| Use | SYNTHESIS OF INTERMEDIATES &
EXPLOSIVES
CHEM INT FOR P-TOLUIDINE, STILBENE DYES, DINITROTOLUENES,
P-NITROBENZALDEHYDE, P-NITROBENZOIC ACID.
FOR PRODUCTION OF TOLUIDINE, FUCHSIN, AND VARIOUS SYNTHETIC DYES.
| Apparent Color | YELLOWISH CRYSTALS ;
COLORLESS RHOMBIC NEEDLES
ORTHORHOMBIC CRYSTALS FROM ALCOHOL & ETHER
|
|---|
| Odor | Weak aromatic ; Bitter almond
|
|---|
| Boiling Point | 238.3 DEG C @ 760 mm Hg
|
|---|
| Melting Point | 53-54 DEG C
|
|---|
| Molecular Weight | 137.14
|
|---|
| Misc | DEN: 1.1038 @ 75 deg/4 deg C
SOLUBILITY: SOL IN ALCOHOL, BENZENE, ETHER, CHLOROFORM, ACETONE ;
SOL IN
CARBON TETRACHLORIDE, PYRIMIDINE, TOLUENE ; 0.004 g/100 g of water at 20
deg C. ; Water Solubility: 442 mg/l at 30 deg C
INDEX OF REFRACTION: 1.5346 @ 62.5 DEG C ; SADTLER REF NUMBER:
4693 (IR, PRISM); 438 (IR, GRATING); MAX ABSORPTION (HEXANE): 265 NM (LOG E=
4.02) ; IR: 5633 (Coblentz Society Spectral Collection) ; UV: 1293 (Sadtler Research
Laboratories Spectral Collection) ; NMR: 677 (Sadtler Research Laboratories Spectral
Collection) ; MASS: 714 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
36.83 dynes/cm @ 60 deg C; 35.64 dynes/cm @ 70 deg C
4.72 (AIR = 1)
0.1 mm Hg at 20 deg C
% IN SATURATED AIR: 0.17 @ 65 DEG C
Boiling point 105 deg C @ 9 mm Hg
VAPOR PRESSURE: 1.3 MM HG AT 65 DEG C
The major hazards encountered in the use and handling of 4-nitrotoluene stem from its
toxicologic properties and explosivity. Toxic by all routes (ie, inhalation, ingestion, and dermal
absorption), exposure to this bitter-almond-smelling, white-to-yellowish, crystalline substance
may occur from its manufacture and use in the synthesis of dinitrotoluene, trinitrotoluene, and
various azo and sulfur dye intermediates such as p-toluidine, p-nitrobenzaldehyde and
4-nitro-2-chlorotoluene. Effects from exposure may include contact burns to the skin and eyes,
headache, weakness, dizziness, nausea, shortness-of-breath, tachycardia, and methemoglobinemia.
The onset of symptoms may be delayed up to 4 hours. OSHA has set a time-weighted-average
(TWA) limit of 2 ppm as a final rule to become effective December 31, 1992. Local exhaust
ventilation should be applied to control airborne 4-nitrotoluene to permissible limits. In activities
and situations where over-exposure may occur, wear a positive pressure self-contained breathing
apparatus and chemical protective clothing which is specifically recommended by the shipper or
manufacturer. If contact should occur, irrigate exposed eyes with copious amounts of tepid water
for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated
clothing should be removed and left at the site for cleaning. While 4-nitrotoluene does not ignite
easily, it may burn with the production of irritating or poisonous gases. Also, containers of this
substance may explode violently in the heat of a fire. For fires involving 4-nitrotoluene, extinguish
with dry chemical, CO2, water spray, fog, or standard foam. Fight fire from as far a distance as
possible, and if fire is advanced, evacuate the area. Dike fire control water. 4-Nitrotoluene should
be stored away from sources of ignition, heat, strong oxidizers, and sulfuric acid. Small spills of
4-nitrotoluene should be carefully shovelled into a clean, dry container and covered loosely
(liquid solutions are taken up with vermiculite, dry sand, or earth). Large dry spills on land
should be covered with a plastic sheet to prevent dissolving in the rain or firefighting water, until
removal is possible. Large liquid solution spills on land should be diked far ahead of the spill and
not allowed to enter water sources or sewers. Spills into bodies of water should be trapped at the
bottom with sand bag barriers and removed with suction hoses, or treated with activated carbon
and the resulting immobilized masses removed with mechanical dredges or lifts.
