Chlorinated benzo-1,2-quinones: an example of chemical transformation of toxicants during tests with aquatic organisms
- Swedish Environmental Research Institute, Stockholm (Sweden)
An analytical procedure specific for chlorinated benzo-1,2-quinones has been developed to examine the stability of these compounds under conditions used for investigating their toxicity to aquatic organisms. Solutions of the compounds in a number of organic solvents were unstable in the light, and addition of acetone solutions to water brought about rapid decomposition of the chloroquinones which had half-lives less than 0.5 hr: the corresponding chlorocatechols were the principal products. The kinetics of decomposition of tetrachlorobenzo-1,2-quinone in aqueous solutions were studied in detail and showed the formation of tetrachlorocatechol, 2,5-dichloro-3,6-dihydroxybenzo-1,4-quinone, 1,2,3-trihydroxy-4,5,6-trichlorobenzene, 1,2,4-trihydroxy-3,5,6-trichlorobenzene, dichloromaleic acid, and a trichlorocyclopentendione. In organic solvents in the light, 3,4,5-trichlorobenzo-1,2-quinone underwent a dismutation reaction with formation of 3,4,5-trichloro- and tetrachlorocatechol; in a comparable reaction, 4,5-dichlorobenzo-1,2-quinone formed 4,5-dichlorocatechol and 3,4,5-trichlorocatechol. The toxicity of aqueous solutions prepared by dilution of freshly prepared acetone solutions of tetrachlorobenzo-1,2-quinone was examined in the zebra fish embryo/larvae test, and it was found that the threshold toxic concentration could be accounted for entirely by the analytically established concentration of tetrachlorocatechol produced as a chemical transformation product. It is concluded that in toxicological examination of reactive compounds, exposure to the toxicant should be assessed from concentrations analytically determined during the experiments and that attention be directed to both the nature and the toxicity of the transformation products.
- OSTI ID:
- 5679337
- Journal Information:
- Ecotoxicology and Environmental Safety; (United States), Journal Name: Ecotoxicology and Environmental Safety; (United States) Vol. 22:3; ISSN EESAD; ISSN 0147-6513
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ACETYLATION
ACYLATION
ANIMALS
AQUATIC ORGANISMS
AQUEOUS SOLUTIONS
AROMATICS
BENZOQUINONES
BIOLOGICAL HALF-LIFE
CHEMICAL REACTIONS
CHEMISTRY
CHLORINATED AROMATIC HYDROCARBONS
CHROMATOGRAPHY
DISPERSIONS
FISHES
GAS CHROMATOGRAPHY
HALOGENATED AROMATIC HYDROCARBONS
MASS SPECTROSCOPY
MIXTURES
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHOTOCHEMISTRY
QUINONES
SENSITIVITY
SEPARATION PROCESSES
SOLUTIONS
SPECTROSCOPY
STABILITY
TOXICITY
VERTEBRATES