p-Phenylenediamine
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p-Phenylenediamine
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CAS No:
106-50-3
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Formula:
C6H8N2
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Chemical Name:
p-Phenylenediamine
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Synonyms:
1,4-Benzenediamine;p-Phenylenediamine;C.I. 76060;BASF Ursol D;Benzofur D;C.I. Developer 13;C.I. Oxidation Base 10;Developer PF;p-Diaminobenzene;Durafur Black R;Fouramine D;Fourrine D;Fourrine 1;Fur Black 41867;Fur Brown 41866;Furro D;Fur Yellow;Futramine D;Nako H;Orsin;Pelagol D;Pelagol DR;Pelagol Grey D;Peltol D;Renal PF;Tertral D;Ursol D;Zoba Black D;4-Aminoaniline;p-Aminoaniline;p-Benzenediamine;1,4-Diaminobenzene;1,4-Phenylenediamine;1,4-Diaminobenzol;PPD;Black for Fur D;Rodol DJ;NSC 4777;(4-Aminophenyl)amine;Rodol D;4-Phenylenediamine;Paramine;PDA;pPDA;56481-76-6;82785-55-5
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CAS No:
Description
It is white to purple red crystal. It will turn purple red or dark brown when exposure to the air. It can be dissolved in water, alcohol, ether, chloroform and benzene. p-Phenylenediamines are white to slightly red crystalline solids. They have been described as gray “light brown” which may result from exposure to air.ChEBI: A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.P-phenylenediamine is one of the simplest aromatic diamine with the pure p
P-phenylenediamine appears as a white to purple crystalline solid (melting point 234 F) that turns purple to black in air. Flash point 309 F. Toxic by skin absorption, inhalation or ingestion. Used for production of aramid fiber, antioxidants, as a laboratory reagent, in photographic developing, and as a dye for hair and furs.|Liquid; PelletsLargeCrystals|WHITE-TO-SLIGHTLY-RED CRYSTALS. TURNS DARK ON EXPOSURE TO AIR.|White to slightly red, crystalline solid.
P-phenylenediamine appears as a white to purple crystalline solid (melting point 234 F) that turns purple to black in air. Flash point 309 F. Toxic by skin absorption, inhalation or ingestion. Used for production of aramid fiber, antioxidants, as a laboratory reagent, in photographic developing, and as a dye for hair and furs.|1,4-phenylenediamine is a phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus. It has a role as a hapten, a dye, a reagent and an allergen.|p-Phenylenediamine is primarily used as a dye intermediate and as a dye. Acute (short-term) exposure to high levels of p-phenylenediamine may cause severe dermatitis, eye irritation and tearing, asthma, gastritis, renal failure, vertigo, tremors, convulsions, and coma in humans. Eczematoid contact dermatitis may result from chronic (long-term) exposure in humans. In rats and mice chronically exposed to p- phenylenediamine in their diet, depressed body weights, but no other clinical signs of toxicity, were observed in several studies. No information is available on the reproductive, developmental, or carcinogenic effects of p-phenylenediamine in humans. EPA has not classified p-phenylenediamine with respect to carcinogenicity.|P-phenylenediamine is a Standardized Chemical Allergen. The physiologic effect of p-phenylenediamine is by means of Increased Histamine Release, and Cell-mediated Immunity.
p-Phenylenediamine Basic Attributes
108.14
108.14
742029
203-404-7
U770QIT64J
0805
4777
1673
DTXSID9021138
WHITE TO SLIGHTLY RED CRYSTALS|WHITE PLATES FROM BENZENE, ETHER
29215119
Characteristics
52
-0.25
White, gray, or purple to brown Powder or Flakes
1.1 g/cm3
145-147 °C
267 °C
156 °C
1.6339 (estimate)
H2O: 47 g/L (25 ºC);soluble in alcohol, chloroform, ether and hot benzene.
2-8°C
1.08 mm Hg ( 100 °C)
3.7 (vs air)
Oral-rat LD50:80 mg/kg;Oral-Mouse LDL0: 100 mg/kg
Open flame, high heat, oxidant is combustible; burning releases toxic nitrogen oxide fumes
vol% in air: 1.5
The pKa value of the conjugate acid is 6.2
Oxidizes on exposure to air. The finely powdered base if suspended in air poses a significant dust explosion hazard. Soluble in water. Even as a solid will spot downwind areas purple/black (Roger Patrick, DuPont Engineer).
Amines, Aromatic
P-PHENYLENEDIAMINE is the stongest of the weak aromatic bases. It neutralizes acids in weak exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Reacts readily with oxidizing agents (NTP, 1992).
400 °C
6.89 eV
Combustible Solid
Dust explosion possible if in powder or granular form, mixed with air.
Safety Information
III
6.1
UN 1673 6.1/PG 3
3
23/24/25-36-43-50/53-63-36/37/38-45-40-48/22-67-52/53
28-36/37-45-60-61-28A-24/25-23-53-26
SS8050000
T,N,T+,Xn
Treasury is ventilated at low temperature and dry; stored separately from oxidants and food additives
Explosive when mixed with air
Stable, but oxidizes when exposed to air. Incompatible with oxidizing agents. Store under inert atmosphere.
P260-P273-P280-P301 + P310-P305 + P351 + P338-P311
H301 + H311 + H331-H317-H319-H370-H410
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.
Contact with strong oxidizers may cause fires and explosions.|Strong oxidizers.