Health Hazards: Poisonous; may be fatal if inhaled, swallowed or absorbed through skin.
Contact may cause burns to skin and eyes. Runoff from fire control or dilution water may give off
poisonous gases and cause water pollution. Fire may produce irritating or poisonous gases.
/Nitrotoluene/
Fire or Explosion: Some of these materials may burn, but none of them ignites readily. Container
may explode violently in heat of fire. /Nitrotoluene/
Emergency Action: Keep unnecessary people away; isolate hazard area and deny entry. Stay
upwind, out of low areas, and ventilate closed spaces before entering. Positive pressure
self-contained breathing apparatus (SCBA) and chemical protective clothing which is specifically
recommended by the shipper or manufacturer may be worn. It may provide little or no thermal
protection. Structural firefighters' protective clothing is not effective for these materials. Remove
and isolate contaminated clothing at the site. CALL CHEMTREC AT 1-800-424-9300 AS
SOON AS POSSIBLE, especially if there is no local hazardous materials team available.
/Nitrotoluene/
Fire: Small Fires: Dry chemical, CO2, water spray or regular foam. Large Fires: Water spray, fog
or regular foam. Move container from fire area if you can do it without risk. Fight fire from
maximum distance. Stay away from ends of tanks. Dike fire-control water for later disposal; do
not scatter the material. /Nitrotoluene/
Spill or Leak: Do not touch spilled material; stop leak if you can do it without risk.
Fully-encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire.
Use water spray to reduce vapors. Small Spills: Take up with sand or other noncombustible
absorbent material and place into containers for later disposal. Small Dry Spills: With clean shovel
place material into clean, dry container and cover loosely; move containers from spill area. Large
Spills: Dike far ahead of liquid spill for later disposal. /Nitrotoluene/
First Aid: Move victim to fresh air and call emergency medical care; if not breathing, give artificial
respiration; if breathing is difficult, give oxygen. In case of contact with material, immediately
flush skin or eyes with running water for at least 15 minutes. Speed in removing material from
skin is of extreme importance. Remove and isolate contaminated clothing and shoes at the site.
Keep victim quiet and maintain normal body temperature. Effects may be delayed; keep victim
under observation. /Nitrotoluene/
Low fire hazard. /Nitrotoluene/
... Contact with strong oxidizers or sulfuric acid may cause fires ... /Nitrotoluene/
Health 3. 3= Materials extremely hazardous to health, but areas may be entered with
extreme care. Full protective clothing, including self-contained breathing apparatus, rubber
gloves, boots and bands around legs, arms, and waist should be provided. No skin surface should
be exposed. /Nitrotoluene/
Flammability: 1. 1= Materials that must be preheated before ignition can occur. Water may cause
frothing of liquids with this flammability rating number if it gets below the surface of the liquid
and turns to steam. However, water spray gently applied to the surface will cause a frothing which
will extinguish the fire. Most combustible solids have a flammability rating of 1. /Nitrotoluene/
Reactivity: 0. 0= Materials which are normally stable even under fire exposure conditions and
which are not reactive with water. Normal fire fighting procedures may be used. /Nitrotoluene/
106 DEG C; 223 DEG F (CLOSED CUP)
WATER OR FOAM MAY CAUSE FROTHING. USE CARBON DIOXIDE OR DRY
CHEMICAL.
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.
/Nitrotoluene/ [R1]
Toxic gases & vapors (such as oxides of nitrogen & carbon monoxide) may be released in
a fire involving nitrotoluene. /Nitrotoluene/
REACTIVITY: INCOMPATIBLE /WITH/ SULFURIC ACID; TETRANITROMETHANE.
para-Nitrotoluene and sulfuric acid exploded @ 80 deg C.
