4,4′-methylenebis (2-chloroaniline)

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Structural formula
Structural formula of 4,4′-methylene-bis (2-chloroaniline)
General
Surname 4,4′-methylenebis (2-chloroaniline)
other names
  • 2,2'-dichloro-4,4'-methylenedianiline
  • MOCA
  • 4,4'-diamino-3,3'-dichlorodiphenylmethane
  • CL-MDA
  • DACPM
  • MbOCA
Molecular formula C 13 H 12 Cl 2 N 2
Brief description

flammable, colorless to yellowish solid

External identifiers / databases
CAS number 101-14-4
EC number 202-918-9
ECHA InfoCard 100.002.654
PubChem 7543
ChemSpider 7262
Wikidata Q2257591
properties
Molar mass 267.16 g mol −1
Physical state

firmly

density

1.44 g cm −3

Melting point

110 ° C

boiling point

decomposes, 370 ° C

solubility
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
08 - Dangerous to health 07 - Warning 09 - Dangerous for the environment

danger

H and P phrases H: 302-341-350-410
P: 201-273-281-308 + 313-501
Authorization procedure under REACH

of particular concern : carcinogenic ( CMR ); subject to approval

MAK

Switzerland: 0.02 mg m −3

Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4,4'-methylene-bis (2-chloroaniline) , short MOCA is a chemical compound that since 1954 as crosslinkers of TDI - polyurethanes is used (PU).

presentation

4,4'-methylenebis (2-chloroaniline) is produced commercially by reacting formaldehyde with ortho-chloroaniline . Technical products typically contain 90–92% 4,4′-methylenebis (2-chloroaniline).

Health hazards

MOCA has long been suspected of being carcinogenic. The International Agency for Research on Cancer of the WHO classifies u. a. Based on reliable knowledge about the mechanism of carcinogenesis in animals, MOCA has been in the highest group 1 since 2012: " carcinogenic for humans". The EU Commission therefore proposed in April 2018 that a new limit value for MOCA should be set by law in the third amendment to the Carcinogens and Mutagens Directive (KM Directive) in order to be able to better protect workers.

Individual evidence

  1. ↑ a b c d e f g Entry on 2,2′-dichloro-4,4′-methylenedianiline in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
  2. ^ A b Richard J. Lewis, Sr .: Hawley's Condensed Chemical Dictionary . 15th edition. Wiley-Interscience, 2007, ISBN 978-0-471-76865-4 (English).
  3. ↑ a b U.S. Department of Health and Human Services, Public Health Service: Toxic Substances Portal - 4,4'-Methylenebis (2-Chloroaniline) (MBOCA). In: Agency for Toxic Substances and Disease Registry. September 1995, accessed September 1, 2013 .
  4. ↑ a b European Chemicals Agency (ECHA): Member state committee support document for identification of 2,2'-DICHLORO-4,4'-METHYLENEDIANILINE (PDF; 81 kB) page 5
  5. ↑ Entry on 4,4′-methylenebis [2-chloroaniline] in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. ↑ Entry in the SVHC list of the European Chemicals Agency , accessed on August 20, 2014.
  7. ↑ Entry in the register of substances subject to authorization of the European Chemicals Agency , accessed on August 20, 2014.
  8. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values , accessed on November 2, 2015.
  9. ↑ 4,4'-methylenebis (2-chloroaniline) . In: WHO International Agency for Research on Cancer Monograph Working Group (Ed.): IARC Monographs on the Evaluation of Carciogenic Risks to Humans . tape 99 , 2010, p. 325–367 , doi : 10.1016 / S1470-2045 (08) 70089-5 ( online [PDF; 406 kB ]).
  10. ↑ Birgit Harreither: A little story about the bad networker MbOCA ( Memento from December 20, 2015 in the Internet Archive ) In: FAPU - specialist magazine for the polyurethane industry , 79, 07-08, 2013.
  11. ↑ Chiu-Shong Liu, Saou-Hsing Liou, Ching-Hui Loh, Yi-Chun Yu, Shi-Nian Uang, Tung-Sheng Shih, Hong-I Chen: Occupational Bladder Cancer in a 4,4′-Methylenebis (2- chloroaniline) (MBOCA) exposed workers . In: Environmental Health Perspectives . tape 113 , no. 6 , February 25, 2005, ISSN  0091-6765 , p. 771-774 , doi : 10.1289 / ehp.7666 , PMC 1257605 (free full text).
  12. ↑ IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Volume 100F (2012), page 73f.
  13. ↑ European Commission: Health Protection at Work: Commission proposes new limit values ​​for five carcinogenic chemicals , April 5, 2018.