2,4-Dinitrophenol

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Use water in large amounts. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rest. Refer immediately for medical attention.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

General First Aid:

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

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/

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P048, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

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/

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

Chemical Treatability of 2,4-Dinitrophenol; Concentration Process: Biological Treatment. Chemical Classification: Phenol; Scale of Study: Respirometer Study; Type of Wastewater Used: Synthetic Wastewater; Results of Study: Max oxygen uptake was 27.7 ppm of aeration.

For more Disposal Methods (Complete) data for 2,4-Dinitrophenol (8 total), please visit the HSDB record page.

There is no specific antidote for 2,4-DNP poisoning. Symptomatic treatment includes replacing oxygen and fluids, controlling temperature by administering sponge baths and ice packs, and using a fan to promote air flow and evaporation. In fully conscious patients, administer cold, sugar-containing liquids by mouth as tolerated. In cases of skin contact, bathe and shampoo contaminated skin and hair promptly. (L179)

2,4-DNP appears to markedly increase the rate of ethanol metabolism in rat liver slices by 100-160% and in rats in vivo by 20-30%. Because 2,4-DNP uncouples mitochondrial electron transport from oxidative phosphorylation, the oxidation of NADH to NAD+ is accelerated in the mitochondria. Reoxidation of NADH rather than the activity of alcohol dehydrogenase is the rate-limiting step in the metabolism of ethanol, and, therefore, the metabolic effect of 2,4-DNP enhances the clearance of ethanol. Because 2,4-DNP is known to augment the rate of respiration and perspiration, .2.7-8.2% of the initial dose of ethanol was also eliminated by expiration and cutaneous evaporation in the rat.

In isolated perfused rat livers, 2,4-DNP caused a depletion of the mitochondrial calcium pool, without altering the extramitochondrial calcium pool. Because 2,4-DNP uncouples oxidative phosphorylation from electron transport by dissipating the electrochemical potential, which provides the energy for the accumulation of calcium in the mitochondrial matrix, only the calcium pool in the mitochondria was affected. 2,4-DNP also caused a rapid increase in NAD, along with a decrease in NADH, a rapid decrease in protein thiol content, but only a slow decrease in nonprotein thiol (e.g., reduced glutathione [GSH]), and an increase in cytoplasmic calcium concentration in isolated rat intestinal cells. This DNP-induced protein thiol loss and/or increase of cytoplasmic calcium concentration induced cell rounding and decreased cell viability. Incubation of salicylate and 2,4-DNP with intestinal cells caused a reduction in the 2,4-DNP-induced increase in cytosolic free calcium concentration by complexation, which facilitated the release of calcium from cells. Salicylate also inhibited DNP-induced cell rounding and increased cell viability in the small intestine.

Salicylate (aspirin), which also uncouples oxidative phosphorylation in mitochondrial preparations (although at much higher concentrations than 2,4-DNP), partially inhibited a protein thiol loss induced by 2,4-DNP, but not nonprotein thiol loss by 2,4-DNP in the small intestine of rats. Although DNP inhibits the absorption of the hydrophilic drug, cefmetazole, incubation of DNP and salicylate removed this inhibitory effect in the small intestine. By preventing the DNP-induced protein thiol loss in the small intestine, salicylate appears to enhance diffusivity of cefmetazole in the small intestines. However, salicylate at very high doses can also increase respiratory rates and produce hyperthermia in humans, and possibly exaggerate these signs in persons acutely exposed to 2,4-DNP.

Pretreatment of rats with haloperidol significantly diminished the hyperpyrexia and lethality of 2,4-DNP by interfering with the uncoupling of oxidative phosphorylation by 2,4-DNP. The protection by haloperidol may have occurred by an indirect action on the mitochondrial membrane.

For more Interactions (Complete) data for 2,4-Dinitrophenol (15 total), please visit the HSDB record page.

2,4-DNP can cause cataracts following ingestion of a small dose for short or long periods. This condition could lead to blindness in both eyes. Breathing in, swallowing, or having skin contact with large amounts of DNP can lead to death.(L168)

LC50; Species: Lepomis macrochirus (bluegill); Concentration: 620 ug/L for 96 hr /Conditions of bioassay not specified in source examined/

LC50; Species: Salmo salar (Atlantic salmon); Concentration: 700 ug/L for 96 hr /Conditions of bioassay not specified in source examined/

LC50; Species: Mysidopsis bahia (Mysid shrimp); Concentration: 4850 ug/L for 96 hr /Conditions of bioassay not specified in source examined/

LC50; Species: Herring embryo; Concentration: 5,500 ug/L for 96 hr /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for 2,4-Dinitrophenol (50 total), please visit the HSDB record page.

