Misplaced Pages

4,4'-Methylenedianiline

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from Methylenedianiline)

4,4′-Methylenedianiline
Names
Preferred IUPAC name 4,4′-Methylenedianiline
Other names MDA

dadpm
4,4′-Diaminodiphenylmethane
4,4′-Methylenebisbenzenamine
para,para′-Diaminodiphenylmethane
Dianilinomethane
4,4′-Diphenylmethanediamine

Bis(4-aminophenyl)methane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.705 Edit this at Wikidata
EC Number
  • 202-974-4
KEGG
PubChem CID
RTECS number
  • BY5425000
UNII
UN number 2651
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2Key: YBRVSVVVWCFQMG-UHFFFAOYSA-N
  • InChI=1/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2Key: YBRVSVVVWCFQMG-UHFFFAOYAE
SMILES
  • c1cc(N)ccc1Cc2ccc(N)cc2
Properties
Chemical formula C13H14N2
Molar mass 198.269 g·mol
Appearance Colorless solid
Odor faint, amine-like
Density 1.05 g/cm (100°C)
Melting point 89 °C (192 °F; 362 K)
Boiling point 398 to 399 °C (748 to 750 °F; 671 to 672 K)
Solubility in water 0.125 g/100 ml (20 °C)
Vapor pressure 0.0000002 mmHg (20°C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards potential carcinogen
GHS labelling:
Pictograms GHS08: Health hazard GHS07: Exclamation mark GHS09: Environmental hazard
Signal word Danger
Hazard statements H317, H341, H350, H370, H373, H411
Precautionary statements P201, P260, P273, P280, P308+P313
Flash point 190 °C; 374 °F; 463 K
NIOSH (US health exposure limits):
PEL (Permissible) TWA 0.010 ppm ST 0.100 ppm
REL (Recommended) Ca
IDLH (Immediate danger) Ca
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

4,4′-Methylenedianiline (MDA) is an organic compound with the formula CH2(C6H4NH2)2. 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. Lower quantities are used as hardeners in epoxy resins and adhesives, as well as in the production of high-performance polymers. Additionally, hydrogenation of MDA can be performed to produce 4,4,diaminodicyclohexylmethane, which is also used in polymer chemistry.

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.

Related compounds

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0415". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Record of 4,4'-Diaminodiphenylmethane in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 12 February 2021.
  3. ^ "Data on manufacture, import, export, uses and release of 4-4' diaminodiphenylmethane" (PDF). Archived from the original (PDF) on 2011-10-01.
  4. Endo T, Higashihara T (2022). "Direct Synthesis of Thermally Stable Semiaromatic Polyamides by Bulk Polymerization Using Aromatic Diamines and Aliphatic Dicarboxylic Acids". ACS Omega. 7 (10): 8753–8758. doi:10.1021/acsomega.1c06983. PMC 8928493. PMID 35309482.
  5. Schoustra S, De Heer Kloots M, Posthuma J, Van Doorn D, Dijksman J, Smulders M (2022). "Raman Spectroscopy Reveals Phase Separation in Imine-Based Covalent Adaptable Networks". Macromolecules. 55 (23): 10341–10355. Bibcode:2022MaMol..5510341S. doi:10.1021/acs.macromol.2c01595. PMC 9753755. PMID 36530523.
  6. ^ "ToxFAQs for 4,4'-Methylenedianiline". Agency for Toxic Substances and Disease Registry.
  7. ^ "Background document for 4,4'-Diaminodiphenylmethane (MDA)" (PDF). European Chemicals Agency. Archived from the original (PDF) on 2017-08-22. Retrieved 2015-02-24.
  8. Roose P, Eller K, Henkes E, Rossbacher R, Höke H (2005). "Amines, Aliphatic". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 3-527-30673-0.
  9. Chisca D, Croitor L, Melnic E, Petuhov O, Kulikova O, Fonari MS (2020). "Six transition metal–organic materials with the ditopic 4,4′-diaminodiphenylmethane ligand: Synthesis, structure characterization and luminescent properties". Polyhedron. 192: 114844. doi:10.1016/j.poly.2020.114844.
  10. "4,4'-Methylenedianiline". NIOSH Pocket Guide on Chemical Hazards.
  11. Kopelman H, Robertson MH, Sanders PG, Ash I (February 1966). "The Epping jaundice". British Medical Journal. 1 (5486): 514–6. doi:10.1136/bmj.1.5486.514. PMC 1843808. PMID 5902696.

External links

Categories: