A three-step process was used to synthesize a derivative of 2,4-methylenedianiline (MDA). The process included a Suzuki coupling between 2-nitrobenzyl bromide and 4-nitrophenyl boronic acid, the reduction of two nitro-groups, and the addition of methyl chloroformate to result in a carbamate containing derivative of 2,4-MDA (2,4-MDC). Commercial MDA is primarily made up of three regioisomers; 2,2’-MDA, 2,4’-MDA, and 4,4’-MDA. A mixture of these regioisomers is used in the synthesis of methylene diphenyl diisocyanate (MDI). MDI is a common precursor for the synthesis of foams and insulation. Residual MDI present in these materials is of toxicological concern to consumers. Here a 2,4’ MDC standard was synthesized and will be used to quantify the amount of residual 2,4 MDI present in polymeric MDI materials. The route developed here could also be adapted to quantify other MDI isomers.

Synthesis of a 2,4-methylenedianiline (MDA) derivative

2019 Spring National Meeting

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