1,3,5-トリニトロ-2-メチルベンゼン

Other Uses -> Explosives

Carcinogens

log Kow = 1.60

1.60

1.86

1.654 at 68 °F (NTP, 1992) - Denser than water; will sink

1.654 at 20 °C/4 °C

1.65 g/cm³

1.65

1.654 @25 °C

1.65

Monoclinic rhombohedra from alc; commercial crystals (needles) are yellow

Colorless to pale-yellow solid or crushed flakes

Insoluble (NTP, 1992)

In water, 115 mg/L at 23 °C

Sol less than 2,4,6-trinitrophenol in alc, ether, carbon disulfide

About 0.01% in water at 25 °C. 1 g/700 ml boiling water

Solubilities in various solvents at 18 °C. [Table#2876]

(Explodes) (NIOSH, 2024)

explodes

? (Explodes)

464 °F at 760 mmHg EXPLODES (NTP, 1992)

240 °C (explodes)

464 °F (explodes)

464 °F (Explodes)

Danger

H201: (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P210, P230, P240, P250, P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P370+P380, P372, P373, P391, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H201 (100%): (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P203, P210, P230, P240, P250, P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P319, P321, P330, P361+P364, P370+P380, P372, P373, P391, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Benzene, 2-methyl-1,3,5-trinitro-

Hazard Traits - Carcinogenicity

Benzene, 2-methyl-1,3,5-trinitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 2-methyl-1,3,5-trinitro- 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)

Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/16165

2,4,6-Trinitrotoluene: Does not have an individual approval but may be used under an appropriate group standard

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.)

Flammable Solid

Explosive 1.1D

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

Flash point data for this chemical are not available. It is explosive. (NTP, 1992)

· Flammable/combustible material.

· Flammable/combustible material.

Many reactions may cause fire or explosion. Risk of fire and explosion on rapid heating or on strong shock. Explosive.

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

SYMPTOMS: Symptoms of exposure to this compound may include headache, weakness, anemia, toxic hepatitis, cyanosis, dermatitis, jaundice, purpura, liver injury, conjunctivitis, irritation of the respiratory tract, constriction in the chest, lack of appetite, nausea, vomiting, diarrhea, petechial hemorrhages in the skin, oliguria, albuminuria, casts in urine, papular dermatitis, and yellow-orange discoloration of the hands, nails, face and hair.

· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic.

· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic.

2,4,6-Trinitrotoluene is a yellow, odorless solid that does not occur naturally in the environment. It is commonly known as TNT and is an explosive used in military shells, bombs, and grenades, in industrial uses, and in underwater blasting. 2,4,6-Trinitrotoluene production in the United States occurs solely at military arsenals.

Toxic hepatitis, aplastic anemia, methemoglobinemia, hemolytic anemia, and cataracts have been reported after occupational exposure. In one case, 43% methemoglobinemia was induced after 24 hours from an inhalation and skin exposure. Exposed workers experienced sneezing, sore throat and skin irritation. In a munitions plant with mean air levels of 2.38 mg/m3, no fatalities or permanent liver damage were reported in workers handling TNT over a period of 20 years. Abnormal liver function tests were found in a study of 43 TNT shell-packers and shell-loaders during a 5-month period in which dust level ranged from 0.3 to 0.8 mg/m3. Hemolytic anemia has been described in workers with a genetic glucose-6-phosphate dehydrogenase (G6PD) deficiency. Reduced hemoglobin values were seen with exposures as low as 0.48 mg/m3. Cataracts were induced in 6 of 12 workers exposed at 0.14 to 0.58 mg/m3 for 6.8 [+/-] 4.7 years and in 7 of 9 workers exposed at 0.10 to 0.35 mg/m3 for 1 to 27 years (average of 14 years). Listed in the table Examples of Industrial Chemicals for Which Methemoglobin Formation is NOT the Principal Cause of Toxicity; [ACGIH] May stain the skin yellow and cause dermatitis; Other potential adverse effects are methemoglobinemia, hemolysis, liver injury, and jaundice. [ICSC]

3366 113

1356 113

1356 113(wet)

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Agency for Toxic Substances and Disease Registry, U.S. Department of Health and Human Services. Toxicological Profile for 2,4,6-Trinitrotoluene (1995)

National Research Council, Washington; Evaluation of the health risks of ordnance disposal waste in drinking water; Rept (NRC-TOX-P897): 58 pages (1982) NTIS# PB83-153635. Drinking water standards and legal and permissible concn of pollutants in ordinance wastes.

