Low-Odor Ether Carboxylate Production via Neutralization

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Solution Overview

Problem

Existing methods for producing ether carboxylates result in products with off-odors, making them unsuitable for direct application on human skin in cosmetics and toiletries, despite their stability in hard water and environmental benefits.

Innovation Solution

A process involving the reaction of C6 to C36 aliphatic monohydric alcohol with C2 to C4 alkylene oxide in the presence of an alkali catalyst, followed by neutralization with specific carboxylic acids and subsequent reaction with monohalogenofatty acids or their salts, or catalytic oxidation to produce a low-odor ether carboxylate.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If ether carboxylate is produced by reacting ether alcohol with monohalogenoacetic acid and alkali metal hydroxide, then the ether carboxylate achieves high stability in hard water, good detergency, and excellent environmental suitability, but the product develops an off-odor that makes it unsuitable for direct application on human skin

Engineering Contradiction:
Improvestability in hard waterVSAvoidoff-odor
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the reaction parameters by using a specific molar ratio of alkali metal hydroxide to monohalogenoacetic acid (1.05:1 to 1.2:1), controlling the reaction temperature (60-80°C), and adjusting the reaction time (2-6 hours) to optimize the ether carboxylate production process. These parameter changes reduce the off-odor while maintaining the stability in hard water, detergency, and environmental suitability of the product.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If ether carboxylate is produced by conventional methods, then the production process is simple and cost-effective, but the product quality is insufficient for cosmetic and toiletry applications due to off-odors

Engineering Contradiction:
Improveproduction process simplicityVSAvoidproduct quality
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The invention optimizes reaction parameters including temperature (60-80°C), time (2-6 hours), and molar ratios (ether alcohol:monohalogenoacetic acid:alkali metal hydroxide = 1:1.05-1.2:1.2-1.5) to simultaneously achieve simple manufacturing process and high product quality suitable for cosmetics and toiletries, eliminating the need for complex additional purification steps while reducing off-odors.

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 process effectively reduces odor in ether carboxylates, making them suitable for use in cosmetics and toiletries with improved foamability and detergency, while maintaining low skin irritation and environmental suitability.

Implementation Method 1

reacting a C6 to C36 aliphatic monohydric alcohol with a C2 to C4 alkylene oxide in the presence of an alkali catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

neutralizing a reaction solution obtained in the step (1) with at least one acid selected from the group consisting of C2 to C10 hydroxycarboxylic acids, C2 to C10 dicarboxylic acids and C2 to C10 tricarboxylic acids to obtain an ether alcohol

Methodology Applied
Scientific EffectNeutralization: Chemical Bonding

Implementation Method 3

reacting the ether alcohol obtained in the step (2) with a C2 to C4 monohalogenofatty acid or a salt thereof, and an alkali metal hydroxide

Methodology Applied
Scientific EffectNucleophilic substitution: Chemical Bonding

Implementation Method 4

subjecting the ether alcohol obtained in the step (2) to catalytic oxidation reaction with oxygen or an oxygen-containing gas in the presence of a catalyst

Methodology Applied
Scientific EffectCatalytic oxidation: Catalysis

Data Source

PatentUS8304575B2Process for production of ether carboxylates
Publication Date: 2012.11.06 KAO CORP

AI summary

The present invention relates to a process for producing an ether carboxylate which includes the steps of (1) reacting an aliphatic monohydric alcohol with an alkylene oxide in the presence of an alkali catalyst; (2) neutralizing a reaction solution obtained in the step (1) with an acid such as hydroxycarboxylic acids to obtain an ether alcohol; and (3-1) reacting the obtained ether alcohol with a monohalogenofatty acid or a salt thereof and an alkali metal hydroxide, or (3-2) subjecting the obtained ether alcohol to catalytic oxidation reaction in the presence of a catalyst. The obtained ether carboxylate has a less odor and a high quality and is therefore suitably used in the applications such as cosmetics and toiletries.