2,4-Dinitrotoluene

Hazardous Air Pollutants (HAPs)

Nitrogen Compounds -> Nitros, Aromatic

Carcinogens

Semi-Volatile Organic Compound (SVOC)

log Kow = 1.98

1.98

2.13

1.379 at 68 °F (USCG, 1999) - Denser than water; will sink

Density = 1.521 g/mL at 15 °C

Density = 1.3208 g/mL at 71 °C

1.52 g/cm³

1.379

1.3208 @ 71°C

Yellow needles or monoclinic prisms

Yellow or orange crystals

less than 0.1 mg/mL at 63 °F (NTP, 1992)

Soluble in ethanol, chloroform, benzene and ethyl ether; very soluble in acetone, pyridine

Ethanol, at 15 °C, 30.46 g/L; diethyl ether, at 22 °C, 94 g/L; carbon disulfide, at 17 °C, 21.9 g/L

In water, 2.70X10+2 mg/L at 22 °C

In water, 200 mg/L at 25 °C

Solubility in water: very poor

405 °F (NTP, 1992)

404 °F (207 °F) (Closed cup)

169 °C c.c.

404 °F

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301+H311+H331 (26.7%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Benzene, 1-methyl-2,4-dinitro-

Hazard Traits - Carcinogenicity; Hematotoxicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity; Reproductive Toxicity

Benzene, 1-methyl-2,4-dinitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1-methyl-2,4-dinitro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Substance: 2,4-dinitrotoluene

2,4-Dinitrotoluene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Nitrogen oxides and dense black smoke are produced in a fire.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. Risk of explosion on contact with many substances.

Ingestion or overexposure to vapors from hot liquid can cause loss of color, nausea, headache, dizziness, drowsiness, collapse. Hot liquid can burn eyes and skin. Prolonged skin contact with solid can give same symptoms as after inhalation or ingestion. (USCG, 1999)

2,4-Dintirotoluene is used as an intermediate in the manufacture of polyurethanes. No information is available on the acute (short-term) effects of 2,4-dinitrotoluene in humans. Chronic (long-term) inhalation exposure to 2,4-dinitrotoluene affects the central nervous system (CNS) and blood in humans. A significant reduction in sperm count and normal sperm morphology was observed in one study of chronically exposed workers, while other studies have not reported this effect. No significant increase in cancer mortality was observed in a study of workers occupationally exposed to 2,4-dinitrotoluene by inhalation. Kidney, liver, and mammary gland tumors were observed in animals orally exposed to 2,4- dinitrotoluene. EPA has not classified 2,4-dinitrotoluene for potential carcinogenicity.

Can induce methemoglobinemia; Can be absorbed through skin; [ICSC] A mucous membrane irritant; May cause methemoglobinemia; [HSDB] Allergic contact dermatitis reported in a worker manufacturing explosives and exposed to 2,4-dinitrotoluene and nitroglycerin; [Kanerva, p. 1788] Chronic exposure may cause liver injury, anemia, and neuritis; [CHRIS] Equivocal evidence for human reproductive toxicity; [ToxPlanet: DOE] No evidence of teratogenicity in rats or mice at doses maternally toxic; A decrease in sperm positive females was observed in a study of rats when males were dosed at 240 mg/kg/day; [REPROTOX] See Dinitrotoluene, all isomers.

USEPA; Ambient Water Quality Criteria Doc: Dinitrotoluene (1980) EPA 440/5-80-045

USEPA; Chemical Hazard Information Profile: 2,4-Dinitrotoluene (1978) EPA-560/11-80-011

Rickett DE et al; CRC Crit Rev Toxicol 13 (3): 217-34 (1984). A review with 86 references on toxicity, mutagenicity, carcinogenicity, and metabolism of 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dinitrotoluene in man and lab animals.

DHHS/ATSDR; Toxicological Profile for 2,4-Dinitrotoluene and 2,6-Dinitrotoluene. NTIS/PB90-171430 (1990).

For more Special Reports (Complete) data for 2,4-DINITROTOLUENE (10 total), please visit the HSDB record page.

U105; As stipulated in 40 CFR 261.33, when 2,4-dinitrotoluene, 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 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).

D030; A solid waste containing 2,4-dinitrotoluene may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste.

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: 3-11-94; Reporting date: 5-10-94.