Nitrotoluene will attack some forms of plastics, rubber, & coatings. /Nitrotoluene/
... Contact with strong oxidizers or sulfuric acid may cause fires and explosions.
Decomposes violently at 279 deg C and will burn even in absence of air.
Irritating to eyes, nose and throat.
Wear butyl rubber gloves, protective clothing and shoes, and self-contained breathing
apparatus.
Respirator Selection: At 50 ppm: Supplied-air respirator or self-contained breathing apparatus. At
200 ppm: Supplied air with a full facepiece, helmet and hood, or a Type C supplied air operated in
pressure-demand or other positive pressure or continuous-flow mode. Escape: Gas mask with an
organic vapor canister (chin-style or front-or back-mounted canister) with a particulate filter, and
self-contained breathing apparatus. /Nitrotoluene/
Respirators may be used when engineering & work practice controls are not technically feasible ...
Respirators may also be used for operations which require entry into tanks or closed vessels, & in
emergency situations. ... Respirators permitted are those that have been approved by the Mine
Safety & Health Admin ... or by the NIOSH. ... Employees should be provided with & required to
use impervious clothing, gloves, face shields (8-inch min), & other appropriate protective clothing
necessary to prevent repeated or prolonged skin contact with solid or liq nitrotoluene. ...
Employees should be provided with & required to use dust- & splash-proof safety goggles where
solid or liq nitrotoluene may contact the eyes. /Nitrotoluene/
Contact lenses should not be worn when working with this chemical. /Nitrotoluene/
The scientific literature supports the wearing of contact lenses in industrial environments, as
part of a program to protect the eye against chemical compounds and minerals causing eye
irritation. However, there may be individual substances whose irritating or corrosive properties
are such that the wearing of contact lenses would be harmful to the eye. In those specific cases
contact lenses should not be worn.
Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and
sewers. Build dikes to contain water flow as necessary. /Nitrotoluene/ [R1]
Avoid breathing vapors or dusts. Do not handle broken packages without protective equipment.
Wash away any material which may have contacted the body with copious amounts of water or
soap and water. [R1]
... A complete respiratory protection program should be instituted which incl regular training,
maintenance, inspection, cleaning, & evaluation. ... Non-impervious clothing which becomes
contaminated ... should be removed ... & not reworn until nitrotoluene is removed. Eating &
smoking should not be permitted in areas where solid nitrotoluene is handled, processed, or
stored. Employees who handle solid or liq nitrotoluene should wash ... hands thoroughly with
soap or mild detergent & water before eating or smoking. /Nitrotoluene/
/Heat contributes/ ... to instability. /Nitrotoluene/
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)./ [R2]
Int'l Air Shipments: Chemical: Nitrotoluenes, liquid or solid. IMO Class: 6.1. UN 1664. Primary
hazard label: Poison (packaging group II). Additional packaging instructions listed in the table
must also be followed. /Nitrotoluenes/
International Water Shipments: Chemical: Nitrotoluenes (ortho-;meta-;para-) IMO Class: 6.1,
poisons. UN 1664. Packaging Group: II. Label(s) required: Poison. /Nitrotoluenes/ [R3]
ST0RAGE: PROTECT AGAINST PHYSICAL DAMAGE. STORE IN COOL, DRY,
WELL-VENTILATED AREA AWAY FROM AREAS OF HIGH FIRE HAZARD.
CLEANUP: 1) Ventilate area of spill or leak. For small quantities of liq nitrotoluene, absorb on
paper
towels. For small quantities of solid nitrotoluene, sweep onto paper or other suitable material.
