P-Phenylenediamine

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

Use water spray, powder.

Fresh air, rest. Half-upright position. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention .

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

Rinse mouth. Give a slurry of activated charcoal in water to drink. 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.

(General first aid procedures)

Keep well closed and protected from light.

IN GENERAL MATERIALS ... TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS ... SHOULD BE STORED IN COOL ... VENTILATED PLACE, OUT OF ... SUN, AWAY FROM ... FIRE HAZARD ... /AND/ BE PERIODICALLY INSPECTED & MONITORED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED.

The following wastewater treatment technologies have been investigated for p-phenylenediamine: biological treatment.

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.

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 absorb in saw-dust or other combustible absorbents.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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.

For more Preventive Measures (Complete) data for 1,4-BENZENEDIAMINE (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.30(2), and a recommended regression-derived equation(3), indicates that 1,4-benzenediamine is expected to have high mobility in soil(SRC); however it may form covalent bonds to humic material which would limit movement through soil(4). Volatilization of 1,4-benzenediamine is not expected from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.7X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Volatilization of 1,4-benzenediamine from dry soil surfaces is not expected(SRC) based on an extrapolated vapor pressure of 0.005 mm Hg(SRC) at 25 °C(6). Biodegradation is expected to occur slowly in soils based on standard biodegradability tests conducted with activated sludge(7-11).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.30(2), and a recommended regression-derived equation(3), indicates that 1,4-benzenediamine is not expected to adsorb to suspended solids and sediment in water(SRC). 1,4-benzenediamine is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 6.7X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Degradation of 1,4-benzenediamine by photochemically produced peroxy radicals will be an important environmental fate process in surface waters(5,SRC). The half-life of this reaction is estimated as 1 day for a solution concentration of 1X10-9 M of peroxy radicals and an estimated rate constant of 1X10+4 L/mol-s(5). According to a classification scheme(6), an estimated BCF value of 0.3(3,SRC), from a measured log Kow of -0.3(2,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Biodegradation in aquatic environments is not expected to be an important environmental fate process(SRC). A 0% theoretical oxygen demand was observed for 1,4-benzenediamine in a Warburg apparatus during a 5 day incubation period(7). A measured pKb value of 6.2 indicates that the protonated form of 1,4-benzenediamine will exist at environmentally significant pH and this may affect the environmental fate of this compound in aquatic environments(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-benzenediamine, which has an extrapolated vapor pressure of 0.005 mm Hg at 25 °C(2,SRC), is expected to exist primarily as a vapor in the ambient atmosphere. Vapor-phase 1,4-benzenediamine 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 about 2 hours(3,SRC).

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

Cough. Dizziness. Headache. Laboured breathing. See Ingestion.

MAY BE ABSORBED! Redness.

Redness. Pain. Swelling of the eyelids. Blurred vision. Loss of vision.

Abdominal pain. Blue lips, fingernails and skin. Convulsions. Drowsiness. Laboured breathing. Shortness of breath. Vomiting. Weakness.

irritation pharynx, larynx; bronchial asthma; sensitization dermatitis

/Annual/ physical examinations of exposed personnel, including blood counts and studies of liver function. Those persons with allergy and with diseases of skin, liver, blood, and lungs should avoid exposure. Sensitized persons should avoid re-exposure.

Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.3(2) and a recommended regression-derived equation(3), indicates that 1,4-benzenediamine is expected to have high mobility in soil(SRC); however it may form covalent bonds to humic material which would limit movement through soil(4).

1,4-Benzenediamine was examined for mutagenic activity in Salmonella typhimurium tester strains TA1535, TA1537, TA1538, TA100, and in Saccharomyces cerevisiae strain D3 with and without metabolic activation provided by phenobarbitol-induced rat liver S9 fraction. The test article was not mutagenic at concentrations ranging from 1 to 1000 ug/ml in the Salmonella strains (plate incorporation assay), or at 0.05% in the Saccharomyces D3 strain (mitotic recombination assay), in the presence or absence of metabolic activation. In preliminary experiments, 1,4-benzenediamine was toxic to Saccharomyces D3 cells at a concentration of 0.1%, however, toxicity to Salmonella was not reported.

para-Phenylenediamine (CAS # 106-50-3) was evaluated as cause for methemoglobinuria in sets of 2 each beagle dogs fed single gavage doses of 1.0, 3.0, and 10.0 mg/kg bodyweight. All dogs exhibited lacrimation, while 10.0 mg/kg dosed dogs showed red and swollen eyes persisting in one dog at 24-hour post-gavage observation. Slight redness was also noted in the eyes of 3.0 mg/kg dogs, but all such signs were resolved by 24 hours after treatment. Methemoglobinemia was not induced at levels producing pharmacotoxic effects in beagle dogs.

