SPECTRUM

Chemical Fact Sheet

Chemical Abstract Number (CAS #) 479458
CASRN 479-45-8
SynonymsN-METHYL-N,2,4,6-TETRANITROANILINE(TETRYL)
2,4,6-Tetryl; 2,4,6-Trinitrophenylmethylnitramine
Molecular FormulaC7H5N5O8

Link to the National Library of Medicine's Hazardous Substances
Database for more details on this compound.

UseUsed as an explosive in detonators and primers; as an intermediary detonating agent for other less sensitive, high explosives, and as a booster charge for military devices; it may also be employed as an explosive charge. [R4,p. 568.1(88)]
Apparent ColorColorless to yellow
OdorOdorless
Boiling Point 187 DEG C (explodes)
Melting Point 130-132 DEG C
Molecular Weight 287.15
MiscIR: 750 (Sadtler Research Laboratories IR Grating Collection); +UV: 9663 (Sadtler Research Laboratories IR Grating Collection); +NMR: 18185 (Sadtler Research Laboratories Spectral Collection); +MASS: 221 (Aldermaston, Eight Peak Index of Mass Spectra, UK); +THE CI-ISOBUTANE MASS SPECTRUM OF TETRYL CONSISTS MAINLY OF 1 MAJOR PEAK AT M/E 243. Dangerous fire ... explosion risk [R7, 1141] Evacuation: If the material is on fire or involved in fire consider evacuation of one mile radius. [R8] Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. [R8] Water may be used on small fires. Do not attempt to extinguish large fires. [R5, 2] Toxic gases and vapors (such as oxides of nitrogen and carbon monoxide) may be released in a fire involving tetryl. [R5, 2] Dangerously explosive. Do not fight fires in a cargo of explosives. [R8] EXPLOSION: SEVERE, WHEN SHOCKED OR EXPOSED TO HEAT OR FLAME. IT IS POWERFUL EXPLOSIVE QUITE SENSITIVE TO PERCUSSION & MORE SENSITIVE TO SHOCK & FRICTION THAN TNT. [R9] Explodes at 187 deg C [R10] Explosion temp (temp required to cause explosion in five seconds): 257 deg C (495 deg F) [R5, 2] Impact sensitivity (minimum fall of a 2 kg weight to cause at least one explosion in ten trials): 26 cm [R5, 2] REACTIVITY: Contact of tetryl with some oxidizable materials may cause fires & explosions. [R5, 2] Contact of hydrazine with N,2,4,6-tetranitroaniline caused ignition. [R11, 1193] Tetryl detonates spontaneously on contact with trioxygen difluoride. [R11, 1065] Tetryl is a skin, eye and respiratory irritant. EQUPMENT: Respirator selection: Upper limit devices recommended by OSHA: up to 7.5 mg/cu m: any dust and mist respirator except single use respirators; up to 15 mg/cu m: any dust and mist respirator except single use and quarter mask respirators or any supplied air respirator or any self contained breathing apparatus; up to 37.5 mg/cu m: any powered air purifying respirator with a dust and mist filter or any supplied air respirator operated in a continuous flow mode; up to 75 mg/cu m: any air purifying full facepiece respirator with a high efficiency particulate filter or any self contained breathing apparatus with a full facepiece or any supplied air respirator with a full facepiece; up to 3000 mg/cu m: any supplied air respirator with a full facepiece and operated in a pressure demand or other positive pressure mode; Emergency or planned entry in unknown concentration or IDLH conditions: any self contained breathing apparatus with a full facepiece and operated in a pressure demand or other positive pressure mode or any supplied air respirator with a full facepiece and operated in a pressure demand or other positive pressure mode in combination with an auxiliary self contained breathing apparatus operated in pressure demand or other positive pressure mode; Escape: any air purifying full facepiece respirator with a high efficiency particulate filter or any appropriate escape type self-contained breathing apparatus. [R12] Skin contact may be minimized by the use of impervious fabric clothing fastened at wrists & neck, rubberized aprons & half sleeves & caps or turbans. [R3] Employees should be provided with and required to use ... gloves, face shields (eight inch minimum), and other appropriate