72 FR 18792 (4/13/2007); Department of Labor; Occupational Safety and Health Administration. Explosives, Proposed Rule. OSHA proposes to revise the explosives and blasting agents standard in subpart H of part 1910. This revision of section 1910.109 is intended to enhance the protections provided to employees engaged in the manufacture, storage, sale, transportation, handling, and use of explosives. The proposal updated and clarifies the regulatory language, addresses regulatory inconsistencies between OSHA and other Federal agencies, incorporates updated consensus standards, and provides the regulated community with greater compliance flexibility.

Ryon MG; Water Quality Criteria for 2,4,6-Trinitrotoluene (TNT) (Final Report) (1987) AD-ORNL-6304. A report with 155 references on environmental effects and fate, aquatic toxicity, mammalian toxicity and human health effects of 2,4,6-trinitrotoluene.

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

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Use water in large amounts. Do not attempt to extinguish large fire, evacuate area. 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 . Wear protective gloves when administering first aid.

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

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Wear protective gloves when inducing vomiting.

· 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.

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

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:

(General first aid procedures)

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.

May explosively decompose on shock, friction, or concussion. Explodes on heating to 240 °C.

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

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

Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or end of shift. [ACGIH]

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. /Trinitrotoluene, wetted or TNT, wetted with not less than 30% water, by mass/

Evacuation: If the material is on fire or involved in fire consider evacuation of one (1) mile radius. /Trinitrotoluene (TNT)/

If material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn. /Trinitrotoluene (TNT)/

Evacuation: If the material is on fire or involved in fire consider evacuation of one (1) mile radius. /Trinitrotoluene (TNT)/

If material on fire or involved in fire: Solid streams of water may spread fire. Use water in flooding quantities as fog. Use dry chemical, graphite, or dry earth. /Trinitrotoluene (TNT), wetted (with not less than 10% water, by mass)/

Physical treatments, such as sorption by activated carbon or ion exchange resins or coagulation and filtration, are effective in removing TNT and other related cmpd present in munitions mfg wastewater.

TNT was removed from wastewater using treatment by amines.

The feasibility was demonstrated of treating explosive-contaminated wastewater using an oxidant (hydrogen peroxide) in conjunction with short wavelength UV light. The process achieves a high degree of decontamination without any troublesome by-products. Water contaminated with TNT ... was successfully treated using this photooxidative method.

Evacuate danger area! Consult an expert! Wet spilled material before picking it up, do not attempt to sweep up dry material. Do NOT wash away into sewer. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment. Chemical protection suit including self-contained breathing apparatus.

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

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

... Bench-scale composting of up to 10% TNT showed that almost complete removal of TNT occurred in 55 days. Many of the toxic transformation products formed in activated sludge and soil were not found in the composted TNT. ... Composted wastes of TNT and other munitions must be examined for the leachability of undecomposed chem and transformation products prior to land treatment.

Pink water (mainly consists of alpha-2,4,6-trinitrotoluene (alpha-TNT) and various concentrations of nitrobodies such as RDX) was successfully oxidized electrochemically from a range of 60-105 ppm TNT to below acceptable disposal concn (0.5 ppm). The oxidation process does not produce any toxic by-products, and at an electrical cost of approximately $2.00 per 1000 gal, is most competitive in comparison to present alternatives.

The following wastewater treatment technologies have been investigated for 2,4,6-trinitrotoluene Biological treatment, Activated Carbon, and Resin adsorption.

