Adipic Acid Hydrogenation Route Using 3-Hydroxyadipic Acid Lactone

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Solution Overview

Problem

Conventional methods for producing adipic acid from biomass resources face challenges such as low yield, low solubility of intermediates, multi-step processes, and the use of toxic chemicals, which are environmentally unfavorable.

Innovation Solution

A method involving the hydrogenation of 3-hydroxyadipic acid-3,6-lactone with hydrogen in an aqueous solvent using a hydrogenation catalyst, preferably supported on a catalyst with acid catalytic activity, to produce adipic acid in a single step without toxic reagents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If adipic acid is produced by fermentation using sugar or fatty acid as raw material, then environmental friendliness is improved, but the yield of adipic acid is low

Engineering Contradiction:
Improvedinitrogen monoxide gas emissionVSAvoidyield of adipic acid
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The invention changes the chemical parameters of the reaction system by using 3-hydroxyadipic acid-3,6-lactone as a specific intermediate and conducting hydrogenation at controlled temperatures (100-350°C) and pressures with specific catalysts, achieving both environmental friendliness and high yield (90% or more based on theoretical value)

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces 3-hydroxyadipic acid-3,6-lactone as a key intermediary substance that bridges biomass resources and adipic acid production, enabling a reaction pathway that avoids dinitrogen monoxide emission while maintaining high productivity through its specific chemical properties

Inventive Principle:
Principle #24Intermediary (Mediator)

2Device complexity

If muconic acid is used as raw material for chemical hydrogenation, then the process is simplified, but the solubility of muconic acid in solvent is low making high-concentration reaction difficult

Engineering Contradiction:
Improvenumber of reaction stepsVSAvoidsolubility of muconic acid
Core Design Contradiction:
Device complexityVSQuantity of substance

Solution Approach 1:

The invention changes the physical parameter of solubility by selecting 3-hydroxyadipic acid-3,6-lactone as the raw material, which has high solubility in water and other solvents, enabling high-concentration reactions without compromising process simplicity

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If homocitric acid is used as raw material, then biomass utilization is improved, but the fermentation yield of homocitric acid is low and multi-step chemical reaction is necessary

Engineering Contradiction:
Improvebiomass utilizationVSAvoidfermentation yield of homocitric acid
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The invention extracts and utilizes the 3-hydroxyadipic acid-3,6-lactone intermediate from the fermentation process, bypassing the need to produce and process homocitric acid, thereby eliminating multi-step reactions and improving overall productivity while maintaining biomass utilization

Inventive Principle:
Principle #2Taking out (Extraction)

4Adaptability or versatility

If sugar is used as raw material for chemical synthesis, then renewable resource utilization is improved, but an equivalent amount of toxic hydrogen bromide must be used

Engineering Contradiction:
Improverenewable resource utilizationVSAvoidtoxic chemical usage
Core Design Contradiction:
Adaptability or versatilityVSObject-affected harmful factors

Solution Approach 1:

The invention converts the fermentation process into a beneficial pathway that produces 3-hydroxyadipic acid-3,6-lactone without requiring toxic chemicals, transforming what would be a complex multi-step chemical synthesis into an environmentally friendly process that maintains renewable resource utilization

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

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

Adipic acid is produced under industrially advantageous conditions with high yield and solubility, eliminating the need for toxic chemicals and reducing environmental impact.

Implementation Method 1

reacting 3-hydroxyadipic acid-3,6-lactone with hydrogen in an aqueous solvent in a presence of a hydrogenation catalyst

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

in the presence of a hydrogenation catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS12528757B2Method for producing adipic acid
Publication Date: 2026.01.20 TORAY INDUSTRIES INC
  • US12528757B2 patent drawing
  • US12528757B2 patent drawing

AI summary

The present invention relates to a method of producing adipic acid, including a step (hydrogenation step) of reacting 3-hydroxyadipic acid-3,6-lactone with hydrogen in an aqueous solvent in a presence of a hydrogenation catalyst. The hydrogenation catalyst preferably includes one kind or two or more kinds of transition metal elements selected from the group consisting of palladium, platinum, ruthenium, rhodium, rhenium, nickel, cobalt, iron, iridium, osmium, copper, and chromium.