Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 13:20, 13 February 2011 editTassedethe (talk | contribs)Autopatrolled, Administrators1,374,192 editsm WPCleaner 0.99 - Repairing link to disambiguation page - (You can help) - REACH← Previous edit		Latest revision as of 03:53, 11 February 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,087 edits Added bibcode. | Use this bot. | #UCB_Other
(74 intermediate revisions by 50 users not shown)
Line 1:		Line 1:
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 407447227
			| Watchedfields = changed
			| verifiedrevid = 413681246
	| ImageFile = Tetrabromobisphenol A.svg		| ImageFile = Tetrabromobisphenol A.svg
			| PIN = 4,4′-(Propane-2,2-diyl)bis(2,6-dibromophenol)
	| IUPACName = 2,2',6,6'-Tetrabromo-4,4'-isopropylidenediphenol
	| OtherNames = 2,2',6,6'-Tetrabromobisphenol A, 2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane, 4,4'-Isopropylidenebis(2,6-dibromophenol)		| OtherNames = 2,2′,6,6′-Tetrabromobisphenol A, 2,2′,6,6′-Tetrabromo-4,4′-isopropylidenediphenol, 2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane, 4,4′-Isopropylidenebis(2,6-dibromophenol)
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| Abbreviations = TBBPA, TBBP-A, TBBA		| Abbreviations = TBBPA, TBBP-A, TBBA
			| CASNo_Ref = {{cascite|correct|CAS}}
	| Formula = C<sub>15</sub>H<sub>12</sub>Br<sub>4</sub>O<sub>2</sub>
	| CASNo_Ref = {{cascite}}
	| CASNo = 79-94-7		| CASNo = 79-94-7
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| EINECS =
	| PubChem =		| ChEBI = 33217
	| SMILES =		| ChEMBL = 184450
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| InChI =
			| ChemSpiderID = 6366
	}}
			| EINECS = 201-236-9
	| Section2 = {{Chembox Properties
			| PubChem = 6618
	| MolarMass = 543.9 g·]<sup>−1</sup>
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| Density = 2,12 g·cm<sup>−3</sup> (20 °C)<ref name="GESTIS">{{GESTIS|Name=Tetrabromobisphenol A|ZVG=24370|Date=2008/2/15}}</ref>
	| Solubility =		| KEGG = C13620
			| MeSHName = C443737
	| MeltingPt = 178 °C<ref name="GESTIS"/>
			| UNII_Ref = {{fdacite|correct|FDA}}
	| BoilingPt = 250 °C (decomposition)<ref name="GESTIS"/>
	| pKa =		| UNII = FQI02RFC3A
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
	| pKb =
			| StdInChI = 1S/C15H12Br4O2/c1-15(2,7-3-9(16)13(20)10(17)4-7)8-5-11(18)14(21)12(19)6-8/h3-6,20-21H,1-2H3
	| IsoelectricPt =
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
	| DeltaHf =
			| StdInChIKey = VEORPZCZECFIRK-UHFFFAOYSA-N
	| DeltaHc =
			| SMILES = CC(C)(c1cc(Br)c(O)c(Br)c1)c1cc(Br)c(O)c(Br)c1
	}}
			}}
	| Section7 = {{Chembox Hazards
			|Section2={{Chembox Properties
	| EUClass =
			| Formula = C<sub>15</sub>H<sub>12</sub>Br<sub>4</sub>O<sub>2</sub>
			| MolarMass = 543.9 g·]<sup>−1</sup>
			| Density = 2,12 g·cm<sup>−3</sup> (20 °C)<ref name="GESTIS">{{GESTIS|Name=Tetrabromobisphenol A|ZVG=24370|Date=2008/2/15}}</ref>
			| Solubility = insoluble
			| MeltingPtC = 178
			| MeltingPt_ref = <ref name="GESTIS"/>
			| BoilingPtC = 250
			| BoilingPt_notes = (decomposition)<ref name="GESTIS"/>
			| pKa =
			| pKb =
			| IsoelectricPt =
			}}
			|Section7={{Chembox Hazards
	| MainHazards = N<ref name="GESTIS"/>		| MainHazards = N<ref name="GESTIS"/>
	| NFPA-H =		| NFPA-H =
	| NFPA-F =		| NFPA-F =
	| NFPA-R =		| NFPA-R =
			| GHSPictograms = {{GHS09}}
	| RPhrases = {{R50/53}}<ref name="GESTIS"/>
			| GHSSignalWord = Warning
	| SPhrases = {{S60}} {{S61}}<ref name="GESTIS"/>
			| HPhrases = {{H-phrases|410}}
	| RSPhrases =
			| PPhrases = {{P-phrases|273|391|501}}
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	| ExploLimits =		| ExploLimits =
	| PEL =		| PEL =
	| RTECS =
	}}		}}
	| Section9 = {{Chembox Related		|Section9={{Chembox Related
	| OtherAnions =		| OtherAnions =
	| OtherCations =		| OtherCations =
	| OtherFunctn =		| OtherFunction =
	| Function =		| OtherFunction_label =
	| OtherCpds =		| OtherCompounds =
	}}		}}
	}}		}}
	'''Tetrabromobisphenol A''' (TBBPA) is a ].
