Esterification Process Using Excess Carboxylic Acid

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Solution Overview

Problem

Current processes for producing carboxylic acid esters, such as ethyl acetate, are inefficient in terms of productivity and energy consumption, and fail to meet the required low acetic acid content for various applications.

Innovation Solution

A process involving a high molar ratio of carboxylic acid to alcohol (at least 16:1) with an acid catalyst, preferably using a protonic acid catalyst like methanesulfonic acid, and a distillation operation to separate and recycle reactants, optimizing energy costs and product purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional molar ratios of carboxylic acid to alcohol are used (1-5), then the process is simpler to operate, but the productivity and energy efficiency are insufficient

Engineering Contradiction:
ImproveproductivityVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by significantly increasing the molar ratio of carboxylic acid to alcohol from conventional values (1-5) to at least 16:1. This parameter modification fundamentally alters the reaction dynamics, enabling higher productivity and better energy efficiency while maintaining operational simplicity through automated feed control

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If conventional molar ratios are used, then the process requires less acid catalyst, but the acetic acid content in the product exceeds the required <0.01% purity level

Engineering Contradiction:
Improveproduct purityVSAvoidacetic acid content
Core Design Contradiction:
Manufacturing precisionVSQuantity of substance

Solution Approach 1:

The patent uses parameter changes by adjusting the molar ratio of carboxylic acid to alcohol to at least 16:1, which fundamentally improves product purity by reducing acetic acid content to below 0.01%. This parameter modification ensures the ester product meets stringent purity requirements for cosmetic and pharmaceutical applications

Inventive Principle:
Principle #35Parameter changes

3Use of energy by moving object

If high molar ratio of carboxylic acid to alcohol (at least 16:1) is used, then energy consumption is reduced and productivity is improved, but the process requires precise control of reactant feeding ratios

Engineering Contradiction:
Improveenergy consumptionVSAvoidoperational simplicity
Core Design Contradiction:
Use of energy by moving objectVSEase of operation

Solution Approach 1:

The patent applies feedback control through automated feed systems that continuously monitor and adjust the molar ratio of carboxylic acid to alcohol input. This feedback mechanism maintains the optimal ratio of at least 16:1 throughout the reaction process, reducing energy consumption while ensuring operational simplicity through automation

Inventive Principle:
Principle #23Feedback

Solution Approach 2:

The patent uses parameter changes by establishing a high molar ratio of at least 16:1 as the operating condition. This parameter modification reduces energy consumption by minimizing excess reactant handling and improving reaction efficiency, while the ratio is maintained through controlled feed rates

Inventive Principle:
Principle #35Parameter changes

4Productivity

If high molar ratio of carboxylic acid to alcohol is used, then the transformation of alcohol to ester is more complete, but the process requires careful management of water separation

Engineering Contradiction:
Improvetransformation efficiencyVSAvoidwater separation requirement
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies discarding and recovering by implementing water separation systems that remove water produced during the esterification reaction. The high molar ratio of at least 16:1 ensures complete alcohol transformation, and the water separation step recovers and manages the water byproduct, maintaining high transformation efficiency while controlling process complexity

Inventive Principle:
Principle #34Discarding and recovering

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

This process significantly reduces energy consumption and achieves high purity of carboxylic acid esters by almost complete transformation of alcohol into ester, meeting stringent acetic acid content requirements.

Implementation Method 1

reaction between a carboxylic acid and an alcohol, in particular in the presence of an acid catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

the liquid reaction mixture previously obtained is then subjected to a distillation operation in order to obtain: a vapor stream comprising mainly the ester of the carboxylic acid

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP2531483B1Method for preparing a carboxylic acid ester
Publication Date: 2015.10.07 RHODIA POLIAMIDA E ESPECIALIDADES LTDA
  • EP2531483B1 patent drawingFigure 1

AI summary

The present invention relates to a method for manufacturing a carboxylic acid ester. The present invention relates to a method for manufacturing a carboxylic acid ester by reacting a carboxylic acid and an alcohol, characterised in that the reaction is performed in the presence of an excess of carboxylic acid.