2-Isopropylnaphthalene

170.255

170.25

217-976-0

4DTR9UN8SR

166466

DTXSID7051844

Clear, yellowish-brown liquid|Colorless liquid

2902909090

0

4.79

0.9753 g/cm³ @ Temp: 20 °C

14.5 °C

268.2 °C

122 deg C (open cup)

1.586

Insoluble in water; very soluble in ethanol, ethyl ether; soluble in benzene.

5.18X10-3 mm Hg @ 25 deg C

Faint sweet odor

475 °C

13,036.9 g cal/g mole

QJ8000000

P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, P391, P501

H317

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 naphthalene: Biological treatment. /Naphthalene/

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/

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, P391, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Avoid inhalation of vapors and prolonged skin contact.

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/

2-Isopropylnaphthalene was identified as a component of waste water effluent from sewage treatment facilities(1).

SEDIMENT: 2-Isopropylnaphthalene was detected in sediment samples at a concn of 50 ng/g dry wt(1) 400 m downstream from a discharge of produced water at midchannel at Pass Fourchon, LA(1). 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 C/L, and is generated as a result of petroleum production(2).

LD50 Mouse oral 5300 mg/kg

2-Isopropylnaphthalene is a natural component of crude oil(1).

2-Isopropylnaphthalene's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9,000(SRC), determined from a structure estimation method(2), indicates that 2-isopropylnaphthalene is expected to be immobile in soil(SRC). Volatilization of 2-isopropylnaphthalene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.5X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 2-Isopropylnaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.18X10-3 mm Hg(4). 2-Isopropylnaphthalene may degrade in the soil environment based on MITI test data using analogous 1- and 2-methylnaphthalenes(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9,000(SRC), determined from a structure estimation method(2), indicates that 2-isopropylnaphthalene 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 8.5X10-4 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 5 hrs and 5 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 78 days if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 730(SRC), from an estimated log Kow of 4.6(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(9). 2-Isopropylnaphthalene may degrade in the aquatic environment based on MITI test data using analogous 1- and 2-methylnaphthalenes; using a freshwater inoculum, 49% and 72% for 1- and 2-methylnaphthalene, respectively, was lost in 28 days under aerobic conditions at 25 °C(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-isopropylnaphthalene, which has a vapor pressure of 5.18X10-3 mm Hg at 25 °C(2), is expected to exist primarily as a vapor in the ambient atmosphere. Vapor-phase 2-isopropylnaphthalene 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 7 hrs(SRC), calculated from its rate constant of 5.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Based upon aqueous photolysis data(4), 2-isopropylnaphthalene may undergo direct photolysis in the atmosphere.

The rate constant for the vapor-phase reaction of 2-isopropylnaphthalene with photochemically-produced hydroxyl radicals has been estimated as 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(2). The rate constant for the direct photolysis of 2-isopropylnaphthalene in a pyrex beaker of distilled water maintained at 20 °C and exposed to a 100W mercury lamp for 96 hours was measured to be 0.31 hr-1; which corresponds to a half-life of about 22.3 hours(3).

An estimated BCF of 730 was calculated for 2-isopropylnaphthalene(SRC), using an estimated log Kow of 4.6(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). However, using a bioaccumulation study, 2-isopropylnaphthalene was not detected in oyster tissue samples following a 14 day exposure to 2-isopropylnaphthalene-contaminated sediment (concn of <10 ng/g dry wt) collected near Port Lachon, LA(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-isopropylnaphthalene can be estimated to be 9,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-isopropylnaphthalene is expected to be immobile in soil.

The Henry's Law constant for 2-isopropylnaphthalene is estimated as 8.5X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-isopropylnaphthalene 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 5 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 5 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 78 days when adsorption is considered(3). 2-Isopropylnaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.18X10-3 mm Hg(4).

GROUNDWATER: 2-Isopropylnaphthalene was detected in an aquifer contaminated by sewage effluent in the People's Rep of China(1).|DRINKING WATER: For a survey of drinking water supplies in the US, 2-isopropylnaphthalene was detected in the treated water at 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). 2-Isopropylnaphthalene was detected in 11 drinking water wells contaminated by sewage effluent in the People's Rep of China(1).

