Esterification Water Removal via Superheated Alcohol Vapor

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Solution Overview

Problem

Current methods for preparing carboxylic acid esters face challenges in efficiently removing water from the reaction mixture, particularly in the esterification of higher aliphatic carboxylic acids and aromatic carboxylic acids, which limits the conversion rate and results in a high acid number in the final product.

Innovation Solution

A process involving the use of superheated alcohol vapor in a reaction system with stirred tank reactors, where the alcohol vapor is introduced to create a large exchange surface area with the liquid reaction mixture, facilitating the removal of water as an alcohol-water azeotrope, and the alcohol phase is partially returned to the system to enhance the esterification process.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional esterification methods are used with alcohol as entraining agent, then the process is relatively simple, but the conversion rate is limited and acid number remains high due to inefficient water removal

Engineering Contradiction:
Improveconversion rateVSAvoidacid number
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent utilizes phase transition of water from liquid to vapor form through sparging with inert gas or steam, enabling efficient removal of water from the reaction mixture. The water is transformed into vapor phase and stripped from the liquid reaction mixture, thereby shifting equilibrium toward ester formation and improving conversion rate while reducing acid number.

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The patent introduces an intermediary substance (inert gas or steam) to facilitate water removal. The inert gas or steam acts as a carrier that transports water vapor from the reaction mixture without participating in the esterification reaction, thus improving water removal efficiency and product quality without interfering with the main reaction.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If more water removal measures are implemented to improve conversion rate, then the acid number decreases, but the process complexity increases

Engineering Contradiction:
Improveesterification efficiencyVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent implements continuous water removal during the esterification process through sparging operations. Instead of batch-wise water removal, the inert gas or steam is continuously passed through the reaction mixture to continuously strip water, maintaining the reaction equilibrium shift throughout the process and improving overall esterification efficiency without requiring complex intermittent operation systems.

Inventive Principle:
Principle #20Continuity of useful action

Solution Approach 2:

The patent employs pneumatic sparging by passing inert gas or steam through the liquid reaction mixture to remove water. This pneumatic method provides efficient mass transfer and water removal while maintaining relatively simple equipment requirements compared to other water removal techniques, thus improving productivity without excessive increase in process complexity.

Inventive Principle:
Principle #29Pneumatics and hydraulics

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 approach significantly increases the conversion rate and reduces the acid number in the final ester product, improving the efficiency of the esterification process and minimizing the formation of by-products.

Implementation Method 1

the water of reaction being distilled off as an alcohol-water azeotrope with the vapor

Methodology Applied
Scientific EffectEvaporation: Evaporation

Implementation Method 2

the water of reaction being distilled off as an alcohol-water azeotrope with the vapor

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 3

the vapor from at least one reactor being at least partially condensed, the condensate being separated into an aqueous phase and an alcohol phase

Methodology Applied
Scientific EffectCondensation: Condensation

Data Source

PatentEP2379482B1Production of carboxylic acid esters by stripping with alcohol vapor
Publication Date: 2015.08.26 BASF SE
  • EP2379482B1 patent drawingFigure 1

AI summary

The invention relates to a method for producing carboxylic acid esters by reacting a reaction mixture, comprising a carboxylic acid and/or a carboxylic acid anhydride, and an alcohol in a reaction system having one or more reactors, wherein reaction water is distilled off as an alcohol/water azeotrope with the exhaust vapor. In addition, the reaction mixture is treated with superheated alcohol vapor. The method allows the production of esters having a low acid number.