protective clothing necessary to prevent repeated or prolonged skin contact with tetryl or liquids containing tetryl. ... Employees should be provided with and required to use splash-proof safety goggles where tetryl or liquids containing tetryl may contact the eyes. [R5, 2] Contact lenses should not be worn when working with this chemical. [R12] Contact lens use in industry is controversial. A survey of 100 corporations resulted in the recommendation that each company establish its own contact lens use policy. One presumed hazard of contact lens use is possible chemical entrapment. /It was/ found that contact lenses minimized injury or protected the eye. The eye was afforded more protection from liquid irritants. Soft contact lenses did not worsen corneal damage from strong chemicals and in some cases could actually protect the eye. Overall, the literature supports the wearing of contact lenses in industrial environments as part of the standard eye protection, eg, face shields; however, more data are needed to establish the value of contact lenses. [R13] If material /is/ not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. [R8] Avoid breathing dusts, and fumes from burning material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing. [R8] ... A complete respiratory protection program should be instituted which incl regular training, maintenance, inspection, cleaning, and evaluation. [R5, 2] Employees who handle tetryl or liquids containing tetryl should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. [R5, 3] If employees' clothing may have become contaminated with tetryl, employees should change into uncontaminated clothing before leaving the work premises. Clothing contaminated with tetryl should be placed in closed containers or storage until it can be discarded or until provision is made for the removal of tetryl from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the tetryl, the person performing the operation should be informed of tetryl's hazardous properties. [R5, 3] To prevent injury to health, atmospheric concn of tetryl should be kept below 1 mg/cu m by automation & enclosure of dust sources such as dryers, sieves, conveyor transfer points, & by remote control of presses, etc. Mechanical exhaust ventilation may not be feasible due to the explosion hazard and plenum ventilation appears to be preferable. Care should be taken to avoid draughts stirring up clouds of tetryl dust ... scrupulous housekeeping & cleaning should be enforced.... Barrier creams & lotions may make other hand protection unnecessary. Adequate sanitary & washing facilities should be provided & workers instructed to observe scrupulous personal hygiene ... indicator soap (sodium sulfite) should be used to verify decontamination. /Some individuals are sensitive to sulfite/. ... Eating and drinking should not be allowed at the workplace. [R3] Is highly stable losing virtually no weight on prolonged storage at 80 deg C. [R14] SHIPPING: No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./ [R15] Int'l Air Shipments: Chemical: Trinitrophenylmethylnitramine is forbidden for transport on passenger and cargo aircraft. [R16] International Water Shipments: Chemical: Trinitrophenylmethylnitramine is in Compatibility Group D. Materials in Group D meet the following criteria: secondary detonating explosive substance or black powder or article containing a secondary detonating explosive substance, in each case without means of initiation and without a propelling charge, or article containing a primary explosive substance and containing two or more independent safety features. IMO Class: 1, Explosive. UN 0208. Label(s) required: Explosive. [R17] STORAGE: KEEP SOLN IN DARK. [R2] Protect from shock. [R5, 2] CLEANUP: If tetryl is spilled, the following steps should be taken: 1. Remove all ignition sources. 2. Ventilate area of spill. 