2,5-디니트로페놀

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Dinitrophenol solutions/

If material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn. /Dinitrophenol, dry or wetted with less than 15% water by weight)

If material on fire or involved in fire: Dangerously explosive. Flood with water. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Dinitrophenol, wetted with at least 15% water/

Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Wet spilled material with water. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. Keep dinitrophenol out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection of your regional office of the federal EPA for specific recommendations.

Environmental considerations: Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be contained with a flexible impermeable membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder. /Dinitrophenol solutions/

Environmental considerations: Water spill: use natural barriers or oil spill control booms to limit spill travel. use surface active agent (e.g., detergent, soaps, alcohols), if approved by EPA. Inject "universal" gelling agent to solidify encircled spill and increase effectiveness of booms. If dissolved in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Dinitrophenol solutions/

Environmental considerations - land spill: dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. /Dinitrophenol, wetted with at least 15% water/

Environmental considerations - water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Dinitrophenol, wetted with at least 15% water/

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Dinitrophenol: Incinerate (1800 °F, 2.0 sec minimum) with adequate scrubbing equipment for the removal of NOx. Dinitrophenol ... /is a/ waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. /Dinitrophenol/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material wet. Wet spilled material before picking it up. Do not attempt to sweep up dry material. /Dinitrophenol, dry or wetted with less than 15% water by weight/

Evacuation: If the material is on fire or involved in fire consider evacuation of one (1) mile radius. /Dinitrophenol, dry or wetted with less than 15% water by weight/

Personnel protection: Avoid breathing dusts, and fumes from burning material. /Dinitrophenol, dry or wetted with less than 15% water by weight/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Dinitrophenol solutions/

For more Preventive Measures (Complete) data for 2,5-Dinitrophenol (13 total), please visit the HSDB record page.

Self-contained breathing apparatus, butyl rubber gloves, goggles, protective shoes and laboratory coat. (USCG, 1999)

Wear appropriate chemical protective clothing. /Dinitrophenol solutions/

Respirator Selection: Where there is potential for exposure to dinitrophenol, use a NIOSH/MSHA approved supplied-air respirator with a full facepiece operated in the positive pressure mode, or with a full facepiece, hood, or helmet in the continuous flow mode; or use a NIOSH/MSHA approved self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode.

People exposed to the solid, or to a strong soln should wear protective clothing, hand protection, and, in confined spaces, the use of respiratory protective equipment. /Dinitrophenol/

The relative potencies of the 6 dinitrophenols in uncoupling phosphorylation in rat liver mitochondria were in declining order 3,5-dinitrophenol, 2,4-dinitrophenol 2,6-dinitrophenol and 3,4-dinitrophenol and 2,3-dinitrophenol and 2,5-dinitrophenol. The relative potency of these phenolic compounds may be determined primarily by their ability to cross a boundary membrane and to bind to a cationic site on a protein normally associated with energy-conservation, rather than merely by their relative acidity or lipid solubility.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a structure estimation method(2), indicates that 2,5-dinitrophenol is expected to have moderate mobility in soil(SRC). The pKa of 2,5-dinitrophenol is 5.21(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because 2,5-dinitrophenol exists as an anion and anions do not volatilize(SRC). 2,5-Dinitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.22X10-4 mm Hg at 20 °C(5). No biodegradation was observed when 2,5-dinitrophenol was incubated with an anaerobic digester sludge over a 90 day period(6). 2,5-Dinitrophenol was stable to biochemical degradation by a mixed culture of phenol-adapted bacteria under aerobic conditions(7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a structure estimation method(2), indicates that 2,5-dinitrophenol is expected to adsorb to suspended solids and sediment(SRC). A pKa of 5.21(3) indicates 2,5-dinitrophenol will exist almost entirely 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(4), an estimated BCF of 7(SRC), from its log Kow of 1.73(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). No biodegradation was observed when 2,5-dinitrophenol was incubated with an anaerobic digester sludge over a 90 day period(7). 2,5-Dinitrophenol was stable to biochemical degradation by a mixed culture of phenol-adapted bacteria under aerobic conditions(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,5-dinitrophenol, which has a vapor pressure of 1.22X10-4 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,5-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 32 days(SRC), calculated from its rate constant of 5.0X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2,5-Dinitrophenol may react with nitrate radicals in the atmosphere(2). 2,5-Dinitrophenol absorbs light at wavelengths of 361 nm in water(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

/AQUATIC SPECIES/ The response of the water receptor of frogs was repressed by nitrophenol derivatives. The order of reversible inhibitory action of the derivatives was 2,4-dinitrophenol (I) > 2,5-dinitrophenol > 2,4,6-trinitrophenol > p-nitrophenol > 2,6-dinitrophenol > m-nitrophenol > o-nitrophenol.

/AQUATIC SPECIES/ A comparison was made between the predicted 96-hr guppy median lethal concn of 110 phenols based upon quant structure-activity relationship (QSAR) equations of J Saarikoski and M Viluksela (1982) and the data from 936 toxicity screening tests for these chems. Test data on up to 8 species of freshwater fishers were available per cmpd. Overall, the experimental toxicity data on these chem were consistent with the QSAR predictions. The 110 phenols occupy a considerably larger range of spanned substituent space than the QSAR training set. One cmpd, 4-aminophenol exhibited lethality at test concn of 35 times below that predicted. The increased fish toxicity of this cmpd is explained in terms of a proelectrophilic mol mechanism, in which the parent cmpd is metabolically oxidized to a para quinoid structure. The resulting electrophilic metabolite is susceptible to attack by nucleophilic moieties present in biological macromols leading to covalent bond formation and inhibition of biochem processes.

