Abstract
Then-butyl ester of 2,4-dichlorophenoxyacetic acid in the liquid and vapor phase was irradiated in a pyrex reactor for 188 hr by ultraviolet light of 300 nm using an intensity similar to that around 300 nm in the solar spectrum. In both phases, the ester was dechlorinated at theortho position together with simultaneous reduction and Photo-Fries rearrangement to produce volatile photo products. Ether bond cleavage to produce chlorophenols, and a Norrish Type II photoprocess, also occurred. A 79% mass balance was accounted for by volatile chlorinated organic residues. HC1 gas was also evolved. The production of Cl was also demonstrated in both vapor and liquid phases. The half time of decomposition was around 13 days. The possible effects of the volatile photoproducts on off-target plants were also noted.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Binkley, R. W., and T. R. Oakes, Photochemical reactions of methyl phenoxyacetates. J. Org. Chem.39, 83 (1974a).
—: Photochemical reactions of alkyl 2,4-dichlorophenoxyacetates. Chemosphere3, 3 (1974b).
Calvert, J. G., and J. N. Pitts: Photochemistry. New York: Wiley and Sons (1966).
Cicerone, R. J., R. S. Stolarski, and S. Walters: Stratospheric ozone destruction by man-made chlorofluoromethanes. Science185, 1165 (1974).
Corner, J., S. S. Que Hee and R. G. Sutherland: Esterification of (2,4-dichlorophenoxy) acetic acid — a quantitative comparison of esterification techniques. Anal. Chem.46, 110 (1974).
Kelly, D. P.., J. T. Pinhey, and R. D. G. Rigbhy: Photochemical rearrangement of aromatic ethers. Aust. J. Chem.22, 977 (1969).
Likens, G. E.., and F. H. Bormann: Acid rain. Serious environmental problem. Science184, 1176 (1974).
Maugh, II, T. H.: The ozone layer: The threat from aerosol cans is real. Science194, 170 (1976).
Molina, M. J., and F. S. Rowland: Stratospheric sink for chlorofluoromethanes. Chlorine atomcatalysed destruction of ozone. Nature249, 810 (1974).
Nordblom, G. D., and L. L. Miller: Photoreduction of 4.4′-dichlorobiphenyl. J. Agr. Food Chem.22, 57 (1974).
Que Hee, S. S., and R. G. Sutherland: The volatility and photodecomposition of various esters of 2,4-dichlorophenoxyacetic acid. Abstr. Chem. Biochem. Herbicides, Regina, Saskatchewan, March 5–6, 1974,1, 13 (1973).
—: Photodecomposition of 2,4-dichlorophenoxyacetic acid and its compounds in the vapor phase and in solution. Abstr. 57th Canadian Chemical Conference, Regina, June 3–5, 1974: 188 (1974a).
—: Volatilization of various esters and salts of 2,4-D. Weed Sci.22, 313 (1974b).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Hee, S.S.Q., Sutherland, R.G. Vapor and liquid phase photolysis of then-butyl ester of 2,4-dichlorophenoxyacetic acid. Arch. Environ. Contam. Toxicol. 8, 247–254 (1979). https://doi.org/10.1007/BF01056329
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01056329