title: Synthesis of the two minor isomers, delta- and epsilon-1,2,5,6,9,10-hexabromocyclododecane, present in commercial hexabromocyclododecane.
abstract: 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.
authors.affiliation: Wellington Laboratories Inc., Research Division, 345 Southgate Drive, Guelph, Ont., Canada N1G 3M5. gilles@well-labs.com
authors.forename: Gilles
authors.initials: G
authors.lastname: Arsenault
authors.forename: Alexandre
authors.initials: A
authors.lastname: Konstantinov
authors.forename: Chris H
authors.initials: CH
authors.lastname: Marvin
authors.forename: Gordia
authors.initials: G
authors.lastname: MacInnis
authors.forename: Alan
authors.initials: A
authors.lastname: McAlees
authors.forename: Robert
authors.initials: R
authors.lastname: McCrindle
authors.forename: Nicole
authors.initials: N
authors.lastname: Riddell
authors.forename: Gregg T
authors.initials: GT
authors.lastname: Tomy
authors.forename: Brian
authors.initials: B
authors.lastname: Yeo
mesh_terms: D002853:Chromatography, Liquid; D005411:Flame Retardants / Q000138:chemical synthesis; D008401:Gas Chromatography-Mass Spectrometry; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005411:Flame Retardants; D006842:Hydrocarbons, Brominated; C089796:hexabromocyclododecane