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-Dinitrotoluene is included on this list. Effective date: 3-11-94; Sunset date: 6-30-98.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

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

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

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

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.

DECOMP IS SELF-SUSTAINING @ 280 °C.

Closed containers may rupture violently when heated.

WATER, DRY CHEMICAL, OR CARBON DIOXIDE FROM PROTECTED LOCATION.

Use extreme caution in approaching a fire as the material may explode when exposed to heat or flame. No attempt should be made to fight advanced or massive fires except for remote manual activation of installed fire extinguishing equipment, or with unmanned fixed turrets and hose nozzles. The surrounding area should be evacuated.

If material on fire or involved in fire: Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Dinitrotoluenes, molten/

If material on fire or involved in fire: Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Dinitrotoluene, liquid; dinitrotoluene, solid/

Use water spray, dry chemical, or carbon dioxide. Fight fire from protected location or maximum possible distance. Use water spray to keep fire-exposed containers cool.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Store away from oxidizing or reducing materials. Protect containers against physical damage.

Normally stored as a molten liquid. Separate from strong oxidizing materials and reducing agents. Hot water coils should not exceed 194 °F (90 °C).

1) REMOVE ALL IGNITION SOURCES. 2) VENTILATE AREA OF SPILL. 3) FOR SMALL QUANTITIES, SWEEP ONTO PAPER OR OTHER SUITABLE MATERIAL & BURN IN SUITABLE COMBUSTION CHAMBER WHICH ALLOWS BURNING IN UNCONFINED CONDITION & IS EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. LARGE QUANTITIES MAY BE RECLAIMED; ... IF ... NOT PRACTICAL, DISSOLVE IN FUEL OIL & ATOMIZE IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated. ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

The adsorption and desorption of 2,4-dinitrotoluene on activated-carbon were investigated. Known amounts of granular FS300, FS400, powdered FS300, and regenerated spent FS300 and FS400 activated carbon were equilibrated with aqueous 2,4-dinitrotoluene solutions. The aqueous phase was analyzed by HPLC or UV spectrophotometry. The solid phases were dried, weighed, and desorbed with water, acetone, a 1:1 acetone/water mixture, and methanol. The solvent extracts were analyzed by UV spectrophotometry, HPLC, and GC/MS. The equilibrium adsorptive capacities of 2,4-dinitrotoluene on the activated carbons were assessed by constructing Freundlich adsorption isotherms. Both types of activated-carbon effectively adsorbed 2,4-dinitrotoluene from the solutions. The adsorptive capacities ranged from 0.21 to 0.30 grams 2,4-dinitrotoluene per gram carbon. Acetone and methanol were better solvents than water for desorbing 2,4-dinitrotoluene. More 2,4-dinitrotoluene could be recovered from spent FS400 than from spent FS300. 2,4-Dinitrotoluene derivatives such as 2,4-dinitrobenzyl alcohol, 2,4-dinitrobenzaldehyde, 2,4-dinitrobenzoic acid, and methyl-2,4-dinitrobenzoate were identified in the extracts. The authors conclude that 2,4-dinitrotoluene contaminated carbons can be regenerated by extracting them with methanol, acetone, or their mixtures with water. Some of the adsorbed 2,4-dinitrotoluene is converted to its derivatives, probably as a result of side chain oxidation.

Environmental considerations - water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. 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. /Dinitrotoluene, liquid; dinitrotoluene, solid/

For more Cleanup Methods (Complete) data for 2,4-DINITROTOLUENE (6 total), please visit the HSDB record page.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U105 and D030, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.[

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1600 °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 liquidsand gases, and longer for solids.

1) BY MAKING PACKAGES OF DINITROTOLUENE IN PAPER OR OTHER FLAMMABLE MATERIAL & BURNING IN SUITABLE COMBUSTION CHAMBER WHICH ALLOWS BURNING IN UNCONFINED CONDITION & IS EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. 2) BY DISSOLVING IN FUEL OIL & ATOMIZING IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. /DINITROTOLUENE/

For more Disposal Methods (Complete) data for 2,4-DINITROTOLUENE (13 total), please visit the HSDB record page.

Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

Eating and smoking should not be permitted in areas where dinitrotoluene or liquids containing dinitrotoluene are handled, processed, or stored. Employees who handle dinitrotoluene or liquids containing dinitrotoluene should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Dinitrotoluene/

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. /Dinitrotoluene, liquid; dinitrotoluene, solid/

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. /Dinitrotoluenes, molten/

For more Preventive Measures (Complete) data for 2,4-DINITROTOLUENE (24 total), please visit the HSDB record page.

Following oral exposure, immediately dilute with 4 to 8 ounces (120 to 240 mL) of water or milk (not to exceed 4 ounces/120 mL in a child). Administer charcoal as a slurry. Gastric lavage and oxygen administration is recommended. Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Following eyes exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water, and administer a benzodiazepine IV in case of irritation. In all those cases, a physician may need to examine the area if irritation or pain persists. (T36)

Ingestion of alcohol has a synergistic effect on the toxicity of 2,4-DNT.

The sulfotransferase inhibitors 2,6-dichloro-4-nitrophenol and pentachlorophenol were used to investigate the role of sulfate ester formation during the in vivo bioactivation of 2,4- and 2,6-DNT. Male F-344 rats were administered one of the sulfotransferase inhibitors (40 umol/kg ip) 45 min prior to oral administration of 28 mg/kg ring-(14)C-2,4-DNT or 3-(3)H-2,6-DNT and killed 12 hr later. Pentachlorophenol had no significant effect on the urinary excretion of the benzyl glucuronide or benzoic acid metabolites of 2,6-DNT. The sulfotransferase inhibitors decreased the total hepatic macromolecular covalent binding of 2,4-DNT by 33%, and of 2,6-DNT by 69%. Hepatic DNA showed covalent binding of 2,4- and 2,6-DNT of 45 and 94 pmol equivalents/mg DNA, respectively. The sulfotransferase inhibitors decreased the binding of the hepatocarcinogen 2,6-DNT to hepatic DNA by greater than 95%. 2,6-Dichloro-4-nitrophenol decreased the binding of 2,4-DNT to DNA by >84% while the decrease due to pentachlorophenol was 33%. These results suggest that sulfation is important in the biotransformation of 2,4- and 2,4-DNT to reactive metabolites which covalently bind to DNA. 3H20 was detected in the urine of rats administered 3-(3)H-2,6-DNT.

EC50; Species: Pseudokirchneriella subcapitata (Green Algae) exponential growth phase; Conditions: freshwater, static, 25 °C, pH 6.0-7.5; Concentration: 14.3 uM for 96 hr (95% confidence interval: 10.5-19.2 uM); Effect: decreased population abundance

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, renewal, 25 °C, pH >7; Concentration: 38000 ug/L for 24 hr; Effect: behavior, equilibrium /formulation/

EC50; Species: Daphnia magna (Water flea) age < or = 24 hr; Conditions: freshwater, static, 25 °C, pH >7.0, dissolved oxygen > or =58%; Concentration: 38000 ug/L for 24 hr; Effect: intoxication, immobilization /formulation/

EC50; Species: Daphnia magna (Water flea) age <24 hr, larvae, 1st instar; Conditions: freshwater, static, 22 °C, pH 7.7 (7.0-8.2), hardness 154.5 (89.5-180) mg/L CaCO3, alkalinity 137.7 (95-156) mg/L CaCO3; Concentration: 26200 ug/L for 48 hr (95% confidence interval: 22500-30500 ug/L); Effect: intoxication, immobilization /formulation/

For more Ecotoxicity Values (Complete) data for 2,4-DINITROTOLUENE (7 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 57-2000, determined from two adsorption studies(2,3), indicates that 2,4-dinitrotoluene can have high to low mobility in soil(SRC). Leaching of 2,4-dinitrotoluene has been observed in soil column transport studies(4) and it has been detected in groundwater samples beneath ammunition plants(5,6) indicating 2,4-dinitrotoluene can leach from soil. Volatilization of 2,4-dinitrotoluene from moist soil surfaces is not expected to be an important fate process(SRC) given a measured Henry's Law constant 5.4X10-8 atm-cu m/mole at 25 °C(7). 2,4-Dinitrotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.47X10-4 mm Hg(8). 2,4-Dinitrotoluene may undergo direct photolysis on soil surfaces, based on observed photolysis of 2,4-dinitrotoluene in water(9). Biodegradation of 2,4-dinitrotoluene is expected to be an important fate process in soil based on results of various screening tests that demonstrated microbial degradation(10-14).