Disposal of 2,4,6-trinitrotoluene has been accomplished effectively by burning in an incinerator equipped with an afterburner and a scrubber ... 2,4,6-Trinitrotoluene has been pretreated before incineration by pouring or sifting onto sodium bicarbonate or a sand-soda ash mixture. The resulting combination is mixed and packaged in heavy paper cartons with plenty of paper packaging to serve as fuel ... 2,4,6-Trinitrotoluene has also been prepared for incineration by mixing with a flammable solvent, such as alcohol or benzene, and spraying the resulting mixture into the fire chamber of an incinerator.

The mixture of the two compounds is designated as LAP (load, assemble, and pack) mixture. The ratio of 2,4,6-trinitrotoluene and 1,3,5-trinitrohexahydro-1,3,5-triazine (RDX) in the LAP mixture in this study was 1.6:1. Acute oral toxicity of the LAP mixture was investigated in rats, mice, and rabbits. The results indicate that there was a distinct species difference regarding acute oral toxicity after exposure to the LAP mixture. The acute oral LD50 values indicate that rats were more susceptible to toxic effects of the LAP mixture than to 2,4,6-trinitrotoluene alone. The opposite was true for mice ... LAP applied to the eyes of rabbits produced conjunctivitis, iritis, and/or corneal opacity. Intermediate oral toxicity was determined in a 90-day exposure study in rats, mice, and dogs. The results indicate that the main target organs for LAP toxicity are the same as those for 2,4,6-trinitrotoluene, namely blood and liver. Mild-to-moderate hemolytic anemia, enlarged spleens and livers, hemosiderosis of the spleen, and colored urine were common effects of intermediate exposure to LAP seen in all three species. LAP-induced testicular atrophy (dogs and rats), uterine hypoplasia (rats), and numerous neurological signs (dogs) were also observed. These observations indicate that 2,4,6-trinitrotoluene was the principal, but not the only factor, contributing to the intermediate oral toxicity of LAP; some of the observed toxicity is due to RDX .

Dermal (Skin), Hematological (Blood Forming), Hepatic (Liver), Ocular (Eyes)

Hepatic

Eyes, skin, respiratory system, blood, liver, cardiovascular system, central nervous system, kidneys

Exposition to high concentrations of 2,4,6-trinitrotoluene in air can lead to several harmful health effects, including anemia and abnormal liver function. Similar blood and liver effects, as well as spleen enlargement and other harmful effects on the immune system, have been observed in animals that ate or breathed 2,4,6-trinitrotoluene. Other effects in humans include skin irritation after prolonged skin contact, and cataract development after long-term (365 days or longer) exposure. It is not known whether 2,4,6-trinitrotoluene can cause birth defects in humans. However, male animals treated with high doses of 2,4,6-trinitrotoluene have developed serious reproductive system effects. Moreover, the EPA has determined that 2,4,6-trinitrotoluene is a possible human carcinogen. (L132)

LC50 Daphnia magna >4.4 mg/l/48 hr at 20 °C /Flow through Bioassay/

LC50 Lepomis macrochirus (bluegill sunfish) is 2.7 mg/l with a mean weight of 0.39 g in a 96 hr at 10 °C /Static Bioassay/

LC50 Pimephales promelas (fathead minnow) 0.46 mg/l/ 96 hr at 24 °C /Flow through, immobilization test/

EC50; Species: Pseudokirchneriella subcapitata (Green algae); Conditions: freshwater; static; Concentration: 2.5 uM (95% confidence limit: 2.1 to 2.9 uM) for 96 hr; Effect: population, abundance /formulated product/

