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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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

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

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...
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Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

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Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
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Distillation: Vapor–Liquid Equilibria01:01

Distillation: Vapor–Liquid Equilibria

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Distillation is a separation technique that takes advantage of the boiling point properties of disparate elements in a mixture. To perform distillation, we begin by heating a miscible mixture of two liquids with a significant difference in boiling points (at least 20°C). As the solution heats up and reaches the bubble point of the more volatile component, some molecules of the more volatile component transition into the gas phase and travel upward into the condenser, which is a glass tube...
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Esters to Carboxylic Acids: Saponification01:25

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...
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Updated: Jan 11, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Energy and Capital Cost Reduction in Ester Transesterification Using an Optimized Reactive Distillation System with

Carles Troyano Ferré1, Ruben Cabello1, Alvaro Risco1

  • 1Faculty of Chemistry, Department of Chemical Engineering and Analytical Chemistry, University of Barcelona, Martí i Franquès Street 1, Sixth Floor, 08028 Barcelona, Spain.

ACS Omega
|November 17, 2025
PubMed
Summary

This study introduces a novel reactive distillation with prefractionation column (RDPFC) system to efficiently recover methanol and n-butyl acetate from poly(vinyl alcohol) waste. The RDPFC system significantly reduces energy consumption by 67% compared to traditional methods.

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Area of Science:

  • Chemical Engineering
  • Process Optimization
  • Separation Technology

Background:

  • Reactive distillation is efficient but challenged by azeotropes in processes like methyl acetate (MeAc) and methanol (MeOH) transesterification.
  • Valorizing waste streams from the poly(vinyl alcohol) industry, containing MeAc and MeOH, is crucial for economic and environmental benefits.

Purpose of the Study:

  • To propose and optimize a reactive distillation with prefractionation column (RDPFC) system.
  • To recover high-purity methanol (MeOH) and n-butyl acetate (BuAc) from industrial waste streams.
  • To minimize the total annual cost (TAC) of the proposed process.

Main Methods:

  • Process modeling and optimization using Aspen Plus version 12.1.
  • Integration of a prefractionation column (PFC) under vacuum and a reactive column (RC) at high pressure.
  • Comparative analysis with traditional reactive and extractive distillation (RED) processes.

Main Results:

  • The RDPFC system achieved a MeAc conversion rate of 99.2 mol %.
  • Product purity exceeded 99.85 wt % for MeOH and 99.5 wt % for BuAc.
  • A significant 67% reduction in energy consumption (2.56 GJ/tBuAc) was observed compared to RED.

Conclusions:

  • The RDPFC system offers a highly efficient and economically viable solution for waste stream valorization.
  • Elimination of entrainer and recovery units contributes to substantial energy savings.
  • This technology presents a promising approach for the poly(vinyl alcohol) industry.