Isosorbide Composition Stabilization with Amine Agents

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Solution Overview

Problem

The storage stability of isosorbide compositions is not effectively improved by existing methods, despite purification efforts, and the use of agents like nitrogen gas or sodium borohydride during distillation does not significantly enhance stability.

Innovation Solution

The use of monoethanolamine, diethanolamine, or triethanolamine as stabilizing agents, introduced after the distillation and purification steps, to improve the storage stability of isosorbide compositions by maintaining pH stability over time.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If purification treatments are applied to isosorbide compositions, then purity is improved, but storage stability is not effectively improved

Engineering Contradiction:
ImprovepurityVSAvoidstorage stability
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent applies preliminary action by adding the stabilizing agent (monoethanolamine, diethanolamine, or triethanolamine) after distillation and purification steps, before storage. This preliminary stabilization prevents degradation during storage without interfering with the purification process, thereby achieving both high purity and improved storage stability.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses an intermediary substance (amine stabilizing agent) that mediates between the purified isosorbide and storage conditions. The amine acts as a buffer and stabilizer, protecting the purified product from degradation during storage while maintaining the purity achieved through distillation and purification steps.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Object-affected harmful factors

If agents like nitrogen gas or sodium borohydride are used during distillation, then oxidation is prevented, but storage stability is not significantly enhanced

Engineering Contradiction:
Improveoxidation preventionVSAvoidstorage stability
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent maintains the inert atmosphere principle during distillation using nitrogen gas, but extends protection by adding chemical stabilizers (amines) that provide ongoing protection during storage. The amine stabilizers continue to prevent oxidation and degradation even when the inert atmosphere is no longer present, significantly enhancing long-term storage stability.

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

Solution Approach 2:

The patent replaces expensive and complex continuous inert atmosphere protection with a simple, inexpensive amine stabilizer that provides long-lasting protection. The amine acts as a disposable protective agent that remains in the product, eliminating the need for continuous external protection during storage.

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

3Productivity

If dehydration reaction is performed on hydrogenated sugars, then isosorbide is produced, but co-products and impurities are generated

Engineering Contradiction:
Improveisosorbide productionVSAvoidpurity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies extraction principles by using distillation to separate isosorbide from co-products and impurities generated during dehydration. The stabilizing agent is then added to the purified distillate, ensuring that the final product has both high purity and improved storage stability without requiring removal of all impurities from the original reaction mixture.

Inventive Principle:
Principle #2Taking out (Extraction)

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 compositions exhibit enhanced stability, with pH remaining consistent for at least 1 month to 1 year at 50°C, significantly extending storage duration and maintaining high purity levels.

Implementation Method 1

The use of monoethanolamine, diethanolamine, or triethanolamine as stabilizing agents, introduced after the distillation and purification steps, to improve the storage stability of isosorbide compositions by maintaining pH stability over time

Methodology Applied
Scientific EffectpH buffering:

Implementation Method 2

a) a step of distilling a medium containing said internal dehydration product with a view to obtaining a distillate enriched in this product

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP2991991B1Method for stabilizing of a composition comprising at least a dehydrating product of a hydrogenated sugar, composition produced according to the method, and use thereof
Publication Date: 2018.09.26 ROQUETTE FRERES SA
  • EP2991991B1 patent drawing

AI summary

The present invention relates to a method for improving the stability of compositions of a product for internal dehydration of a hydrogenated sugar, in particular an isosorbide composition, said method involving the use of monoethanolamine, diethanolamine, triethanolamine and the mixtures thereof as a stabilisation agent. The invention also relates to the resulting compositions and to the various uses thereof.