dechlorane plus
{{short description|Polychlorinated flame retardant}}
{{Other uses|Dechlorane (disambiguation){{!}}Dechlorane}}
{{Chembox
| ImageFile = Dechlorane plus.png
| ImageSize =
| IUPACName = 1,2,3,4,7,8,9,10,13,13,14,14-dodecachloro-1,4,4a,5,6,6a,7,10,10a,11,12,12a-dodecahydro-1,4,7,10-dimethanodibenzo[a,e]cyclooctene
| OtherNames = Dechloran A
|Section1={{Chembox Identifiers
| ChemSpiderID = 24323
| InChI = 1/C18H12Cl12/c19-9-10(20)15(25)7-3-4-8-6(2-1-5(7)13(9,23)17(15,27)28)14(24)11(21)12(22)16(8,26)18(14,29)30/h5-8H,1-4H2
| InChIKey = UGQQAJOWXNCOPY-UHFFFAOYAP
| CASNo = 13560-89-9
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 193G0ER097
| EINECS = 236-948-9
| PubChem = 26111
| SMILES = Cl\C2=C(/Cl)C3(Cl)C1CCC4C(CCC1C2(Cl)C3(Cl)Cl)C5(Cl)C(\Cl)=C(\Cl)C4(Cl)C5(Cl)Cl
}}
|Section2={{Chembox Properties
| Formula = C18H12Cl12
| MolarMass = 653.72 g/mol
| Appearance = white, crystalline solid
| Density = 1.8 g/cm3
| MeltingPtC = 350
| MeltingPt_notes = (decomposes)
| BoilingPt =
| Solubility = 0.044–249 μg/L}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Dechlorane plus (abbrev. DDC-CO{{Cite journal | doi = 10.1016/j.envint.2012.08.003| pmid = 22982223| pmc = 3483428| title = A novel abbreviation standard for organobromine, organochlorine and organophosphorus flame retardants and some characteristics of the chemicals| journal = Environment International| volume = 49| pages = 57–82| year = 2012| last1 = Bergman | first1 = Å. | last2 = Rydén | first2 = A. | last3 = Law | first3 = R. J. | last4 = De Boer | first4 = J. | last5 = Covaci | first5 = A. | last6 = Alaee | first6 = M. | last7 = Birnbaum | first7 = L. | last8 = Petreas | first8 = M. | last9 = Rose | first9 = M. | last10 = Sakai | first10 = S. | last11 = Van Den Eede | first11 = N. | last12 = Van Der Veen | first12 = I. }}) is a polychlorinated flame retardant produced by Oxychem.
Its log P is 11.27±0.94.{{Cite web|url=https://echa.europa.eu/registration-dossier/-/registered-dossier/11906/4/8|title=1,6,7,8,9,14,15,16,17,17,18,18-dodecachloropent... - Registration Dossier - ECHA|website=echa.europa.eu|language=en-GB|access-date=2020-03-18}}
It is produced by the Diels-Alder reaction of two equivalents of hexachlorocyclopentadiene with one equivalent of cyclooctadiene. The syn and anti isomer are formed in the approximate ratio of 1:3.{{Cite journal | doi = 10.1021/es2003028| pmid = 21574656| title = Dechlorane Plus and Related Compounds in the Environment: A Review| journal = Environmental Science & Technology| volume = 45| issue = 12| pages = 5088–5098| year = 2011| last1 = Sverko | first1 = E. | last2 = Tomy | first2 = G. T. | last3 = Reiner | first3 = E. J. | last4 = Li | first4 = Y. F. | last5 = McCarry | first5 = B. E. | last6 = Arnot | first6 = J. A. | last7 = Law | first7 = R. J. | last8 = Hites | first8 = R. A. | bibcode = 2011EnST...45.5088S}}{{Cite journal | doi = 10.1016/S0040-4039(00)92688-1| title = Tandem reverse-electron-demand diels-alder reactions of 1,5-cyclooctadiene| journal = Tetrahedron Letters| volume = 32| issue = 28| pages = 3289–3292| year = 1991| last1 = Garcia | first1 = J. G. | last2 = Fronczek | first2 = F. R. | last3 = McLaughlin | first3 = M. L. }}
Dechlorane plus syn isomer.svg|syn isomer
Dechlorane plus anti isomer.svg|anti isomer
Environmental concerns
