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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 

 
Title
Formation of Polybrominated Dibenzo-p-dioxins/Furans (PBDDs/Fs) by the Pyrolysis of 2,4-Dibromophenol, 2,6-Dibromophenol, and 2,4,6-Tribromophenol
Author
Yun-Cheol Na, JongKi Hong, Kang-Jin Kim*
Keywords
Pyrolysis, Bromophenol, GC/MS, Formation mechanism
Abstract
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.
Page
547 - 552
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