Title of project

The two-step synthesis of 2,2'- methylene dianiline

Faculty Advisor

James Wollack

Department

Chemistry

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The two-step synthesis of 2,2'- methylene dianiline

Methylene dianiline (MDA) is principally used to produce 4,4’- methylene dianiline diisocyanate and other polymeric isocyanates, which are used to manufacture polyurethane foams. Methylene dianiline is also used as a curing agent for epoxy resins and urethane elastomers, as a corrosion preventative for iron, as an antioxidant for lubricating oils, as a rubber processing chemical, and as an intermediate in the manufacture of elastomeric fibers. Methylene dianiline (2,2’ – MDA) can be produced in a two-step synthesis from 2-nitrophenyl boronic acid and 2-nitrobenzyl bromide. First, 2-nitrophenyl boronic acid is combined with 2-nitrobenzyl bromide using a Suzuki reaction to produce bis (2-nitrophenyl) methane. Next, the nitro groups on the bis (2-nitrophenyl) methane are reduced using a catalytic hydrogenation reaction to produce the compound methylene dianilene (2,2’ – MDA). Once produced this compound can be used as a standard to measure the by-products of 2,2’ – MDA created in the manufacturing process, since it can have hazardous health effects such as irritation to the skin and eyes, liver damage through acute oral or dermal exposure, and it is a possible human carcinogen.