Oil-Based Esterquat Preparation With Low Triesterquat Formation

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Solution Overview

Problem

Existing methods for producing esterquats used in fabric softeners result in high levels of triesterquats, which are inactive, and require expensive fatty acids, complex processes, and low-molecular alcohol solvents that cause undesirable side reactions and increased costs.

Innovation Solution

A transesterification process involving the stepwise addition of fatty acid oils to hydroxy alkyl tertiary amines under atmospheric pressure, followed by quaternization without low-molecular alcohol solvents, to enhance selectivity towards mono- and diesterquats and reduce equipment and operating costs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If fatty acids are used as starting material, then the fabric softener material can be produced, but the production cost increases due to expensive fatty acids

Engineering Contradiction:
Improveproduction costVSAvoidstarting material availability
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The invention changes the starting material from pure fatty acids to fatty acid-containing oils, which are cheaper and more readily available. This parameter change in raw material selection reduces production cost while still enabling the transesterification reaction to produce the desired esterquat fabric softener material

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses cheaper fatty acid-containing oils (such as vegetable oils or animal fats) instead of expensive pure fatty acids. These oil-based starting materials are more economical and can be easily obtained, reducing the overall production cost while maintaining product effectiveness

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

2Productivity

If low-molecular alcohol solvents are used in quaternization reaction, then the reaction can proceed, but undesirable side reactions occur generating unpleasant odor

Engineering Contradiction:
Improvequaternization reaction efficiencyVSAvoidunpleasant odor from side reactions
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention extracts or removes the low-molecular alcohol solvent from the quaternization reaction system. By conducting the reaction without these solvents, the harmful side reactions that generate unpleasant odors are eliminated, while the quaternization reaction still proceeds effectively to produce the desired esterquat product

Inventive Principle:
Principle #2Taking out (Extraction)

3Manufacturing precision

If high vacuum conditions are applied during transesterification, then the reaction can be controlled, but the process complexity and operating costs increase

Engineering Contradiction:
Improvetransesterification reaction controlVSAvoidvacuum equipment requirements
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention enables the transesterification reaction to proceed effectively under atmospheric pressure without requiring high vacuum conditions. The reaction system is self-sufficient and can be controlled using simple equipment, eliminating the need for complex vacuum apparatus while still achieving the desired reaction outcomes and product quality

Inventive Principle:
Principle #25Self-service

4Reliability

If trialkanolamine reacts with fatty acids to produce fabric softener, then the softening effect is achieved, but the amount of inactive triesterquat increases reducing product efficiency

Engineering Contradiction:
Improvefabric softening effectVSAvoidactive compound concentration
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention segments the fatty acid starting material into a mixture of different chain lengths and structures within the fatty acid-containing oil. This segmentation approach, combined with controlled transesterification, produces a more favorable distribution of mono- and diesterquats (active compounds) while reducing triesterquat formation, thereby increasing the concentration of effective softening agents in the final product

Inventive Principle:
Principle #1Segmentation

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 increases the selectivity of mono- and diesterquats, reduces the formation of unwanted by-products, and lowers production costs by using fatty acid oils instead of expensive fatty acids, while eliminating the need for vacuum conditions and low-molecular alcohol solvents.

Implementation Method 1

a transesterification reaction of a hydroxy alkyl tertiary amine with a fatty acid oil or a mixture comprising one or more fatty acid oils and one or more fatty acids

Methodology Applied
Scientific EffectTransesterification reaction: Chemical Bonding

Implementation Method 2

followed by quaternization without low-molecular alcohol solvents

Methodology Applied
Scientific EffectQuaternization reaction: Chemical Bonding

Data Source

PatentUS11434193B2Preparation method for esterquats based on oil
Publication Date: 2022.09.06 EVONIK OPERATIONS GMBH
  • US11434193B2 patent drawing
  • US11434193B2 patent drawing
  • US11434193B2 patent drawing

AI summary

The present invention relates to a process for producing an esterquat by a transesterification reaction of a fatty acid oil or a mixture comprising one or more fatty acid oils and one or more fatty acids with a tertiary hydroxy amine and then a quaternization reaction. Esterquats obtained by the method of the invention show beneficial properties in particular when used as active component in fabric softener materials.