N-phenyl-2-naphthylamine

H315: Causes skin irritation [Warning Skin corrosion/irritation]

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H351: Suspected of causing cancer [Warning Carcinogenicity]

H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P203, P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H351 (99.8%): Suspected of causing cancer [Warning Carcinogenicity]

H411 (99.8%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Aggregated GHS information provided per 650 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

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

Fresh air, rest. Seek medical attention if you feel unwell.

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.

Seek medical attention if you feel unwell.

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)

(General first aid procedures)

Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.

Skin: Soap wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.

Breathing: Respiratory support

Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

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

Use water spray, powder, foam, carbon dioxide.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

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 containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

The worker should immediately wash the skin when it becomes contaminated.

The worker should wash daily at the end of each work shift.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

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.

STORAGE PRECAUTIONS: You should store this material under ambient temperatures and protect it from light. (NTP, 1992)

Separated from oxidants. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.

...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH...DECOMP INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT...SHOULD BE STORED IN COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, &...PERIODICALLY INSPECTED & MONITORED.

Ca* See Appendix A [*Note: Since metabolized to β-Naphthylamine.]

A potential occupational carcinogen. (NIOSH, 2024)

NIOSH considers N-phenyl-beta-naphthylamine to be a potential occupational carcinogen. [Note: Since metabolized to beta-Naphthylamine].

Ca [N.D.]

See: IDLH INDEX

Exposure by all routes should be carefully controlled to levels as low as possible.

A4; Not classifiable as a human carcinogen.

A4 (not classifiable as a human carcinogen).

skin absorption (H); sensitization of skin (SH); carcinogen category: 1; germ cell mutagen group: 3A

A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

The substance may be irritating to the skin and eyes.

Repeated or prolonged contact may cause skin sensitization. This substance is possibly carcinogenic to humans.

Excerpt from NIOSH Pocket Guide for N-Phenyl-beta-naphthylamine:

Skin: PREVENT SKIN CONTACT - Wear appropriate personal protective clothing to prevent skin contact.

Eyes: PREVENT EYE CONTACT - Wear appropriate eye protection to prevent eye contact.

Wash skin:

• WHEN CONTAMINATED - The worker should immediately wash the skin when it becomes contaminated.

• DAILY - The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.

Remove: WHEN WET OR CONTAMINATED - Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Change: DAILY - Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Provide:

• EYEWASH - Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substances; this is irrespective of the recommendation involving the wearing of eye protection.

• QUICK DRENCH - Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2024)

Wear appropriate personal protective clothing to prevent skin contact.

Wear appropriate eye protection to prevent eye contact.

Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.

Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]

For more Personal Protective Equipment (PPE) (Complete) data for 2-NAPHTHYLAMINE, N-PHENYL- (6 total), please visit the HSDB record page.

At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentration:

(APF = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode

(APF = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus

(APF = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having an N100, R100, or P100 filter.

Click here for information on selection of N, R, or P filters.

Any appropriate escape-type, self-contained breathing apparatus

Important additional information about respirator selection

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. Prevent build-up of electrostatic charges (e.g., by grounding).

AVOID ALL CONTACT!

Use closed system, local exhaust or breathing protection.

Protective clothing. Protective gloves.

Wear safety goggles.

N-phenyl-2-naphthylamine is a light gray to gray powder. Solutions show blue fluorescence. (NTP, 1992)

White to yellow crystals or gray to tan flakes or powder. [Note: Commercial product may contain 20-30 ppm of Beta-Naphthylamine.]; [NIOSH]

WHITE-TO-GREY SOLID IN VARIOUS FORMS.

White to yellow crystals or gray to tan flakes or powder.

White to yellow crystals or gray to tan flakes or powder. [Note: Commercial product may contain 20-30 ppm of β-Naphthylamine.]

NEEDLES FROM METHANOL

WHITE TO YELLOWISH CRYSTALS

GRAY TO TAN FLAKES OR POWDER

White to yellow crystals or gray tan flakes or powder [Note: Commercial product may contain 20-30 ppm of beta naphthylamine].

743 °F at 760 mmHg (NTP, 1992)

395.5 °C

226 °F (NTP, 1992)

less than 1 mg/mL at 66 °F (NTP, 1992)

SOLUBILITY IN ETHANOL 50 G/L, IN BENZENE 27 G/L, IN ACETONE 640 G/L

INSOL IN WATER; SOL IN ALC, ETHER, ACETIC ACID (BLUISH FLUORESCENCE)

Solubility in water at 25 °C: none

Insoluble

1.24 (NTP, 1992) - Denser than water; will sink

1.2 g/cm³

0.00000829 [mmHg]

log Kow = 4.38

WHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF /NITROGEN OXIDES/.

