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4,4'-Methylenedianiline

MDA

dadpm

4,4′-Diaminodiphenylmethane

4,4′-Methylenebisbenzenamine

para,para′-Diaminodiphenylmethane

Dianilinomethane

4,4′-Diphenylmethanediamine

Bis(4-aminophenyl)methane

4,4′-Methylenedianiline (MDA) is an organic compound with the formula . It is a colorless solid, although commercial samples can appear yellow or brown. It is produced on an industrial scale, mainly as a precursor to polyurethanes.

Synthesis and applications

In the industrial production, MDA is produced by reaction of formaldehyde and aniline in the presence of hydrochloric acid.

MDA is a common monomer in the synthesis of polymer materials. These include polyamides, polyimides and polyimines. MDA is also used extensively as a precursor to methylene diphenyl diisocyanate (MDI). Here, MDA is treated with phosgene to produce MDI. MDI, in turn, is a precursor to many polyurethane foams.

MDA can also be applied as a bidentate (bridging) ligand in the formation of metal-coordination complexes.

Safety

MDA is considered a potential occupational carcinogen by the US National Institute for Occupational Safety and Health. The Occupational Safety and Health Administration has set a permissible exposure limit at 0.01 ppm over an eight-hour time-weighted average, and a short-term exposure limit at 0.1 ppm.

It is suspected carcinogen. It is included in the "substances of very high concern" list of the European Chemicals Agency (ECHA). The compound was blamed in a mass poisoning in the vicinity of Epping, Essex, United Kingdom during 1965 during which 84 individuals were poisoned through accidental contamination of flour used to make bread.

References

References

  1. {{GESTIS
  2. {{PGCH. 0415
  3. "Data on manufacture, import, export, uses and release of 4-4' diaminodiphenylmethane".
  4. (2022). "Direct Synthesis of Thermally Stable Semiaromatic Polyamides by Bulk Polymerization Using Aromatic Diamines and Aliphatic Dicarboxylic Acids". ACS Omega.
  5. (2022). "Raman Spectroscopy Reveals Phase Separation in Imine-Based Covalent Adaptable Networks". Macromolecules.
  6. (2005). "Amines, Aliphatic". Wiley-VCH.
  7. (2020). "Six transition metal–organic materials with the ditopic 4,4′-diaminodiphenylmethane ligand: Synthesis, structure characterization and luminescent properties". Polyhedron.
  8. "4,4'-Methylenedianiline". NIOSH Pocket Guide on Chemical Hazards.
  9. "ToxFAQs for 4,4'-Methylenedianiline". Agency for Toxic Substances and Disease Registry.
  10. "Background document for 4,4'-Diaminodiphenylmethane (MDA)". European Chemicals Agency.
  11. (February 1966). "The Epping jaundice". British Medical Journal.
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