Acylamino Acid Stock Solution Preparation via High-Boiling Solvent Extraction

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Solution Overview

Problem

Acylamino acids and their derivatives are difficult to purify and isolate from reaction mixtures due to their intractable solid form, which hinders their industrialization and incorporation into edible products effectively.

Innovation Solution

A method involving the addition of an extraction solvent with a higher boiling point to the reaction mixture before solvent removal, allowing for the recovery of acylamino acids in a stock solution form, particularly using propylene glycol to facilitate concentration and purification, and further processing into powder form without affecting the physical properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional solvent removal by evaporation is used, then the reaction solvent can be removed, but the acylamino acids form an intractable solid mass that is difficult to purify and isolate

Engineering Contradiction:
Improvepurification and isolationVSAvoidisolation efficiency
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent changes the physical state parameter of the acylamino acids from solid to liquid by dissolving them in a suitable solvent to form a stock solution. This parameter change enables easy purification and isolation, as the liquid solution can be conveniently handled, concentrated, and stored without forming intractable solid masses, thereby resolving the contradiction between ease of manufacture and productivity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a solvent as an intermediary medium to facilitate the purification and isolation process. The solvent acts as a mediator that dissolves the acylamino acids, allowing them to be separated from reaction mixtures and other components. This intermediary approach enables efficient isolation while maintaining high productivity, as the solvent-based system allows for straightforward concentration and storage operations.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If the compounds are recovered as solid mass, then they can be isolated from reaction mixture, but they form an intractable solid form that hinders industrialization

Engineering Contradiction:
Improveisolation efficiencyVSAvoidindustrialization
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the physical state from solid to liquid by forming a stock solution, which fundamentally improves ease of manufacture for industrial applications. The liquid form enables scalable processing, convenient storage, and flexible formulation into various edible products, removing the hindrance that intractable solid forms pose to industrialization while maintaining high isolation efficiency.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent transitions from a static solid form to a dynamic liquid solution that can be easily manipulated, concentrated, and stored. This dynamic approach facilitates industrialization by allowing flexible processing methods, efficient scaling, and adaptable formulation, thereby improving both productivity and ease of manufacture simultaneously.

Inventive Principle:
Principle #15Dynamics

3Ease of operation

If a stock solution is formed in an extraction solvent, then the compounds can be easily formulated into edible products, but the solvent selection becomes complex due to multiple constraints

Engineering Contradiction:
Improveformulation into edible productsVSAvoidsolvent selection process
Core Design Contradiction:
Ease of operationVSDevice complexity

Solution Approach 1:

The patent identifies a universal solvent class (water-miscible organic solvents) that satisfies multiple constraints simultaneously: appropriate boiling point for separation, solvating properties for dissolution, and compatibility with food applications. This universal solvent category simplifies the selection process while enabling easy formulation into diverse edible products, resolving the contradiction between ease of operation and device complexity.

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

Solution Approach 2:

The patent establishes specific parameter ranges for solvent selection (boiling point higher than reaction solvent, water-miscible organic solvent) that transform a complex multi-constraint problem into a systematic parameter-based selection process. This parameterization simplifies solvent choice while maintaining ease of operation for formulation, as the constrained parameter space points to suitable solvents like propylene glycol and glycerol.

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

Enables efficient isolation and formulation of acylamino acids into stock solutions and powders suitable for industrial use, maintaining their taste-modifying properties and ease of incorporation into various food and beverage products.

Implementation Method 1

an extraction solvent for the compound, having a higher boiling point than the reaction solvent, is added to the reaction mixture, and wherein after separation of the compound from the reaction solvent, the compound of formula (I) is recovered in the form of a stock solution in said extraction solvent

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

prior to removal of the reaction solvent by evaporation

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentUS10975018B2Organic compounds
Publication Date: 2021.04.13 GIVAUDAN SA
  • US10975018B2 patent drawing
  • US10975018B2 patent drawing
  • US10975018B2 patent drawing

AI summary

A stock solution comprising a compound of formula (I)WhereinR1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR2R3, in which R3 is H or together with R2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.