/AQUATIC SPECIES/ The 96-hr median lethal concn (LC50) of 21 substituted phenols (I, R= H, alkyl, Cl, or NO2; R1= H, Cl, OH, methoxy, alkyl, or NO2; n= 0-5; m= 0 to 5-n) for the guppy (Poecilia reticulata) were detd at pH 6-8 and related to the lipohilicity defined as log P from the 1-octanol/water system, and to the DELTApKa value (pKa of phenol - pKa). Log P was the more important parameter and exhibited a good correlation with log (1/LC50) at all pH levels. The contribution of DELTApKa when introduced as a 2nd parameter into the regression equation was dependent on the pH of water: at pH 6, it was pos but turned neg as the pH was raised to 8. If the LC50 were correlated for ionization using an empirically formulated relation between toxicity and pH, the resulting regression equation could be used to predict the toxicity at any pH from 6 to 8. When corrected for ionization, log BCF (the bioconcn factor) of 8 phenols was highly correlated with log P but not with DELTApKa. The regression of log BCF on log P sufficed to explain the regression of toxicity on lipophilicity.

/AQUATIC SPECIES/ The effects of the uncoupling reagents 2,4- and 2,5-dinitrophenol (DNP) on the ontogenesis of herring (Culpea harengus) were investigated. Eggs of the Baltic spring and autumn spawning herring were artificially fertilized, attached to glass plates and incubated in 1-L aerated containers (14 to 16% water salinity) for 30, 48 or 55 hr prior to incubation in 0.005, 0.01, 0.015, 0.02, 0.025, 0.03, 0.05, 0.075 and 0.10 mM 2,4- or 2,5-DNP/l. The solution temperatures were maintained at about 10.8 and 11.8 °C for the spring and autumn spawners, respectively. The effects of the DNP concentrations on the embryonic development were determined by measuring the activity of the embryo, the heartbeat rate and the mutagenic and mortality rates. The rate of mortality was shown to be dependent on the age of the embryo at the start of exposure and on the concentration of the DNP. Exposure at 30 and 48 hr resulted in 100% mortality at 0.025 and 0.03 mM/l, respectively. When the embryos were first exposed at 55 hr, highest concentration (0.10 mM DNP/l) produced 92.6% mortality. DNP also increased the occurrence of malformations which were in the form of anophthalmy, symmetrical and unilateral microphthalmy, curled bodies and dedifferentiations.

In exposed workers, blood concentration of /dinitro-derivatives/ should not exceed 10 ug/g. A white cell count should be performed if the exposed person has an unexplained persistent fever. Individuals who have a fall in white blood cell counts should avoid further exposure. /Dinitro-derivatives/

Consider skin, eyes, thyroid, blood, central nervous system, liver and kidney function, as well as general health in placement and periodic examination. Dinitrophenols can be measured in urine as such or as an aminophenol.

/Workers/ regularly exposed to dinitrophenol should have their urine tested regularly for dinitrophenol or amino-nitrophenol by polarography or Derrien's test. /Dinitrophenol/

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,5-dinitrophenol can be estimated to be 460(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,5-dinitrophenol is expected to have moderate mobility in soil. The pKa of 2,5-dinitrophenol is 5.21(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

/SIGNS AND SYMPTOMS/ Short Term Exposure: Dinitrophenol can affect you when breathed and by passing through skin ... May affect the metabolism, causing very high body temperature. May affect the peripheral nervous system causing numbness, "pins and needles," and/or weakness of the hands and feet. Exposure can cause a bluish color to skin and lips, headaches, temperature rise, dizziness, collapse, convulsions, coma, and even death. Exposure may irritate the lungs, causing caoughing and shortness of breath. Higher levels can cause a build up of fluid in the lungs, a medical emergency which can cause death. Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis with rash and drying and itching of the skin. Dinitrophenol may have effects on the dyes, causing cataracts. Exposure can damage the liver and kidneys, and affect the thyroid gland. May cause lung irritation and the development of bronchitis with coughing and shortness of breath. May damage the nervous system. High exposure may damage the developing fetus.

/SIGNS AND SYMPTOMS/ 2,4-dinitrophenol does not produce methemoglobin, but the 2,3-, 2,5-, 2,6-, and 3,4-isomers do produce it.

The ... wastewaters (COD 4.4-6 g/L) contained nitrobenzene and 2,4-dinitrophenol. These compounds are biodegradable ... and account for 50% of the Chemical Oxygen Demand. The remainder of the Chemical Oxygen Demand reflects the presence of ... 2,5- and 2,6-dinitrophenol, which are not biodegradable.

AEROBIC: 2,5-Dinitrophenol was stable to biochemical degradation by a mixed culture of phenol-adapted bacteria under aerobic conditions (0% COD chemical oxygen demand) removal after 20 days)(1).

AEROBIC: A low degree of degradability was observed for 2,5- and 2,6-dinitrophenol, whereas 2,4-dinitrophenol was readily degraded /by adapted activated sludge/.

ANAEROBIC: No biodegradation was observed when 2,5-dinitrophenol was incubated with an anaerobic digester sludge over a 90 day period(1).

An estimated BCF of 7 was calculated in fish for 2,5-dinitrophenol(SRC), using a log Kow of 1.75(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

A pKa of 5.21(1) indicates 2,5-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). 2,5-Dinitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.22X10-4 mm Hg(2).

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Dinitrophenol is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance. /Dinitrophenol; CAS No. 51-28-5/

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Nitrophenols/

Used as an indicator and to make dyes and other organic chemicals; [Merck Index]

In manufacture of dyes and organic chemicals, as an indicator.