For more Ecotoxicity Values (Complete) data for 2,4,6-TRINITROTOLUENE (43 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an average Koc value of 1,600(2) indicates that 2,4,6-trinitrotoluene is expected to have low mobility in soil(SRC). Volatilization of 2,4,6-trinitrotoluene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), derived from its vapor pressure of 8.02X10-6 mm Hg(3) and water solubility of 115 mg/L(4). 2,4,6-Trinitrotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation of 2,4,6-trinitrotoluene in soil will be of minor importance; however 2,4,6-trinitrotoluene is readily reduced under anaerobic conditions(5). Microbial transformation of 2,4,6-trinitrotoluene leads to a variety of reduction products, including 2-amino and 4-amino dinitrotoluene and azoxydimers(3,5,7). Limited information regarding photolytic processes in soil suggest that 2,4,6-trinitrotoluene in surface layers is photolyzed to trinitrobenzene and trinitrobenzaldehyde(8). Gas chromatography-electron capture measurements demonstrated that a sea water solution at a pH of 8.1 with 95 ppm 2,4,6-trinitrotoluene underwent no change in concn after 108 days(7), thus evidencing the stability of 2,4,6-trinitrotoluene against hydrolysis in water under neutral conditions(9).

TERRESTRIAL FATE: Phytoremediation of 2,4,6-trinitrotoluene has shown that metabolism takes place in three stages; transformation (formation of 2-amino-4,6-dinitrotoluene and 4-amino-2,6-dinitrotoluene), conjugation, and sequestration (formation of bound residues within the plant)(1). Hybrid poplar trees planted in 2,4,6-trinitrotoluene contaminated soil from Iowa Army Ammunition Plant showed an uptake of 25% 2,4,6-trinitrotoluene in 20 days(2). 75% of the 2,4,6-trinitrobenzene was found in the roots, 17% in the stems and 6% in the leaves(2).

AQUATIC FATE: Based on a classification scheme(1), an average Koc value of 1,600(2) indicates that 2,4,6-trinitrotoluene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), derived from its vapor pressure of 8.02X10-6 mm Hg(4) and water solubility of 115 mg/L(5). According to a classification scheme(6), an estimated BCF of 3.4(SRC), from its log Kow of 1.60(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The capability of microorganisms to biotransform 2,4,6-trinitrotoluene seems well established(2,9-11); however, reduction rates under aerobic conditions are very slow. Photolysis studies comparing river waters and distilled water have shown that the rate of 2,4,6-trinitrotoluene photolysis is directly related to increases in pH(10-11) and organic matter content(2). In the presence of oxygen, 10 ppm of 2,4,6-trinitrotoluene added to a freshwater bay sample remained unchanged for 20 days then following first order kinetics with an estimated half-life of 25 days and dropped to 3 ppm within 64 days(2). 2,4,6-Trinitrotoluene at an initial concn of 20 ppm within the dark control bottle of a river die away study underwent a 90% reduction within 30 days(11). However biotransformation was identified to be 100-1000 times slower than photolytic processes(2,11). Gas chromatography-electron capture measurements demonstrated that a sea water solution at a pH of 8.1 with 95 ppm 2,4,6-trinitrotoluene underwent no change in concn after 108 days(12), thus evidencing the stability of 2,4,6-trinitrotoluene against hydrolysis in water under neutral conditions(13).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4,6-trinitrotoluene, which has a vapor pressure of 8.02X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,4,6-trinitrotoluene 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 120 days(SRC), calculated from its rate constant of 1.4X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2,4,6-trinitrotoluene may be removed from the air by wet or dry deposition(SRC). The rate constants for river water, seawater, pond water and distilled water were 1.2X10-3, 1.5X10-4, 5.8X10-4 and 1.7X10-5/sec, respectively, which correspond to half-lives of about 10 min, 1.3 hrs, 20 min and 11.3 hrs(4).

Lab scale compost systems can be used for the estimation of the degradation rates of hazardous materials in a compost and to identify the degradation products. Composting /consisted of/ chopped alfalfa hay 45, horse feed 45, and soil 10% contaminated with explosives ... TNT was rapidly transformed into nonextractable cmpd which resembled humus matrials. ... TNT showed no ring degradation. The amount of leachable TNT declined with its increasing biotransformation.

