Phenyl-1-naphthylamine

log Kow = 4.20

4.2

4.2

Prisms or needles from alcohol; leaflets from ligroin.

Tan to purple crushed solid or crystals.

White to yellowish crystals

In its pure form crystallizes into lemon yellow prisms or needles ... marketed in the form of brown to dark violet crystals or light brown to light violet granules

less than 1 mg/mL at 70 °F (NTP, 1992)

Soluble in ethanol, ethyl ether, benzene, carbon tetrachloride, chloroform, acetic acid.

In water, 60 mg/L @ 25 °C

Solubility in water: none

1.5 [ug/mL] (The mean of the results at pH 7.4)

635 °F at 528 mmHg (NTP, 1992)

335 °C @ 558 mm Hg

144 °F (NTP, 1992)

61 °C

62-63 °C

0.00000829 [mmHg]

1.13X10-5 mm Hg @ 25 °C /Extrapolated/

This chemical does not meet GHS hazard criteria for 0.3% (5 of 1663) of reports.

Warning

H302 (90.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P319, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1663 reports by companies from 50 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: 1-Naphthalenamine, N-phenyl-

1-Naphthalenamine, N-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Naphthalenamine, N-phenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 11-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/18078

1-Naphthylamine, N-phenyl-: Does not have an individual approval but may be used under an appropriate group standard

Flash point data for this compound are not available. It is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N-Phenyl-1-naphthylamine is included on this list.

N-PHENYL-1-NAPHTHYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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 .

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.

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.

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.

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

EC50 Tetrahymena pyriformis (inhibition of cell proliferation) 2 mg N-phenyl-1-naphthylamine/L/48 hr; static, solubilizer: acetone

LC50 Daphnia magna 0.06 mg/L/21 day; semi-static

LC50 Goldfish 4.4 mg/L/48 hr /Conditions of bioassay not specified in source examined/

LC50 Xenopus laevis (Clawed frog, larvae) 2.3 mg/L/48 hr /Conditions of bioassay not specified in source examined/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a log Kow of 4.20(2) and a regression-derived equation(3), indicates that N-phenyl-1-naphthylamine is expected to have slight mobility in soil(SRC). The pKa of N-phenyl-1-naphthylamine is 4.93 at 25 °C(4) indicating that this compound will partially exist in the cation form in the environment(5). Volatilization of N-phenyl-1-naphthylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.13X10-5 mm Hg(6), and water solubility, 60 mg/L(7). N-Phenyl-1-naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(7). A 17% CO2 evolution when incubated in temperate soil after 11 days(8) indicates that N-phenyl-1-naphthylamine biodegradation in soil is not a major environmental fate process(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a log Kow of 4.20(2) and a regression-derived equation(3), indicates that N-phenyl-1-naphthylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.13X10-5 mm Hg(4), and water solubility, 60 mg/L(5). According to a classification scheme(6), a BCF range of 427 to 2,730(5), suggests bioconcentration in aquatic organisms is high to very high(SRC). Measured photochemical degradation half-lives in water of 8.4 and 5.7 minutes have been reported(7). Biodegredation in water is moderate(SRC) as indicated by a theoretical BOD in freshwater of 50% after 10 days(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-phenyl-1-naphthylamine, which has an extrapolated vapor pressure of 1.1X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase N-phenyl-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 1 hr(SRC), calculated from its rate constant of 3.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase N-phenyl-1-naphthylamine may be removed from the air by wet and dry deposition(SRC). Based on its uv adsorption spectrum, direct photolysis of this compound is expected(4).

/AQUATIC SPECIES/ Sublethal N-phenyl-1-naphthylamine concentrations of approximately 5.2 and 5.6 mg/L had teratogenic effects on embryos and larvae, respectively, of the clawed frog (Xenopus laevis). Concentrations above 6.2 mg/L were lethal (100% death of larvae within 24 hr) for both. ...For larvae of the leopard frog (Rana pipiens), a 48-hr LC100 of 5 mg/L was reported ...

Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.

MAY BE ABSORBED!

See Inhalation.

The Koc of N-phenyl-1-naphthylamine is estimated as 4,600(SRC), using a measured log Kow of 4.2(1), and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that N-phenyl-1-naphthylamine is expected to have slight mobility in soil. The pKa of N-phenyl-1-naphthylamine is 4.93 at 25 °C(4) indicating that this compound will partially exist in the cation form in the environment(3) Since N-phenyl-1-napthylamine exists in the protonated form, it will adsorb more strongly to organic carbon and clay than its neutral counterparts(5).

