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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

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The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

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Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Published on: October 30, 2018

Continuous reaction-separation process for enzymatic esterification in supercritical carbon dioxide.

A Marty¹, D Combes, J S Condoret

¹Institut National des Sciences Appliquées, Département de Génie Biochimique et Alimentaire, Complexe Scientifique de Rangueil, 31077 Toulouse, France.

Biotechnology and Bioengineering

|March 15, 1994

Summary

This study optimized enzymatic esterification using immobilized lipase in continuous flow systems. Researchers achieved satisfactory modeling and efficient product separation in supercritical carbon dioxide, demonstrating a viable industrial process.

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor

A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor

Published on: February 10, 2023

Area of Science:

Biocatalysis and enzyme technology
Chemical engineering and process intensification
Supercritical fluid technology

Background:

Previous research established enzymatic esterification using immobilized lipase in batch systems with supercritical carbon dioxide (SCCO(2)) and n-hexane.
Industrial application requires scalable and continuous processes for enzymatic esterification.

Purpose of the Study:

To extend previous findings to a continuous operation model for enzymatic esterification.
To develop and validate a plug flow model for the reaction vessel.
To investigate and optimize the postreactional separation process in SCCO(2).

Main Methods:

Continuous operation in a tubular fixed bed reactor.
Modeling of the reaction vessel using a plug flow model and kinetic equations.
Experimental investigation of postreactional separation in SCCO(2).

Main Results:

The plug flow model coupled with kinetic equations provided a satisfactory representation of the continuous reaction vessel operation.
Experimental studies demonstrated good selectivities and high product recovery during postreactional separation in SCCO(2).

Conclusions:

Continuous operation of enzymatic esterification using immobilized lipase in SCCO(2) is feasible and effectively modeled.
Efficient product separation in SCCO(2) is achievable, making the process attractive for industrial applications.