1-나프틸아민

log Kow = 2.25

2.25

1.12 at 77 °F (USCG, 1999) - Denser than water; will sink

1.114 g/cu cm

1.12 g/cm³

1.12

1.0228 @ 20°C

1.12

Needles from ethanol (aq) or ether

YELLOW RHOMBIC NEEDLES

White crystals becoming red on exposure to air

Needles, becoming red on exposure to air, or a reddish, crystal mass

Colorless crystals; darkens in air to a reddish-purple color

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

Crystal powder; becomes bluish on exposure to air and light. Sol in about 27 parts water; sol in alcohol and ether /Hydrochloride/

Sol in chloroform

Freely sol in alcohol and ether

In water, 1.7X10+3 mg/L @ 20 °C

Solubility in water: none

315 °F (NTP, 1992)

157 °C

157 °C, 315 °F, (closed cup)

157 °C c.c.

315 °F

315 °F

574 °F at 760 mmHg (NTP, 1992)

300.7 °C

300.8 °C

573 °F

300.7 °C @760 [mm Hg]

573 °F

122 °F (NTP, 1992)

49.2 °C

50.0 °C

122 °F

49.2 °C

122 °F

4.93 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

4.93 (Air= 1)

Relative vapor density (air = 1): 4.93

4.93

1 mmHg at 219.7 °F ; 5 mmHg at 279.9 °F (NTP, 1992)

0.00418 [mmHg]

4.18X10-3 mm Hg @ 25 °C /Extrapolated/

Vapor pressure, Pa at 20 °C: 0.53

1 mmHg at 220 °F

(220 °F): 1 mmHg

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]；H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Danger

Chemical: 1-Naphthalenamine

Hazard Traits - Carcinogenicity；Authoritative List - Prop 65；Report - regardless of intended function of ingredient in the product

Status: Cease Manufacture Update: 04-10-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1659；Status: Active Update: 25-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/20391

1-Naphthalenamine: HSNO Approval: HSR001523 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Toxic nitrogen oxides are produced in a fire. (USCG, 1999)

· Combustible material: may burn but does not ignite readily.；· When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.；· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.；· Corrosives in contact with metals may evolve flammable hydrogen gas.；· Containers may explode when heated.；· Runoff may pollute waterways.；· Substance may be transported in a molten form.

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

Inhalation may cause cyanosis (blue color in lips and under finger nails). Contact with liquid causes local irritation of eyes. Neither ingestion nor contact with skin produces any recognized immediate effects. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.；· Methyl bromoacetate (UN2643) is an eye irritant/lachrymator (causes flow of tears).；· Contact with molten substance may cause severe burns to skin and eyes.；· Avoid any skin contact.；· Fire may produce irritating, corrosive and/or toxic gases.；· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.

2077 153

2077 153

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).

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:；SMALL FIRE: Dry chemical, CO2 or water spray.；LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.；FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

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.；· Keep unauthorized personnel away.；· Stay upwind, uphill and/or upstream.；· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.；· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.；· Stop leak if you can do it without risk.；· Prevent entry into waterways, sewers, basements or confined areas.；· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.；· DO NOT GET WATER INSIDE CONTAINERS.

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.；INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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.；OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

General First Aid:；· Call 911 or emergency medical service.；· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.；· Move victim to fresh air if it can be done safely.；· Administer oxygen if breathing is difficult.；· If victim is not breathing:；-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.；-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).；-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.；· Remove and isolate contaminated clothing and shoes.；· For minor skin contact, avoid spreading material on unaffected skin.；· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.；· For severe burns, immediate medical attention is required.；· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.；· Keep victim calm and warm.；· Keep victim under observation.；· For further assistance, contact your local Poison Control Center.；· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.；Specific First Aid:；· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.

(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.

· Wear positive pressure self-contained breathing apparatus (SCBA).；· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.；· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

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.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:；ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

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).

Chemical: 1-Naphthalenamine

Hazard Traits - Carcinogenicity；Authoritative List - Prop 65；Report - regardless of intended function of ingredient in the product

Status: Cease Manufacture Update: 04-10-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1659；Status: Active Update: 25-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/20391

1-Naphthalenamine: HSNO Approval: HSR001523 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

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).

... n-(1-naphthyl)-hydroxylamine was present in smaller concentration than was n-(2-naphthyl)-hydroxylamine after administration ... to the dog, and ... no 1-nitrosonaphthalene was formed. ... significant amounts of n-(1-naphthyl)-hydroxylamine and 1-nitrosonaphthalene were excreted only when a high dose of 1-naphthylamine was administered to dogs. This contrasts with behavior of 2-naphthylamine. Diphosphate ester of 1-amino-2-naphthol has not been identified in urine of dogs.

Doses of 250 mg 1-naphthylamine given to 4 patients resulted in excretion of N-hydroxy-1-naphthylacetamide either in free state or as a glucuronic acid conjugate.

Alpha-naphthylamine is metabolized, by rats and other mammals, into 1-amino-2-naphthol and 1-amino-4-naphthol which are excreted in urine as glucuronide and sulfate conjugates, together with n-glucuronide, the n-sulfate, and somewhat unexpectedly, the n-glucoside of 1-naphthylamine.

1-Naphthylamine was metabolized to 2-amino-1-naphthyl monophosphate ester and para-hydroxy conjugates. 1-Naphthylamine and 2-naphthylamine are hydroxylated, but 2-naphthylamine was oxidized to 2-nitrosonaphthalene, showing that this further n-oxidative step does not appear to occur with the more stable n-1-naphthylhydroxylamine. Thus the aromatic amines in the urine were metabolized but the active carcinogens of these aromatic amines are still to be found.

For more Metabolism/Metabolites (Complete) data for 1-NAPHTHYLAMINE (11 total), please visit the HSDB record page.

1-Naphthylamine is absorbed through the skin and by inhalation.

1-Naphthylamine is partly oxidized to 1-amino-2-naphthol, which is eliminated in the urine but mainly as a glucuronide. 0.2% from 5.0 mg dose was shown to be excreted in the urine. A part of 1-naphthylamine is excreted unchanged.

/In rhesus monkeys/ the N-hydroxy-N-glucuronide of 2-naphthylamine was ... excreted at a rate ... 6.8 times that of the 1-naphthylamine isomer. Furthermore, the unoxidized 1-naphthylamine is excreted at a level 10 times that of 2-naphthylamine, indicating that it may be a poor substrate for the oxidative metabolic enzymes of the monkey.

After oral administration of 71.6 mg/kg bw to female beagle dogs, a blood concentration of about 0.015 mg/mL after 60-80 min could be detected. ...Within 8 hr, 25 mg unchanged 1-naphthylamine, and 0.5 mg of N-oxidation products were excreted in the urine.

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.