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

inhalation, skin absorption, ingestion, skin and/or eye contact

Oral (L131) ; inhalation (L131) ; dermal (L131)

2,4,6-Trinitrotoluene is a competitive inhibitor with respect to NADPH and a noncompetitive inhibitor with respect to L-arginine. It binds to the P450 reductase domain of the eNOS and suppresses l-citrulline formation by shunting electrons away from the normal catalytic pathway. The reduction of TNT then produces reactive oxygen species (ROS), such as superoxide (O2.−), and hydrogen peroxide (H2O2). The overproduction of superoxide is associated with oxidative stress-mediated induction of cataracts. The inhibition of the eNOS activity occurs in a concentration-dependent manner. (A110, A111)

/BIRDS and MAMMALS/ Considerable concentrations of the explosive, 2,4,6-trinitrotoluene (TNT) have been found in the soil at many installations where explosives have been used, manufactured, assembled, or destroyed. To evaluate risk to avian receptors, measures of exposure are compared with a threshold level of sublethal toxicity. To date, a single feeding study has evaluated the responses of oral TNT exposure to birds with equivocal results regarding sublethal effects. The present study followed a controlled dosing regime comprising four dose groups and a control (200, 120, 70, 20, and 0 mg TNT/kg body weight-day) in the common pigeon (Columba livia) for 60 days. Overt signs of toxicity occurred with both sexes between 2 and 3 weeks of exposure. Signs included weight loss, neuromuscular effects (e.g., ataxia, tremors, etc.), and scant red feces (chromaturia). Emetic events following dosing were common and proportional to dose; however, attempts to quantify vomitus compound concentration suggests that birds were marginally successful at removing TNT following administration. Eight of 12 and 2 of 12 males and females died or were moribund in the 200 and 120 mg/kg-day groups, respectively. Changes in hematological parameters, liver, kidney, and ovary weights were related to treatment. Dose-related changes in plasma albumin and sodium concentrations were also observed. These results suggest that subchronic exposure to TNT can adversely affect the central nervous system and hematological parameters in birds. Chemical analysis of blood detected concentrations of the two primary reduction metabolites, but not parent compound, suggesting that toxicity may be due to the bioaccumulation of a toxic intermediate.

/BIRDS and MAMMALS/ Subchronic dietary exposure to TNT was ... evaluated in a species of management concern at military installations, the northern bobwhite (Colinus virginianus). Adult male and female quail (n = 5/sex/dose) were given commercial feed containing 3,000, 1,500, 750, and 100 mg/kg TNT for 90 days following the determination of an acute lethal dose and a 14-day range finding study. Dietary TNT intake caused a dose-dependent decrease in total red blood cell counts, packed cell volume, total plasma protein, blood prolymphocytes, and blood lymphocytes. An increased trend in late apoptotic/necrotic blood leukocytic cells was also observed in TNT-exposed birds, as was hemosiderosis in the liver. With the exception of hemosiderosis, these trends were statistically significant yet of questionable biological significance. Since treatment-related responses in this preliminary study were variable, a conservative interpretation is suggested. However, since these treatments had concentrations that were a log-fold or more than doses in similar studies using mammals, these data suggest that northern bobwhite are less sensitive to oral exposures of TNT than mammals.

/AQUATIC SPECIES/ In /Kyoto, Japan/, relatively high concentrations of ... trinitrotoluene (TNT), /and its metabolites/ ... 2-amino-4,6-dinitrotoluene (2ADNT), and 4-amino-2,6-dinitrotoluene (4ADNT) ... have been identified from field samples. /The author/ used a standardized assay with Xenopus laevis embryos (frog embryo teratogenesis assay--Xenopus, FETAX) to examine the developmental toxicity of these compounds. ... The TNT (96-hr LC50 = 16.7 uM) was more lethal than 2ADNT (96-hr LC50 = 166 uM) or 4ADNT (96-hr LC50 = 115 uM). Although 4ADNT (96-hr EC50 = 85.8 uM) induced various tadpole malformations, it was a weak teratogen compared with TNT (96-hr EC50 = 9.78 microM) and 2ADNT (96-hr EC50 = 16.9 microM). The most typical malformations observed were axial malformations, eye abnormalities (TNT), edema, and irregular gut coiling (2ADNT and 4ADNT). The 96-hr LC50 and 96-hr EC50 values of TNT, 2ADNT, and 4ADNT were lower than their saturated concentrations in water. Therefore, these nitroaromatic compounds may show lethal or teratogenic effects on aquatic animals if their habitats are severely contaminated with TNT.

