Synthesis of the two minor isomers, δ- and ε-1,2,5,6,9,10-hexabromocyclododecane, present in commercial hexabromocyclododecane

Autor: Alan McAlees, Chris Marvin, Alexandre Konstantinov, Nicole Riddell, Gregg T. Tomy, Gilles Arsenault, Robert McCrindle, Gordia MacInnis, Brian Yeo
Rok vydání: 2007
Předmět:
Zdroj: Chemosphere. 68:887-892
ISSN: 0045-6535
DOI: 10.1016/j.chemosphere.2007.02.005
Popis: Hexabromocyclododecane (HBCD) is prepared commercially by bromination of cis,trans,trans-cyclododecatriene (ctt-CDT) and widely used as a flame retardant, particularly in polystyrene foams. Commercial HBCD consists largely of three diastereomers, alpha-, beta-, and gamma-HBCD, the structures of which have been known for many years. Recently, the presence in the mixture of small amounts of two minor diastereomers, delta- and epsilon-HBCD, has been reported. Bearing in mind the manner in which commercial HBCD is generated, it was anticipated that these components are probably formed by bromination of trans,trans,trans-cyclododecatriene (ttt-CDT), a common contaminant in commercial ctt-CDT. Indeed, when a sample of ttt-CDT was brominated it gave two products, the NMR spectra and LC/MS and GC/MS behaviour of which confirmed that they are identical to the minor components, delta- and epsilon-HBCD, present in commercial HBCD.
Databáze: OpenAIRE