Hexabromobiphenyl

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of 2,2 ', 4,4', 5,5'-hexabromobiphenyl
Mixture of substances -
one of 42 congeners
General
Surname Hexabromobiphenyl
other names
  • Hexabromo-1,1'-biphenyl
  • FireMaster BP-6b
  • FireMaster FF-1b
Molecular formula C 12 H 4 Br 6
Brief description

white solid

External identifiers / databases
CAS number
  • 36355-01-8
  • 59536-65-1 (BP-6)
  • 67774-32-7 (FF-1)
PubChem 154482
Wikidata Q27095544
properties
Molar mass 627.59 g mol −1
Physical state

firmly

Melting point

72 ° C

solubility

practically insoluble in water, soluble in acetone and benzene

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexabromobiphenyl is a mixture of up to 42 chemical compounds ( congeners ) from the group of aromatic halogenated hydrocarbons , more precisely the polybrominated biphenyls (PBB). It has a biphenyl backbone (two benzene rings linked by a single bond ) on which six hydrogen atoms have been replaced by bromine atoms . Production and use have been banned worldwide since 2010.

Extraction and presentation

In general, PBB are produced by bromination of biphenyl using aluminum chloride (AlCl 3 ) as a catalyst . The reaction also produces other polybrominated biphenyls, which means that the technical products such as FireMaster FF-1 and FireMaster BP-6 also contain a number of other PBBs in addition to the congeners, especially pentabromobiphenyls and heptabromobiphenyls, but also other compounds such as hexabromonaphthalene . The main components of these two products are the congeners 2,2 ', 4,4', 5,5'-hexabromobiphenyl (BB-153) with a proportion of about 50% and 2,2 ', 3,4,4', 5, 5'-heptabromobiphenyl (BB-180) with a proportion of 7 to 25%.

use

Hexabromobiphenyl has been used as a flame retardant in many plastics and textiles since the 1970s and is the most common from PBB. In electronic waste an average concentration of 3 was used in a 2011 study conducted  ppm found what the presence of HBB confirmed in electronic devices.

safety instructions

PBB are long-lived organic pollutants (POP) and are suspected of being toxic , carcinogenic and liver-damaging . In addition, toxic properties with consequences such as memory and muscle weakness and immune deficiencies are suspected. Therefore, since July 1, 2006, according to the Electrical and Electronic Equipment Act (ElektroG of March 16, 2005) and EU Regulation 2002/95 / EC ( RoHS ), it has been prohibited to put new electrical and electronic devices on the market that have more than 0 , 1 percent by weight of PBB per homogeneous material. The use of textiles is prohibited. In the wild, hexabromobiphenyl has been linked to increased cancer rates in Tasmanian devils . In May 2009, hexabromobiphenyl was included in Appendix A of the Stockholm Convention , so its manufacture and use has been banned worldwide since 2010.

Congeners

The congeners of hexabromobiphenyl are:

  • BB-128, 2,2 ', 3,3', 4,4'-hexabromobiphenyl, CAS number: 82865-89-2
  • BB-129, 2,2 ', 3,3', 4,5-hexabromobiphenyl
  • BB-130, 2,2 ', 3,3', 4,5'-hexabromobiphenyl, CAS number: 82865-90-5
  • BB-131, 2,2 ', 3,3', 4,6-hexabromobiphenyl,
  • BB-132, 2,2 ', 3,3', 4,6'-hexabromobiphenyl, CAS number: 119264-50-5
  • BB-133, 2,2 ', 3,3', 5,5'-hexabromobiphenyl, CAS number: 55066-76-7
  • BB-134, 2,2 ', 3,3', 5,6-hexabromobiphenyl,
  • BB-135, 2,2 ', 3,3', 5,6'-hexabromobiphenyl, CAS number: 119264-51-6
  • BB-136, 2,2 ', 3,3', 6,6'-hexabromobiphenyl,
  • BB-137, 2,2 ′, 3,4,4 ′, 5-hexabromobiphenyl, CAS number: 81381-52-4
  • BB-138, 2,2 ', 3,4,4', 5'-hexabromobiphenyl, CAS number: 67888-98-6
  • BB-139, 2,2 ', 3,4,4', 6-hexabromobiphenyl,
  • BB-140, 2,2 ', 3,4,4', 6-hexabromobiphenyl,
  • BB-141, 2,2 ', 3,4,5,5'-hexabromobiphenyl, CAS number: 120991-47-1
  • BB-142, 2,2 ′, 3,4,5,6-hexabromobiphenyl,
  • BB-143, 2,2 ', 3,4,5,6'-hexabromobiphenyl,
  • BB-144, 2,2 ′, 3,4,5 ′, 6-hexabromobiphenyl, CAS number: 119264-52-7
  • BB-145, 2,2 ', 3,4,6,6'-hexabromobiphenyl,
  • BB-146, 2,2 ', 3,4', 5,5'-hexabromobiphenyl,
  • BB-147, 2,2 ', 3,4', 5,6-hexabromobiphenyl,
  • BB-148, 2,2 ', 3,4', 5,6'-hexabromobiphenyl,
  • BB-149, 2,2 ′, 3,4 ′, 5 ′, 6-hexabromobiphenyl, CAS number: 69278-59-7
  • BB-150, 2,2 ', 3,4', 6,6'-hexabromobiphenyl, CAS number: 93261-83-7
  • BB-151, 2,2 ′, 3,5,5 ′, 6-hexabromobiphenyl, CAS number: 119264-53-8
  • BB-152, 2,2 ', 3,5,6,6'-hexabromobiphenyl
  • BB-153, 2,2 ', 4,4', 5,5'-hexabromobiphenyl, CAS number: 59080-40-9
  • BB-154, 2,2 ', 4,4', 5,6'-hexabromobiphenyl, CAS number: 36402-15-0
  • BB-155, 2,2 ', 4,4', 6,6'-hexabromobiphenyl, CAS number: 59261-08-4
  • BB-156, 2,3,3 ′, 4,4 ′, 5-hexabromobiphenyl, CAS number: 77607-09-1
  • BB-157, 2,3,3 ', 4,4', 5'-hexabromobiphenyl, CAS number: 84303-47-9
  • BB-158, 2,3,3 ', 4,4', 6-hexabromobiphenyl
  • BB-159, 2,3,3 ', 4,5,5'-hexabromobiphenyl, CAS number: 120991-48-2
  • BB-160, 2,3,3 ', 4,5,6-hexabromobiphenyl
  • BB-161, 2,3,3 ', 4,5', 6-hexabromobiphenyl
  • BB-162, 2,3,3 ', 4', 5,5'-hexabromobiphenyl
  • BB-163, 2,3,3 ', 4', 5,6-hexabromobiphenyl
  • BB-164, 2,3,3 ′, 4 ′, 5 ′, 6-hexabromobiphenyl, CAS number: 82865-91-6
  • BB-165, 2,3,3 ', 5,5', 6-hexabromobiphenyl
  • BB-166, 2,3,4,4 ', 5,6-hexabromobiphenyl
  • BB-167, 2,3 ', 4,4', 5,5'-hexabromobiphenyl, CAS number: 67888-99-7
  • BB-168, 2,3 ′, 4,4 ′, 5 ′, 6-hexabromobiphenyl, CAS number: 84303-48-0
  • BB-169, 3,3 ', 4,4', 5,5'-hexabromobiphenyl, CAS number: 60044-26-0

Analytical evidence

The chemical-analytical detection in environmental samples, food and animal feed is carried out after suitable sample preparation to separate the matrix and gas chromatographic separation of minor components by high-resolution mass spectrometry techniques such as flight mass spectrometry (Time-Of-Flight mass spectrometry).

Individual evidence

  1. ↑ Emerging Contaminants - Polybrominated Diphenyl Ethers (PBDEs) and Polybrominated Biphenyls (PBBs) (PDF; 79 kB).
  2. ↑ a b c Agency for Toxic Substances and Disease Registry: Polybrominated Biphenyls (PDF; 345 kB).
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ^ Environmental Health Criteria (EHC) for POLYBROMINATED BIPHENYLS , accessed November 19, 2014.
  5. ^ Ruedi Taverna, Rolf Gloor, Urs Maier, Markus Zennegg, Renato Figi, Edy Birchler: Material flows in Swiss electronic waste . Metals, non-metals, flame retardants and polychlorinated biphenyls in small electrical and electronic devices . Federal Office for the Environment , Bern 2017. Environmental status No. 1717: 164 p.
  6. ^ Entry on hexabromobiphenyl in the GESTIS substance database of the IFA , accessed on June 16, 2009(JavaScript required) .
  7. ↑ Innovation report: Flame retardants kill rare Tasmanian devils .
  8. ↑ Secretary-General of the United Nations: Reference: CN524.2009.TREATIES-4 (Depositary Notification) , August 26, 2009.
  9. ↑ Eric J. Reiner, Adrienne R. Boden, Tony Chen, Karen A. MacPherson and Alina M. Muscalu: Advances in the Analysis of Persistent Halogenated Organic Compounds . In: LC GC Europe . 23 (2010) 60-70.