Remove to safe place (such as fume hood) & burn. Large quantities of liq nitrotoluene can be
collected & atomized in suitable combustion chamber equipped with appropriate effluent gas
cleaning device. Large quantities of solid nitrotoluene can be reclaimed; ... If not practical,
dissolve in flammable solvent (such as alcohol) & atomize in suitable combustion chamber
equipped with appropriate effluent gas cleaning device. /Nitrotoluene/
Land Spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material /SRP: If
time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an
impermeable flexible membrane liner./ Cover solids with plastic sheet to prevent dissolving in rain
or fire fighting water. /Nitrotoluene/ [R1]
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, apply activated
carbon at ten times the spilled amount in region of 10 ppm or greater concentration. Use
mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
/Nitrotoluene/
DISPOSAL: 1) For liq nitrotoluene, by absorbing it in vermiculite, dry sand, earth or similar
material &
disposing in secured sanitary landfill. 2) By atomizing liq nitrotoluene in suitable combustion
chamber equipped with appropriate effluent gas cleaning device. 3) By making packages of solid
nitrotoluene in paper or other suitable material or by dissolving in a flammable solvent (such as
alcohol) & burning in a suitable combustion chamber equipped with appropriate effluent gas
cleaning device. /Nitrotoluene/
The following wastewater treatment technologies have been investigated for 4-nitrotoluene:
Concentration process: Biological treatment. [R4]
Initial Medical Exam: A complete history & physical exam: ... Exam of blood, nervous
system, GI system, & cardiovascular system should be stressed. Skin should be exam for evidence
of chronic disorders. ... A complete blood count should be performed, including red cell count, a
white cell count, a differential count of stained smear, as well as hemoglobin & hematocrit.
Periodic Medical Exam: The ... /initial medical exam/ should be repeated on an annual basis.
Methemoglobin determinations should be performed if overexposure is suspected or signs &
symptoms of toxicity occur. /Nitrotoluene/
Routine checking of lips, tongue, and nail beds of exposed personnel for signs of cyanosis.
/Nitrotoluene/
TOXICITY IDENTICAL WITH O-NITROTOLUENE. O-NITROTOLUENE
PRODUCES METHEMOGLOBIN CAUSING HYPOXIA, BUT OF LOW POTENCY. IT IS
ALSO SUSPECTED OF CAUSING ANEMIA IN CHRONIC EXPOSURES.
... Cases of poisoning from nitrotoluene are uncommon. Some authorities considered it only
slightly toxic, esp in comparison with nitrobenzene. There is some evidence that the different
isomers vary ... in toxicity. ... It is stated that nitrotoluene is a methemoglobin former of
apparently low grade. /Nitrotoluene/
... The onset of symptoms of methemoglobinemia is insidious and may be delayed up to 4 hours;
headache is commonly the first symptom and may become quite intense as the severity of
methemoglobinemia progresses. ... Cyanosis develops early in the course of intoxication, first the
lips, the nose, and the ear lobes, and is usually recognized by fellow workers. ... Until the
methemeglobinemia concentration approaches approximately 40%, the individual usually feels
well, has no complaints, and will insist that nothing is wrong . ... Over 40% ... weakness and
dizziness; at up to 70% ... there may be ataxia, dyspnea on mild exertion, tachycardia, nausea,
vomiting, and drowsiness. /Nitrotoluene/
TOXIC BY INHALATION, INGESTION, SKIN ABSORPTION.
Target Organs: Blood, central nervous system, gastrointestinal, cardiovascular system, and skin.
