The Environmental Behavior of Methylene-4,4'-dianiline

Rev Environ Contam Toxicol. 2018 Jun 24. doi: 10.1007/398_2018_13. Online ahead of print.

Abstract

Methylene-4,4'-dianiline (MDA, CAS-No. 101-77-9) is a high production volume intermediate that is mainly processed to diisocyanates and finally polyurethanes. This review summarizes available data concerning the environmental behavior. When released into the environment, MDA distributes into water and subsequently sediment and soil compartments; the air is of little relevance, owed to the low vapor pressure and short atmospheric half-life, which renders MDA non-critical for long-range transport. Biodegradation data present a diverged picture; in some tests, MDA is not readily biodegradable or even not inherent biodegradable; in other tests, MDA turned out to be readily biodegradable (but failing the 10-d window). The history and composition of the inoculum used for testing seem to play an important role, which is underlined by good test results with adapted inoculum. In soil, initially a rapid mineralization is observed, which slows down within the first days due to competitive chemical absorption. The latter results in degradation rates comparable to that of natural organic matter. Under anaerobic conditions, mineralization is poor. Irreversible chemisorption occurs unless soils/sediments are highly reduced. Half-lives due to primary decay do not indicate MDA to be persistent according to the regulatory guidance used in then EU, Canada, or the USA; in Japan, however, due to test results in MITI degradation tests, MDA would be regarded as persistent. The identification of microbial MDA metabolites deserves further research. MDA is not bioaccumulative, but it is toxic to aquatic organisms and mammals. MDA in pore water of soils is rapidly adsorbed on the surface of plant roots. Test runs were too short to draw a final conclusion with regards to transport to stem, leaves, and fruits. Data from structurally similar compounds indicate that such transport would account for less than 1% of the root-adsorbed material.

Keywords: 4,4′-Diaminodiphenylmethane; Abiotic degradation; Anaerobic biodegradation; Bioaccumulation; Biodegradation in sediment; Biodegradation in soil; Biodegradation simulation test; Covalent binding; Distribution; Environmental modeling; Inherent biodegradability; K oc; K ow; MDA; Methylene-4,4′-dianiline; NER; Non-extractable residues; Persistency; Photodegradation; Primary aromatic amines; Ready biodegradability; Soil absorption; Soil adsorption; Soil organic matter; Soil reactivity; Soil–water distribution.