AQUATIC FATE: Based on a classification scheme(1), a Koc range of 57-2000, determined from two adsorption studies(2,3), indicates that 2,4-dinitrotoluene is expected to be susceptible to some adsorption to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 5.4X10-8 atm-cu m/mole at 25 °C(5). According to a classification scheme(6), an estimated BCF of 9(SRC), from its log Kow of 1.98(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low. Photolysis of 1.0 ppm 2,4-dinitrotoluene in distilled and natural waters gave half-lives of 43 hrs in distilled water and 2.7, 9.6, and 3.7 hrs in river, bay and pond waters, respectively(9). 2,4-Dinitrotoluene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(4). Biodegradation of 2,4-dinitrotoluene is expected to be an important fate process in water based on results of various screening tests that demonstrated microbial degradation(10-14).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-dinitrotoluene, which has a vapor pressure of 1.47X10-4 mm Hg at 22 °C(2), is expected to exist solely as a vapor in the ambient atmosphere at 22 °C. However, at 15 °C, 2,4-dinitrotoluene has a vapor pressure of 6X10-5 mm Hg(3) which indicates it will exist in both the vapor and particulate phases in the ambient atmosphere. 2,4-Dinitrotoluene has been detected in atmospheric particulate matter(4). Vapor-phase 2,4-dinitrotoluene 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 75 days(SRC), calculated from its rate constant of 2.2X10-13 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(5). Particulate-phase 2,4-dinitrotoluene may be removed from the air by wet or dry deposition(SRC). 2,4-Dinitrotoluene is susceptible to direct photolysis in sunlight(6).

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

Dermal (T44) ; eye contact (T44) ; inhalation (T44) ; oral (T44)

2,4-DNT may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia. Some metabolites of 2,4-DNT are also transported back from the bile to the liver, where the amine group is N-hydroxylated by cytochrome P-450 to form an unstable sulfate conjugate. The sulfate conjugate is degraded into carbonium or nitrenium ions. These ions covalently bind to hepatic macromolecules (DNA, RNA), leading to mutations and subsequently liver tumors. They also bind to DNA of the lung and the intestine. (L276, T45, A171, L280)

/BIRDS and MAMMALS/ ...A controlled dosing regime (gavage) /was followed/ using 2,4-dinitrotoluene (2,4-DNT) in the Northern Bobwhite (Colinus virginianus) for 60 days following a 14-day range-finding study and the determination of a LD50 using the up/down method. The LD50 was determined to be 55 mg/kg using corn oil as a vehicle. Individuals dosed exceeding this level were moribund or died within 60 hr of exposure. Morbidity and death occurred during the 14-day range-finding study at dosing regimens of 35 and 55, but not at 15, 5, and 0.5 mg/kg/day. Compound-related morbidity/mortality occurred in the 60-day study during the first week of exposure at 25 and 15, but not at 5, 1, and 0 mg/kg/day. Overt signs of toxicity occurred with both sexes at the onset of exposure. Signs included weight loss, diarrhea, and lethargy. Dose-related changes in egg production, ovary, kidney, and brain mass, and body weight, but not feed consumption, were found. Changes in kidney mass and histological observations suggest accumulation of nitrogenous waste may be the cause of morbidity. These data suggest that oral 2,4-DNT exposures are more acutely toxic and has a different etiology than 2,4,6-trinitrotoluene in birds.

/AQUATIC SPECIES/ 2,4-Dinitrotoluene (DNT) was tested for the induction of sex-linked recessive mutations in Drosophila melanogaster using a standard protocol approved by the National Toxicology Program. Canton-S wild-type males were treated with concentrations of DNT that resulted in approximately 30% mortality and were mated individually to 3 harems of Basc virgin females to produce 3 broods for analysis. DNT was positive at dose of 10,000 ppm when administered to males by injection.