/HUMAN EXPOSURE STUDIES/ N-Phenyl-1-naphthylamine, mixed with oil or water, was not irritating when applied to the skin of volunteers (no data on concentrations available). Skin eczema in workers has been attributed to repeated exposure to high levels of N-phenyl-1-naphthylamine, possibly in combination with other substances. Reportedly, the content of N-phenyl-1-naphthylamine in a special antirust oil had to be lowered from 2% to 0.5% because of skin problems. Workers, who did not wear gloves, were exposed during the packaging of bearing rings covered with antirust-oil containing N-phenyl-1-naphthylamine.

/SIGNS AND SYMPTOMS/ Acute hazards/Symptoms of Inhalation exposure: Blue lips or finger nails. Blue skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness. /from table/

/CASE REPORTS/ At a manufacturing firm making rollers for conveyor belts, the lubricant used was a fire resistant (FR) grease. Alvania Grease-RA was also used. It appeared that three employees were suffering from contact dermatitis and were patch tested. Two were allergic to phenyl-alpha-naphthylamine (PAN) which was present in both greases at 1%. There was no cross reactivity demonstrated with other naphthylamines. Brief histories of the two workers were provided. One was a 58 yr old welder and the other was a 61 yr old roller assembly worker. Despite improved protection for each of these workers, they continue to be afflicted by eczema. One required regular moderately potent topical applications of a steroid to control the condition. Both were diagnosed as having developed allergic contact dermatitis from the FR and Alvania greases as a result of sensitization to PAN, and also aryl phosphate ester mix in the second case. The authors note that testing with the routinely available phenyl-beta-naphthylamine and di-beta-naphthyl-p-phenylenediamine is not an adequate screen for detecting PAN sensitivity. They emphasize the risk of extrapolating data from animal models.

/CASE REPORTS/ N-Phenyl-1-naphthylamine was also reported to have sensitizing properties in humans. Case-studies on patients with contact dermatitis, potentially associated with occupational exposure to N-phenyl-1-naphthylamine in greases or oils, have been identified. The majority of these patients also had a positive reaction to other substances in the test series, such as mercaptobenzothiazole or p-phenylenediamine. Lower incidences were reported in patients with past exposure to rubber materials. Because of the chemical's incorporation into the polymer matrix, exposure to N-phenyl-1-naphthylamine in rubber materials is assumed to be lower than exposure from greases or oils.

/EPIDEMIOLOGY STUDIES/ An increased occurrence of cancers in a small packaging unit in a Swedish engineering company was reported in a cohort study. Between 1954 and 1957, a special anticorrosive oil, which contained 0.5% N-phenyl-1-naphthylamine in addition to other chemicals, had been used in this unit. In 12 of 78 women in this unit (group A: 78 women/20 men), cancers were diagnosed between 1964 and 1973 in several organs (predominantly the uterus and ovary). The staff performing the actual packaging, and thus in contact with the oil, were mainly women. Morbidity and mortality from cancer were 3.1- and 3.5-fold higher, respectively, than expected, based upon age-specific and sex-specific data from the Swedish Cancer Register (the standard cancer rates for the period 1974-1976 were estimated on the basis of the 1973 rate). In the males of group A, no significant differences were established. In another unit (reference group B: 25 women/8 men) where anticorrosive oil without N-phenyl-1-naphthylamine had been used, morbidity and mortality from cancer were not elevated. This was also true for reference group C (8 women/23 men), from units that had been in contact with N-phenyl-1-naphthylamine-containing anticorrosive oil for a short period of time only, because they had demonstrated allergic reactions. The authors concluded that, apart from exposure to N-phenyl-1-naphthylamine, the formation of N-nitroso-N-phenyl-1-naphthylamine from sodium nitrite originating from the packaging paper used may be a possible explanation for the increased frequency of cancer in group A.

N-Phenyl-1-naphthylamine's production and use as an antioxidant in various lubrication oils and as both a protective agent and antioxidant in rubber and rubber mixtures for various products, including tires(1) may result in its release to the environment through various waste streams(SRC).

AEROBIC: N-Phenyl-1-naphthylamine, present at 100 mg/L, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). In contrast, another test showed a 50% theoretical BOD in 5 days using a freshwater inoculum(2). Using an activated sewage inoculum, N-phenyl-1-naphthylamine (concentration of 2 ug/g) reached 70% of its theoretical BOD in 2 days(2). In screening tests, N-phenyl-1-naphthylamine present in a concentration of 2 ug/mL, reached 50% of its theoretical BOD in 10 days in Oneida Lake, NY water(2). Using acclimated lake water supplemented with nutrient broth, N-phenyl-1-naphthylamine (concentration of 2 ppm) reached 90% of its theoretical BOD after 10 days. N-Phenyl-1-naphthylamine was observed to degrade in a soil study, based on carbon dioxide evolution at rates of 7 and 17% 14CO2 evolution (40 nCi of 14CO2%-test compound/g soil) after 2 and 11 days, respectively(2).