Occupational exposure to 2-isopropylnaphthalene may occur through inhalation and dermal contact with this compound at workplaces where 2-isopropylnaphthalene is produced or used. Monitoring data indicate that the general population may be exposed to 2-isopropylnaphthalene via ingestion of contaminated drinking water and recreational activities on contaminated waterways. (SRC)

Pulmonary toxicity of 2-isopropylnaphthalene (2-IPN) and its photoproducts was studied in mice. Twenty-four hours after the intraperitoneal injection of 2-IPN or its photoproducts, 2-isopropenylnaphthalene (2-IPeN) (1000 mg/kg), 2-acetonaphthone (2-AN) (700 mg/kg), beta-naphthol (BN) (50 mg/kg), phthalide (PH) (500 mg/kg) and phthalic acid (PA) (100 mg/kg) produced pulmonary damage, but 2-IPN (3000 mg/kg) and 2-(2-naphthyl)-2-propanol (2-NP) (100 mg/kg) did not produce pulmonary damage. The maximum levels of 2-IPN in the lung, liver and kidney were observed 6 h after the administration, and then the levels decreased with time. The concentrations of 2-IPeN, 2-NP, 2-AN, BN, PH and PA in the tissues, reached the maximum levels within 1 or 2 hr, and then rapidly decreased with time. The binding of both 2-AN and BN to lung slices was greater than that of other compounds. The injections of 2-IPN, 2-IPeN, BN and PH caused considerable depletion of pulmonary GSH (reduced glutathione).|Over 95% of orally admin 2-isopropylnaphthalene was absorbed within 24 hr from the GI tract in rats. Peak levels in the blood, liver, kidneys, brain, heart, spleen, and muscle were observed at 2 hr, whereas peak levels in the adipose tissue and skin were observed at 4-6 hr. Amount of unchanged 2-isopropylnaphthalene in urine was small. In rats fed the experimental diet containing 0.1% for 14 or 28 days, 2-isopropylnaphthalene in the adipose tissue decreased to 1/3 within 24 hr after halting continuous ingestion.

Metabolism of 2-isopropylnaphthalene in rats proceeded through oxidation of isopropyl chain of the molecule. Four unconjugated metabolites were isolated from urine and identified: 2-(2-naphthyl)propionic acid, 2-(2-naphthyl)-2-propanol, 2-(2-naphthyl)-1,2-propanediol and 2-(2-naphthyl)-2-hydroxypropionic acid, together with a small amount of unchanged compound.

10.00 Days

The intraperitoneal administration of 2-isopropylnaphthalene (2-IPN) (3000 mg/kg) to rats resulted in an increase of phospholipids and phosphatidylcholine in the pulmonary lavage fluid. The fatty acid composition of the phosphatidylcholine in the fluid of rats so treated, however, was unchanged from that of untreated animals. Prior treatment of rats with piperonyl butoxide, a known cytochrome P-450 inhibitor, resulted in an inhibition of the above increase of phospholipids and phosphatidylcholine. In contrast, prior treatment with diethyl maleate, which induced depletion of reduced glutathione (GSH) in the tissue, enhanced the effect of 2-IPN on phospholipid and phosphatidylcholine contents in the pulmonary lavage fluid.

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/|Maintain an open air way and assist ventilation if necessary. Treat coma and seizures if they occur. Treat hemolysis and resulting hemoglobinuria if they occur by intravenous hydration and urinary alkalinization. There is no specific antidote. Administer activated charcoal if available. Do not induce vomiting, because of the risk of lethargy and seizures. Do not administer milk, fats or oils, which may enhance absorption /Naphthalene/|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/

2-isopropylnaphthalene

Naphthalene, 2-(1-methylethyl)-: ACTIVE|Naphthalene, isopropylated: INACTIVE

Method: EPA-EAD 1625, Semivolatile Organic Compounds by Isotope Dilution GC/MS; Analyte: 2-Isopropylnaphthalene; Matrix: Water.