1,6-Dimethylnaphthalene

156.22

156.22

209-385-1

DXN13WI5EY

52966

DTXSID7022415

2902909090

0

4.37

1,6-dimethylnaphthalene is a clear pale yellow liquid. (NTP, 1992)

1.003 g/cm³ @ Temp: 20 °C

-16.9 °C

264 °C

112°C

1.605

Insoluble in water; sol in ether and benzene

You should store this chemical at ambient temperatures and away from oxidizing materials. STORE AWAY FROM SOURCES OF IGNITION.

1.46X10-2 mm Hg @ 25 deg C

Hydroxyl radical reaction rate constant = 6.34X10-11 cu cm/molec-sec @ 25 °C

Insoluble in water.

Hydrocarbons, Aromatic

1,6-DIMETHYLNAPHTHALENE can react with strong oxidizing agents. (NTP, 1992)

IRRITANT

NONH for all modes of transport

3

23-24/25

This chemical is stable under normal laboratory conditions. Solutions of this chemical in water, DMSO, 95% ethanol or acetone should be stable for 24 hours under normal lab conditions.

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.|The following wastewater treatment technology has been investigated for dimethylnaphthalene: Activated carbon. /Dimethlynaphthalene/|The following wastewater treatment technology has been investigated for naphthalene: Biological treatment. /Naphthalene/

This compound can react with strong oxidizing agents.

SCHMELTZ I ET AL; VOL 3, POLYNUCLEAR AROMATIC HYDROCARBONS. SECOND INTERNATIONAL SYMPOSIUM ON ANALYSIS, CHEMISTRY, & BIOLOGY. SEPT 1977, ISBN 0-89004-241-1: 47-60 (1978). BIOASSAYS OF NAPHTHALENE FOR COCARCINOGENIC ACTIVITY RELATION TO TOBACCO CARCINOGENESIS WAS DISCUSSED. /NAPHTHALENE & ALKYL NAPHTHALENES/

This chemical is probably combustible. (NTP, 1992)

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be use. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical at ambient temperatures and away from oxidizing materials. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

It is probably combustible.

If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

... Skin irritant ... /Methylated naphthalene/

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Alkyl naphthalenes is produced, as an intermediate or a final product, by process units covered under this subpart. /Alkyl Naphthalenes/

The major hazards encountered in the use and handling of 1,6-dimethylnaphthalene stem from its toxicologic properties. Toxic primarily via dermal contact and inhalation. Exposure to this substance may occur from its presence as a combustion product of fossil fuels such as coal, gasoline, and heating oil. Effects from exposure include skin irritation and photosensitization. Before implementing land disposal of waste 1,6-dimethylnaphthalene, consult with environmental regulatory agencies for guidance.

1,6-Dimethylnaphthalene was identified as a stack emission(1) and a component of fly ash(2) from waste incinerators. The compound was detected at a total concn of 0.16 mg/mile in conjunction with the 1,7- and 1,3-isomers from gasoline-fueled high-emitter light duty motor vehicle exhaust sampled during summer near Denver, CO(3).|Alkylaromatics, alkanes, aldehydes, dimethyl polysulfides and miscellaneous compounds were determined over 15 months at a coastal site, Vineyard Sound, Massachusetts. Alkylnaphthalenes showed a contrasting pattern with highest levels occurring during the winter months and the lowest in summer; this was best explained by a dominant wintertime source such as space heating oil use(1). A mean seawater concentration of 1.9 ng/liter and a range of 0.0-4.2 ng/liter was reported for 1,6-dimethylnaphthalene(1).

SEDIMENT: Of 492 streambed sediments sampled in the US from 1992-1995, 1,6-dimethylnapthalene was detected in 6.3% of the samples, with <50, <50, 56, and 680 ug/kg measured at the 75th percentile, 90th percentile, 95th percentile, and maximum, respectively(1). 1,6-Dimethylnaphthalene was detected in sediment samples at a concn of 65 ng/g dry wt 400 m downstream from a discharge of produced water at midchannel at Pass Fourchon, LA(2). Produced water is a complex chemical mixture that can contain petroleum organics, heavy metals, radionuclides, treating chemicals, salts, and dissolved nonvolatile organic matter of unknown chemical composition at concns as high as 750 mg Carbon/liter, and is generated as a result of petroleum production(3).