/AQUATIC SPECIES/ ...The purpose of this study is to characterize the effects of 2,4-dinitrotoluene and the associated mechanisms of toxicity in the freshwater fish species, fathead minnow (Pimephales promelas), through the use of DNA microarray technology. ...A fathead minnow cDNA microarray containing 5,000 anonymous ESTs made from RNA extracted from fish at different developmental stages from embryo to adult /was used/. Adult fish were exposed to four concentrations of 2,4- DNT (11, 22, 44, 88 uM respectively) for 10 days. RNA extracted from the liver of exposed fish and from unexposed control fish were converted into cDNA, labeled using Cy3 and Cy5 and hybridized to the cDNA microarrays. Statistical analysis of hybridization signals was used to identify 72 cDNAs that are affected by exposure to different concentrations of 2,4-DNT. Sequence analysis of the cDNA revealed that several apolipoprotein subunit genes as well as a fatty acid binding protein were down-regulated in the livers of exposed fish suggesting that 2,4-DNT interferes with lipid metabolism. ...Results also indicate that 2,4-DNT interferes with oxygen transport in the blood as suggested by its effect on the expression of the hemoglobin alpha chain gene, two transferrin genes as well as genes coding for mitochondrial respiratory chain components. These observations correlate well with the results of a 2,4-DNT toxicity study which indicated that high doses of 2,4-DNT cause methemoglobinemia and anemia in exposed animals as well as an almost total absence of body fat. Our study on 2,4-DNT toxicity using a fathead minnow microarray platform suggests that cDNA microarrays can be useful to identify the mechanisms of toxicity and as a predictive tool for toxicity in mammals.

/AQUATIC SPECIES/ The individual and joint toxicities of binary mixtures of 2,4-Dinitrotoluene (2,4-DNT) and 8 nitrobenzenes and anilines to Vibrio fischeri were determined respectively and their mixture toxicity effects were assessed using the Additivity Index (Al). ... The joint toxic effects derived from AI values show that the mixture toxicity of 2,4-DNT and the other nitrobenzenes is synergistic (AI>0), whilst the mixture toxicity of 2,4-DNT and the anilines is antagonistic (AI<0). These results confirm that the mixture toxicity is mainly related to intracellular oxidation and reduction. -E(LUMO) values of nitrobenzenes are higher. The nitrobenzenes when mixed with 2,4-DNT make the mixture systems easily reduced; the mixture toxicity effect is synergism. On the other hand, -E(LUMO) values of anilines are lower. The anilines when mixed with 2,4-DNT can make the mixture systems less easily reduced, and the mixture toxicity effect is antagonism.

For more Ecotoxicity Excerpts (Complete) data for 2,4-DINITROTOLUENE (14 total), please visit the HSDB record page.

Blue lips, fingernails and skin. Headache. Dizziness. Nausea. Confusion. Convulsions. Unconsciousness.

MAY BE ABSORBED! See Inhalation.

See Inhalation.

Symptoms of 2,4-dinitrotoluene poisoning include blue lips or finger nails, blue skin, vertigo, fatigue, dizziness, weakness, nausea, vomiting, dyspnea, arthralgia, insomnia, tremor, paralysis, unconsciousness, chest pain, shortness of breath, palpitation, anorexia, and loss of weight. (T45, L272)

U105; As stipulated in 40 CFR 261.33, when 2,4-dinitrotoluene, 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 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).

D030; A solid waste containing 2,4-dinitrotoluene may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste.

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: 3-11-94; Reporting date: 5-10-94.

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-Dinitrotoluene is included on this list. Effective date: 3-11-94; Sunset date: 6-30-98.

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. Dinitrotoluene is produced, as an intermediate or a final product, by process units covered under this subpart. /Dinitrotoluene/

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).

2,4-Dinitrotoluene 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.

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

(FL) FLORIDA 0.05 ug/L

(NH) NEW HAMPSHIRE 0.11 ug/L

(ME) MAINE 0.5 ug/L

(WI) WISCONSIN 0.05 ug/L

METAB OF (14)C-LABELED 2,4-DNT TO 2,4-DINITROBENZYL ALCOHOL BY POSTMITOCHONDRIAL LIVER FRACTION FROM RABBITS, DOGS & MONKEYS WAS GREATER THAN BY FRACTIONS FROM MICE & RATS. ONLY CONSISTENT SEX DIFFERENCE WAS FORMATION OF MORE AMINOTOLUENES BY MALE LIVERS FOLLOWING A NITROGEN FLUSH.

