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What is the nitration process of Methyl benzoate?

Nov 2，2024

Methyl m-nitrobenzoate (methyl 3-nitrobenzoate) is an organic synthesis intermediate. It can be used as a starting material for the preparation of dyes and crop agents. Currently, it is obtained by nitrating methyl benzoate with mixed acid 2 (an aqueous mixture of nitric acid and sulfuric acid). Nitration is an exothermic reaction and, like polymerization, is one of the most dangerous reactions at the industrial level.

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The synthetic reaction steps of methyl 3-nitrobenzoate are as follows:

Weigh 2.0 g of methyl benzoate into a dry conical flask, slowly swirl 4 cm3 of concentrated sulfuric acid into the methyl benzoate, mix thoroughly and cool in an ice bath. Then transfer 1.5 cm3 of concentrated nitric acid to a dry test tube. Immerse the nitric acid partially in an ice-water bath to cool, then slowly add 1.5 cm3 of concentrated sulfuric acid, mix and shake well, and cool. Get a nitration mixture. Finally, slowly add the nitration mixture into a conical flask while stirring (keep the temperature below 6 °C). After standing at room temperature for 15 minutes, add ice and filter, and recrystallize in hot ethanol to obtain the product.

References:

[1] ILARIA DI SOMMA*. Kinetic and Safety Characterization of the Nitration Process of Methyl Benzoate in Mixed Acid[J]. Organic Process Research & Development, 2012. DOI:10.1021/op300043x.

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