80 male and female young adult golden Syrian hamsters were divided into groups. Group A was the control group. Groups B, C, and D were treated by painting of the left buccal pouch 3 times/wk with a 0.5% solution of 7,12-dimethylbenz(a)anthracene in heavy mineral oil. Group C was painted with mineral oil containing 0.3% 1,4-dimethylnaphthalene. This group showed intermediate tumor numbers and sizes. Apparently 1,4-dimethylnaphthalene retards development of epidermoid carcinomas in hamster buccal pouches induced by 7,12-dimethylbenz(a)anthracene. /1,4-Dimethylnaphthalene/

1,6-Dimethylnaphthalene is a natural component of crude oil(1). 1,6- Dimethylnaphthalene is also a product of combustion and can be released to the environment via natural fires associated with lightening, volcanic activity, and spontaneous combustion(SRC).

1,6-Dimethylnaphthalene's formationtion during petroleum refining and coal tar distillation(1), as a result of gasoline, diesel, and heating fuel combustion(2), and from municipal waste incinerator activities(3,4) may result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,900(SRC), determined from a structure estimation method(2), indicates that 1,6-dimethylnaphthalene is expected to have slight to no mobility in soil(SRC). Volatilization of 1,6-dimethylnaphthalene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.2X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1,6-Dimethylnaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.46X10-2 mm Hg(4). A 54.5% loss after 7 days in a marine water die-away study with sediment inoculum from Dunstaffnage Bay, Scotland(5), indicates that biodegradation may be an important fate process in the terrestrial environment.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,900(SRC), determined from a structure estimation method(2), indicates that 1,6-dimethylnaphthalene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.2X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 hrs and 6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 51 days if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 520(SRC), from an estimated log Kow of 4.3(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). A 54.5% loss after 7 days in a marine water die-away study with sediment inoculum from Dunstaffnage Bay, Scotland(9), indicates that biodegradation may be an important fate process in the aquatic environment.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,6-dimethylnaphthalene, which has a vapor pressure of 1.46X10-2 mm Hg at 25 °C(2), is expected to exist primarily as a vapor in the ambient atmosphere. Vapor-phase 1,6-dimethylnaphthalene 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 5 hrs(SRC), calculated from its rate constant of 6.34X10-11 cu cm/molecule-sec at 25 °C(3). Based upon aqueous photolysis data for 1- and 2-methylnaphthalene(4), 1,6-dimethylnaphthalene may undergo direct photolysis in the atmosphere(SRC).

The rate constant for the vapor-phase reaction of 1,6-dimethylnaphthalene with photochemically-produced hydroxyl radicals has been estimated as 6.3X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Polycyclic aromatic hydrocarbons are generally resistant to hydrolysis(3). Based upon direct aqueous photolysis half-lives of 71 and 54 hrs for 1- and 2-methylnaphthlene, respectively, at midday, midsummer sunlight at 40 deg N latitude(4), 1,6-dimethylnaphthalene may photolyze in the environment.

An estimated BCF of 520 was calculated for 1,6-dimethylnaphthalene(SRC), using an estimated log Kow of 4.4(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). 1,6-Dimethylnaphthalene was detected in muscle tissue samples of male winter flounder (Pseudopleuronectes americanus) following 4 month (Jan-April) exposure to various concns of Hibernia crude oil in sediments(4). 50, 100, and 250 ml of Hibernia crude oil resulted in sediment concns of 10, 65, and 135 ng/g and muscle concns of 10, 42, and 95 ng/g, respectively; however, 1,6-dimethylnpahthalene was not discerned from 1,7-dimethylnapthalene(4). Using a bioaccumulation study, 1,6-dimethylnaphthalene was detected in oyster tissue samples at a concn of 40 ng/g following a 14 day exposure to 1,6-dumethylnaphthalene-contaminated sediment collected near Port Lachon, LA(5).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1,6-dimethylnaphthalene can be estimated to be 4,900(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,6-dimethylnaphthalene is expected to have slight to no mobility in soil.

The Henry's Law constant for 1,6-dimethylnaphthalene is estimated as 4.2X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,6-dimethylnaphthalene is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 6 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 51 days if adsorption is considered(3). 1,6-Dimethylnaphthalene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1,6-Dimethylnaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.46X10-2 mm Hg(4).

DRINKING WATER: From a survey of drinking water supplies in the US, 1,6-dimethylnaphthalene was detected in the treated water at 5 of 18 water treatment facilities from the cities of Pomona, Escondido, Lake Tahoe and Orange Co, CA and Dallas, Washington, DC, Cincinnati, Philadelphia, Miami, New Orleans, Ottumwa, IA, and Seattle(1).|GROUNDWATER: 1,6-Dimethylnaphthalene was detected in a coal tar contaminated aquifer in St. Louis Park, MN(1).

