4,4'-Methylenedianiline

4,4'-Methylenedianiline
IUPAC name

Bis(4-aminophenyl)methane
Other names

4,4'-Diaminodiphenylmethane; 4,4'-Methylenebisbenzenamine; MDA
Identifiers
CAS number 101-77-9 Y
PubChem 7577
UNII GG5LL7OBZC Y
EC number 202-974-4
KEGG C14288 N
ChEMBL CHEMBL85728 N
RTECS number BY5425000
Jmol-3D images Image 1
Properties
Molecular formula C13H14N2
Molar mass 198.26 g mol−1
Density 1.05 g/cm3 (100°C)
Melting point

89 °C, 362 K, 192 °F
Boiling point

398-399 °C, 671-672 K, 748-750 °F
Solubility in water 0.125 g/100 ml (20 °C)
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

4,4'-Methylenedianiline (MDA) is a suspected carcinogen.[1] It is included in the "substances of very high concern" list of the European Chemicals Agency (ECHA).[2] The compound was involved in an accidental 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.[3]

Contents

Synthesis

In the industrial production, MDA is synthesised by reaction of formaldehyde and aniline in the presence of hydrochloric acid.[4]

Uses

MDA is used primarily for making polyurethane foams in which case it is first reacted with phosgene to create 4,4 ́-methylene diphenyl diisocyanate (MDI) prior to polymerization with a polyol.[1][2] Lower quantities are used as hardeners in epoxy resins and adhesives, as well as in the production of high-performance polymers.[4]

References

  1. ^ a b ToxFAQs for 4,4'-Methylenedianiline, Agency for Toxic Substances and Disease Registry
  2. ^ a b Background document for 4,4’-Diaminodiphenylmethane (MDA)
  3. ^ The Epping jaundice outbreak: a 24 year follow up
  4. ^ a b Data on manufacture, import, export, uses and release of 4-4’ diaminodiphenylmethane as well as ... [1]

External links