1,4-Phenylenediamine (CAS # 106-50-3) was evaluated for neurotoxic effects in groups of Crl:CDBR rats (12/sex/group) administered single gavage doses in sterile water of 0, 20, 40, and 80 mg/kg bodyweight. Neurotoxicity was assessed by functional operational battery and motor activity tests performed prior to treatment (baseline assessment) and at approximately 1.5 hours (time of maximal clinical signs), 24 hours, and 4 days post-gavage. Both females of all dose levels and males of 40 and 80 mg/kg dosage groups exhibited signs of a systemic toxicity with significantly reduced weight gain. These deviations from control were echoed in significantly reduced food consumption in all except 20 mg/kg females after Day 1 and in males of 80 mg/kg doses. No other clinical signs of toxicity were significantly dose-related. Upon the functional observation batteries through post-treatment Day 4, females only demonstrated significant dose-related malaise, postural changes, palpebral closure, and diminished arousal. Males showed similar functional aberrations which were not statistically significant relative to controls. Treatment was not significantly reflected in fore- or hind-limb grip strength or foot splay. Measurements of decreased motor activity in treated rats were significantly dose-related, except after Day 1 in both 20 mg/kg groups.

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. p-Phenylenediamine is included on this list.

Manufacturers and processors of para-phenylenedimine are required to conduct health efffects, chemical fate and environmental effects testing under TSCA section 4.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 1,4-Benzenediamine is included on this list.

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 5000 lb or 2270 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).

CIR ingredient: p-Phenylenediamine

p-Phenylenediamine is primarily used as a dye intermediate and as a dye (e.g., hair dyes and dyes used for dyeing furs), as well as a photographic developing agent and a chemical intermediate. p-Phenylenediamine is also used as a vulcanization accelerator and as an antioxidant in rubber compounds.

Used to dye hair and fur; also used to develop photographs and to synthesize other organic compounds; [ACGIH] Occupational asthma reported in fur dyers; [Malo] Allergic contact dermatitis in hairdressers, mechanics, printers, and textile workers; [Marks] Used to dye leather; [PMID 21938525]

Leather Tanning and Processing [Category: Industry]

Dyeing furs; also in photochemical measurements, accelerating vulcanization; manuf azo dyes.

CHEM INT FOR DYES (EG, DIRECT BLACK 19, 78 & 80); OXIDN BASE 10 & DEVELOPER 13 FOR DYES; CHEM INT FOR ARAMID FIBERS (USED IN TIRE CORD); CHEM INT FOR N,N'-DISUBSTITUTED-P-PHENYLENEDIAMINES; COMPONENT OF GASOLINE ANTIOXIDANTS.

(1978) 1.50X10+6 G (PRINCPL CUSTMS DISTS)

(1982) 9.99X10+4 G (PRINCPL CUSTMS DISTS)

2023: 10,000,000 - <50,000,000 lb

(1978) PROBABLY GREATER THAN 4.54X10+6 G

(1982) PROBABLY GREATER THAN 4.54X10+6 G

REDUCTION OF 1-AMINO-4-NITROBENZENE WITH IRON AND HYDROCHLORIC ACID.

Prepn: A. Rinne, T. Zincke, Ber. 7, 869 (1874); Ger. pat. 202,170 (1907 to BASF), C. A. 3, 382 (1909); A.J. Quick, J. Am. Chem. Soc. 42, 1033 (1920); J.F. Norris, E.O. Cummings, Ind. & Eng. Chem. 17, 305 (1925). See also: Beilstein XIII, 61 (1930).

ONE TECHNICAL GRADE OF PARA-PHENYLENEDIAMINE AVAILABLE IN THE USA HAS THE FOLLOWING SPECIFICATIONS: PURITY, 99.2% MINIMUM; MOISTURE CONTENT, 0.1% MAXIMUM; ORTHO-PHENYLENEDIAMINE (1,2-DIAMINOBENZENE) CONTENT, 0.1% MAXIMUM; AND IRON CONTENT, 50 MG/KG MAXIMUM.

Cosmetics product ingredient: p-Phenylenediamine

Information on 206 consumer products that contain p-Phenylenediamine in the following categories is provided:

Organic Fiber Manufacturing

1,4-Benzenediamine: ACTIVE

ALL COLORING AGENTS CONTAINING PARA-PHENYLENEDIAMINE OR ONE OF ITS HOMOLOGS MUST INCL STATEMENT ON PACKAGE RELATIVE TO SENSITIZING PROPERTIES ... & ITS ABILITY TO CAUSE BLINDNESS IF IT CONTACTS EYES. LAW ... REQUIRES THAT PATCH TEST BE CONDUCTED 24 HR BEFORE ... DYE IS APPLIED /TO HAIR/.

Formerly: as an eyelash dye ... sold under proprietary name Lash Lure.