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

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

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.

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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 Mechanism

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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.

Esters to Carboxylic Acids: Saponification

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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.
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Acid Halides to Esters: Alcoholysis

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Towards optimizing short-chained PFCA esterification in water.

Susanna K Maisto¹, Doris Hong¹, Fabian S Menges²

¹Department of Chemical and Environmental Engineering, Yale University, New Haven, CT, 06511, USA.

|July 9, 2026

Summary

Short-chained perfluorocarboxylic acids (PFCAs) can be removed from water via esterification and emulsion formation. This study optimized the process, achieving over 70% removal of PFHxA and PFBA using tailored conditions.

Keywords:

NMR Perfluorocarboxylic acids Physicochemical transformations Short-chained PFAS

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Area of Science:

Environmental Chemistry
Water Treatment Technologies

Background:

Short-chained perfluorocarboxylic acids (PFCAs) are persistent and mobile contaminants in aqueous environments.
Effective treatment technologies are needed to mitigate rising PFCA emissions from industrial sources.

Purpose of the Study:

To expand the esterification-based removal of per- and polyfluoroalkyl substances (PFAS) to short-chained PFCAs.
To develop and utilize a quantitative 19F NMR method for in-situ measurement of PFAS partitioning and transformation.
To systematically evaluate influencing factors for optimizing PFCA removal.

Main Methods:

Esterification reaction with decanol within spontaneously formed emulsions.
Development of a quantitative 19F NMR method for in-situ PFAS analysis.
Systematic evaluation of water constituents (e.g., NaCl) and reaction additives (e.g., alcohol chain length).

Main Results:

PFCA removal is driven by both chemical transformation (esterification) and emulsion formation/stabilization.
Higher ionic strengths (NaCl, Na2SO4) hinder PFCA partitioning and esterification, while humic acid shows minimal inhibition.
PFCA mixtures showed improved removal (11-15%) compared to single solutes.
Optimized conditions achieved ≥70% total removal yields for perfluorohexanoic acid (PFHxA) and perfluorobutanoic acid (PFBA).

Conclusions:

The esterification-based approach, coupled with emulsion stabilization, is effective for removing short-chained PFCAs.
Optimizing reactant concentrations and temperature is crucial for maximizing removal efficiency.
This method offers a promising strategy for treating industrial wastewater contaminated with short-chained PFCAs.