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 °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 °C) and its presence in solution primarily as an anion strongly favor a partitioning tendency toward water rather than air.

For more Environmental Fate (Complete) data for 2,4-Dinitrophenol (6 total), please visit the HSDB record page.

The substance can be absorbed into the body through the skin and by ingestion.

Oral (L170); inhalation (L170) ; dermal (L170)

Acute 2,4-dinitrophenol poisoning (from ingestion) involves uncoupling of oxidative phosphorylation, which presumably reduces body's reservoirs of high-energy phosphate. This stimulates oxidative metabolism and, in turn, the heat production of the body. Oxygen consumption, body temperature, respiration and heart rate are all increased. 2,4-Dinitrophenol has been suggested to bind serum proteins such as transthyretin. In fact it was proposed as a therapeutic agent for the prevention/inhibition of amyloid diseases through stabilization of the native fold of transthyretin. (T21, A126, A127)

/BIRDS and MAMMALS/ In a study where bobwhite quail were exposed to 2,4-DNP in the diet, 1 of 6 hens in a group consuming 56.1 mg/kg/day died on the eighth and final day of exposure. Necropsy revealed a marked scarcity of subcutaneous fat, reduced visceral fat, and possibly some shrinkage of leg and breast muscles.

/BIRDS and MAMMALS/ Bobwhite quail were exposed to 2,4-dinitrophenol (DNP) in a respirometer designed to continuously monitor exchange of O2 and CO2, from which metabolic rates (MR) were estimated. After 14-16 days of acclimation to the system (temperature 22 °C, light cycle 8L:14D), hens received feed amended with 0, 625 ppm, or 1250 ppm DNP ad libitum for eight days, followed by 2-5 days of 0 ppm feed. The 625 ppm treatment produced dark period MR 31-41% higher than corresponding control values, and light period MR 23-32% higher than controls. The 1250 ppm treatment produced dark period MR 48-77% higher than control values, and light period MR 41-67% higher than control. Over the eight days of testing, the 625 ppm treatment hens expended 32% more energy than the control hens and hens consuming 1250 ppm feed expended 60% more energy than control hens and lost most of their body fat. In general, the risk of being unable to meet energy demands for survival or reproduction would probably be substantially increased by the observed elevation in MR.

/BIRDS and MAMMALS/ Ducklings fed 2,4-dinitrophenol at a concentration of 2,500 ppm developed cataracts within 24 hr ... Chickens were also susceptible. Cataract was observed in duckling only 3.5 hr after crop intubation. With no further dosing, the lesion cleared within 3 days.

/BIRDS and MAMMALS/ The effects of pharmacologically elevated metabolism on respiratory adjustments were studied in chickens. Adult female white leghorn chickens were decerebrated and allowed to recover from anesthesia. In experiment 1, birds were injected with 2.5 mg/kg 2,4-dinitrophenol. Respiratory and cardiovascular measurements were monitored continuously. After steady state conditions were reestablished, another 2.5 mg/kg 2,4-dinitrophenol injection was given and measurements were taken again. Injections and measurements continued until no further oxygen consumption increase occurred. Some birds received a single 5 mg/kg 2,4-dinitrophenol injection. Measurements were repeated every 5 minutes. In experiment 2, birds had control measurements and arterial blood samples taken at approximately 20 °C. Birds were cooled to 2 °C. After a steady respiratory response was established, measurements were taken. Successive 2,4-dinitrophenol doses caused a progressive oxygen consumption increase in the decerebrated chickens; a 7.5 to 10 mg/kg dose of 2,4-dinitrophenol elicited the maximal oxygen consumption response, approximately 275% of control values. A single 5 mg/kg 2,4-dinitrophenol injection increased oxygen consumption and the respiratory exchange ratio and increased minute ventilation. Ventilation significantly increased within 10 seconds of the start of 2,4-dinitrophenol injection. A steady state was reached approximately 10 minutes after the start of injection. Birds hyperventilated about 45 minutes after injection when the temperature reached approximately 42.3 °C. The respiratory and cardiovascular effects of the increased metabolism during cold exposure was similar to the initial elevated metabolism responses elicited by 2,4-dinitrophenol. Oxygen consumption increased to approximately 185% of control values; V1 increased in a way that oxygen extraction remained unchanged. /It was concluded/ that 2,4-dinitrophenol induced hyper metabolism in the decerebrated chicken is an acceptable model to study respiratory control and gas exchange during exercise in birds.

