4,4'-Methylenedianiline enables eco-friendly polyurea polymer synthesis

Description

4,4'-Methylenedianiline is a colorless solid, although commercial samples can appear yellow or brown. It is very slightly soluble in water (does not mix well with water), readily soluble in alcohol, benzene, and ether, and does not readily evaporate at room temperature.

Applications in organic synthesis

4,4'-Methylenedianiline(MDA) is primarily used to produce 4,4-'methylenedianiline diisocyanate and other polymeric isocyanates which are used to manufacture polyurethane foams.

MDA 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, as an intermediate in the manufacture of elastomeric fibers (e.g., Spandex), and in the preparation of azo dyes.1

Environmental hazards

When released into the air, 4,4'-Methylenedianiline exists in both vapor and particulate phases, where it can be degraded by photochemically-produced hydroxyl radicals, with a half-life of approximately 12.8 hours. In soil, 4,4'-Methylenedianiline is expected to have slight to no mobility and limited volatilization, while biodegradation is not a significant fate process. Upon release into water, 4,4'-Methylenedianiline is anticipated to adsorb to suspended solids and sediment, with low bioconcentration in aquatic organisms and minimal biodegradation. The compound's lack of hydrolysis potential further contributes to its environmental persistence. Occupational exposure can occur through inhalation and dermal contact, and the general population may also be exposed via consumer products containing 4,4'-Methylenedianiline. 2

Reference

1. U.S. Environmental Protection Agency. Health and Environmental Effects Profile for Benzenamine, 4,4'- Methylenebis. EPA/600/x-84/231. Environmental Criteria and Assessment Office, Office of Health and Environmental Assessment, Office of Research and Development, Cincinnati, OH. 1984.

2. PubChem Annotation Record for 4,4'-DIAMINODIPHENYLMETHANE. National Center for Biotechnology Information, 2023, Source: Hazardous Substances Data Bank.

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