151.3 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4021131]

149.2 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID4021131]

150.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID4021131]

MAY BE OXIDIZED TO 7-PHENYL-7H-DIBENZO[C,G]CARBAZOLE

Angular frequency

Boiling point

Crystal structure

External quantum efficiency

Formula unit

Heat of sublimation

Luminescence

Luminescence emission linewidth

Polarization degree

Space group

Unit cell

Unit cell parameter

Vapor pressure

Nitrogen Compounds -> Naphthylamines

Insoluble in water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].

Amines, Phosphines, and Pyridines

N-PHENYL-2-NAPHTHYLAMINE may react with strong oxidizing agents (NTP, 1992). 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.

Oxidizers.

Oxidizers

Inadequate evidence of carcinogenicity in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

A4; Not classifiable as a human carcinogen.

N-Phenyl-2-naphthylamine

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

N-Phenyl-2-Naphthylamine

TR-333: Toxicology and Carcinogenesis Studies of N-Phenyl-2-Naphthylamine (CASRN 135-88-6) in F344/N Rats and B6C3F1 Mice (Feed Studies) (1988 )

03/04/87

No Evidence

Equivocal Evidence

Under the conditions of these 2-year feed studies, there was no evidence of carcinogenic activity for male or female F344/N rats fed diets containing 2,500 or 5,000 ppm N-phenyl-2-naphthylamine. Decreased incidences of several neoplasms were observed in dosed rats: thyroid gland C-cell neoplasms in males and females and mononuclear cell leukemia, pituitary gland adenomas, and mammary gland fibroadenomas in females. There was no evidence of carcinogenic activity for male B6C3F1 mice fed diets containing 2,500 or 5,000 ppm N-phenyl-2-naphthylamine. There was equivocal evidence of carcinogenic activity of N-phenyl-2-naphthylamine for female B6C3F1 mice as indicated by the occurrence of two rare kidney neoplasms. Chemical-related nonneoplastic lesions (nephropathy, karyomegaly, and hyperplasia) occurred in the kidney of rats and mice.

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

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

Redness.

Redness. Pain.

Irritation; leucoplakia; acne, hypersensitivity to sunlight; [potential occupational carcinogen]

Eyes, skin, bladder

[bladder cancer]

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

ACGIH Carcinogen - Not Classifiable.

LD50 Rat oral 8730 mg/kg

LD50 Mouse oral 1450 mg/kg

TREATMENT: SYMPTOMATIC & SUPPORTIVE.

LEUCOPLAKIA, ACNE & HYPERSENSITIVITY TO SUNLIGHT...OBSERVED IN 36 WORKERS EXPOSED FOR PROLONGED PERIODS TO N-PHENYL-2-NAPHTHYLAMINE...

OUT OF 57 CU-SMELTING WORKERS SUFFERING FROM INFLAMMATORY LESIONS OF MUCOUS MEMBRANE & SKIN OF LIPS, 22 HAD INCR SENSITIVITY TO RUBBER AS MAIN CAUSE OF CHEILITIS.

OCCUPATIONAL ALLERGIC DERMATOSIS WAS OBSERVED IN RUBBER WORKERS DUE TO ADDITIVES SUCH AS NEOZON D.

IT HAS BEEN REPORTED THAT COMMERCIAL N-PHENYL-2-NAPHTHYLAMINE IS CONTAMINATED WITH 20-30 MG/KG OF CARCINOGEN 2-NAPHTHYLAMINE...

For more Human Toxicity Excerpts (Complete) data for 2-NAPHTHYLAMINE, N-PHENYL- (6 total), please visit the HSDB record page.

...GROUPS OF 18 MALE & 18 FEMALE (C57BL/6XC3H/ANF)F1 MICE.../&/ (C57BL/6XAKR)F1 MICE...GIVEN SINGLE SC.../DOSE/ OF 464 MG/KG... N-PHENYL-2-NAPHTHYLAMINE IN DIMETHYL SULFOXIDE...ON 28TH DAY OF LIFE... OBSERVED UP TO 80 WK OF AGE, @ WHICH TIME 16, 17, 16 & 18 MICE IN 4 GROUPS, RESPECTIVELY, WERE STILL ALIVE.

