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Alkaline Hydrolysis of Methyl Decanoate in Surfactant-Based Systems

Alkaline Hydrolysis of Methyl Decanoate in Surfactant-Based Systems

Marcel Schmidt, Johannes Deckwerth, Reinhard Schomäcker, Michael Schwarze

J Org Chem. 2018 Jul 20;83(14):7398-7406.

PMID: 29762024

Abstract:

Surfactant-modified reaction systems are one approach to perform organic reactions with water as the solvent involving hydrophobic reactants. Herein, the alkaline hydrolysis of the long-chain methyl decanoate in cationic and nonionic surfactant-modified systems is reported. The physicochemical behavior of the reaction mixture and the performance of the alkaline hydrolysis were systematically investigated. In water as the solvent, the reaction is slow, but at elevated temperatures, the alkaline hydrolysis of methyl decanoate is accelerated because the reaction product sodium decanoate acts as an ionic surfactant, leading to an increased solubility of methyl decanoate in the aqueous phase. The rate can be significantly increased by the addition of surfactants as solubilizers. In nonionic TX-100 solutions, the reaction rate can be increased by a factor of about 100 for a surfactant concentration of 5 wt %. If cationic surfactants are applied, the reaction rate can be further increased due to the electrostatic interaction between the hydroxide ions in solution and the charged head groups of the cationic micelles.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP110429-A	Methyl decanoate		110-42-9	Price

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