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Tetrabromobisphenol A

Tetrabromobisphenol A

IUPAC name	2,2',6,6'-Tetrabromo-4,4'-isopropylidendiphenol
Other names	2,2',6,6'-Tetrabromobisphenol A, 2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane, 4,4'-Isopropylidenebis(2,6-dibromophenol)
Abbreviations	TBBPA, TBBP-A, TBBA
Molecular formula	C₁₅H₁₂Br₄O₂
Molar mass	543.9 g·mol⁻¹
CAS number	79-94-7
Density	2,12 g·cm⁻³
Melting point	181–182 °C
Boiling point	316 °C
Hazards
Main hazards	N
R-phrases	R50/53
S-phrases	S60 S61
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Tetrabromobisphenol A (TBBPA) is a brominated flame retardant.

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Synthesis

TBBPA is a derivative of bisphenol A and is synthesized from this substance. Most commercial TBBPA products are of a relatively low purity, in fact containing a mixture of products brominated to varying extents. This is not generally considered to be a drawback, since in most applications of this substance (i.e. flame-retarding) it is the average %Br that is of importance. The mixture resulting from the bromination of bisphenol A is therefore not purified, allowing a more efficient, lower cost product.

Uses

TBBPA can be used as reactive and additive flame retardant. In the reactive application, TBBPA is bound chemically to the polymers. The main use are epoxy resins of printed circuit boards. As an additive flame retardant it is used in acrylonitrile butadiene styrene, which are used e.g. in TVs. The annual consumption worldwide has been estimated as 119,600 tons in 2001, of which 11,600 tons were used by the European industry.^[1]

Relevance

TBBPA emits from different processes to the environment and can be found in trace concentration the atmosphere, hydrosphere, soil, and sediments. It also occurs in sewage sludge and house dust.^[2] In an investigation carried out by the WWF, TBBPA was found in blood samples of EU parliamentarians.^[3]

References

^ Bromine Science and Environmental Forum: Major Brominated Flame Retardants Volume Estimates – Total Market Demand By Region in 2001
^ Kuch B, Körner W, Hagenmaier H (2001): Monitoring von bromierten Flammschutzmitteln in Fliessgewässern, Abwässern und Klärschlämmen in Baden-Württemberg. Umwelt und Gesundheit, Universität Tübingen.
^ WWF Detox Campaign (2004): Bad Blood? A Survey of Chemicals in the Blood of European Ministers

Category: Organobromides