Obtaining benzotriazole

Objective

The purpose of this practice is to obtain a simple nitrogenous heterocycle, in this case a triazole (five-membered ring with three nitrogens) fused to a six-membered aromatic ring, benzotriazole.

Background

Benzotriazole is a heterocyclic compound that is used as a starting product in the manufacture of some pharmaceuticals, in photography as a component of developers, or as a component of metal coatings to prevent corrosion, especially of copper and copper alloys. Benzotriazole can be found as an additive in dish detergents, automotive antifreeze, or as an additive in lubricants.

Experimental procedure

Dissolve 5.4 g of o-phenylenediamine in a mixture of 6 g (5.5 ml) of glacial acetic acid and 15 ml of water in a 250 ml Erlenmeyer flask. Heat slightly if necessary to achieve total dissolution of the mixture.

Cool the solution in a cold water bath and add at once a solution of 3.8 g of sodium nitrite in 8 ml of water. Proceed with manual stirring and avoid magnetic stirring. It is observed that the reaction mixture heats up reaching approximately 85 ºC.

At this point it cools down again, and a change in the coloration of the reaction mixture (from dark red to light brown) can be observed.

The cooling-heating-cooling sequence is critical for good performance. Therefore, if the initial or final cooling process is not very efficient, performance decreases.

Stirring is continued for 15 min. and the mixture is placed in an ice bath for another 30 min.

The solid that appears is filtered under vacuum and washed three times with cold deionized water in the Büchner. The solid obtained is benzotriazole. It is recrystallized in water.

International Chemical Identifier

The IUPAC InChI key identifiers for the main compounds used in this experiment are provided to facilitate the nomenclature and formulation of chemical compounds and the search for information on the Internet for these compounds.

benzotriazoleQRUDEWIWKLJBPS-UHFFFAOYSA-N
o-fhenylenediamineGEYOCULIXLDCMW-UHFFFAOYSA-N

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