Chlorinated benzo-1,2-quinones: an example of chemical transformation of toxicants during tests with aquatic organisms

Journal Article · Sun Dec 01 00:00:00 EST 1991 · Ecotoxicology and Environmental Safety; (United States)

DOI:https://doi.org/10.1016/0147-6513(91)90082-Z· OSTI ID:5679337

Remberger, M; Hynning, P A; Neilson, A H ^[1]

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1. 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), Vol. 22:3; ISSN 0147-6513
• Country of Publication: United States
• Language: English

Related Subjects

63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
BENZOQUINONES
TOXICITY
CHLORINATED AROMATIC HYDROCARBONS
FISHES
SENSITIVITY
ACETYLATION
AQUEOUS SOLUTIONS
BIOLOGICAL HALF-LIFE
GAS CHROMATOGRAPHY
MASS SPECTROSCOPY
PHOTOCHEMISTRY
STABILITY
ACYLATION
ANIMALS
AQUATIC ORGANISMS
AROMATICS
CHEMICAL REACTIONS
CHEMISTRY
CHROMATOGRAPHY
DISPERSIONS
HALOGENATED AROMATIC HYDROCARBONS
MIXTURES
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
QUINONES
SEPARATION PROCESSES
SOLUTIONS
SPECTROSCOPY
VERTEBRATES
560300* - Chemicals Metabolism & Toxicology