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

  • Thomas SchuppEmail author
  • Hans Allmendinger
  • Christian Boegi
  • Bart T. A. Bossuyt
  • Bjoern Hidding
  • Summer Shen
  • Bernard Tury
  • Robert J. West
Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 246)


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.


4,4′-Diaminodiphenylmethane Abiotic degradation Anaerobic biodegradation Bioaccumulation Biodegradation in sediment Biodegradation in soil Biodegradation simulation test Covalent binding Distribution Environmental modeling Inherent biodegradability Koc Kow 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 



This work was sponsored by the International Isocyanate Institute, Inc. The views presented in this paper are those of the authors and not necessarily those of the sponsor.

Conflict of Interest

T. Schupp worked for BASF, an MDA producer, until 2012.

H. Allmendinger is a consultant for Currenta GmbH & Co. OHG.

S. Shen is working for Dow, an MDA producer.

B. T. A. Bossuyt is working for Huntsman, an MDA producer.

C. Boegi and B. Hidding are working for BASF, an MDA producer.

B. Tury and R. J. West have been employed by the International Isocyanate Institute, Inc.


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Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  • Thomas Schupp
    • 1
    Email author
  • Hans Allmendinger
    • 2
  • Christian Boegi
    • 3
  • Bart T. A. Bossuyt
    • 4
  • Bjoern Hidding
    • 5
  • Summer Shen
    • 6
  • Bernard Tury
    • 7
  • Robert J. West
    • 8
  1. 1.Faculty of Chemical EngineeringMuenster University of Applied ScienceSteinfurtGermany
  2. 2.Currenta GmbH & Co. OHGLeverkusenGermany
  3. 3.BASF SE, FEP/PA - Z570LudwigshafenGermany
  4. 4.Huntsman EuropeEverbergBelgium
  5. 5.BASF SE, RB/TC - Z570LudwigshafenGermany
  6. 6.Dow Chemical (China) Investment Limited CompanyShanghaiChina
  7. 7.(former) International Isocyanate Institute Inc.BoontonUSA
  8. 8.International Isocyanate Institute Inc.BoontonUSA

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