			'''Tetrabromobisphenol A''' ('''TBBPA''') is a ]. The compound is a white solid (not colorless), although commercial samples appear yellow. It is one of the most common ]s.<ref name=Ullmann>{{ Ullmann | author = Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. | title = Bromine Compounds | doi = 10.1002/14356007.a04_405 }}</ref>
	== Synthesis ==
	TBBPA is a ] of ] 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 ==		==Production and use==
			TBBPA is produced by the reaction of bromine with ]. Most commercial TBBPA products consist of a mixture that differ in the degree of bromination with the formula C<sub>15</sub>H<sub>16−x</sub>Br<sub>x</sub>O<sub>2</sub> where x = 1 to 4. Its fire-retarding properties correlate with its bromine content. The annual consumption in Europe has been estimated as 6200 tons in 2004.<ref>{{cite web |title=RISK ASSESSMENT OF 2,2',6,6'-TETRABROMO-4,4'-ISOPROPYLIDENE DIPHENOL (TETRABROMOBISPHENOL-A) |url=https://echa.europa.eu/documents/10162/17c7379e-f47b-4a76-aa43-060da5830c07 |publisher=Environment Agency (UK) |date=June 2007}}</ref>
	TBBPA can be used as reactive and additive ]. In the reactive application, TBBPA is bound chemically to the ]s. The main use are ]s of ]s. As an additive flame retardant it is used in ], 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.<ref>Bromine Science and Environmental Forum: ''''</ref>
			TBBPA is mainly used as a reactive component of polymers, meaning that it is incorporated into the polymer backbone. It is used to prepare fire-resistant ]s by replacing some bisphenol A. A lower grade of TBBPA is used to prepare ]s, used in ]s.<ref name=Ullmann/>
	== Relevance ==
			]<br>
	TBBPA emits from different processes to the environment and can be found in trace concentration in the ], ], ], and ]s. It also occurs in ] and ].<ref>Kuch B, Körner W, Hagenmaier H (2001): ''''. Umwelt und Gesundheit, Universität Tübingen.</ref> TBBPA has been the subject of an eight year evaluation under the EU Risk Assessment procedure which reviewed over 460 studies. The Risk Assessment was published on the EU Official Journal in June 2008.<ref>Official Journal of the European Union: '''', 18.6.2008</ref> TBBPA will now go through ] registration.
	== References ==		==Toxicity==
			A study was published by the European Food Safety Authority (EFSA) in December 2011 on the exposure of TBBPA and its derivatives in food. The study, which examined at 344 food samples from the fish and other seafood food group, concluded that “current dietary exposure to TBBPA in the European Union does not raise a health concern.” EFSA also determined that “additional exposure, particularly of young children, to TBBPA from house dust is unlikely to raise a health concern”.<ref>EFSA Scientific Opinion on Tetrabromobisphenol A (TBBPA) and its derivatives in food (2011) https://efsa.onlinelibrary.wiley.com/doi/abs/10.2903/j.efsa.2011.2477. See page 1.</ref>
	<references/>
			Some studies suggest that TBBPA may be an ] and immunotoxicant. As an endocrine disruptor, TBBPA may interfere with both ]s and ]s.<ref name=HFR1>{{cite journal|last=Shaw|first=S.|author2=Blum, A. |author3=Weber, R. |author4=Kannan, K. |author5=Rich, D. |author6=Lucas, D. |author7=Koshland, C. |author8=Dobraca, D. |author9=Hanson, S. |author10=Birnbaum, L. |title=Halogenated flame retardants: do the fire safety benefits justify the risks?|journal=Reviews on Environmental Health|year=2010|volume=25|issue=4|pages=261–305|doi=10.1515/REVEH.2010.25.4.261|pmid=21268442|s2cid=20573319}}</ref> Further, TBBPA structurally mimics the thyroid hormone ] (T<sub>4</sub>) and can bind more strongly to the transport protein ] than T<sub>4</sub> does, likely interfering with normal T<sub>4</sub> activity. TBBPA likely also suppresses immune responses by inhibiting expression of ] receptors on ]s, preventing their activation, and by reducing ] activity.<ref>{{cite journal|last=Pullen|first=S|author2=Boecker R. |author3=Tiegs G |title=The flame retardants tetrabromobisphenol A and tetrabromobisphenol A–bisallylether suppress the induction of interleukin-2 receptor α chain (CD25) in murine splenocytes|journal=Toxicology|year=2003|volume=184|issue=1|pages=11–22|doi=10.1016/S0300-483X(02)00442-0|pmid=12505372}}</ref><ref>{{cite journal|last=Kibakaya|first=EC|author2=Stephen K |author3=Whalen MM |title=Tetrabromobisphenol A has immunosuppressive effects on human natural killer cells|journal=Journal of Immunotoxicology|year=2009|volume=6|issue=4|pages=285–292|doi=10.3109/15476910903258260|pmid=19908946|pmc=2782892}}</ref>
