Hydroxycarboxylic Acid Esters with Pulsed Microwave Chain Control

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Solution Overview

Problem

Existing methods for producing polymeric hydroxycarboxylic acid esters, such as citric acid esters, face challenges with uncontrolled chain length formation, decomposition, and the production of uncontrolled byproducts due to conventional heating methods, leading to high viscosity and unsuitability as complexing agents.

Innovation Solution

A pulsed temperature method, utilizing microwave radiation, is employed to control the esterification reaction of aliphatic hydroxycarboxylic acids with alkylene glycols, resulting in low-molecular-weight compounds with defined chain lengths, preventing decomposition and polymerization.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional heating methods are used for esterification reaction, then the reaction can proceed, but uncontrolled chain length formation and decomposition occur

Engineering Contradiction:
Improvechain length controlVSAvoidreaction control
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent applies periodic microwave irradiation in pulsed mode rather than continuous heating. The reaction mixture is irradiated in periodic pulses with controlled duration and intensity, allowing the esterification reaction to proceed while preventing excessive temperature buildup and decomposition. This periodic action enables precise control over chain length formation and prevents uncontrolled side reactions.

Inventive Principle:
Principle #19Periodic action

Solution Approach 2:

The patent changes the heating parameters from conventional continuous heating to pulsed microwave irradiation. By controlling the pulse duration, intensity, and frequency of microwave irradiation, the reaction temperature and energy input are precisely regulated. This parameter change enables controlled esterification with defined chain lengths while preventing decomposition and uncontrolled polymerization.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If heating is applied to promote esterification, then reaction yield improves, but viscosity increases and free-flowing property is lost

Engineering Contradiction:
Improvereaction yieldVSAvoidviscosity control
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent uses periodic pulsed microwave irradiation to promote esterification reaction without causing excessive temperature rise. The pulsed nature of the heating allows the reaction to proceed efficiently while giving the system time to cool between pulses, preventing runaway reactions and excessive viscosity buildup. This maintains the free-flowing property of the product while achieving high reaction yield.

Inventive Principle:
Principle #19Periodic action

Solution Approach 2:

The patent applies intense microwave irradiation in short pulses to rapidly drive the esterification reaction to completion. By concentrating the energy input into brief, intense pulses rather than prolonged heating, the reaction achieves high yield quickly without allowing viscosity to increase excessively. The reaction is rushed through the critical temperature range before viscosity problems can develop.

Inventive Principle:
Principle #21Skipping (Rushing through)

3Speed

If high temperature is used for esterification, then reaction speed increases, but decomposition and byproduct formation occur

Engineering Contradiction:
Improvereaction speedVSAvoiddecomposition
Core Design Contradiction:
SpeedVSObject-generated harmful factors

Solution Approach 1:

The patent employs periodic pulsed microwave irradiation to achieve high reaction speed without sustained high temperature. The brief pulse duration limits the time at which decomposition can occur, while the high intensity during the pulse provides sufficient energy for rapid esterification. The periodic cooling between pulses prevents thermal accumulation that would lead to decomposition and byproduct formation.

Inventive Principle:
Principle #19Periodic action

Solution Approach 2:

The patent uses intense pulsed microwave energy to rush the esterification reaction through the critical high-temperature phase quickly. By concentrating the energy input into short, intense pulses, the reaction achieves high speed before the temperature can cause decomposition. The brief exposure time to high temperature minimizes harmful decomposition reactions while maintaining rapid productivity.

Inventive Principle:
Principle #21Skipping (Rushing through)

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 produces low-viscosity, free-flowing compounds that effectively complex with metal ions, particularly alkaline earth metals, suitable for use in detergents and cleaning agents.

Implementation Method 1

A pulsed temperature method, utilizing microwave radiation, is employed to control the esterification reaction

Methodology Applied
Scientific EffectMicrowave radiation: Microwave Radiation

Implementation Method 2

The esterification reaction is carried out by heating the starting components

Methodology Applied
Scientific EffectDielectric heating: Dielectric Heating

Data Source

PatentEP3786150B1Detergents and cleaning agents containing hydroxycarboxylic acid esters and use of hydroxycarboxylic acid esters
Publication Date: 2025.07.30 WEYLCHEM PERFORMANCE PRODUCTS GMBH
  • EP3786150B1 patent drawing
  • EP3786150B1 patent drawing
  • EP3786150B1 patent drawing

AI summary

Hydroxycarboxylic acid esters, processes for their preparation and their use. Compounds of formula (I) (R1OOC)aR 2(OH)c-COO-(CnH2n-O)m-OC-R3(OH)d-(COOR4)b are described, wherein R1 and R4 independently represent hydrogen, a cation of a metal, an ammonium cation, C1-C6 alkyl, cycloalkyl with three to nine ring carbon atoms, aryl with five to ten ring carbon atoms, aryl substituted with one or two alkyl groups, aryl linked to the carboxyl group via an alkylene group, -(CnH2n-O)mH or -O-R2(COOR1)a+1, R2 and R3 independently represent aliphatic hydrocarbon residues with one to four carbon atoms, a and b independently represent integers from 1 to 4, and c represents an integer from 0 to 4 is, d is an integer from 1 to 4, n means 2, 3 or 4, and m is 1, 2, 3 or 4, with the proviso that R1 and R4 within a molecule may be different within the given definitions.These compounds are characterized by a very good complexing capacity for metal cations and can be used in detergents and cleaning agents, in petroleum production and for water softening.