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Related Concept Videos

Esters to Carboxylic Acids: Saponification01:25

Esters to Carboxylic Acids: Saponification

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...
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

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 Overview01:20

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.
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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

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.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

Esters to β-Ketoesters: Claisen Condensation Mechanism

Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the intermediate restores...

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Enzymatic esterification in aqueous miniemulsions.

Eugen M Aschenbrenner1, Clemens K Weiss, Katharina Landfester

  • 1Max-Planck-Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 22, 2009
PubMed
Summary

Enzyme-catalyzed esterification using miniemulsions achieved high conversions of carboxylic acids and alcohols. This efficient method offers a faster alternative to acid catalysis, even with significant water presence.

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Area of Science:

  • Biocatalysis
  • Green Chemistry
  • Organic Synthesis

Background:

  • Enzyme-catalyzed esterification offers a sustainable alternative to traditional chemical synthesis.
  • Miniemulsion technology provides a unique reaction medium for biocatalytic processes, enhancing stability and efficiency.
  • Controlling reactant hydrophilicity and enzyme specificity is crucial for optimizing esterification yields.

Purpose of the Study:

  • To synthesize monoesters from carboxylic acids and phenyl-labeled alcohols using lipases in aqueous miniemulsions.
  • To investigate the impact of reactant properties and enzyme specificity on esterification efficiency.
  • To compare enzyme-catalyzed esterification with acid-catalyzed methods in a miniemulsion system.

Main Methods:

  • Synthesis of monoesters via lipase-catalyzed esterification in aqueous miniemulsions.
  • Dispersion of reactants in nonionic surfactant solutions to form stable miniemulsions.
  • Optimization of reaction parameters for the model system using Lipase PS.

Main Results:

  • Achieved significant esterification conversions (around 90%) for various carboxylic acids and alcohols.
  • Identified Lipase PS as the most effective catalyst, yielding up to 80% conversion in under an hour for a model reaction.
  • Demonstrated that enzyme-catalyzed reactions in miniemulsions are significantly faster than acid-catalyzed equivalents.

Conclusions:

  • The miniemulsion technique is highly effective for direct, enzyme-catalyzed esterification of carboxylic acids and alcohols.
  • This approach facilitates efficient biocatalysis even in the presence of substantial amounts of water.
  • The study highlights the potential of miniemulsion-based enzymatic synthesis for green chemical production.