Dechlorane plus was first found in the environment in 2006 in air around the Great Lakes.{{cite journal|last=Hoh|first=Eunha|author2=Lingyan Zhu |author3=Ronald A. Hites |title=Dechlorane Plus, a chlorinated flame retardant, in the Great Lakes|journal=Environmental Science & Technology|year=2006|volume=40|issue=4|pages=1184–1189|doi=10.1021/es051911h|pmid=16572773|bibcode=2006EnST...40.1184H}} Since then, its environmental occurrence has been further documented in several studies including sediments of the Great Lakes;{{cite journal|last=Sverko|first=Ed|author2=Gregg T. Tomy |author3=Chris H. Marvin |author4=Donna Zaruk |author5=Eric Reiner |author6=Paul A. Helm |author7=Brad Hill |author8=Brian E. McCarry |title=Dechlorane plus levels in sediment of the lower Great Lakes|journal=Environmental Science & Technology|year=2007|volume=42|issue=2|pages=361–366 |doi=10.1021/es0710104|pmid=18284131}} zooplankton, fish, and mussels in Lake Winnipeg and Lake Ontario;{{cite journal|last=Tomy|first=Gregg|author2=Kerri Pleskach |author3=Nargis Ismail |author4=D. Michael Whittle |author5=Paul A. Helm |author6=E. D. Sverko |author7=Donna Zaruk |author8=Chris H. Marvin |title=Isomers of dechlorane plus in Lake Winnipeg and Lake Ontario food webs|journal=Environmental Science & Technology|year=2007|volume=41|issue=7|pages=2249–2254|doi=10.1021/es062781v|pmid=17438771|bibcode=2007EnST...41.2249T}} air and seawater from the Arctic to Antarctica;{{cite journal|last=Möller|first=Axel|author2=Zhiyong Xie |author3=Renate Sturm |author4=Ralf Ebinghaus |title=Large-scale distribution of Dechlorane Plus in air and seawater from the Arctic to Antarctica|journal=Environmental Science & Technology|year=2010|volume=44|issue=23|pages=8977–8982|doi=10.1021/es103047n|pmid=21047104|bibcode=2010EnST...44.8977M}} and Chinese air.{{cite journal|last=Ren|first=Nanqi |author2=Ed Sverko |author3=Yi-Fan Li |author4=Zhi Zhang |author5=Tom Harner |author6=Degao Wang |author7=Xinnan Wan |author8=Brian E. McCarry|title=Levels and isomer profiles of Dechlorane Plus in Chinese air|journal=Environmental Science & Technology|year=2008|volume=42|issue=17|pages=6476–6480|doi=10.1021/es800479c|pmid=18800517 |bibcode=2008EnST...42.6476R }} In 2011, modeling data indicated that Dechlorane Plus may be persistent, bioaccumulative, and subject to long-range transport.{{cite journal|last=Sverko|first=Ed |author2=Gregg T. Tomy |author3=Eric J. Reiner |author4=Yi-Fan Li |author5=Brian E. McCarry |author6=Jon A. Arnot |author7=Robin J. Law |author8=Ronald A. Hites|title=Dechlorane plus and related compounds in the environment: a review|journal=Environmental Science & Technology|year=2011|volume=45|issue=12|pages=5088–5098|doi=10.1021/es2003028|pmid=21574656 |bibcode=2011EnST...45.5088S }} The 2023 Conference of the Parties of the United Nations Stockholm Convention on Persistent Organic Pollutants took the decision to eliminate the use of Dechlorane Plus, by listing this chemical in Annex A to the Convention.{{cite web |title=Governments accelerate action and take bold decisions to address pollution from chemicals and wastes |url=https://www.brsmeas.org/MediaHub/News/PressReleases/OutcomesCOPs2023/tabid/9569/language/en-US/Default.aspx |publisher=Secretariat of the Basel, Rotterdam and Stockholm Conventions |access-date=6 July 2023 |date=May 15, 2023}}
Dechlorane plus was added to the list of REACH Substances of Very High Concern on January 15, 2018.{{cite web|url=https://echa.europa.eu/candidate-list-table/-/dislist/details/0b0236e181f392bf|website=European Chemicals Agency|title=1,6,7,8,9,14,15,16,17,17,18,18-Dodecachloropentacyclo[12.2.1.16,9.02,13.05,10]octadeca-7,15-diene ("Dechlorane Plus"™) - Candidate List of substances of very high concern for Authorisation - ECHA|publisher=ECHA|accessdate=January 16, 2018}}
Literature
- {{cite web|url=http://www.epa.gov/HPV/pubs/summaries/dechlorp/c15635.pdf |title=Dechlorane Plus High Production Volume (HPV) Chemical Challenge Program Test Plan. 201-15635 |last=ENVIRON Health Sciences Institute |url-status=dead |archiveurl=https://web.archive.org/web/20121023010826/http://www.epa.gov/HPV/pubs/summaries/dechlorp/c15635.pdf |archivedate=2012-10-23 }}
References
{{DEFAULTSORT:Dechlorane Plus}}
Category:Persistent organic pollutants under the Stockholm Convention