1-Naphthylamin

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

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.

General First Aid:

General First Aid:

General First Aid:

General First Aid:

(General first aid procedures)

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

Powder, alcohol-resistant foam, water spray, carbon dioxide.

Dry chemical, carbon dioxide, mist, spray.

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.

Keep well closed and protected from light.

Store containers in well-ventilated area.

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses.

Environmental considerations: Land spill: Dig a pit, pond, lagoon, 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 a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete.

Do NOT wash away into sewer. Sweep spilled substance into sealable containers. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U167, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

A degradation method involving the oxidation of aromatic amines with potassium permanganate/sulfuric acid was examined for possible treatment of laboratory wastes including benzidine, ortho-toluidine, ortho-dianisidine, 3,3'-dichlorobenzidine, 4-aminobiphenyl, 1-naphthylamine, 2-naphthylamine, 4,4'-methylene-bis(2-chloroaniline), and meta-toluenediamine. Three requirements were sought for a degradation method: first, degradation of the compounds must be complete; second, the oxidation products formed must be nonmutagenic; and third, the method must be applicable and reproducible in its results. Two methods were used for the degradation. In the first method, 5 ml of a solution of 0.005M aromatic amine was treated with 5 ml of 0.2M solution of potassium permaganate in the presence of 10 ml of a 1M solution of sulfuric acid for 8 hours. In the second method, 10 ml of a solution of 0.005 M aromatic amine was treated with 5 ml of a 2M solution of sulfuric acid for 8 hours. At the end of the 8 hours, the reaction was stopped by adding just enough solid ascorbic acid to obtain complete decolorization of the solution. The pH was adjusted to 7 and 20 microliter aliquots injected into a high pressure liquid chromatography apparatus. Salmonella typhimurium strains (TA-100), (TA-98), and (TA-97) were used for mutagenicity studies. Degradation of 99.8% of all materials was achieved. Only 4-aminobiphenyl showed residual mutagenic activity, and further degradation with twice the amount of oxidant eliminated the activity. The method is recommended for use in treatment of solid compounds, solutions in volatile organic solvents, aqueous solutions, solutions in oil and for decontamination of glassware and spills.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

LD50 Cyprinus carpio oral 91-109 mg/kg bw/70 hr /Conditions of bioassay not specified in source examined/

LC50 Oryzias latipes (Medaka) 15 mg/L/24 hr; static

LC50 Oryzias latipes (Medaka) 7 mg/L/48 hr; static

LD50 Rat (Norway, wild) oral 300 mg/kg bw

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 2,688 to 3,777, using a batch equilibrium technique(2), indicate that 1-naphthylamine is expected to have low mobility in soil(SRC). Results of a batch equilibrium study with various soils indicated that 1-naphthylamine binds to soil in two phases with an initial rapid and reversible equilibrium established between the amine and the inorganic and organic components of soil followed subsequently by a strong association with the humic fraction of soil via covalent binding(3,4). Volatilization of 1-naphthylamine from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 4.6X10-7 atm-cu(SRC), derived from its vapor pressure, 4.18X10-3 mm Hg(5), and water solubility 1.7X10+3 mg/L(6). 1-Naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.18X10-3 mm Hg(4). The pKa of 1-naphthylamine is 3.92(7), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(8). At the end of a 200 day experiment, 86 percent of the 1-naphthylamine in the soil had degraded. This degradation was due to the bacteria native to the soil(9).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 2,688 to 3,777, using a batch equilibrium technique(2), indicate that 1-naphthylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 4.6X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 4.18X10-3 mm Hg(4), and water solubility 1.7X10+3 mg/L(5). The pKa of 1-naphthylamine is 3.92(6), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb more strongly to suspended solids and sediment than their neutral counterparts(7). According to a classification scheme(8), an estimated BCF of 11(SRC), its log Kow(2) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The rate of biodegradation of 1-naphthylamine in water was found to be 1.4 ug/hr(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-naphthylamine, which has a estimated vapor pressure of 4.18X10-3 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-naphthylamine 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 2 hrs(SRC), calculated from its rate constant of 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Blue lips, fingernails and skin. Confusion. Dizziness. Headache. Shortness of breath. Weakness.

MAY BE ABSORBED! Redness.

Redness. Pain.

Blue lips, fingernails and skin. Dizziness. Headache. Nausea.

dermatitis; hemorrhagic cystitis; dyspnea (breathing difficulty), ataxia, methemoglobinemia; hematuria (blood in the urine); dysuria; [potential occupational carcinogen]

1-Naphthylamine was qualitatively found in waste streams at a coal gasification facility in Chicago(1). Concentrations of 3 ppm was detected in the process water from an oil shale facility in Australia(2). 1-Naphthylamine was not detected at a detection limit of 1.0 ug/L in the tire leachate water from an unspecified location in the United States(3).

Using a batch equilibrium technique, 1-naphthylamine Koc values of 2,688 and 3,173 were determined for two sandy-silt soils and a Koc value of 3,777 was determined for a silty-clay soil(1). According to a classification scheme(2), this estimated Koc value suggests that 1-naphthylamine is expected to have low mobility in soil. Results of a batch equilibrium study with various soils indicated that 1-naphthylamine binds to soil in two phases with an initial rapid and reversible equilibrium established between the amine and the inorganic and organic components of soil followed subsequently by a strong association with the humic fraction of soil via covalent binding(3,4). In laboratory study, 1-naphthyalmine was found to have a relatively moderate tendency to adsorb to lignite coal in subsurface areas where it may be present as a contaminant from coal-gasification plants(5).

The pKa of 1-naphthylamine is 3.92(1), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(2). Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), also suggesting that mobility may be much lower in some soils(SRC).

U167; As stipulated in 40 CFR 261.33, when 1-naphthalenamine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

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 100 lb or 45.5 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).

Former uses included: a chemical intermediate for the synthesis of dyes, rubber antioxidants, and pesticides; [HSDB]

See 29CFR1910.1003 (Code of Federal Regulations}

Toning prints made with cerium salts.

Chemical intermediate for dyes, eg, azoic diazo component; chemical intermediate for azo dye coupling agents, for n-1-naphthylphthalmic acid herbicide, for n-phenyl-1-naphthylamine rubber antioxidant, for an imidazoline adrenergic agent; chemical intermediate for 1-naphthylthiourea rodenticide and for a fluoroacetamide miticide. /SRP60: Former/

1-Naphthylamine is used as an intermediate in the synthesis of dyes, antioxidants, herbicides, some drugs, and other chemicals. /SRP60: Former/

In agricultural chemicals

(1977) 5.16X10+7 G (PRINCPL CUSTMS DISTS)

(1982) 9.91X10+7 G (PRINCPL CUSTMS DISTS)

(1978) PROBABLY GREATER THAN 2.27X10+6 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

(1985) Data not reported

Reduction of 1-nitronaphthalene by catalytic hydrogenation with a nickel catalyst ... .

Prepared by reducing alpha-nitronaphthalene with iron and hydrochloric acid.

Naphthalene is nitrated with H2SO4-HNO3 at 50-60 °C. The crude product (mp 52 °C) is separated, washed with hot water, and further purified by crystallization or sweating (draining of the lower melting point isomer) to remove 2-nitronaphthalene (3%) and traces of 2,4-dinitronaphthalene. purified 1-nitronaphthalene was traditionally reduced with iron in boiling dilute hydrochloric acid, but modern plants use hydrogenation with nickel catalyst. The 1-naphthylamine produced is further purified by distillation under vacuum. The content of 2-naphthylamine in the commercial product is specified at less than 10 ppm.