/Nitrotoluene/
WHEN ADMIN ORALLY AT DOSES CORRESPONDING TO 0.1-0.2 LD50
VALUES IN RATS FOR 1-3 MO, THE HEMOTOXICITY OF TOLUENE DERIV DECR IN
THE ORDER: TRINITROTOLUENE, DINITROTOLUENE, M-NITROTOLUENE,
P-NITROTOLUENE, AND O-NITROTOLUENE. THEY CAUSED ANEMIA
ACCOMPANIED BY RETICULOCYTOSIS AND A DECR IN THE LEVEL OF SH-GROUPS
AND AN INCR OF FIBRINOGEN IN THE BLOOD. [R5]
The mutagenicities of the o, m, and p-isomers of nitrotoluene ... were tested with or without S9
mix and norharman in the Salmonella assay system. None of the compounds were mutagenic
without norharman. ... The induction of mutagenesis with norharman was strong for the o-isomer,
weak for the p-isomer, and was not observed for the m-isomer. [R6]
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. [R7]
To determine whether hepatic macromolecular covalent binding of mononitrotoluene isomers to
hepatic DNA in vivo was decreased by inhibitors of sulfotransferase, male Fischer-344 rats were
given a single oral dose of ring-U-(14)C-labeled 2-, 3-, or 4-nitrotoluene, and were killed at
various times thereafter. Livers were removed and analyzed for total and covalently bound
radiolabel. Maximal concentrations of total radiolabel were observed between 3 and 12 hr after
the dose, and there were no large differences among the 3 isomers in peak concentrations
achieved. Covalent binding to hepatic macromols was maximal 12 hr after administration for all 3
isomers. Thereafter, concn of administration for all 3 isomers. Thereafter, concn of covalently
bound 2-nitrotoluene derived material were always 2-6 times higher than those of 3- or
4-nitrotoluene derived material. When DNA was isolated from livers of rats given
mononitrotoluene isomers 12 hr previously, only 2-nitrotoluene was observed to covalently bind
at concns above the limits of detection of the assay. The covalent binding of 2-nitrotoluene, but
not that of 3- or 4-nitrotoluene, to both total hepatic macromols and DNA was markedly
decreased by prior administration of pentachlorophenol or 2,6-dichloro-4-nitrophenol. Covalent
binding to hepatic DNA was decreased by >96%. Thus, 2-nitrotoluene, but not 3- or
4-nitrotoluene, induces DNA excision repair. Furthermore, 2-nitrotoluene, like the
hepatocarcinogen 2,6-dinitrotoluene, may require the action of sulfotransferase for its conversion
to a species capable of covalently binding to hepatic DNA. [R8]
The log of the lowest concn of 4-nitrotoluene tested that significantly (p< 0.01) lowered
the population growth constant of Daphnia after 21 days was 1.61 umol/l. This same concn was
the lowest concn to significantly (p< 0.01) lower the mean length of Daphnia after 21 days.
[R9, (1989]
The log of the concn of 4-nitrotoluene causing a decr of 50% in the maximum density (yield) of
Chlorella pyrenoidosa populations after 96 hr exposure (96 hr EC50) was 2.21 umol/l. [R9,
(1989)]
The log of the concn of 4-nitrotoluene causing a 50% decr of Photobacterium phosphoreum
bioluminescence after 15 min of exposure was 1.90 umol/l. [R9, (1989)]
The log of the 48 hr immobilization concn (IC50) of Daphnia magna was 2.14 umol/l for
4-nitrotoluene in static tests. Using a semi-static procedure, the log of the 21 day IC50 was 1.71
umol/l for 4-nitrotoluene. [R9, (1989)]
Persons with blood disorders may be at increased risk from exposure. /Nitrotoluene/
Toxic on ingestion, inhalation, or by absorption thru the skin.
YIELDS P-NITROBENZYL ALCOHOL IN RABBITS. ... YIELDS
P-NITROBENZYL ALCOHOL IN RATS AND MICE ... . /FROM TABLE/
EEL LIVER HOMOGENATES METABOLIZE METHYL GROUP OF P-NITROTOLUENE,
MODEL CMPD OF TOLUENE, MORE SLOWLY THAN RAT LIVER HOMOGENATES.
[R10]
COMPARATIVE STUDIES ON ANILINE HYDROXYLATION & P-NITROTOLUENE
HYDROXYLATION BY THE LIVER ARE PRESENTED. [R11]
VERTEBRATE LIVER ENZYMES & INTACT GRASS GRUBS OXIDIZED METHYL
GROUPS OF P-NITROTOLUENE INTO CARBOXY GROUPS @ DIFFERENT RATES.