3. Attempt to reclaim spilled material; however, do not sweep or burn unless this is supervised by explosives experts. [R5, 3] BOTH ACTIVATED CARBON AMBERLITE XAD-4 REMOVED TNT, HEXAHYDRO-1,3,5-TRINITRO-1,3,5- TRIAZINE (RDX) , & OCTAHYDRO-1,3,5,7-TETRANITRO-1,3,5,7-TETRAZOCINE (HMX) FROM PINK WATER TO A LEVEL OF LESS THAN 1 PPM. ACTIVATED CHARCOAL HAS LOWER CAPACITY FOR TNT, & A HIGHER CAPACITY FOR RDX, HMX, & TETRYL, THAN AMBERLITE XAD-4. DECOLORIZATION OF THE EFFLUENT WITH AMBERLITE XAD-4 ALONE WAS NOT COMPLETE. BOTH AMBERLITE XAD-4 & ACTIVATED CARBON PROVIDED SIMILAR NITROBODY LEAKAGE FOR SIMILAR STREAMS. [R18] DISPOSAL: Tetryl may be disposed of only by explosives experts. [R5, 3] Because job rotation incr the number of workers at risk, it may favor sensitization and retard "hardening". [R3] 1. Initial medical exam: A complete history and physical exam: The purpose is to detect existing conditions that might place the exposed employee at incr risk, and to establish a baseline for future health monitoring. Persons with a history of asthma ... or known sensitization to tetryl may be at increased risk from exposure. Exam of the resp tract, eyes, liver, central nervous system, and kidneys should be stressed. The skin should be examined for evidence of chronic disorders. ... Tetryl has been shown to cause anemia in humans. A complete blood count should be performed incl a red cell count, a white blood count, a differential count of a stained smear, as well as hemoglobin and hematocrit. 2. The aforementioned medical exam should be repeated on an annual basis. [R5, 1] Tetryl ... dust stains the skin yellow and causes a sensitization-type dermatitis which may involve the eyelids. Conjunctivitis, keratitis, and iridocyclitis are also said to have occurred. [R19] ON INITIAL EXPOSURE TETRYL PRODUCES ACUTE IRRITATION OF NASAL & PHARYNGEAL MUCOUS MEMBRANES. WITHIN FEW DAYS, THE HANDS, FACE, SCALP & HAIR OF EXPOSED WORKERS ARE STAINED A YELLOWISH COLOR. ... DURING FIRST 2-3 WK OF EXPOSURE, WORKERS MAY DEVELOP DERMATITIS IN FORM OF ERYTHEMA, PARTICULARLY IN THE REGION OF THE NECK, CHEST, BACK, AND THE INSIDE SURFACE OF THE FOREARMS. AFTER A FEW DAYS THE ERYTHEMA MAY REGRESS LEAVING MODERATE DESQUAMATION. [R3] AFTER ONLY 3 TO 4 DAYS EXPOSURE TO HIGH DUST CONCN, WORKERS MAY COMPLAIN OF HEADACHE FOLLOWED BY PERIODIC NOSEBLEEDING. UPPER RESPIRATORY TRACT IRRITATION DOES NOT FREQUENTLY EXTEND TO BRONCHI ... HOWEVER, DRY COUGH & BRONCHIAL SPASMS HAVE BEEN OBSERVED. DIARRHEA & MENSTRUAL DISORDERS MAY OCCUR OCCASIONALLY. [R3] MANY OF DISORDERS CAUSED BY TETRYL ARE TO BE ATTRIBUTED TO IRRITANT ACTION OF CRYSTALS. IN SOME CASES, DERMATITIS IS ALLERGIC ... FOLLOWING SEVERE, PROLONGED EXPOSURE TETRYL CAUSES CHRONIC POISONING WITH DIGESTIVE DISORDERS SUCH AS LOSS OF APPETITE, ABDOMINAL PAIN, VOMITING, LOSS OF WEIGHT, CHRONIC HEPATITIS, CNS IRRITATION WITH INSOMNIA, EXAGGERATED REFLEXES, & MENTAL EXCITATION. CASES OF LEUKOCYTOSIS WITH OCCASIONAL SLIGHT ANEMIA ... REPORTED. [R3] THERE IS EVIDENCE THAT HEAVY EXPOSURES TO TETRYL MAY CAUSE LIVER DAMAGE ... [R20] ... Reported effects from accidental exposures of 11 persons to tetryl. Of those exposed, 2 had died, 1 had a disability, and 8 had no detected permanent disability. ... In addition, 1 worker developed pulmonary pathologic changes, presumably attributable to exposure to tetryl irritation. Irritation of the mucous membranes of the upper resp tract was noteworthy, resulting in sore throats, nosebleeds, and coughing of varying degrees of severity. [R4,p. 568.2(88)] ANIMAL EXPERIMENTS INDICATE RENAL TUBULE DAMAGE. [R3] IN ANESTHETIZED CATS, NITRAMINE AT 10-30 MG/KG DECREASED ARTERIAL PRESSURE 15-40%. THE HIGHER DOSE ALSO INCREASED THE AMPLITUDE AND FREQUENCY OF RESPIRATION. [R21] Persons with a history of asthma, allergies, or known sensitization to tetryl may be at increased risk from exposure. [R5, 1] ABSORBED BY SKIN. [R7, 1212] Tetryl can be released to the environment from various wastewater streams generated at sites where it is