Abstract
The polybrominated biphenyl (PBB) fire retardant, FireMaster FF-1, was pyrolyzed for 20 min at 380-400 degrees C in open glass tubes and in tubes sealed after nitrogen flushing. The pyrolyzed residue was extracted with benzene, and extracts were cleaned up on columns of graphite (Carbopack A) and alumina. Analysis was carried out by low resolution direct probe mass spectrometry (MS). Spectra from extracts of the open tube pyrolyzed material had a series of ions characteristic of tetra- and pentabrominated dibenzofurans as evidenced by comparison with spectra from 2,3,7,8-tetrabromodibenzofuran (TBDF). Confirmatory evidence for the brominated dibenzofurans was obtained by high resolution MS dual ion analysis of certain fragment and molecular ions. Recovery values of TBDF through the cleanup procedure averaged 50% and, using this recovery value and TBDF as an external standard, dual ion analyses indicated that 40 ppm tetra- and 4 ppm pentabrominanted dibenzofuran were produced based on the PBB level used in the pyrolysis experiments. Additional analysis of the open tube pyrolyzed material by gas chromatography/mass spectrometry provided evidence that there was one tetrabromodibenzofuran compound with a retention time equal to that of TBDF. Trace levels (less than 1 ppm) of the molecular ion of tetrabrominated dibenzofuran were found after analysis by low resolution MS of the PBB pyrolyzed under nitrogen in sealed tubes. The experimental evidence is consistent with a mechanism for brominated dibenzofuran formation involving attack of oxygen on PBB compounds.
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Selected References
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- Andersson K., Norström A., Rappe C., Rasmuson B., Swahlin H. Photochemical degradation of PCB, PBB and other flame retardants. Environ Qual Saf Suppl. 1975;3:798–802. [PubMed] [Google Scholar]
- Bowes C. W., Mulvihill M. J., Simoneit B. R., Burlingame A. L., Risebrough R. W. Identification of chlorinated dibenzofurans in American polychlorinated biphenyls. Nature. 1975 Jul 24;256(5515):305–307. doi: 10.1038/256305b0. [DOI] [PubMed] [Google Scholar]
- Bowes G. W., Simoneit B. R., Burlingame A. L., de Lappe B. W., Risebrough R. W. The search for chlorinated dibenzofurans and chlorinated dibenzodioxins in wildlife populations showing elevated levels of embryonic death. Environ Health Perspect. 1973 Sep;5:191–198. doi: 10.1289/ehp.7305191. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Carter L. J. Michigan's PBB Incident: Chemical Mix-Up Leads to Disaster. Science. 1976 Apr 16;192(4236):240–243. doi: 10.1126/science.192.4236.240. [DOI] [PubMed] [Google Scholar]
- Hass J. R., McConnell E. E., Harvan D. J. Chemical and toxicologic evaluation of firemaster BP-6. J Agric Food Chem. 1978 Jan-Feb;26(1):94–99. doi: 10.1021/jf60215a006. [DOI] [PubMed] [Google Scholar]
- Jacobs L. W., Chou S. F., Tiedje J. M. Fate of polybrominated biphenyls (PBB's) in soils. Persistence and plant uptake. J Agric Food Chem. 1976 Nov-Dec;24(6):1198–1201. doi: 10.1021/jf60208a005. [DOI] [PubMed] [Google Scholar]
- Kay K. Polybrominated biphenyls (PBB) environmental contamination in Michigan, 1973-1976. Environ Res. 1977 Feb;13(1):74–93. doi: 10.1016/0013-9351(77)90006-8. [DOI] [PubMed] [Google Scholar]
- Kimbrough R. D. The toxicity of polychlorinated polycyclic compounds and related chemicals. CRC Crit Rev Toxicol. 1974 Jan;2(4):445–498. doi: 10.3109/10408447309025705. [DOI] [PubMed] [Google Scholar]
- Roach J. A., Pomerantz I. H. The finding of chlorinated dibenzofurans in a Japanese polychlorinated biphenyl sample. Bull Environ Contam Toxicol. 1974 Sep;12(3):338–342. doi: 10.1007/BF01709129. [DOI] [PubMed] [Google Scholar]
- Vos J. G., Koeman J. H., van der Maas H. L., ten Noever de Brauw M. C., de Vos R. H. Identification and toxicological evaluation of chlorinated dibenzofuran and chlorinated naphthalene in two commercial polychlorinated biphenyls. Food Cosmet Toxicol. 1970 Dec;8(6):625–633. doi: 10.1016/s0015-6264(70)80451-5. [DOI] [PubMed] [Google Scholar]