NINE METABOLITES OF 2,4-DINITROTOLUENE IN RAT URINE WERE DETECTED BY TLC AFTER REPEATED ORAL ADMIN TO MALE RATS. 2-AMINO-4-NITROTOLUENE, 4-AMINO-2-NITROTOLUENE, 2,4-DIAMINOTOLUENE, 2,4-DINITROBENZYL ALC, 2-AMINO-4-NITROBENZYL ALC, 4-AMINO-2-NITROBENZYL ALC, 2-NITRO-4-ACETYLAMINOTOLUENE, 2-AMINO-4-ACETYLAMINOTOLUENE, & 2-AMINO-4-ACETYLAMINOBENZOIC ACID WERE IDENTIFIED.

2,4-DNT TREATMENT HAD LITTLE EFFECT ON THE ACTIVITY OF SOME HEPATIC XENOBIOTIC METABOLIZING ENZYMES IN RATS, AND WAS READILY METABOLIZED BY LIVER PREPN IN VITRO. THE PATHWAYS OF IN VITRO METABOLISM WERE DEPENDENT ON OXYGEN TENSION. THIS IN VITRO METAB PRODUCED MOSTLY POLAR METABOLITES WHICH DID NOT BIND APPRECIABLY TO MICROSOMAL MACROMOLECULES.

IN RATS, THE REDUCTIVE METABOLIC CAPACITY OF CECAL CONTENTS ON PER G WT BASIS EXCEEDS THAT BY LIVER MICROSOMES BY FACTOR OF 1000, SUGGESTING THAT CECUM REPRESENTS MAJOR SITE OF REDUCTIVE METABOLISM OF DNT. LIVER & CECAL MICROFLORA ACTING IN CONCERT REPRESENT MAJOR SITES FOR FORMATION OF DINITROTOLUENE METABOLITES WHICH MAY BE RESPONSIBLE FOR ITS CARCINOGENIC ACTIVITY.

For more Metabolism/Metabolites (Complete) data for 2,4-DINITROTOLUENE (16 total), please visit the HSDB record page.

2,4-Dinitrotoluene can be inhalated as fumes or dust, ingested, or absorbed after contact with the skin. Bioactivation of 2,4-DNT is thought to occur by the following processes: The methyl group is oxidized to an alcohol by a cytochrome P-450 dependent pathway; the benzyl alcohol is conjugated with glucuronic acid and excreted in the bile. Intestinal microflora hydrolyzes the glucuronide and reduces one nitro group, forming an aminonitrobenzyl alcohol which can be readsorbed from the intestine. The amino group is oxidized to an hydroxylamine by hepatic enzymes and conjugated with sulfate, by sulfotransferase. Decomposition of the sulfate ester yields a highly electrophilic nitrenium (or carbonium) ion which can react with DNA and other biological nucleophiles. The major metabolite found in human urine is 2,4-dinitrobenzyl alcohol or its glucuronide conjugate. Other urinary metabolites include 2,4-dinitrobenzoic acid, 4-(N-acetyl)amino-2nitrobenzoic acid, and 2-amino-4-nitrobenzoic acid. The latter two are clearly the product of both oxidative and reductive metabolism. Metabolism is also believed to involve O-acetyltransferase (which transfers the acetyl group of 2,4-DNT) and cytosolic xanthine oxidase (which reduces 2,4-DNT). Small traces of unmetabolized 2,4-DNT can be observed in the urine too. (L276, A169, T47, A170, A177, A178)

AFTER SINGLE ORAL ADMIN OF (3)H 2,4-DNT TO RATS, RADIOACTIVITY IN BLOOD REACHED MAX 6 HR AFTER ADMIN WITH A HALF-LIFE OF APPROX 22 HR, MAX LEVEL IN LIVER OCCURRED AFTER 6 HR. ABOUT 10% EXCRETED INTO BILE WITHIN 24 HR. FECAL EXCRETION MAX 6-9 HR & URINARY WAS MAX 6 HR AFTER ADMIN.

IN STRAIN A MICE, THE URINE WAS THE MAJOR ROUTE OF ELIMINATION FOR 2,4-DINITROTOLUENE (2,4-DNT), WITH 52.5, 60.1, AND 70.0% OF IP DOSES OF 1, 10, AND 100 MG/KG, RESPECTIVELY, EXCRETED WITHIN 4 HR AFTER ADMIN. AT ALL DOSES RAPID AND EXTENSIVE METAB BY THE LIVER AND SMALL INTESTINE WAS OBSERVED.

