Technical Fact Sheet – Dinitrotoluene (DNT) - US EPA

1 Technical Fact Sheet . Dinitrotoluene (DNT). November 2017. Technical FACT Sheet DNT. Introduction At a Glance This fact Sheet , developed by the Environmental Protection Agency Nitroaromatic explosive that (EPA) Federal Facilities Restoration and Reuse Office (FFRRO), provides a exists as six isomers: 2,4- and summary of Dinitrotoluene (DNT), including physical and chemical properties;. 2,6-DNT are the most environmental and health impacts; existing federal and state guidelines;. common forms. detection and treatment methods; and additional sources of information. This Not naturally found in the fact Sheet is intended for use by site managers and field personnel who may environment.

2 Address DNT contamination at cleanup sites or in drinking water supplies. Used as an intermediate in The widespread use of DNT in manufacturing munitions, polyurethane foams, the production of ammunition, and other chemical products has contributed to extensive soil and polyurethane polymers, dyes, groundwater contamination. DNT can be transported in surface water or plasticizers and automobile groundwater because of its moderate solubility and relatively low volatility, airbags. unless degraded by light, oxygen or biota. As a result, releases to water are Found in waste streams of important sources of human exposure and remain a significant environmental DNT manufacturing or concern.

3 DNT is considered toxic to most organisms, and chronic exposure processing facilities. may result in organ damage. EPA currently classifies DNT as a priority pollutant. Expected to remain in water for long periods of time because of its relatively low What is DNT? volatility and moderate water DNT is a nitroaromatic explosive that exists as six isomers: 2,4- and 2,6- solubility. DNT are the two major forms; 2,3-DNT, 2,5-DNT, 3,4-DNT and 3,5-DNT. Adverse effects identified in are minor isomers (ATSDR 2016; Lent and others 2012a). the blood, nervous system, Technical grade DNT (Tg-DNT) is about 2,4-DNT, 2,6-DNT, liver and kidney in animals and minor isomers ( 3,4-DNT, 2,3-DNT, 2,5- after exposure.)

4 DNT, and 3,5-DNT (ATSDR 2016; Lent and others 2012a). Classified as a Class B2 DNT is not found naturally in the environment. It is usually produced by (probable human) carcinogen. mixing toluene with nitric and sulfuric acids and is an intermediate in 2,4,6- Health-based goals, exposure trinitrotoluene (TNT) manufacturing (ATSDR 2016; EPA 2008). limits, screening levels and A mixture of DNTs is sold as an explosive and is a starting material for the state drinking water guidelines production of 2,4,6-TNT. The mixture is also used as a modifier for have been developed. smokeless powders in the munitions industry, in airbags of automobiles, as Standard detection methods a chemical intermediate for the production of toluene diisocyanate (TDI), include gas chromatography dyes and urethane foams (ATSDR 2016; EPA 2008).

5 (GC) and high-performance There are currently a small number of DNT manufacturing facilities in the liquid chromatography United States (EPA 2008). (HPLC). Common treatment technologies include Disclaimer: The EPA prepared this fact Sheet using the most recent publicly- adsorption, chlorination, available scientific information; additional information can be obtained from the source ozonation, ultraviolet documents. This fact Sheet is not intended to be used as a primary source of radiation, alkaline hydrolysis information and is not intended, nor can it be relied upon, to create any rights and bioremediation. enforceable by any party in litigation with the United States.

6 Mention of trade names or commercial products does not constitute endorsement or recommendation for use. United States Office of Land and Emergency EPA 505-F-17-010. Environmental Protection Agency Management (5106P) November 2017. 1. Technical Fact Sheet DNT. Exhibit 1: Physical and Chemical Properties of 2,4- and 2,6-DNT. (ATSDR 2016; EPA 2008). Property 2,4-DNT 2,6-DNT. Chemical Abstracts Service (CAS) number 121-14-2 606-20-2. Physical description (physical state at room Yellow solid Yellow to red solid temperature and atmospheric pressure). Molecular weight (g/mol) Water solubility (mg/L) 270 at 22 oC 180 at 20 oC. Melting point (oC) 71 66. Boiling point (oC) 300 285.

7 Vapor pressure at 20 oC (mm Hg) x 10-4 x 10-4. Specific gravity/Density at 71 oC at 111 oC. Octanol-water partition coefficient (log Kow) Organic-carbon partition coefficient (log Koc) Henry's law constant (atm-m3/mol) x 10-8 x 10-7. Abbreviations: g/mol grams per mole; mg/L milligrams per liter; oC degree Celsius; mm Hg millimeters of mercury;. atm-m3/mol atmosphere-cubic meters per mole. Existence of DNT in the environment DNT is commonly found in surface water, broken down by photodegradation (EPA 2008;. groundwater and soil at hazardous waste sites HSDB 2013). that contain buried ammunitions waste or waste Photolysis is the primary means for DNT. from facilities that manufacture or process DNT degradation in oxygenated water.

8 The (EPA 2008; Darko-Kagya and others 2010; Lent photodegradation of 2,6-DNT was assessed under and others 2012a). simulated solar radiation in a seawater solution. As of 2016, DNT has been identified at 56 sites on Within 24 hours, 2,6-DNT had been reduced by 89. the EPA National Priorities List (NPL) (EPA 2016). percent and after 72 hours had been fully Because of their low vapor pressures and low degraded (EPA 2008; NAVFAC 2003). Henry's Law constants, 2,4- and 2,6-DNT do not Biodegradation of 2,4- and 2,6-DNT in water can usually volatize from water or soil. The isomers occur under both aerobic and anaerobic conditions are usually released to air in the form of dusts or (EPA 2008).

9 Aerosols from manufacturing plants or adsorbed to Microorganisms indigenous to surface soil and other suspended particles (EPA 2008). aquifer materials collected at a munitions- 2,4- and 2,6-DNT have only a slight tendency to contaminated site were able to transform 2,4- and sorb to sediments, suspended solids or biota 2,6-DNT to amino-nitro intermediates within 70. based on their relatively low organic-carbon days (Bradley and others 1994). partition coefficients (EPA 2008). 2,4- and 2,6-DNT have relatively low octanol-water The retention of DNT in soil depends on the partition coefficients and, as a result, are not chemistry and content of the soil organic matter expected to bioaccumulate significantly in animal (Clausen and others 2011; Singh and others tissue (ATSDR 2016).)

10 2010). As a result of its moderate solubility, DNT can be Unless broken down by light, oxygen or biota, transferred to plants via root uptake from soil and DNT is expected to remain in water for long is expected to accumulate readily in plant periods of time because of its relatively low materials (EPA 2008). volatility and moderate water solubility. As a result, DNT's bioavailability and toxicity to plants are DNT has the potential to be transported by greatly altered by soil properties. Studies have groundwater or surface water (ATSDR 2016; EPA found that the toxicity of 2,4- and 2,6-DNT for 2008). various plant species is significantly and inversely Vapor-phase 2,4- and 2,6-DNT have an estimated correlated with soil organic matter content half-life of 75 days in the atmosphere and are (Rocheleau and others 2010).