Dihydroxyindole Extraction via Segmented Solvent Displacement

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Solution Overview

Problem

Existing methods for producing dihydroxyindoles are limited by the insolubility of melanin in water and organic solvents, making it difficult to use as a dye or in other applications, and there is a challenge in reducing cyanide content during the production process.

Innovation Solution

A method involving a three-step process: reacting 3-(3,4-dihydroxyphenyl)alanine with hexacyanoferrate(III) to produce dihydroxyindoles, extracting them with an organic solvent having an octanol/water distribution coefficient between 0 and 4.0, and then evaporating the solvent to obtain a water-soluble dihydroxyindole solution, with the extraction and solvent displacement processes conducted in separate tanks to minimize cyanide contamination.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If hexacyanoferrate(III) is used to oxidize 3-(3,4-dihydroxyphenyl)alanine to produce dihydroxyindoles, then the yield of dihydroxyindoles is improved, but cyanide content in the solution increases

Engineering Contradiction:
Improveyield of dihydroxyindolesVSAvoidcyanide content
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent extracts dihydroxyindoles from the aqueous reaction solution containing cyanide by adding an organic solvent. The dihydroxyindoles are transferred to the organic phase, separating them from the cyanide-containing aqueous phase, thereby reducing cyanide content in the final product while maintaining high yield

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent divides the solution into two separate phases (aqueous and organic) through solvent extraction. This segmentation allows the dihydroxyindoles to be isolated in the organic phase while cyanide remains in the aqueous phase, enabling simultaneous achievement of high yield and low cyanide content

Inventive Principle:
Principle #1Segmentation

2Stability of the object's composition

If melanin is used as a dye without treatment, then the natural pigment properties are preserved, but insolubility in water and organic solvents prevents dyeing applications

Engineering Contradiction:
Improvenatural pigment propertiesVSAvoidsolubility for dyeing
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent changes the solubility parameter of dihydroxyindoles by extracting them into an organic solvent phase. This parameter change enables the compounds to be dissolved and applied in dyeing processes while maintaining their natural pigment properties and stability

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 method enhances the yield of dihydroxyindoles while reducing cyanide content, making them more suitable for applications such as hair dyeing and ensuring safety by minimizing cyanide residues.

Implementation Method 1

3-(3,4-dihydroxyphenyl)alanine (DOPA) as a substrate compound is oxidized by catalysis of tyrosinase as a melanogenesis enzyme to generate a dihydroxyindoles

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

causing at least a material selected from the group consisting of 3-(3,4-dihydroxyphenyl)alanine and a derivative of 3-(3,4-dihydroxyphenyl)alanine to react with hexacyanoferrate(III)

Methodology Applied
Scientific EffectRedox Reactions: Redox Reactions

Implementation Method 3

an oleaginous second solution in which the dihydroxyindoles are extracted in an extraction solvent by mixing the first solution obtained in the step 1 with the extraction solvent

Methodology Applied
Scientific EffectLiquid-Liquid Extraction: Liquid-Liquid Extraction

Implementation Method 4

a step 3 of obtaining an aqueous third solution by evaporating the extraction solvent from a mixture of the second solution obtained in the step 2 and water

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentEP3689852B1Method for producing dihydroxyindoles
Publication Date: 2024.05.29 KAO CORP
  • EP3689852B1 patent drawingFigure 1
  • EP3689852B1 patent drawingFigure 2A
  • EP3689852B1 patent drawingFigure 2B

AI summary

A method for producing dihydroxyindoles includes: a step 1 of obtaining an aqueous first solution including DHIs obtained by causing DOPAs to react with hexacyanoferrate(III); a step 2 of obtaining an oleaginous second solution in which DHIs are extracted in an extraction solvent by mixing the first solution obtained in the step 1 with the extraction solvent; and a step 3 of obtaining an aqueous third solution by evaporating the extraction solvent from a mixture of the second solution obtained in the step 2 and water. The extraction of DHIs in the step 2 is performed in a tank A. After the second solution is discharged from the tank A, the second solution is supplied to a tank B, and then the step 3 is performed in the tank B.