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Related Concept Videos

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.
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 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.
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 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...
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.

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Defining Substrate Specificities for Lipase and Phospholipase Candidates
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Defining Substrate Specificities for Lipase and Phospholipase Candidates

Published on: November 23, 2016

Advances in lipase-catalyzed esterification reactions.

Panagiota-Yiolanda Stergiou1, Athanasios Foukis, Michalis Filippou

  • 1University of Ioannina, Department of Chemistry, Group of Enzyme Biotechnology and Genetic Engineering, Ioannina 45110, Greece.

Biotechnology Advances
|August 20, 2013
PubMed
Summary

Lipase-catalyzed esterification is crucial for industrial applications like biofuel production. This review evaluates trends, factors affecting enzymatic esterification, and biocatalysis using whole cells or purified lipases.

Keywords:
BiofuelEster yieldEsterificationInfluence of pHLipase immobilizationLipasesWater activityWhole cell biocatalysis

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Area of Science:

  • Biochemistry
  • Chemical Engineering
  • Industrial Biotechnology

Background:

  • Lipase-catalyzed esterification is a significant industrial process.
  • Organic esters are increasingly used in biotechnology and the chemical industry.
  • Lipases function in multi-phase environments where reactant distribution changes.

Purpose of the Study:

  • To provide a comprehensive review of enzymatic esterification trends and perspectives.
  • To focus on biofuel production applications.
  • To highlight factors influencing lipase-catalyzed esterification.

Main Methods:

  • Review of applied trends and perspectives in enzymatic esterification.
  • Evaluation of factors affecting lipase-catalyzed reactions.
  • Review of whole-cell and purified lipase biocatalysis from bacterial and fungal sources.

Main Results:

  • Enzymatic esterification, particularly for biofuel production, is a key area of research.
  • Understanding factors influencing reaction kinetics is essential.
  • Both whole-cell and purified lipases offer viable biocatalysis options.

Conclusions:

  • Lipase-catalyzed esterification is vital for industrial applications, especially biofuels.
  • Further research into reaction kinetics and optimization is warranted.
  • Bacterial and fungal lipases, in various forms, are effective biocatalysts.