B1 patent drawingFigure 2
  • EP3357898B1 patent drawing

AI summary

Provided is a method for producing an organic compound, wherein the organic compound is an industrially useful compound, and a deodorization step, for removing from a reaction solution odorants that are generated in or remaining after a reac - tion process, is performed by using flow reaction within a flow channel.