2,4-Dinitrophenol

CAS RN: 51-28-5

Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc values of 13.5(2) and 16.6(3), indicate that 2,4-dinitrophenol is expected to have very high mobility in soil(SRC). The pKa of 2,4-dinitrophenol is 4.09(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). This can be seen in the measured Koc values(SRC). 2,4-Dinitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.9X10-4 mm Hg at 20 deg C(6). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation is not an important environmental fate process in soil(SRC). However, the biodegradation half-life of 2,4-dinitrophenol in an acidic soil was reported as 32.1 days and the biodegradation half-life in a basic soil was reported as 4.6 days(8).
TERRESTRIAL FATE: 2,4-Dinitrophenol is a moderately weak acid that is expected to be highly labile (leachable and plant available) in high-pH soils. The adsorption and degradation behavior of 2,4-dinitrophenol in two sludge-amended, calcareous soils was determined and used to explain 2,4-dinitrophenol uptake by plants grown in the soils in the greenhouse. The 2,4-dinitrophenol adsorption was minor in both soils and was only slightly affected by sludge. The 2,4-dinitrophenol degradation was rapid in both soils and was unaffected by sludge. Thus, despite limited soil adsorption, plant uptake of 2,4-dinitrophenol was minor in all crops and plant parts owing to rapid soil 2,4-dinitrophenol degradation. Even if a municipal sludge highly contaminated with 2,4-dinitrophenol was identified (an unlikely occurrence), concerns over possible plant contamination should not limit sludge applications to calcareous soils at agronomic rates. Rapid degradation will minimize opportunities for plant uptake of 2,4-dinitrophenol from contaminated soils or leaching of 2,4-dinitrophenol to groundwater given careful water management.
AQUATIC FATE: Based on a classification scheme(1), a Koc values of 13.5(2) and 16.6(3), indicate that 2,4-dinitrophenol is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.09(4) indicates 2,4-dinitrophenol will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(5), BCFs of <0.4-0.7 and <3.7(6), suggest the bioconcentration in aquatic organisms is low(SRC). The biodegradation half-life of 2,4-dinitrophenol was reported as 68 days and 2.8 days in aerobic and anaerobic waters, respectively(7).
AQUATIC FATE: ... The high solubility of 2,4-dinitrophenol in water (5,600 mg/L at 18 deg C) and its presence in solution primarily as an anion strongly favor a partitioning tendency toward water rather than air.
AQUATIC FATE: Laboratory experiments were performed to investigate the behavior of six phenols /including/ 2,4-dinitrophenol ... in dolomite aquifers. ... The experimental results, with the exception of the chlorinated phenols, indicate that little, if any, of the phenols adsorb onto dolomite at temperatures of 5 deg and 22 deg C and at concentrations from 0.1 to 10 mg/L. ... No processes of phenol degradation were detected in the experiments, with some experiments lasting 21 days.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-dinitrophenol, which has a vapor pressure of 3.9X10-4 mm Hg at 20 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dinitrophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 24 days(SRC), calculated from its rate constant of 6.6X10-13 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). 2,4-Dinitrophenol may react with nitrate radicals in the atmosphere(2). 2,4-Dinitrophenol does absorb light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
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