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2-Methyl-dibenzothiophene (2-MDT) is an organic compound with the chemical formula C12H10S2.
It is a colorless liquid with a characteristic odor and is commonly used as a solvent and in the production of chemicals and materials.
The synthetic routes of 2-MDT can be broadly classified into three categories: synthesis via the sulfur route, synthesis via the condensation route, and synthesis via the oxidation route.
Synthesis via the Sulfur Route:
The sulfur route is the most common method for the synthesis of 2-MDT.
This route involves the reaction of benzene with a sulfur compound, such as sulfur or thiophene, in the presence of a solvent and a catalyst.
The reaction proceeds through the following steps:
- Benzene is treated with sulfur to form a sulfur-benzene complex.
- The sulfur-benzene complex is then treated with a catalyst, such as aluminum chloride, to form a benzene sulfonate.
- The benzene sulfonate is then treated with thiophene in the presence of a solvent, such as dichloromethane, to form a benzothiophene sulfonate.
- The benzothiophene sulfonate is then hydrolyzed to form 2-MDT.
The reaction is typically carried out under mild conditions and can be catalyzed by a variety of metal salts, such as aluminum chloride, iron(III) chloride, and zinc chloride.
The reaction can be performed in a variety of solvents, such as dichloromethane, chloroform, and carbon tetrachloride.
The yield of 2-MDT can be improved by using a solvent that is miscible with water, as this allows for more efficient hydrolysis of the intermediate benzothiophene sulfonate.
Synthesis via the Condensation Route:
The condensation route involves the reaction of two or more aromatic compounds to form 2-MDT.
This route can be carried out by using a variety of aromatic compounds, such as benzene, toluene, and xylene, as starting materials.
The reaction proceeds through the following steps:
- The aromatic compounds are heated in the presence of a solvent, such as benzene or toluene, and a catalyst, such as sulfuric acid, in a reactor.
- The aromatic compounds undergo dimerization to form a solid product, which is then dissolved in a solvent, such as dichloromethane or chloroform.
- The solution is then treated with a base, such as sodium hydroxide, to hydrolyze the product and form 2-MDT.
The reaction can be carried out at temperatures between 100 and 200°C and the choice of solvent and catalyst can significantly affect the yield of 2-MDT.
The yield of 2-MDT can also be improved by using a solvent that is miscible with water, as this allows for more efficient hydrolysis of the intermediate product.
Synthesis via the Oxidation Route:
The oxidation route involves the oxidation of an aromatic compound, such as benzene or toluene, to form 2-MDT.
This route can be carried out by using a variety of oxidizing agents, such as potassium permanganate, chromic acid, and ozone.
The reaction proceeds through the following steps:
- The aromatic compound is treated with the oxidizing agent in the presence of a solvent, such as water or acetic acid, to form a product.
- The product is then hydrolyzed to form 2-MD