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Related Concept Videos

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

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

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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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Esters to Carboxylic Acids: Saponification01:25

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

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

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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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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

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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...
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Preparation of Binary and Ternary Deep Eutectic Systems
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Designed Reactive Natural Deep Eutectic Solvents for Lipase-Catalyzed Esterification.

Alina Ramona Buzatu1,2, Anamaria Todea1, Raluca Pop3

  • 1Department of Applied Chemistry and Engineering of Organic and Natural Compounds, Faculty of Industrial Chemistry and Environmental Engineering, University Politehnica Timişoara, Carol Telbisz 6, 300001 Timisoara, Romania.

Molecules (Basel, Switzerland)
|February 26, 2025
PubMed
Summary

Reactive natural deep eutectic solvents (R-NADESs) enhance lipase performance in synthesizing biosurfactants. These green solvents improve enzyme stability and activity for sustainable biorefinery applications.

Keywords:
carbohydratescatalytic activitycholine chlorideimmobilized lipaselipaselipase stabilitymolecular propertiesreactive NADES

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Area of Science:

  • Green Chemistry and Biorefining
  • Biocatalysis and Enzyme Technology
  • Sustainable Solvent Systems

Background:

  • Natural deep eutectic solvents (NADESs) offer sustainable alternatives for extraction and reaction media.
  • Enzymatic reactions benefit from NADESs due to improved substrate solubility, enzyme stability, and efficiency.
  • NADESs can act as multi-functional media, serving as substrates and catalysts, known as reactive solvents.

Purpose of the Study:

  • To investigate the impact of designed reactive natural deep eutectic solvents (R-NADESs) on lipase activity and stability.
  • To explore the synthesis of polyol- and carbohydrate-based biosurfactants using R-NADESs with lipases.
  • To characterize novel R-NADES systems and their physicochemical properties.

Main Methods:

  • Manufactured and characterized 16 binary and ternary R-NADES systems using choline chloride (ChCl) as HBA and various HBDs (carbohydrates, urea, water).
  • Determined physicochemical, thermal, and molecular properties (viscosity, polarizability, hydrogen bonding) of R-NADESs.
  • Evaluated the esterification activity and thermal stability of free and immobilized lipases in R-NADESs.

Main Results:

  • R-NADES properties were effectively controlled by composition, molar ratio, molecular characteristics, temperature, and water content.
  • Many lipases, both free and immobilized, exhibited high thermal stability in the developed R-NADESs.
  • Remarkable catalytic performance of lipases was observed in R-NADESs for esterification reactions.

Conclusions:

  • Designed R-NADESs are beneficial for enzymatic esterification reactions, particularly in biosurfactant synthesis.
  • These novel solvent systems enhance lipase stability and catalytic efficiency, supporting green chemistry principles.
  • The tunable properties of R-NADESs make them versatile media for biocatalytic applications in biorefineries.