Malaprade oxidation

What is Malaprade oxidation?

Malaprade oxidation is a chemical reaction that involves the conversion of an alkyl aryl ether into a dialkyl aryl ether by reacting it with oxygen in the presence of a catalyst. This reaction was discovered by the French chemist, Henry Malaprade, in the early 20th century and has since been widely used in the synthesis of a variety of organic compounds..

Malaprade oxidation
Malaprade oxidation

The mechanism of the Malaprade oxidation involves the formation of an alkyl hydroperoxide intermediate, which is then cleaved into the final dialkyl aryl ether product. The alkyl hydroperoxide intermediate is formed through the oxygenation of the alkyl aryl ether by the oxygen molecule, which is facilitated by the presence of a catalyst. The catalyst used in the Malaprade oxidation is typically a copper compound, such as copper oxide or copper acetate..

The Malaprade oxidation has several advantages over other methods of synthesizing dialkyl aryl ethers. It is a simple and efficient process that can be carried out under mild conditions, and it allows for the selective synthesis of specific dialkyl aryl ethers. In addition, the reaction has a high yield and produces a high-quality product..

The Malaprade oxidation has a wide range of applications in the synthesis of organic compounds, including the synthesis of pharmaceuticals, fragrances, and plasticizers. It is also used in the synthesis of surfactants and detergents, which are used in a variety of personal care and household products..

Summary

The Malaprade oxidation is an important chemical reaction that has had a significant impact on the synthesis of a variety of organic compounds. It is a simple, efficient, and widely used method for synthesizing dialkyl aryl ethers, and it has a wide range of applications in the chemical industry..

Example

One example of Malaprade oxidation is the oxidation of propene (propylene) to propylene glycol described as follows:

C3H6 + O2 –> C3H8O2

Mechanism of reaction

The Malaprade oxidation mechanism is described as follows:

  • The alkyl aryl ether is mixed with oxygen and a catalyst, such as copper oxide or copper acetate..
  • The oxygen molecule is activated by the catalyst, allowing it to react with the alkyl aryl ether..
  • The oxygen molecule is incorporated into the alkyl aryl ether, forming an alkyl hydroperoxide intermediate..
  • The alkyl hydroperoxide intermediate is cleaved into the final dialkyl aryl ether product..

The overall reaction can be summarized as follows:

Alkyl aryl ether + O2 + catalyst -> Dialkyl aryl ether

The Malaprade oxidation is a simple and efficient process that can be carried out under mild conditions. It allows for the selective synthesis of specific dialkyl aryl ethers and has a high yield and produces a high-quality product. It is widely used in the synthesis of a variety of organic compounds and has a range of applications in the chemical industry..

References

  • L. Malaprade, Bull. Soc. Chim. France 43, 683 (1928)
  • L. Malaprade, Compt. Rend. 186, 382 (1928)
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