55720-44-0Relevant academic research and scientific papers
Synthesis of chlorinated biphenyls by Suzuki cross-coupling using diamine or diimine-palladium complexes
Kylmaelae, Tuula,Kuuloja, Noora,Xu, Youjun,Rissanen, Kari,Franzen, Robert
experimental part, p. 4019 - 4024 (2009/04/11)
Several novel diimines (Salen-type ligands) 2a-2i and their reduced diamine counterparts 3b,3d-3g and 3i form complexes 4a-4i, 5b,5d-5g, and 5i with PdCl2 in DMF or methanol. Using 1 mol-% of the isolated complexes 4e and 5f many polychlorinated biphenyls (PCBs) can be prepared in moderate to excellent yields according to the Suzuki cross-coupling protocol with contact to air. Several 4-acetylbiphenyls prepared by this method can be converted in moderate yields into the corresponding biphenylcarboxylic acids (BCAs) by alkaline cleavage. An X-ray crystal structure determination confirms the structure of complex 5f. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Polychlorinated biphenyl reductive dechlorination by vitamin B12s: Thermodynamics and regiospecificity
Woods, Sandra L.,Trobaugh, Darin J.,Carter, Kim J.
, p. 857 - 863 (2007/10/03)
Microbial reductive dechlorination reactions play an important role in determining the environmental fate of polychlorinated biphenyls (PCBs), especially for PCB congeners with more than four chlorines. Powerful chemical catalysts such as vitamin B12s provide an effective tool for the study of reductive dechlorination reactions. The reductive dechlorination of PCBs by titanium(III) citrate-reduced vitamin B12s was studied in batch reactors. Long-term experiments demonstrated reductive dechlorination of aqueous and sediment-sorbed 2,3,4,5,6-pentachlorobiphenyl (2,3,4,5,6-PeCB) to tetra-, tri-, di-, and monochlorobiphenyl products. Approximately 10% chlorine removal was observed in 36 days in aqueous experiments at 20°C; the sediment experiment showed 40% chlorine removal in 42 days at 30°C. Nearly all possible intermediates were produced and reductively dechlorinated, with no apparent accumulation of individual congeners. Short-term experiments were conducted to determine the pathway forvitamin B12s-catalyzed reductive dechlorination of aqueous 2,3,4,5,6-PeCB and its dechlorinated products; relative product distributions were measured for all possible tetra-and trichlorobiphenyl reductive dechlorination reactions. Theoretical product distributions based on free energies of formation agreed with observed product distributions for short-and long-term experiments. Reductive dechlorination was favored at positions with adjacent chlorines; on average, chlorines were removed equally from ortho, meta, and para positions.
Phototransformations of polychlorobiphenyls in brij 58 micellar solutions
Chu, Wei,Jafvert, Chad T.,Diehl, Claude A.,Marley, Karen,Larson, Richard A.
, p. 1989 - 1993 (2007/10/03)
Our purpose in conducting these studies was to examine photolysis as a destructive process for polychlorobiphenyls (PCBs) extracted from soils with surfactant solutions. Surfactants have shown promise as agents for removing free phase and sorbed contaminants from soils, yet information on ultimate disposal options and recycle/recovery strategies for the surfactants is generally lacking. For arylhalides, photodechlorination may result in decontamination, eliminating the need to physically separate these contaminants from the washing solution. Photochemical reactions of the PCB congener mixture, Aroclor 1254, and the specific congener, 2,3,4,5- tetrachlorobiphenyl (2,3,4,5-TeCB), were investigated in aqueous solutions containing surfactant micelles with UV light at 253.7 nm. Photoreduction through photodechlorination was shown to be the main decay pathway in which lesser chlorinated congeners were formed as intermediates. In experiments with 2,3,4,5-TeCB, final noncarbon-containing products included Cl- and H+, both produced nearly stoichiometrically from the starting materials. The quantum yield for decay of 0.1 μM 2,3,4,5-TeCB in 0.5 mM Brij 58 micellar solutions was over six times greater than in water alone. Sequential extraction from a soil and photoreduction of 2,3,4,5-tetrachlorobiphenyl by Brij 58 solutions proved to be limited by surfactant loss to the soil. Our purpose in conducting these studies was to examine photolysis as a destructive process for polychlorobiphenyls (PCBs) extracted from soils with surfactant solutions. Surfactants have shown promise as agents for removing free phase and sorbed contaminants from soils, yet information on ultimate disposal options and recycle/recovery strategies for the surfactants is generally lacking. For arylhalides, photodechlorination may result in decontamination, eliminating the need to physically separate these contaminants from the washing solution. Photochemical reactions of the PCB congener mixture, Aroclor 1254, and the specific congener, 2,3,4,5-tetrachlorobiphenyl (2,3,4,5-TeCB), were investigated in aqueous solutions containing surfactant micelles with UV light at 253.7 nm. Photoreduction through photodechlorination was shown to be the main decay pathway in which lesser chlorinated congeners were formed as intermediates. In experiments with 2,3,4,5-TeCB, final noncarbon-containing products included Cl- and H+, both produced nearly stoichiometrically from the starting materials. The quantum yield for decay of 0.1 μM 2,3,4,5-TeCB in 0.5 mM Brij 58 micellar solutions was over six times greater than in water alone. Sequential extraction from a soil and photoreduction of 2,3,4,5-tetrachlorobiphenyl by Brij 58 solutions proved to be limited by surfactant loss to the soil.
Physical, spectral and chromatographic properties of all 209 individual PCB congeners
Bolgar,et al.
, p. 2687 - 2705 (2007/10/03)
Through the use of two capillary GC columns: 40% octadecyl/ 15% phenyl methyl siloxane and 50% phenyl methyl siloxane, it was possible to separate 201 PCB congeners with only four unresolved pairs. The data compiled in this study for all 209 congeners will aid in the identification of selected individual components of these environmental pollutants. The use of this data also presents the opportunity for the improved quantification of the commercial PCB formulations. -from Authors