/AQUATIC SPECIES/ Synthetic condensate wastewater prepared to simulate the composition of condensate wastewater from TNT manufacture and containing 32 compounds showed acute toxic concentrations for bluegills (Lepomis macrochirus), scud (Hyalella azteca), and green algae (Selenastrom capricornutum) of 7.1 mg/L, 22.8 mg/L, and 10 mg/L respectively.

For more Ecotoxicity Excerpts (Complete) data for 2,4,6-TRINITROTOLUENE (25 total), please visit the HSDB record page.

TNT

A Commercial Grade

5000

A Commercial Grade

400

Explosive chemical that can be released at a facility.

(FL) FLORIDA 10 ug/L

(ME) MAINE 3.5 ug/L

... The hypothesis that 2,4,6-trinitrotoluene induces anemia by causing hemolysis through oxidative damage which is mediated by 2,4,6-trinitrotoluene and/or its metabolites ... is ... supported by the presence of methemoglobinemia, produced by the oxidation of the heme iron, observed when 2,4,6-trinitrotoluene was fed to rats at 300 mg/kg/day for 13 weeks ... to rats at 10 or 50 mg/kg/day for 24 months ... and to dogs at 32 mg/kg/day for 6 months ...

One of the proposed mechanisms of 2,4,6-trinitrotoluene-induced toxicity is an increase in free radical levels which occurs after exposure. Superoxide radicals and hydrogen peroxide were measured in mitochondria and microsomes from livers of monkeys treated with 0, 60, or 120 mg/kg/day of 2,4,6-trinitrotoluene for 12 weeks ... The amount of superoxide radicals was indirectly measured by the formation of adrenochrome from adrenalin, and hydrogen peroxide production was evaluated by the conversion of methanol to formaldehyde. There was a dose-dependent increase in superoxide radicals and hydrogen peroxide production in liver mitochondria and microsomes ... These findings were confirmed when mitochondria and microsomes obtained from various organs were treated in vitro with 0, 0.04, 0.2, or 1 mmol of 2,4,6-trinitrotoluene and then tested for adrenochrome and formaldehyde production. Different amounts of hydrogen peroxide were produced in the mitochondria of the various organs. The highest amount of hydrogen peroxide was present in the liver followed by brain, testicle, kidney cortex, and kidney medulla ...

A theory of the mechanism of toxicity by 2,4,6-trinitrotoluene is that the parent compound and some metabolic intermediates are active oxygen generators ... and are involved in lipid peroxidation in the liver and in oxygenation of the lens to form cataracts ...

The metabolism of 2,4,6-trinitrotoluene (TNT) was studied in rats, mice, rabbits, and dogs following oral, dermal, or intratracheal admin of single doses of (14)C-ring labeled compound. TNT was extensively metabolized in all species; radioactivity was excreted in urine primarily as the glucuronide conjugates. Most metabolites were reduction products including the 2- and 4-hydroxylamine and 2- and 4-monoaminodinitro and 2,6- and 4,6-diaminomononitro derivatives. Trace quantities of TNT, trinitrobenzyl alcohol, and trinitrobenzoic acid were detected occasionally.

At levels of 1x10-4 to 1x10-3 g 2,6-dinitro-4-aminotoluene, the major known metabolite of TNT, was found in urine samples of munitions workers.

TNT undergoes both oxidative and reductive metabolism in animals and humans. The nitro groups are reduced through intermediate hydroxylamines to amines. The methyl group can be oxidized to an alcohol and an acid, both of which can be conjugated with glucuronic acid and excreted in the urine. 4-Amino-2,6-dinitrotoluene (4-A), 6- amino-2,4-dinitrotoluene, and 4-hydroxylamino-2,6- dinitrotoluene (4-HA) were found in the urine of rabbits fed TNT.

