High-Pressure Isosorbide Dehydration Using Organic Sulfonic Acid Catalysts

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Solution Overview

Problem

Current methods for producing isosorbide under high-pressure conditions using sulfuric acid catalysts result in low yields and high operating costs due to side reactions and equipment corrosion, while vacuum reactions offer higher yields but are energy-intensive and costly.

Innovation Solution

A method involving dehydration of sugar alcohol at high pressure (10-50 bar) using a catalyst with a boiling point of 160°C or higher, acidity between -3.0 and 3.0, and reacting in a homogeneous phase to suppress side reactions and increase isosorbide yield.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If sulfuric acid catalyst is used in high-pressure reaction, then reaction can proceed at high temperature, but side reactions increase and yield decreases

Engineering Contradiction:
Improvereaction temperatureVSAvoidisosorbide yield
Core Design Contradiction:
TemperatureVSProductivity

Solution Approach 1:

The patent changes the chemical parameter of the catalyst from sulfuric acid (strong acid) to organic sulfonic acid catalysts with controlled acidity (pKa between 0 and 3). This parameter change allows the reaction to proceed at high temperatures (150-350°C) while suppressing side reactions that occur with stronger acids, thereby maintaining high isosorbide yield.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses organic sulfonic acid catalysts that are less acidic and can be used in high-pressure reactions without causing severe corrosion. These catalysts enable high-temperature operation with acceptable stability, allowing the process to achieve high yields without requiring expensive corrosion-resistant equipment for extended periods.

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

2Productivity

If sulfuric acid catalyst is used, then dehydration reaction is effective, but equipment corrosion increases

Engineering Contradiction:
Improvedehydration efficiencyVSAvoidequipment corrosion
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the acidity parameter of the catalyst from sulfuric acid (pKa ≈ -3) to organic sulfonic acids with pKa between 0 and 3. This reduction in acidity maintains sufficient catalytic activity for dehydration while significantly reducing the corrosiveness to reaction equipment, eliminating the need for expensive corrosion-resistant reactors.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If vacuum reaction is used, then isosorbide yield is high, but energy consumption increases

Engineering Contradiction:
Improveisosorbide yieldVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

Instead of using vacuum conditions to remove water and drive the dehydration reaction forward, the patent inverts the approach by using high pressure (1-20 MPa) combined with a carefully selected organic sulfonic acid catalyst. This catalyst enables the reaction to proceed efficiently under high pressure without requiring vacuum conditions, thereby eliminating the high energy consumption associated with maintaining vacuum while still achieving high isosorbide yields.

Inventive Principle:
Principle #13The other way round (Inversion)

4Speed

If high-pressure reaction with sulfuric acid is used, then reaction rate increases, but operating cost increases

Engineering Contradiction:
Improvereaction rateVSAvoidoperating cost
Core Design Contradiction:
SpeedVSLoss of energy

Solution Approach 1:

The patent changes the catalyst from sulfuric acid to organic sulfonic acids with controlled pKa values (0-3). These catalysts maintain high reaction rates under high-pressure conditions while being less corrosive and requiring less expensive equipment. The reduced equipment cost and lower energy requirements for pressure maintenance result in lower operating costs despite maintaining high reaction rates.

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

The method achieves isosorbide yields comparable to vacuum reactions while reducing energy consumption and equipment costs by using a less acidic catalyst that maintains activity and prevents by-product formation, thereby enhancing process efficiency and cost-effectiveness.

Implementation Method 1

dehydrating sugar alcohol at high pressure (10-50 bar) in the presence of a catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

dehydration of sugar alcohol at high pressure (10-50 bar) using a catalyst with a boiling point of 160°C or higher, acidity between -3.0 and 3.0

Methodology Applied
Scientific EffectDehydration reaction: Chemical Bonding

Data Source

PatentUS10752638B2Method for producing anhydrosugar alcohol by high-pressure reaction
Publication Date: 2020.08.25 SK INNOVATION CO LTD

AI summary

The present invention relates to a method of producing anhydrosugar alcohol by dehydrating sugar alcohol at high pressure in the presence of a catalyst which is less acidic than a conventional sulfuric acid catalyst and which can suppress side reactions at high temperature. According to the present invention, anhydrosugar alcohol can be produced in a yield similar to that in a vacuum reaction.