IN FEMALES OF.../(C57BL/6XC3H/ANF)F1 STRAIN OF MICE/, FREQUENCY OF TUMOR-BEARING ANIMALS WAS SIGNIFICANTLY GREATER.../THAN/ WITH CONTROL ANIMALS (UNTREATED OR GIVEN DMSO BY INJECTION: 5/18 VERSUS 9/154, P LESS THAN 0.01... ). /TREATED MICE GIVEN SINGLE DOSE 464 MG/KG SC ON DAY 28 OF LIFE & OBSERVED UP TO 80 WK OF AGE./

...THERE WAS...A STATISTICALLY SIGNIFICANT INCR IN FREQUENCY OF HEPATOMAS IN MALES OF...STRAIN /(C57BL/6XAKR)F1 MICE GIVEN SINGLE SC DOSE OF 464 MG/KG N-PHENYL-2-NAPHTHYLAMINE IN DIMETHYL SULFOXIDE ON DAY 28 OF LIFE & OBSERVED UP TO 80 WK OF AGE/ (2/18 VERSUS 1/16, P LESS THAN 0.05)... /SEE TABLES/

DAILY INHALATION BY RATS OF...AEROSOL (900 MG/CU M) FOR 14 DAYS CAUSED WT LOSS, SLIGHT ERYTHROCYTOPENIA & PULMONARY EMPHYSEMA... MICE EXPOSED DAILY FOR 4 HR DURING 1 MO TO...12 MG/CU M N-PHENYL-2-NAPHTHYLAMINE /IN AIR/ & 339 MG/CU M 1,3-BUTADIENE SHOWED SLIGHT LEUCOPENIA & IRRITATION OF RESP TRACT...

For more Non-Human Toxicity Excerpts (Complete) data for 2-NAPHTHYLAMINE, N-PHENYL- (20 total), please visit the HSDB record page.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=135-88-6]

Under the conditions of these 2 year studies, there was no evidence of carcinogenic activity for male or female F344/N rats fed diets containing 2,500 or 5,000 ppm N-phenyl-2-naphthylamine. Decreased incidence of several neoplasms were observed in dosed rats: thyroid gland C-cell neoplasms in males and females and mononuclear cell leukemia, pituitary gland adenomas, and mammary gland fibroadenomas in females. There was no evidence of carcinogenic activity for male B6C3Fl mice fed diets containing 2,500 or 5,000 ppm N-phenyl-2-naphthylamine. There was equivocal evidence of carcinogenic activity of N-phenyl-2-naphthylamine for male B6C3F1 mice as indicated by the occurrence of two rare kidney neoplasms.

The substance is toxic to aquatic organisms. Bioaccumulation of this chemical may occur in fish. The substance may cause long-term effects in the aquatic environment.

N-Phenyl-2-naphthylamine is probably released to the environment in waste streams from its production and use. In the atmosphere, it should exist in the vapor and particulate phases. Vapor phase N-phenyl-2-naphthylamine is expected to degrade rapidly (estimated half-life of 55 minutes) by reaction with photochemically produced hydroxyl radicals. Particulate-phase N-phenyl-2-naphthylamine may be removed via dry deposition. If released to soil, N-phenyl-2-naphthylamine may undergo a covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and prevent leaching. In the absence of covalent bonding, N-phenyl-2-naphthylamine will be immobile in soil. Photolysis may be important on soil surfaces. N-Phenyl-2-naphthylamine should rapidly biodegrade to beta-naphthylamine at concns <5 ppm in soil and water; however, the apparent covalent bonding and adsorption may reduce biodegradation. In water, covalent bonding with humic materials in the water column and sediments may result in partitioning from the water column to sediments. By analogy to the aromatic amine chemical class, N-phenyl-2-naphthylamine may be susceptible to photolysis and photooxidation via hydroxyl and peroxy radicals in water. Experimental data suggest that bioconcentration in aquatic organisms will not be an important fate process. Hydrolysis and volatilization from water should not be important. In occupational settings, workers may be exposed to N-phenyl-2-naphthylamine through inhalation and through eye and skin contact. (SRC)

N-Phenyl-2-naphthylamine is used as an antioxidant, lubricant, and inhibitor(1) and, therefore, it may be released to the environment during its production and use(SRC).

