Reactions of PCBs and other polychlorinated aromatics with sodium and potassium salts of polyethylene glycols
Polychlorinated biphenyls (PCBs) are of major environmental and toxicological concern for several reasons. PCBs are generally water-insoluble and fat-soluble, therefore they accumulate in living tissue. A variety of toxic responses to PCBs by humans and animals has been reported. PCBs are also very resistant to thermal and chemical degradation. They are, however, easily attacked by reactive species such as alkali metals and strong bases. The high solubility of PCBs in PEGs facilitates the nucleophilic substitution of chloride by strong base in PEG solution. Chlorinated aromatic compounds undergo chlorine substitution by a variety of mechanisms. The bimolecular S/sub N/Ar mechanism is the preferred route in the presence of alkali metal hydroxides and primary alkoxides activated by cation-complexing agents such as polyethylene glycols (PEG). The chloride is preferentially displaced by the alkoxide group from a reagent comprising an alkali metal hydroxide solution in the cation-complexing alcohol. Cleavage of the ether substitutent occurs with excess alkaline PEG reagent, producing the phenoxide ion. This reaction competes with further chloride substitution on polychlorinated benzenes and biphenyls.
- OSTI ID:
- 5622548
- Country of Publication:
- United States
- Language:
- English
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63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ALCOHOLS
ALKALI METAL COMPOUNDS
AROMATICS
BASES
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORINATED AROMATIC HYDROCARBONS
DATA
EXPERIMENTAL DATA
GLYCOLS
HALOGENATED AROMATIC HYDROCARBONS
HYDROXY COMPOUNDS
INFORMATION
KINETICS
NUMERICAL DATA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC POLYMERS
POLYETHYLENE GLYCOLS
POLYMERS
POTASSIUM COMPOUNDS
REACTION INTERMEDIATES
REACTION KINETICS
SODIUM COMPOUNDS