1,6-Dimethylnaphthalene was found to be a volatile component in steamed meat from a southeast Asian crab, Charybidis feriatus. Concentrations in the leg, body, and carapace were 1.9, 1.1, and 18.9 ug/g, respectively(1).|1,6-Dimethylnaphthalene was identified in stored liquid smoke flavorings obtained from oak, cherry, beech, poplar, and vine shoots at concns of 3.38, 2.28, 1.84, 15.03, and 4.22 ug/kg, obtained at max temps of 530, 550, 532, 536, and 559 °C, respectively(1). Concns decreased when stored in polyethylene flasks - 1.60 for beech, 1.09 for poplar, and 1.36 ug/kg(1).

Occupational exposure to 1,6-dimethylnaphthalene may occur through inhalation and dermal contact with this compound at workplaces where 1,6-dimethylnaphthalene is produced(SRC). Exposure levels to flight-related and ground-support personal for C-130H aircraft at an Air National Guard base were measured at 29.2 ng/cu m (hanger/background), 73.0 ng/cu m (hanger/taxiing) to 196.6 ng/cu m (engine run-up), sampling done on May 5, 1999(1). Concns of 879.2 ng/cu m was measured downwind of aerospace ground equipment and 475.7 ng/cu m during an engine runinng on/off loading maneuver(1). Monitoring data indicate that the general population may be exposed to 1,6-dimethylnaphthalene via ingestion of smoked foods and contaminated drinking water, and via inhalation of vehicle exhaust(SRC).

The distribution, excretion and metabolism of 1,6-dimethylnaphthalene following i.p. administration of a single dose of 20 mg/kg to rats, was investigated using radiotracer (3H) and a gas chromatography-mass spectrometry technique (GC-MS). After 72 hr, about 94% of the given dose was excreted in urine and feces. In organs and tissues, the highest concentration during the first hours after administration was detected in fat, liver, spleen and kidneys. Then gradual decline of tritium was noticed in all examined tissues.

Yields 5-methyl-2-naphthoic acid in Nocardia... /from table/|In /rat/ urine, the following substances were identified and quantified by GC peak areas: unchanged 1,6-dimethylnaphthalene, 1-methyl-hydroxynaphthalenes, 1-hydroxymethyl-6-methylnaphthalene, 1,6-dimethyl-thionaphthalene, 6-methyl-1-naphthoic aldehyde, 6-methyl-1-naphthoic acid, 1,6-dimethyl-thionaphthalene and 1,6-dimethyl-methylthionaphthalene.

SYMPTOMS: Symptoms of exposure to this compound may include irritation. ACUTE/CHRONIC HAZARDS: This compound may be harmful by ingestion, inhalation or skin absorption. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Naphthalene and Related Compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Start an IV with lactated Ringer's. Adequate hydration must be maintained to prevent renal failure secondary to myoglobinuria unless signs of cerebral or pulmonary edema are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Naphthalene and related compounds/|Basic Treatment: Establish a patent airway. Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Irritating materials/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation at the first sign of upper airway obstruction may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/|NAPHTHALENE toxicosis caused by vapor inhalation can usually be managed simply by removing the individual to fresh air. Skin contamination should be removed promptly by washing with soap and water. Eye contamination should be removed by flushing with copious amounts of clear water. Irritation may be severe, and if it persists, should receive medical attention. SRP: /It may be helpful to empty stomach and administer dose of activated charcoal/ Examine the plasma for evidence of hemolysis: a reddish-brown tinge. Examine the blood smear for "ghosts" and Heinz bodies. If /hemolysis is/ present, monitor red blood cell count and hematocrit for anemia, urine for protein, and cells. Measure direct- and indirect-reacting bilirubin in the plasma. Monitor fluid balance and blood electrolytes. If possible, monitor urinary excretion of naphthol to assess severity of poisoning and clinical progress. If hemolysis is clinically significnt, administer intravenous fluids to accelerate urinary excretion of the naphthol metabolite and protect the kidney from products of hemolysis. Use Ringer's-lactate or sodium bicarbonate to keep urine pH above 7.5. Consider use of mannitol, or furosemide, to promote diuresis. If urine flow declines, intravenous infusions must be carefully monitored to avoid fluid overload. Institute hemodialysis. Consider charcoal hemoperfusion in tandem to extract naphthalene and end-products. If anemia is severe, blood transfusions may be needed. Hydrocortisone may be of some benefit if significant hemolysis is present. /Fumigant poisoning/

/HUMAN EXPOSURE STUDIES/ In contrast to naphthalene, the only reported effects of methylated naphthalene in man are skin irritation and skin photosensitization. /methylated naphthalene/

1,6-dimethylnaphthalene

CMPD ISOLATED /FROM MINERAL OIL FRACTIONS OF CRUDE PETROLEUM/ INCLUDED ... DI-, TRI-, AND TETRAMETHYLNAPHTHALENES ... /DIMETHYLNAPHTHALENES/