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N-Phenyl-1-naphthylamine is included on this list.

Mono- and dihydroxy-derivatives of N-phenyl-1-naphthylamine have been identified in in vitro metabolic studies conducted with rat liver microsomes. /It was/ suggested that the hydroxyl group in the mono-hydroxy derivative is in the naphthalene moiety at a para-position to the amino group, whereas at least one hydroxyl group in the dihydroxy-derivative is at the available para-position in the naphthyl ring. Pretreatment of male rats with phenobarbital or 3-methylcholanthrene increased the rate of microsomal metabolism, indicating that more than one P-450 enzyme is involved in the metabolism of N-phenyl-1-naphthylamine.

...In the ether extract of the urine /of male Sprague-Dawley rats administered a single oral dose of 160 mg [14C] N-phenyl-1-naphthylamine/kg bw/, at least five radioactive metabolites were detected but not identified.

In studies conducted with human volunteers or laboratory animals, the isomer N-phenyl-2-naphthylamine was partially metabolized to the known human carcinogen 2-naphthylamine following ingestion or inhalation. Although data concerning the formation of this metabolite are not available for N-phenyl-1-naphthylamine, it should be noted that, based on its chemical structure, it is unlikely that N-phenyl-1-naphthylamine is metabolized to 2-naphthylamine. /N-phenyl-2-naphthylamine/

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.

In male Sprague-Dawley rats administered a single oral dose of 160 mg [14C] N-phenyl-1-naphthylamine/kg bw, the chemical was well absorbed, metabolized almost completely, and excreted primarily in the feces. Radioactivity was detected in plasma within 60 min, with the maximum concentration measured after 4 hr. After 24 hr, 20% of the radioactivity was found in the GI tract (including contents), 2.4% in fatty tissue, 0.4% in the liver, and 0.1% in the kidneys. 90% of the administered radioactivity was excreted within 48 hr; 95% was excreted within 72 hr (60% in the feces and 35% in the urine).

High performance liquid chromatographic and gas chromatographic methods for the determination of N-phenyl-1-naphthylamine (I) in biological fluid and tissues were developed, and the biological fate of I was studied in male rats following single and multiple oral administration. It was assumed that the intestinal absorption of I was excellent, because the fecal excretion of unchanged I was extremely low (0.4% of dose), and there was little unchanged I excreted in the urine (0.01% of dose). A large amount of glucuronide and sulfate metabolites was excreted in the urine. After single or multiple (6 days) oral administration, a small amount of unchanged I was distributed in fat, but the distribution of unchanged I in liver, kidney, spleen, heart and lung was extremely low.

Used as a stabilizer for synthetic rubbers, an antioxidant in lubrication oils and rubber mixtures, and an intermediate for dyes and other chemicals; [HSDB] Caused contact dermatitis in workers manufacturing rollers for conveyor belts exposed to fire-resistant greases containing this chemical; [Kanerva, p. 1826]

Used as a stabilizer for various synthetic rubber. A thermostabilizer for vulcanizates and polyethylene.

/Synthesis of/ dyes and other organic chemicals, rubber antioxidant.

N-Phenyl-1-naphthylamine is used as an antioxidant in gear, hydraulic, lubrication, and bearing oils and as a protective agent and antioxidant in rubbers and rubber mixtures.

N-Phenyl-1-naphthylamine... used as an antioxidant in various lubrication oils and as both a protective agent and antioxidant in rubber and rubber mixtures for various products, including tires.

The commercial product has a typical purity of >99%. Named impurities from three manufacturers are 1-naphthylamine (<100-500 mg/kg), 2-naphthylamine (<3-50 mg/kg), aniline (<100-2500 mg/kg), 1-naphthol (<5000 mg/kg), 1,1-dinaphthylamine (<1000 mg/kg), and N-phenyl-2-naphthylamine (500-<5000 mg/kg).

Trade names: Antioxidant PAN; Neozone A; Nonox AN.

The commercial product has a typical purity of >99%.

Petroleum Lubricating Oil and Grease Manufacturing

1-Naphthalenamine, N-phenyl-: ACTIVE