TERRESTRIAL FATE: One screening study observed that N-phenyl-2-naphthylamine is readily biodegradable to beta-naphthylamine at concns <5 ppm(2). Higher concns appear to be toxic to microorganisms(2,SRC). Because N-phenyl-2-naphthylamine absorbs UV light >290 nm(3), photolysis may be important if N-phenyl-2-naphthylamine is spilled on terrestrial surfaces(SRC). By analogy to other aromatic amines(1), when released to soil, N-phenyl-2-naphthylamine may undergo covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and result in tight adsorption. When covalently bound in this latent form, leaching in soil systems is not expected to occur. This covalent bonding proceeds in two steps: a rapid and reversible bonding followed by a slower and much less reversible reaction(1,SRC). In the absence of covalent bonding, leaching would not be possible based on an estimated Koc of 12,500(4-6).

The substance is toxic to aquatic organisms. Bioaccumulation of this chemical may occur in fish. The substance may cause long-term effects in the aquatic environment.

N-Phenyl-2-naphthylamine is probably released to the environment in waste streams from its production and use. In the atmosphere, it should exist in the vapor and particulate phases. Vapor phase N-phenyl-2-naphthylamine is expected to degrade rapidly (estimated half-life of 55 minutes) by reaction with photochemically produced hydroxyl radicals. Particulate-phase N-phenyl-2-naphthylamine may be removed via dry deposition. If released to soil, N-phenyl-2-naphthylamine may undergo a covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and prevent leaching. In the absence of covalent bonding, N-phenyl-2-naphthylamine will be immobile in soil. Photolysis may be important on soil surfaces. N-Phenyl-2-naphthylamine should rapidly biodegrade to beta-naphthylamine at concns <5 ppm in soil and water; however, the apparent covalent bonding and adsorption may reduce biodegradation. In water, covalent bonding with humic materials in the water column and sediments may result in partitioning from the water column to sediments. By analogy to the aromatic amine chemical class, N-phenyl-2-naphthylamine may be susceptible to photolysis and photooxidation via hydroxyl and peroxy radicals in water. Experimental data suggest that bioconcentration in aquatic organisms will not be an important fate process. Hydrolysis and volatilization from water should not be important. In occupational settings, workers may be exposed to N-phenyl-2-naphthylamine through inhalation and through eye and skin contact. (SRC)

N-Phenyl-2-naphthylamine is used as an antioxidant, lubricant, and inhibitor(1) and, therefore, it may be released to the environment during its production and use(SRC).

TERRESTRIAL FATE: One screening study observed that N-phenyl-2-naphthylamine is readily biodegradable to beta-naphthylamine at concns <5 ppm(2). Higher concns appear to be toxic to microorganisms(2,SRC). Because N-phenyl-2-naphthylamine absorbs UV light >290 nm(3), photolysis may be important if N-phenyl-2-naphthylamine is spilled on terrestrial surfaces(SRC). By analogy to other aromatic amines(1), when released to soil, N-phenyl-2-naphthylamine may undergo covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and result in tight adsorption. When covalently bound in this latent form, leaching in soil systems is not expected to occur. This covalent bonding proceeds in two steps: a rapid and reversible bonding followed by a slower and much less reversible reaction(1,SRC). In the absence of covalent bonding, leaching would not be possible based on an estimated Koc of 12,500(4-6).

AQUATIC FATE: Based on analogy to other aromatic amines(1), N-phenyl-2-naphthylamine may undergo covalent bonding with humic materials in the water column and in sediment; therefore, partitioning from the water column to sediment and suspended material may be important. N-Phenyl-2-naphthylamine may be susceptible to photooxidation via hydroxyl and peroxy radicals based on analogy to other aromatic amines(2,SRC). Because N-phenyl-2-naphthylamine abosorbs UV light >290 nm(4), photolysis may be important in near-surface water. A BCF value of 147(3,SRC) suggests that N-phenyl-2-naphthylamine will have low potential to bioconcentrate in aquatic organisms(SRC). Aquatic hydrolysis and volatilization do not appear to be environmentally important removal processes of N-phenyl-2-naphthylamine in water(SRC). It appears that N-phenyl-2-naphthylamine is readily biodegradable to beta-naphthylamine at concns <5 ppm(5).

ATMOSPHERIC FATE: Based on a modified regression-derived equation(1,SRC), the vapor pressure for N-phenyl-2-naphthylamine can be estimated to be 8.3X10-6 mm Hg at 25 °C(SRC). According to a suggested classification scheme(2), this vapor pressure value suggests that N-phenyl-2-naphthylamine will exist in both the vapor and particulate phases in the ambient atmosphere. Particulate-phase N-phenyl-2-naphthylamine will probably be removed from air via dry deposition. Vapor-phase N- phenyl-2-naphthylamine is degraded rapidly in an average ambient atmosphere by reaction with photochemically produced hydroxyl radicals at an estimated half-life of about 55 minutes(3,SRC).