produced or through leaching from contaminated soil deposits. Direct release to the oceans has occurred through intentional dumping to dispose of unwanted munitions supplies. If released to water, tetryl may be degraded by hydrolysis and photolysis. The hydrolysis half-life at 20 deg C and pH 6.8 has been estimated to be 305 days; however, the hydrolysis rate is expected to increase in more alkaline water. In seawater at 25 deg C (pH 8.1), the hydrolysis half-life is about 33 days. Under ambient lighting conditions and pH 6, the photolysis rate has been observed to be at least an order of magnitude faster than hydrolysis. If released to soil, tetryl is expected to be susceptible to slow hydrolysis in acidic and neutral soils; however, in highly alkaline soils, hydrolysis may be relatively rapid. Moderate leaching can be expected to occur in soil. Insufficient data are available to predict the relative importance of biodegradation in either soil or water. If released to air, tetryl is expected to exist primarily in the particulate phase where it can be physically removed by wet and dry deposition. Occupational exposure to tetryl may be possible through dermal contact or inhalation of dusts at sites where it is manufactured or used in explosives. (SRC) The Joliet Army Ammunition Plant, which produced tetryl until production ceased in July 1973, released tetryl to the environment in various wastewater stream emissions generated at the plant(1); wastewater streams were released via drainage ditches with wastewaters typically containing 400-460 ppm tetryl(1); even after production had terminated, tetryl releases to surface and ground waters were still possible via runoff and leaching from contaminated soils at the plant site(1). [R22] In 1963, the US Navy initiated a program in which old liberty ships were loaded with munitions and deliberately sunk in the ocean to dispose of the unwanted munitions(1); tetryl was one of the most common and abundant explosives disposed of in this manner(1). [R23] FATE: TERRESTRIAL FATE: Tetryl has an estimated Koc value of 406, which indicates that it has medium mobility in soil(1,SRC); collection of tetryl contaminated water in seepage holes dug at a contaminated soil site have shown that leaching can occur(2). Based on hydrolysis studies in water(3), tetryl may be susceptible to slow hydrolysis in acidic and neutral soils; however, in highly alkaline soils, hydrolysis may be relatively rapid. Insufficient data are available to predict the relative importance of biodegradation in soil. Tetryl may be susceptible to photolysis on sunlit surfaces(SRC). [R24] AQUATIC FATE: Hydrolysis and photolysis appear to be important degradation processes for tetryl in water. At 20 deg C and pH 6.8, the hydrolysis half-life of tetryl has been estimated to be 305 days(1). Under ambient lighting conditions and pH 6, tetryl has been observed to photolyze at least an order of magnitude faster than it hydrolyzes(1); therefore, photolysis may be the dominant degradation process in sunlit water. The rate of hydrolysis at 40 deg C is about 100 times faster at pH 8.96 than at pH 6.88(1); therefore, the hydrolysis rate can be expected to increase in alkaline waters. The hydrolysis half-life in seawater at 25 deg C (pH 8.1) is 33 days(2). Insufficient data are available to predict the relative importance of biodegradation in water. Aquatic volatilization, bioconcentration, and adsorption to sediment are not expected to be important(SRC). [R25] ATMOSPHERIC FATE: Based on an estimated Henry's Law Constant on the order of 1.0X10-11 atm cu m/mole(1,SRC) and a measured water solubility of 75 ppm at 20 deg C(2), the vapor pressure of tetryl can be calculated to be less than 1X10-8 mm Hg(SRC). This vapor pressure suggests that tetryl will exist primarily in the particulate-phase in the ambient atmosphere(2,SRC). Particulate matter can be physically removed from air by dry deposition and/or by wet deposition