[R12]
... The metabolism and excretion of 2-, 3-, and 4-nitrotoluene were studied in male Fischer 344
rats. ... The major metabolites excreted in urine in 72 hr after administration of 4-nitrotoluene
were: 4-nitrobenzoic acid (28% of the dose), 4-acetamidobenzoic acid (27% of the dose) and
4-nitrohippuric acid (13% of the dose). [R13]
The major sources of release of 4-nitrotoluene to the environment appear to be
production and use facilities and plants which produces this compound as a by-product. This
would include manufacturers of dinitrotoluene, trinitrotoluene and azo and sulfur dye
intermediates such as p-toluidine, p-nitrobenzaldehyde and 4-nitro-2-chlorotoluene.
4-Nitrotoluene may also enter the environment from the disposal of waste products containing
p-nitrotoluene. If released to soil, 4-nitrotoluene should be resistant to oxidation and chemical
hydrolysis. This compound is reported to biodegrade under anaerobic conditions to form toluidine
and one study on 4-nitrotoluene under aerobic conditions in mineral salts and a mixed culture of
soil microorganisms resulted in persistence > 64 days. 4-Nitrotoluene is expected to be
moderately to highly mobile in soil and to volatilize slowly from dry soil surfaces. If released to
water, 4-nitrotoluene would be susceptible to photolysis, volatilization (estimated half-life 25
hours in water 1 m deep flowing 1 m/sec with a wind speed of 3 m/sec) and possibly aerobic
biodegradation provided suitable acclimation has taken place. Oxidation, chemical hydrolysis,
adsorption to suspended solids and sediments and bioaccumulation in aquatic organisms are not
expected to be significant aquatic fate processes. Toluidine has been identified as an anaerobic
biodegradation product of 4-nitrotoluene; however, insufficient data are available to indicate the
significance of anaerobic biodegradation as a possible removal mechanism. Based on monitoring
data, the half-life of 4-nitrotoluene in a river 4 to 5 m deep has been estimated to be 2.7 days. If
released to the atmosphere, p-nitrotoluene is expected to exist almost entirely in the vapor phase.
The dominant removal mechanisms would be reaction with photochemically generated hydroxyl
radicals (estimated half-life 19.9 days) and direct photolysis. 4-Methyl-2-nitrophenol is a
photoproduct of 4-nitrotoluene. The most probable routes of human exposure to 4-nitrotoluene
are inhalation and dermal contact of workers involved in the production and use of this
compound, dinitrotoluene and trinitrotoluene. (SRC)
4-Nitrotoluene may be released to the environment by manufacturers of dinitrotoluene,
trinitrotoluene and various azo and sulfur dye intermediates such as p-toluidine,
p-nitrobenzaldehyde and 4-nitro-2-chlorotoluene(1,SRC). 4-Nitrotoluene may also enter the
environment from the disposal of waste products in which it is contained(SRC). [R14]
TERRESTRIAL FATE: If released to soil, 4-nitrotoluene should be resistant to oxidation
and chemical hydrolysis. This compound is reported to biodegrade under anaerobic conditions to
form toluidine and one study on 4-nitrotoluene under aerobic conditions in mineral salts and
mixed culture of soil microorganisms resulted in persistence > 64 days. 4-Nitrotoluene is expected
to be moderately to highly mobile in soil and volatilize slowly from dry soil surfaces(SRC). 0.5
ug/l 4-nitrotoluene was detected in Rhine River water before infiltration and less than 0.01 ug/l
(detection limit) was found after bank filtration (filtration time = 1-12 months) and after dune
filtration (filtration time = 2-3 months)(1). [R15]
AQUATIC FATE: Based on monitoring data, the half-life of 4-nitrotoluene in a river 4 to 5 m
deep has been estimated to be 2.7 days(1). If released to water, 4-nitrotoluene would be
susceptible to photolysis, volatilization (estimated half-life 25 hr in water 1 m deep flowing 1
m/sec with a wind speed of 3 m/sec) and possibly aerobic biodegradation provided suitable
acclimation has taken place. Oxidation, chemical hydrolysis, adsorption to suspended solids and
