Selective Catalytic Dehydroxylation of Aldaric Acids

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Solution Overview

Problem

Current methods for producing muconic acid and furan chemicals from aldaric acids are inefficient, requiring high temperatures, excessive use of fossil alcohols, and generating significant waste, while also being incompatible with the petroleum-based industry due to their oxygen-rich nature.

Innovation Solution

A selective catalytic dehydroxylation method using a transition metal catalyst, such as rhenium, with hydrogen as a reductant and adjusting reaction temperatures between 90°C to 300°C to produce muconic acids and furans from aldaric acids like galactaric acid, allowing for easy scalability and low energy consumption.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If high temperatures (155°C) are used for muconic acid production via DODH, then conversion efficiency is improved, but energy consumption increases

Engineering Contradiction:
Improveconversion efficiencyVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The invention changes the temperature parameter from conventional high temperatures (155°C) to mild temperatures (25-100°C), thereby reducing energy consumption while maintaining high conversion efficiency through the use of a novel catalyst system

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention replaces thermal energy input (mechanical heating) with catalytic action, where the catalyst system enables the reaction to proceed at low temperatures, substituting the need for high thermal energy with chemical catalysis

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

2Productivity

If fossil pentanol is used as reductant in DODH reaction, then muconic acid production is achieved, but environmental sustainability deteriorates due to use of finite resources

Engineering Contradiction:
Improvemuconic acid productionVSAvoidenvironmental sustainability
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the reductant from fossil-based pentanol to renewable alcohol feedstocks, altering the material input parameter to improve environmental sustainability while maintaining production efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses readily available, renewable alcohol feedstocks that can be sustainably replenished, replacing expensive and finite fossil resources with more sustainable alternatives

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Productivity

If 3-pentanol or 1-butanol are used as reductants in DODH, then muconic acid is produced, but material waste increases due to stoichiometric sacrifice (2-4 moles of alcohol per mole of product)

Engineering Contradiction:
Improvemuconic acid productionVSAvoidalcohol waste
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention employs a catalyst system that enables the reaction to proceed with minimal reductant consumption, where the catalyst continuously facilitates the conversion without being consumed, thereby reducing material waste

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The invention changes the stoichiometric ratio parameter by using a more efficient catalyst system that reduces the amount of reductant needed per mole of product, thereby minimizing material waste

Inventive Principle:
Principle #35Parameter changes

4Productivity

If strong mineral acids are used for dehydroxylation of aldaric acids to produce furans, then furan chemicals are produced, but reaction time increases significantly (up to 40 hours)

Engineering Contradiction:
Improvefuran chemical productionVSAvoidreaction time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The invention replaces strong mineral acids with an organic catalyst system, substituting harsh chemical conditions with milder catalytic action that achieves the same transformation much faster

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

Solution Approach 2:

The invention changes the chemical environment parameter from strongly acidic conditions to milder catalytic conditions, thereby reducing reaction time from 40 hours to a much shorter duration

Inventive Principle:
Principle #35Parameter changes

5Productivity

If conventional catalytic oxidation and hydrodeoxygenation are used to convert glucose to adipic acid, then adipic acid is produced, but process complexity increases due to multiple reaction steps

Engineering Contradiction:
Improveadipic acid productionVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention merges multiple reaction steps (oxidation and hydrodeoxygenation) into a single dehydroxylation step, combining what were previously separate processes into one unified reaction

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention uses a single catalyst system that performs multiple functions (oxidation and deoxygenation) in one reaction, making the process more versatile and less complex

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

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

The method achieves efficient production of industrially significant chemicals with low energy consumption and waste production, using renewable resources and enabling the conversion of non-edible carbohydrates into valuable intermediates for pharmaceutical and chemical synthesis.

Implementation Method 1

selective catalytic dehydroxylation

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

hydrogen as a reductant

Methodology Applied
Scientific EffectReduction: Reduction

Implementation Method 3

transfer-hydrogenation reaction

Methodology Applied
Scientific EffectRedox Reactions: Redox Reactions

Data Source

PatentEP3154927B1Method for producing muconic acids and furans from aldaric acids
Publication Date: 2020.11.25 TEKNOLOGIAN TUTKIMUSKESKUS VTT OY
  • EP3154927B1 patent drawingFigure 1
  • EP3154927B1 patent drawing
  • EP3154927B1 patent drawing

AI summary

The present invention relates to selective catalytic dehydroxylation method of aldaric acids for producing muconic acid and furan chemicals, which can be used directly in fine chemical and polymer applications (FCA/FDCA) and as intermediates in the preparation of industrially significant chemicals, such as terephthalic acid, adipic acid, caprolactone, caprolactam, nylon 6.6, 1,6-hexanediol and multiple pharmaceutical building blocks (MA/MAME).