THE CHANGE IN THE URINARY AND FECAL EXCRETIONS AND DISTRIBUTION OF (3)H LABELED 2,4-DNT IN RATS INGESTING A 0.5% 2,4-DNT DIET FOR 4 MO WAS STUDIED. EXCRETION AND DISTRIBUTION STUDIES SHOWED THAT THE LIVER, SKIN, AND THE ADIPOSE TISSUE ACCUMULATED THE UNCHANGED 2,4-DNT AND/OR ITS METABOLITES.

Excretion of dinitrotoluene in excess of 25 mg/L indicates significant absorption /in industrial exposed populations/. /Dinitrotoluene/

For more Absorption, Distribution and Excretion (Complete) data for 2,4-DINITROTOLUENE (6 total), please visit the HSDB record page.

The predominant use of 2,4-dinitrotoluene is as an intermediate in the manufacture of polyurethanes.

Used to make dyes, explosives, munitions, propellants, rubber chemicals, plastics, and other chemicals; [HSDB] The technical grade (approximately 80/20 of the 2,4/2,6 isomers) is used primarily as an intermediate for toluene diamines and diisocyanates; [IARC]

2,4-Dinitrotoluene is used by the munitions industry as a modifier for smokeless powders and, to a limited extent, as a gelatinizing and waterproofing agent in military and commercial explosive compositions.

Intermediate in the manufacture of toluene diisocyanate and polyurethanes.

Organic synthesis, toluidines.

Most of the 2,4-dinitrotoluene produced is hydrogenated to 2,4-diaminotoluene (m-tolylenediamine) for conversion to toluene diisocyanate (TDI), which is a component of a polyurethane; a much smaller amount is used in explosives and for further nitration to TNT.

2023: 150,000,000 - <500,000,000 lb

(1977) AT LEAST 4.54X10+10 G

(1982) PROBABLY GREATER THAN 3.27X10+9 G-MIXT

(1975) ... Combined production of 272,610,000 lb for 2,4- and 2,6-dinitrotoluene.

(1991) Exceeded 5000 lb or US $5000 in value

For more U.S. Production (Complete) data for 2,4-DINITROTOLUENE (7 total), please visit the HSDB record page.

Manufacture of toluene diisocyanate consumes much of the 2,4-DNT produced. In 1976, 560 million lb of toluene diisocyanate was produced. This production consumed roughly 389 million lb of toluene. A total of 389 million lb of toluene would produce approximately 740 million lb of 2,4-DNT, assuming 96% yield.

Dinitration of toluene results in the formation of a number of isomeric products, and with a typical sulfuric-nitric acid nitrating mixture the following mixture of isomers is obtained: 75 wt% 2,4-dinitrotoluene, 19 wt% 2,6-dinitrotoluene, 2.5 wt% 3,4-dinitrotoluene, 1 wt% 2,3-dinitrotoluene, and 0.5 wt% 2,5-dinitrotoluene.

4-Nitrotoluene is nitrated with mixed acid (containing equimolar HNO3) under controlled conditions and continuous operation to give a 96% yield of 2,4-dinitrotoluene. In Meissner units, for tighter control of the whole process, cocurrent flow is used in each step to separate mono- and dinitration, but countercurrent flow is used between them to prevent under or overnitration; this is also done in one-step nitration plants. After nitration, if separation of the resulting emulsion is difficult, the introduction of pure product can give ... rapid separation.

Available in solid, liquid & granular technical grades

A commercial grade, consisting of a mixture of the three isomers, in an oily liquid.

All Other Basic Organic Chemical Manufacturing

Benzene, 1-methyl-2,4-dinitro-: ACTIVE

Analysis of technical grade dinitrotoluene yielded the following results: 76.49% 2,4-DNT, 18.83% 2,6-DNT, 0.65% 2,5-DNT, 2.43% 3,4-DNT, 1.54% 2,3-DNT, 0.040% 3,5-DNT, 0.050-trinitrotoluene, 0.005 cresols, 0.003 mononitrobenzene, and 0.003%, 0.0005%, and 0.006%, for ortho-, meta-, and para-, mononitrotoluenes, respectively.

Dinitrification of toluene typically yields 75% 2,4-dinitrotoluene by weight