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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 4
BKCSDE 28(4)
April 20, 2007 

Formation of Polybrominated Dibenzo-p-dioxins/Furans (PBDDs/Fs) by the Pyrolysis of 2,4-Dibromophenol, 2,6-Dibromophenol, and 2,4,6-Tribromophenol
Yun-Cheol Na, JongKi Hong, Kang-Jin Kim*
Pyrolysis, Bromophenol, GC/MS, Formation mechanism
This study examined the thermal reactions of 2,4-dibromophenol (diBP), 2,6-diBP and 2,4,6-triBP. The products obtained under pyrolytic conditions were analyzed by gas chromatography/mass spectrometry (GC/MS). 2,7-dibromodibenzo-p-dioxin (diBDD) was the major compound produced from the thermal reaction of 2,4-diBP. In addition, monoBDD and triBDDs were obtained through a process of debromination and bromination, respectively. The pyrolysis of 2,6-diBP and 2,4,6-triBP produced two major brominated dioxin isomers through direct condensation and a Smiles rearrangement. The two ortho-Brs in 2,6-diBP and 2,4,6-triBP mainly led to the production of dioxins, whereas in addition to 2,7-diBDD, 2,4-diBP produced two furans as minor products, 2,8-dibromodibenzofuran (diBDF) and 2,4,8-triBDF, through the intermediate dihydroxybiphenyl (DOHB). The maximum yield of the major dioxins was obtained at 400 oC, and decomposition by debromination at 500 oC resulted in less substituted bromodioxins.
547 - 552
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