	== External links ==
	*
	*
			A 2013 literature review on TBBPA concludes that TBBPA does not produce “adverse effects that might be considered to be related to disturbances in the endocrine system”.<ref>{{cite journal | last1 = Colnot | first1 = Thomas | last2 = Kacew | first2 = Sam | last3 = Dekant | first3 = Wolfgang | year = 2013 | title = Mammalian toxicology and human exposures to the flame retardant 2,2′,6,6′-tetrabromo-4,4′-isopropylidenediphenol (TBBPA): implications for risk assessment | journal = Archives of Toxicology | volume = 88| issue = 3| pages = 553–73 | doi=10.1007/s00204-013-1180-8| pmid = 24352537 | s2cid = 15254375 }}</ref> Therefore, in accordance with internationally accepted definitions, TBBPA should not be considered an “endocrine disruptor”. Furthermore, TBBPA is rapidly excreted in mammals and therefore does not have a potential for bioaccumulation. Measured concentrations of TBBPA in house dust, human diet and human serum samples are very low. Daily intakes of TBBPA in humans were estimated to not exceed a few ng/kg bw/day. Exposures of the general population are also well below the derived-no-effect-levels (DNELs) derived for endpoints of potential concern in REACH.
	]
	]
	]
	]
			TBBPA degrades to bisphenol A and to TBBPA dimethyl ether, and experiments in ] (''Danio rerio'') suggest that during development, TBBPA may be more toxic than either BPA or TBBPA dimethyl ether.<ref>{{cite journal|last=McCormick|first=J|author2=Paiva MS |author3=Häggblom MM |author4=Cooper KR |author5=White LA |title=Embryonic exposure to tetrabromobisphenol A and its metabolites, bisphenol A and tetrabromobisphenol A dimethyl ether disrupts normal zebrafish (Danio rerio) development and matrix metalloproteinase expression|journal=Aquatic Toxicology|year=2010|volume=100|issue=3|pages=255–262|doi=10.1016/j.aquatox.2010.07.019|pmid=20728951|pmc=5839324|bibcode=2010AqTox.100..255M}}</ref>
	]
	]
			===Occurrence===
	]
			TBBPA emits can be found in trace concentration in the ], ], and ]s.<ref>{{cite journal |last1=Covaci |first1=Adrian |last2=Voorspoels |first2=Stefan |last3=Abdallah |first3=Mohamed Abou-Elwafa |last4=Geens |first4=Tinne |last5=Harrad |first5=Stuart |last6=Law |first6=Robin J. |title=Analytical and environmental aspects of the flame retardant tetrabromobisphenol-A and its derivatives |journal=Journal of Chromatography A |date=January 2009 |volume=1216 |issue=3 |pages=346–363 |doi=10.1016/j.chroma.2008.08.035|pmid=18760795 }}</ref> It also occurs in ] and ].<ref>Kuch B, Körner W, Hagenmaier H (2001): '' {{Webarchive|url=https://web.archive.org/web/20031229161020/http://www.bwplus.fzk.de/berichte/SBer/BWB99011SBer.pdf |date=2003-12-29 }}''. Umwelt und Gesundheit, Universität Tübingen.</ref> TBBPA has been the subject of an eight-year evaluation under the EU Risk Assessment procedure which reviewed over 460 studies. The Risk Assessment was published on the EU Official Journal in June 2008.<ref>''''</ref> The conclusions of the Risk Assessment were confirmed by the European Commission SCHER Committee (Scientific Committee on Health and Environmental Risks<ref>European Union Risk Assessment Report on TBBPA (2008) http://echa.europa.eu/documents/10162/32b000fe-b4fe-4828-b3d3-93c24c1cdd51</ref>). TBBPA has been registered under REACH.<ref>TBBPA REACH Registration webpage http://echa.europa.eu/web/guest/information-on-chemicals/registered-substances</ref>
	]
	]
			==See also==
			* ]
			==Further reading==
			* Early work on bromination of BPA: {{cite journal | last=Zincke |first=T. |title=Ueber die Einwirkung von Brom und von Chlor auf Phenole: Substitutionsprodukte, Pseudobromide und Pseudochloride | journal=] | year = 1905 | pages = 75–99 | doi = 10.1002/jlac.19053430106 | volume = 343|url=https://zenodo.org/record/1427557 }}
			==References==
			{{Reflist}}
			==External links==
			* BSEF,
			* BSEF, industry page on TBBPA:
			]
			]
			]
			]
			]
			]