The phytotoxic nitrophenols were analyzed in beech tree leaves (Fagus sylvatica) from two different alpine forests (Val Gerola and Val Masino) in the Lombardy Region (Northern Italy) which are in decline due to adverse effects of air pollution. Leaves from the more damaged site (Val Gerola) had higher mean total nitrophenol concentrations (313 ng/g) than the Val Masino samples (148 ng/g). 2,4-Dinitrophenol concentrations reported in beach leaves from Val Gerola and Val Masino were 8.2 and 4.1 ng/g dry weight, respectively; sampling was conducted from 1994-1995(1).

See Ingestion.

MAY BE ABSORBED! Redness. Roughness. Yellow staining of the skin. Further see Inhalation.

Yellow vision. Redness. Conjunctivitis.

Nausea. Sweating. Severe thirst. Fever. Increased heart rate. Vomiting. Shock or collapse.

Dermal contact may results in redness, roughness, yellow staining of the skin. Nausea, vomiting, palpitations, collapse, sweating occur after inhalation or ingestion. (L170)

P048; As stipulated in 40 CFR 261.33, when 2,4-dinitrophenol, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,4-Dinitrophenol is included on this list. Effective date 9/30/91; Sunset date: 12/19/95.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91; Reporting date: 11/27/91.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. 2,4-Dinitrophenol is found on List B. Case No: 2195; Pesticide type: Insecticide, fungicide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 2,4-dinitrophenol; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 2,4-Dinitrophenol is included on this list.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 2,4-Dinitrophenol is produced, as an intermediate or a final product, by process units covered under this subpart.

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/

For the protection of human health from the toxic properties of dinitrophenols ... ingested throughwater and contaminated aquatic organisms, the ambient water criteria /is/ determined to be 70 ug/l ... ingested through contaminated aquatic organisms alone /is/ determined to be 14.3 mg/l ... . /Dinitrophenols/

(AZ) ARIZONA 14 ug/L

(FL) FLORIDA 30 ug/L

(ME) MAINE 14 ug/L

(MN) MINNESOTA 10 ug/L

2,4-Dinitrophenol is used in the manufacture of dyes and wood preservatives, as a pesticide, and as an indicator for the detection of potassium and ammonium ions. During the 1930s, 2,4-dinitrophenol was used as a diet pill, but this use was stopped in 1938.

Used as a chemical intermediate (dyes and photographic developers), biocide in metal-working fluids, wood preservative, insecticide, polymerization inhibitor (styrene production), and veterinarian medication; [HSDB]

Its use as a pesticide was cancelled. [HSDB]

Metal Machining [Category: Heat or Machine]

For 2,4-dinitrophenol (USEPA/OPP Pesticide Code: 037509) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

(1977): < 1000 pounds

(1978): > 600,000 lb /From table/

For more U.S. Production (Complete) data for 2,4-Dinitrophenol (6 total), please visit the HSDB record page.

HYDROLYSIS OF 2,4-DINITRO-1-CHLOROBENZENE WITH SODIUM HYDROXIDE.

(a) By heating phenol with dilute sulfuric acid, cooling the product, and then nitrating, keeping the temperature approximately 50 °C; (b) by nitration with mixed acid with careful temperature control. /Dinitrophenol/

2,4-Dinitrochlorobenzene is hydrolyzed by heating with 6% aqueous sodium hydroxide at 95 - 100 °C for 4 hr. The product is precipitated by addition of acid, filtered off, and washed to remove acid and also a small quantity of the more soluble 2,6-isomer. The yield is 95 %.

85% with 15% water.

Osmoplastic-R wood preserving compound, solution-ready to use; 45.62% creosote oil (derived from any source), 2.0% dinitrophenol, 3.1% potassium dichromate, 44.42% sodium fluoride.

Cobra salts (Impregna salts), soluble concentrate; 20.0% arsenic trioxide, 21.5% dinitrophenol, 51.0% sodium fluoride.

Shirakiku brand mosquito coils, impregnated materials; 0.42% Allethrin (Allyl homolog of cinerin I), 78.78% Allethrin coil, 0.2% dinitrophenol, 20.6% pyrethrum powder other than pyrethrins.

For more Formulations/Preparations (Complete) data for 2,4-Dinitrophenol (6 total), please visit the HSDB record page.

Phenol, 2,4-dinitro-: ACTIVE

Commercial product is a mixture of 2,3-, 2,4- and 2,6- isomers. /Dinitrophenol/