4,4'-Methylenedianiline
 | |
| Names | |
|---|---|
| IUPAC name
Bis(4-aminophenyl)methane | |
| Other names
4,4'-Diaminodiphenylmethane; 4,4'-Methylenebisbenzenamine; MDA; para, para'-Diaminodiphenyl-methane; Dianilinomethane; 4,4'-Diphenylmethanediamine | |
| Identifiers | |
101-77-9  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:32506  |
| ChEMBL | ChEMBL85728 |
| ChemSpider | 7296 |
| ECHA InfoCard | 100.002.705 |
| EC Number | 202-974-4 |
| KEGG | C14288 |
| PubChem | 7577 |
| RTECS number | BY5425000 |
| UNII | GG5LL7OBZC |
| UN number | 2651 |
| |
| |
| Properties | |
| C13H14N2 | |
| Molar mass | 198.27 g·mol−1 |
| Appearance | Pale brown, crystalline solid |
| Odor | faint, amine-like[1] |
| Density | 1.05 g/cm3 (100°C) |
| Melting point | 89 °C (192 °F; 362 K) |
| Boiling point | 398 to 399 °C (748 to 750 °F; 671 to 672 K) |
| 0.125 g/100 ml (20 °C) | |
| Vapor pressure | 0.0000002 mmHg (20°C)[1] |
| Hazards | |
| Main hazards | potential carcinogen[1] |
| Flash point | 190 °C; 374 °F; 463 K [1] |
| US health exposure limits (NIOSH): | |
| PEL (Permissible) |
TWA 0.010 ppm ST 0.100 ppm[1] |
| REL (Recommended) |
Ca[1] |
| IDLH (Immediate danger) |
Ca [N.D.][1] |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
4,4'-Methylenedianiline (MDA) is a suspected carcinogen.[2] It is included in the "substances of very high concern" list of the European Chemicals Agency (ECHA).[3] 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.[4]
Synthesis
In the industrial production, MDA is synthesised by reaction of formaldehyde and aniline in the presence of hydrochloric acid.[5]
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.[2][3] Lower quantities are used as hardeners in epoxy resins and adhesives, as well as in the production of high-performance polymers.[5]
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 0.10 ppm.[6]
References
- 1 2 3 4 5 6 7 "NIOSH Pocket Guide to Chemical Hazards #0415". National Institute for Occupational Safety and Health (NIOSH).
- 1 2 ToxFAQs for 4,4'-Methylenedianiline, Agency for Toxic Substances and Disease Registry
- 1 2 Background document for 4,4’-Diaminodiphenylmethane (MDA)
- ↑ The Epping jaundice outbreak: a 24 year follow up
- 1 2 Data on manufacture, import, export, uses and release of 4-4’ diaminodiphenylmethane as well as ...
- ↑ NIOSH Pocket Guide on Chemical Hazards
External links
- International Labor Organisation icsc1111
- Centers for Disease Control and Prevention NIOSH Pocket Guide to Chemical Hazards
- European Union Risk Assessment Report
- J.H. Petersen, S.K. Mortensen, G.A. Pedersen, Memorandum for the Danish Veterinary and Food Administration on An acute case of primary aromatic amines migrating from cooking utensils, Danish Institute for Food and Veterinary Research, 12 October 2004