TNT itself as well as 2-amino-4,6- dinitrotoluene (2-A), 4-A, and 2,4-diamino-6- nitrotoluene were found in the urine of rats given TNT orally. 4-HA and 4-A were found in the urine of dogs fed TNT. 4-A, 2-A, hydroxylaminodinitrotoluenes, and diaminonitro compounds were found in the urine of TNT-exposed munitions workers.

For more Metabolism/Metabolites (Complete) data for 2,4,6-TRINITROTOLUENE (18 total), please visit the HSDB record page.

2,4,6-Trinitrotoluene rapidly and completely enters the body through inhalation or ingestion, but more slowly through the skin. Once 2,4,6-trinitrotoluene is in the blood, it travels throughout the body to all of the organs. When it reaches the liver, it breaks down and changes into several different substances, such as 4-aminodinitrotoluene, 2-aminodinitrotoluene and 2,4-diamino-6-nitrotoluene. Most of these substances travel in the blood until they reach the kidneys. Almost all of the 2,4,6-trinitrotoluene that enters the body breaks down and leaves the body in the urine within 24 hours. (L132)

Substances that are energetically unstable and can produce a sudden expansion of the material, called an explosion, which is accompanied by heat, pressure and noise. Other things which have been described as explosive that are not included here are explosive action of laser heating, human performance, sudden epidemiological outbreaks, or fast cell growth.

Trinitrotoluene (TNT) absorption was assessed in workers at two explosives factories by measuring urinary concentrations of dinitroaminotoluene dinitroaminotoluene metabolites. The range of atmospheric concentrations was 0.02-5.73 mg/cu m in static samples and <0.01 to 0.71 mg/cu m in personal samples. In postshift urine samples, the mean concentration of dinitroaminotoluene was 9.7 mg/l (standard deviation= 7.9, n= 219). TNT was shown to be absorbed rapidly during the exposure period. A wide variation among individuals in the rate of clearance of TNT metabolites was seen. For the group as a whole the daily mean urinary total dinitroaminotoluene concentrations in preshift samples were lower than those in postshift samples although in some cases higher concentrations of metabolites were seen in samples taken the morning after exposure. Urine samples collected after 17 days away from the workplace still showed detectable levels of dinitroaminotoluene (mean 0.06 mg dinitroaminotoluene/l) indicating that a proportion of TNT or its metabolites is slowly excreted.

... Two surveys of 2,4,6-trinitrotoluene-exposed workers /were performed/. Air concentrations of 2,4,6-trinitrotoluene were found to range from 0.6 to 4.0 mg/cu m. The urinary excretion of 2,6-dinitro-4-aminotoluene was 2.5 and 6.5 mg/L, respectively.

The disposition and metabolism of 2,4,6-trinitrotoluene (TNT) was studied in rats, mice, rabbits, and dogs following oral, dermal, or intratracheal administration of single doses of 14-C-ring labeled compound. The objective was to determine possible species and sex differences as a function of route of admin as a rationale for the design of chronic studies. TNT was absorbed in all species by all routes of admin with the most extensive absorption occurring after intratracheal instillation. Dermal absorption was the highest in rabbits followed by mice, rats, and dogs. Species differences in the rate of oral absorption could not be accurately assessed. Excretion was primarily in urine and to a lesser extent in feces. Extensive biliary excretion was also noted. Blood and tissue levels in females were generally higher than in males.

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

For more Absorption, Distribution and Excretion (Complete) data for 2,4,6-TRINITROTOLUENE (17 total), please visit the HSDB record page.

An explosive that requires a high-velocity initiator or efficient concussion to detonate; [ACGIH]

2,4,6-Trinitrotoluene is used as a high explosive in military and industrial applications. It has been widely used for filling shells, grenades and airborne demolition bombs, as it is sufficiently insensitive to the shock of ejection from a gun barrel but can be exploded on impact by a detonator mechanism. It has been used either as the pure explosive or in binary mixtures ... Small amounts of 2,4,6-trinitrotoluene have been used for industrial explosive applications, such as deep-well and underwater blasting ...