sediments and bioaccumulation in aquatic organisms are not expected to be significant fate
processes. Toluidine has been identified as an anaerobic biodegradation product of 4-nitrotoluene;
however, insufficient data are available to indicate the significance of anaerobic biodegradation as
a possible removal mechanism(SRC). [R15]
ATMOSPHERIC FATE: If released to the atmosphere 4-nitrotoluene is expected to exist almost
entirely in the vapor phase(1,SRC). The dominant removal mechanisms would be reaction with
photochemically generated hydroxyl radicals (estimated half-life 19.9 days)(2) and direct
photolysis. 4-Methyl-2-nitrophenol is a photoproduct of 4-nitrotoluene(SRC). [R16]
100 ppm 4-nitrotoluene inoculated with 30 ppm activated sludge under aerobic conditions
at 25 deg C was < 30% degraded after 2 week(1,2). 4-Nitrotoluene (200 mg/l COD) inoculated
with adapted activated sludge under aerobic conditions at 20 deg C underwent 98% degradation
in 5 days as measured by COD removal(3). 4-Nitrotoluene should be degraded by biological
sewage treatment provided suitable acclimation can be achieved(5). 10 ug/l 4-nitrotoluene
inoculated in mineral salts and a mixed culture of soil microorganisms under aerobic conditions
persisted > 64 days as measured by UV absorbance(4). In general, anaerobic biodegradation of
nitroaromatic compounds results in the reduction of the nitro group to an amino group(6).
Toluidine has been identified as an anaerobic biodegradation product of 4-nitrotoluene(7).
[R17]
Fate of Atmos Pollut (1986)] Chemical hydrolysis and oxidation of 4-nitrophenol are
not expected to be important removal processes since this compound contains no functional
groups which are susceptible to these types of reactions(1,SRC). Absorption of UV light in the
environmentally significant range (> 290 nm) by 4-nitrotoluene in cyclohexane(2), indicates that
the potential exists for photolysis in water and air(SRC). Irradiation (at > 300 nm) of
4-nitrotoluene vapor in air for 5 hr resulted in 38% loss of 4-nitrotoluene initially present and
formation of 4-methyl-2-nitrophenol (6.1% yield)(3). The half-life for 4-nitrotoluene vapor
reacting with photochemically generated hydroxyl radicals in the atmosphere has been estimated
to be 19.9 days based on a reaction rate constant of 8.05X10-13 cu cm/molecules-sec at 25 deg C
and an ambient hydroxyl radical concn of 5.0X10-5 molecules/cu cm(4). [R18]
The bioconcentration factor (BCF) for 4-nitrotoluene has been measured to be less than
100 in carp (Carprinus carpio)(1,2). BCF values of 37 and 20 have been calculated based on a log
octanol/water partition coefficient (log Kow) of 2.37 and a measured water solubility of 442 mg/l
at 30 deg C(3,4,5,SRC). These BCF values suggest that 4-nitrotoluene will not bioaccumulate
significantly in aquatic organisms(SRC). [R19]
The soil adsorption coefficient for 4-nitrotoluene has been calculated to be 464 and 153
based on a log octanol/water partition coefficient (log Kow) of 2.37 and a measured water
solubility of 442 mg/l at 30 deg C, respectively(1,2,3,SRC). These Koc values suggest that
4-nitrotoluene would be moderately to highly mobile in soil and would adsorb slightly to
suspended solids and sediments in water(4,SRC). [R20]
Henry's Law constant for 4-nitrotoluene has been calculated to be 5X10-5 atm-cu m/mole
at 25 deg C using a method of structural contributions to compounds with intrinsic hydrophilic
character(1,SRC). Based on this value for Henry's Law constant the volatilization half-life of
4-nitrotoluene from water 1 m deep, flowing 1 m/sec with a wind speed of 3 m/sec has been
calculated to be 25 hr (2,SRC). A vapor pressure of 0.1 mm Hg at 20 deg C for 4-nitrotoluene
suggests that this compound will volatilize slowly from dry soil surfaces(3,SRC). [R21]
During 1974, 2- and 4-nitrotoluene were detected in the river Waal (Netherlands), avg
concn 4.5 ug/l, max concn 18.1 mg/l, and in the river Maas (Netherlands), max concn 0.3 ug/l(1).