such as rainfall. The relatively small amounts of vapor phase tetryl which may exist in air are expected to be degraded by reaction with photochemically formed hydroxyl radicals(4,SRC); the half-life for this reaction in average air has been estimated to be approximately 11 days(4,SRC). [R26] In a hydrolysis study of tetryl in seawater (pH 8.1) at 25 deg C, 88% of initial tetryl hydrolyzed in 101 days yielding picric acid as a hydrolysis product(1); this hydrolysis rate corresponds to a first-order half-life of 33 days(SRC). In a buffered aqueous solution at 40 deg C and pH 6.88, the hydrolysis half-life of tetryl was determined to be approximately 63 days(2); the hydrolysis half-life at 40 deg C and pH 8.96 was determined to be approximately 16-17 hours(2); hydrolysis products formed during the buffered hydrolysis studies included picrate ion, N-methylpicramide, methylnitramine, nitrate ion, and nitrite ion(2); based on activation energies, the hydrolysis half-life of tetryl at pH 6.8 and 20 deg C was estimated to be 302 days(2); comparison of hydrolysis rates (initial pH of about 6) under ambient lighting conditions and under dark conditions indicated that under ambient lighting conditions tetryl photolyzes at least an order of magnitude faster than it hydrolyzes(2); the major photolysis product was N-methylpicramide(2). [R27] The rate constant for the vapor-phase reaction of tetryl with photochemically produced hydroxyl radicals has been estimated to be 1.44X10-12 cu cm/molecule-sec at 25 deg C which corresponds to an atmospheric half-life of about 11 days at a normal atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). [R28] Based on a water solubility of 75 ppm at 20 deg C(1), the BCF for tetryl can be estimated to be 54 from a recommended regression-derived equation(2,SRC). This BCF value does not suggest a potential for significant bioconcentration in aquatic organisms(SRC) [R29] Based on a water solubility of 75 ppm at 20 deg C(1), the Koc for tetryl can be estimated to be 406 from an appropriate regression-derived equation(2,SRC). This Koc value indicates medium mobility in soil(3). [R30] The Henry's Law Constant for tetryl can be estimated to be on the order of 1.0X10-11 atm-cu m/mole using a structure estimation method(1,SRC). This value of Henry's Law Constant indicates that a pollutant is essentially non-volatile from environmental waters(2). [R31] GROUND WATER: Seepage water collected in a hole dug at the Joliet Army Ammunition Plant in Aug 1973 contained a tetryl concn of 44 ppm(1). [R32] SEA WATER: Tetryl was not detected (detection limit of 0.02 ppb) in seawater samples collected from the Atlantic Ocean (about 200 miles off the coast of Florida) and from the Pacific Ocean (about 45 miles west of San Francisco) in Sep 1971 at sites where old ships containing munitions (including tetryl) were deliberately sunk as a disposal method(1). [R23] The Joliet Army Ammunition Plant, which produced tetryl until production ceased in July 1973, released tetryl to the environment in various wastewater stream emissions generated at the plant(1); wastewater streams were released via drainage ditches with wastewaters typically containing 400-460 ppm tetryl(1). [R22] Analysis of surface soil collected from the Joliet Army Ammunition Plant in Aug 1973 detected tetryl levels of 472-562 mg/kg soil(1); analysis of subsurface soil detected levels of 1.45-84.4 g/kg soil(1). It was estimated that approximately 31,000 pounds of tetryl was contained in the soil at the Joliet Army Ammunition Plant site in Aug 1973, less than one month after tetryl production had been terminated(1). [R33] Inhalation, skin absorption, ingestion and skin and/or eye contact. [R12] Tetryl has been used as booster explosive, which is the explosive ignited by a detonation charge which in turn detonates the bursting charge(1). Occupational exposure to tetryl may be possible through dermal contact or inhalation of dusts