Explosive. Intermediate in dyestuffs and photographic chemicals

2,4,6-Trinitrotoluene is an explosive used in military shells, bombs, and grenades, in industrial uses, and in underwater blasting. Exposure may results from drinking contaminated water that has migrated from chemical waste disposal sites, breathing contaminated air, eating contaminated foods such as fruits and vegetables, and/or eating contaminated soil. (L132)

Tetranitromethane /is/ an impurity /of crude 2,4,6-trinitrotoluene/.

2,4,6-Trinitrotoluene is purified by the addn of a concn soln of sodium sulfite to extract isomers and impurities.

(1972) 9.9X10+8 G

(1975) 2.64X10+9 G

(1986) 4.6X10+6 lb

2023: 4,000,000 - <5,500,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2875]

PREPARED BY NITRATION OF TOLUENE WITH MIXED ACID (NITRIC ACID + SULFURIC ACID) IN THREE STEPS OR BY CONTINUOUS FLOW ACCORDING TO THE SCHMID-MEISSNER & BIAZI PROCESSES

Bofors Norell process ... includes both continuous nitration of toluene or mononitrotoluene to trinitrotoluene and continuous crystallization ... from dilute nitric acid.

The Swedish Nobel Chematur Process as modified by Canadian Industry LTD (using sodium sulfate instead of nitric acid in the purification step) ... was /futher modified and/ resulted in the first continuous operation of 2,4,6-trinitrotoluene manufacture in the United States in 1968 at Radford Army Ammunition Plant.

Nitration of toluene with mixed acid. Small amounts of the 2,3,4-and 2,4,5-isomers are produced which may be removed by washing with aqueous sulfite solution.

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

2,4,6-Trinitrotoluene is available commercially in the following forms: dry or wetted with < 10%, < 30% or > 30% water by weight. Military-grade flaked trinitrotoluene is available with the following specifications: setting-point, 80.2 °C; water, 0.10% max.; acidity (as H2SO4), 0.02% max.; alkalinity, none; materials insoluble in benzene, 0.05% max.; and sodium, 0.001% max. Commercial-grade trinitrotoluene (Nitropel) is available with the following specifications: setting-point, 80.1 °C; and water, 1.2% max.

Grade: Technical

Trade names for 2,4,6-trinitrotoluene include Entsufon, Gradetol, Nitropel, Tolit, Tolite, Trilit, Tritol, Trotyl and Trotyl oil.

2,4,6-Trinitrotoluene ... has been used either as the pure explosive or in binary mixtures. The most common binary mixtures of 2,4,6-trinitrotoluene are cyclotols (mixtures with RDX (cyclotrimethylenetrinitramine or 1,3,5- trinitrohexahydro-1,3,5-triazine)), octols (mixtures with HMX (cyclotetramethylenetetranitramine or 1,3,5,7-tetranitro-1,3,5,7-tetraazocyclooctane)), amatols (mixtures with ammonium nitrate) and tritonals (mixtures with aluminium).

Explosives Manufacturing

Benzene, 2-methyl-1,3,5-trinitro-: ACTIVE

TRINITROTOLUENE EXISTS IN 5 ISOMERS; 2,4,6-TRINITROTOLUENE IS THE MOST COMMONLY USED

Trinitrobenzene occurs as a by-product of trinitrotoluene (TNT) production and as a contaminant in water systems where it is formed by photolysis of TNT.

Small amounts of the 2,3,4- and 2,4,5-isomers are produced /by the Schmid-Meissner and Biazi processes/, which can be removed by washing with aqueous sodium sulfite solution.

Numerous other compounds are also formed during the nitration of toluene including unsymmetrical isomers of 2,4,6-trinitrotoluene, and oxidation products such as tetranitromethane, nitrobenzoic acid, nitrocresol, and partially nitrated toluenes ...