4-Nitrotoluene has been detected in Rhine River water at a concn of 10 ug/l(2). [R22]
4-Nitrotoluene has been found in the effluent from a plant manufacturing trinitrotoluene
(TNT) in Radford, VA, 0.12 to 9.2 mg/l detected(1). 4-Nitrotoluene has been detected in the
wastewater resulting from the production and purification of 2,4,6-trinitrotoluene, 0.01 to 0.17
mg/l detected, 43% of samples pos(2). 4-Nitrotoluene has also been detected in the raw effluent
from a plant manufacturing dinitrotoluene, 8.8 mg/l detected, and in a waste treatment lagoon of a
chemical company, 0.04 mg/l(1). [R23]
4-Nitrotoluene has been detected in the ambient air at the Dupont plant in Deepwater, NJ
at a concn ranging from 59 to 89 ng/cu m(1). [R24]
The most probable routes of human exposure to 4-nitrotoluene are inhalation and dermal
contact of workers involved in the production and use of this compound, dinitrotoluene and
trinitrotoluene. (SRC)
200 ppm /Nitrotoluene/
OSHA: 8 hr Time-Weighted avg: 5 ppm (30 mg/cu m). /Transitional limits/ must continue to be
achieved by any combination of engineering controls, work practices, and personal protective
equipment during the phase-in period, Sept 1, 1989 through Dec 30, 1992. Final rule limits
become effective Dec 31, 1992. Skin absorption designation in effect as of Sept 1, 1989.
[R25]
8 hr Time-Weighted avg: 2 ppm (11 mg/cu m). /Final rule limits/ shall be achieved by any
combination of engineering controls, work practices and personal protective equipment during the
phase-in period, Sept 1, 1989 through Dec 30, 1992. Final rule limits become effective Dec 31,
1992. Skin absorption designation in effect as of Sept 1, 1989. [R25]
Time Weighted Avg (TWA) 2 ppm, 11 mg/cu m, skin (1982) /Nitrotoluene/
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.
/Nitrotoluene/
BEI (Biological Exposure Index): Methemoglobin in blood during or end of shift is 1.5% of
hemoglobin. The determinant is usually present in a significant amt in biological specimens
collected from subjects who have not been occupationally exposed. Such background levels are
incl in the BEI value. The determinant is nonspecific, since it is observed after exposure to some
other chemicals. These nonspecific tests are preferred because they are easy to use and usually
offer a better correlation with exposure than specific tests. In such instances, a BEI for a specific,
less quantitative biological determinant is recommended as a confirmatory test. The biological
determinant is an indicator of exposure to the chemical, but the quantitative interpretation of the
measurements is ambiguous. /Methemoglobin inducers/
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 1000 lb or 454 kg. The toll free number
of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The
rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
[R26]
4-NITROTOLUENE WAS REMOVED FROM AIR BY ABSORPTION ON
FLUIDIZED BED AND DETERMINED BY THIN-LAYER CHROMATOGRAPHY.
[R27]
A METHOD WAS DEVELOPED FOR DETERMINING O- & P-NITROTOLUENE IN SOLN
& IN AIR BASED ON REDUCTION TO TOLUIDINE.[R28]
KNOWN MIXT OF O-NITROTOLUENE, M-NITROTOLUENE, AND P-NITROTOLUENE
IN AIR OF INDUSTRIAL INSTALLATIONS WERE ANALYZED BY GAS
CHROMATOGRAPHY. THE MINIMUM CONCN OF THE ISOMERS WAS 1X10-6 G/ML,
TIME FOR EACH DETERMINATION 10 MIN, AND THE ABSOLUTE ERROR 9%. [R29]
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