Using an initial concn of 100 mg/L N-phenyl-2-naphthylamine, 0 %BOD was observed after a 2 week period in a biodegradation screening test using 30 mg/L sludge(1). N-Phenyl-2-naphthylamine, initial concn of 100 ppm, exhibited a 0-29 % Theoretical BOD in a Japanese MITI test after 14 days of incubation at 25 °C(2). N-phenyl-2-naphthylamine was shown to degrade to beta-naphthylamine in a screening study using activated sludge inoculum at 21 °C(3). In this study, 44.2 and 9.3 %CO2 production was observed in 1 day at initial concns of 2 and 5 ppm, respectively(3). At an initial concn of 8 ppm, N-phenyl-2-naphthylamine was observed to be inhibitory to microorganisms under the same test conditions(3). Furthermore, adsorption to solids was found to occur and, hence, reduce biodegradation(3).

The rate constant for the vapor-phase reaction of N-phenyl-2-naphthylamine with photochemically produced hydroxyl radicals has been estimated to be 4.18X10-10 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 55 min at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Aromatic amines are generally resistant to aqueous environmental hydrolysis(2); therefore, N-phenyl-2-naphthylamine is not expected to hydrolyze in water(SRC). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically produced hydroxyl radicals and peroxy radicals(3); typical half-lives for hydroxyl radical and peroxy radical reaction are on the order of 19-30 sunlight hours(3); however, rate data specific to N-phenyl-2-naphthylamine were not located(SRC). Photolysis may be important(SRC), since N-phenyl-2-naphthylamine absorbs UV radiation > 290 nm(4).

The BCF value for N-phenyl-2-naphthylamine was determined to be 147 with the fathead minnow (Pimephales promelas) in a 32 day exposure flow-through test of Lake Superior water at 25 °C(1).

Aromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(4). In the absence of covalent bonding, one can estimate the adsorption potential based on the Koc value. Based on an experimental log octanol-water partition coefficient of 4.38(2) and a recommended regression-derived equation(1), the Koc value for N-phenyl-2-naphthylamine can be estimated to be 12,500(SRC). According to a suggested classification scheme(3), this Koc value indicates that N-phenyl-2-naphthylamine will be immobile in soil.

The Henry's Law constant for N-phenyl-2-naphthylamine can be estimated to be 1.03X10-7 from a chemical structure estimation method(1). According to a suggested classification scheme(2), this Henry's Law constant indicates that N-phenyl-2-naphthylamine is essentially nonvolatile from water.

Human exposure to 2-naphthylamines in the past was primarily via inhalation and dermal routes(1).

IT SHOULD BE POSSIBLE TO DESIGNATE A TLV FOR PBNA WHICH WOULD ENSURE SAFETY OF WORKERS IF ADHERED TO, PROVIDED ABSORPTION FROM OTHER SOURCES WAS ALSO PREVENTED. ...EXTREME PRECAUTIONS NEEDED IN HANDLING BNA, WHOSE MFR & USE HAVE BEEN PROHIBITED IN SEVERAL JURISDICTIONS, APPEAR UNNECESSARY FOR PBNA.

WHEN SAMPLES OF 1,3-BUTADIENE RUBBER WERE HEATED TO 220 °C, EVOLVED FUMES CONTAINED 0.012 MG/G (12 MG/KG) OF AIR N-PHENYL-2-NAPHTHYLAMINE... STUDIES CONDUCTED IN SEVERAL SYNTHETIC RUBBER PLANTS IN USSR DETECTED.../THIS COMPD/ IN AIR...

IN US...NIOSH...RECOMMENDED...EMERGENCY TEMPORARY STD TO REGULATE...EXPOSURE TO N-PHENYL-2-NAPHTHYLAMINE BE ISSUED, IN LIGHT OF...FINDINGS INDICATING...IT IS METABOLIZED IN HUMAN BODY TO FORM CARCINOGEN, 2-NAPHTHYLAMINE... NIOSH EST THAT 15,000 WORKERS IN US...POTENTIALLY EXPOSED...DURING ITS MFR & USE (NIOSH, 1976).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 368 workers are potentially exposed to N-phenyl-2-naphthylamine in the USA(1).

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Corrosive

UN Hazard Class: 9; UN Pack Group: III