at sites where it is manufactured or used in explosives(SRC). [R34] The following list includes some common operations in which exposure to tetryl may occur ... use in the manufacture of explosives ... and as a primer for less sensitive explosives; use during the formulation of binary explosives; use as a pH indicator. [R5, 3] OSHA: 8 hr Time-Weighted avg: 1.5 mg/cu m. Skin absorption designation. [R35] Meets criteria for OSHA medical records rule. [R36] +8 hr Time Weighted Avg (TWA) 1.5 mg/cu m (1986) [R37, 32] +Excursion Limit Recommendation: Excursions in worker exposure levels may exceed three times the TLV-TWA for no more than a total of 30 min during a work day, and under no circumstances should they exceed five times the TLV-TWA, provided that the TLV-TWA is not exceeded. [R37, 5] NIOSH S225: Analyte: tetryl; matrix: air; sampler: cellulose membrane filter. [R38] Described are sampling & preservation protocols for munitions in water. [R39] A microfilter extraction assembly containing a mixture of alumina and octadecylsilylsilica is used in the preparation of small volumes of cleaned-up extract from handswabs for their screening for explosive components by high-performance liquid chromatography at a pendent mercury drop electrode. [R40] THE ANALYSIS OF TETRYL IN SEAWATER, BY VAPOR PHASE CHROMATOGRAPHY & ELECTRON CAPTURE DETECTOR IS DESCRIBED. LIMIT OF DETECTION IS 20 PARTS PER TRILLION. [R41] ORGANIC EXPLOSIVE RESIDUES, EG 2,4,6-TRINITROTOLUENE, WERE DETECTED BY THIN LAYER CHROMATOGRAPHY. [R42] AN AUTOMATED SYSTEM FOR ANALYSIS OF NITRO CMPD IN WATER IS PRESENTED. COLORIMETRIC ANALYTICAL SYSTEM UTILIZED 2 CHANNELS, 1 TO REACT ONLY WITH NITROAROMATIC CMPD CONTAINING AT LEAST 3 RING-SUBSTITUTED NITRO GROUPS. TNT & SIMILAR CMPD, WITH STRONG BASE, FORMED A MEISENHEIMER COMPLEX. THE 2ND CHANNEL REACTED WITH ALL OTHER CONTAMINANTS CAPABLE OF FORMING NO2- WHICH WAS DETERMINED WITH A MODIFIED SALTZMAN DIAZO-COMPLEX REACTION. THE REACTION WAS SENSITIVE TO TETRYL. [R43] MINIATURIZED TLC KIT FOR IDENTIFICATION OF EXPLOSIVES IN THE FIELD IS DESCRIBED. [R44] HIGH PERFORMANCE LIQUID CHROMATOGRAPHY TECHNIQUES WERE USED IN THE LOW LEVEL DETERMINATION OF TETRYL & THE 6 ISOMERIC DINITROTOLUENES. [R45] A SCHEME FOR THE IDENTIFICATION OF EXPLOSIVE RESIDUES FROM POSTEXPLOSION SCENES IS DESCRIBED. AFTER EXTRACTION, IDENTIFICATION OF RESIDUES IS BY TLC, GLC, IR & UV SPECTROSCOPY & CHEM TESTS. [R46] NIOSH S225: Analyte: tetryl; Matrix: air; Procedure: colorimetric; absorbance, 420 nm; Range: 0.882-4.51 mg/cu m; Precision: 0.065. [R38] Fused SiO2 (silica) capillary gas chromatography columns coated with OV-101 were used for the analysis of explosives at the low picogram level. To improve the chromatographic separation of explosive mixtures, high helium carrier gas flow rates of 30 ml/min were used. [R47] A method is described for the preparation and analysis of explosive bearing soils for trace amt of poly-nitro cmpd. To impart a uniformity to the analysis, the soils were stabilized at 20-30% moisture and the samples homogenized. Extractions with acetonitrile and separations utilizing reverse phase liquid chromatography were followed by determination by UV spectrometry. [R48] High performance liquid chromatography on a reverse phase cartridge with acetonitrile-water (7:3) was used to separate nitroglycerin, ethylene glycol dinitrate, cyclotrimethylenetrinitramine, cyclotetramethylenetetranitramine, pentaerythritol tetranitrate and tetryl within 7 minutes. Limits of detection were 0.0001-0.01 mg, as compared with 0.2-0.5 mg for TLC (thin-layer chromatography). [R49] A microfilter extraction assembly containing a mixture of alumina and octadecylsilylsilica is used in the preparation of small volumes of cleaned-up extract from handswabs for their screening for explosive components by high-performance liquid chromatography at a pendent mercury drop electrode. [R40]

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