TSCA CHIPs present a preliminary assessment of 1,4-Benzenediamine's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404.|Waters MD et al; The Genetic Toxicology of Gene-Tox Non-Carcinogens; Mutat Res 205(1-4): 139-82 (1988).|USEPA; PHENYLENEDIAMINES; RESPONSE TO INTERAGENCY TESTING COMMITTEE; FED REGIST 47(5) 973 (1982). EVIDENCE IS GIVEN SUPPORTING TESTING OF THE CLASS OF COMPOUNDS PHENYLENEDIAMINES FOR THEIR TOXIC EFFECTS ON HUMAN HEALTH AND THE ENVIRONMENT. THE RESULTS OF TOXICITY TESTING OF 22 COMPOUNDS ARE TABULATED AS ARE THE EFFECTS FOR WHICH TESTING IS BEING CONSIDERED FOR 13 COMPOUNDS, AND THE USES OR POTENTIAL USES OF 47 PHENYLENEDIAMINES.|Fukunaga T, et al; Contact Dermat 35 (3): 185-6 (1996). Contact anaphylaxis due to para-phenylenediamine.|Yagi H et al; Hum Exp Toxicol 15 (8): 617-18 (1996). Paraphenylenediamine induced optic atrophy following hair dye poisoning.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. 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. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. Risk of fire and explosion on contact with strong oxidizing agents.
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P333+P313, P337+P313, P361, P363, P391, P403+P233, P405, and P501|H301+H311+H331 (14.44%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P311, P312, P321, P322, P330, P333+P313, P337+P313, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 568 companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P280, P285, P301+P310, P302+P352, P304+P340, P304+P341, P305+P351+P338, P307+P311, P311, P314, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P272, P280, P285, P301+P310, P302+P352, P304+P312, P304+P340, P304+P341, P305+P351+P338, P307+P311, P310, P312, P314, P321, P330, P332+P313, P333+P313, P342+P311, P362, P363, P405, and P501|P260, P261, P264, P270, P271, P272, P273, P280, P285, P301+P310, P302+P352, P304+P340, P304+P341, P305+P351+P338, P307+P311, P311, P314, P321, P330, P333+P313, P337+P313, P342+P311, P363, P391, P403+P233, P405, and P501
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an 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, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck 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, 2016)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in 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, 2016)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. (NIOSH, 2016)|Employees should be provided with and required to use impervious clothing, gloves, face shields (eight-inch minimum), and other protective clothing necessary to prevent skin contact ... .|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Recommendations for respirator selection. Max concn for use: 2.5 mg/cu m. Respirator Class(es): Any supplied-air respirator operated in a continuous flow mode. Eye protection needed.|For more Personal Protective Equipment (PPE) (Complete) data for 1,4-BENZENEDIAMINE (8 total), please visit the HSDB record page.|(See protection codes)
COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME.
Minimum explosive concentration: 0.025 g/l|The finely powdered base is a significant dust explosion hazard.|Explosive limits , vol% in air: 1.5-?
WATER, CARBON DIOXIDE, DRY CHEM ... .
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.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Phenylenediamines/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: 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. 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. /Phenylenediamines/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Phenylenediamines/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Phenylenediamines/|For more DOT Emergency Guidelines (Complete) data for 1,4-BENZENEDIAMINE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
... Is a skin and respiratory system sensitizer ...|Eye irritation.
Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 0.1 mg/cu m. Skin Designation.
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 0.1 mg/cu m, skin.
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.
Separated from strong oxidants, strong acids, acid anhydrides and food and feedstuffs. Keep in the dark. Well closed.
A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
The substance is irritating to the eyes. Inhalation of dust may cause asthmatic reactions. Ingestion could cause swelling of mouth and throat. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure could cause death.
Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma. The substance may have effects on the kidneys. This may result in kidney impairment.
NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
STRICT HYGIENE!
Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety spectacles, face shield or eye protection in combination with breathing protection.
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.
p-Phenylenediamine is primarily used as a dye intermediate and as a dye. Acute (short-term) exposure to high levels of p-phenylenediamine may cause severe dermatitis, eye irritation and tearing, asthma, gastritis, renal failure, vertigo, tremors, convulsions, and coma in humans. Eczematoid contact dermatitis may result from chronic (long-term) exposure in humans. In rats and mice chronically exposed to p- phenylenediamine in their diet, depressed body weights, but no other clinical signs of toxicity, were observed in several studies. No information is available on the reproductive, developmental, or carcinogenic effects of p-phenylenediamine in humans. EPA has not classified p-phenylenediamine with respect to carcinogenicity.
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).
Toxicity
highly
LDLo Rat oral 100 mg/kg|LDLo Rat ip 50 mg/kg|LDLo Rat sc 170 mg/kg|LD50 Dog iv 17 mg/kg|For more Non-Human Toxicity Values (Complete) data for 1,4-BENZENEDIAMINE (8 total), please visit the HSDB record page.
P-PHENYLENEDIAMINE OR ITS INTERMEDIARY OXIDN PRODUCTS APPEAR NOT TO BE PARTICULARLY CAUSTIC OR INJURIOUS, EXCEPT WHEN THERE IS HYPERSENSITIVITY TO THEM. APPARENTLY HYPERSENSITIVITY IS SPONTANEOUSLY PRESENT IN SOME INDIVIDUALS & IS READILY DEVELOPED IN MANY OTHERS.
1,4-Benzenediamine is not known to occur as a natural product(1).
1,4-Benzenediamine may be released in emissions and wastewater during its production and use in the manufacture of diisocyanates for polyurethanes (largest volume use) such as Kevlar(1) and as an intermediate in manufacture of antioxidants and accelerators for rubber. It is used in manufacture of azo dyes and as a component of dye mixtures for hair and fur(2). Its derivatives are also used as developers for black-and-white and color photographs(3).
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 rate constant for the vapor-phase reaction of 1,4-benzenediamine with photochemically-produced hydroxyl radicals has been estimated as 2.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). A measured pKb value of 6.2 indicates that 1,4-benzenediamine is expected to exist in the protonated form at environmentally significant pH values(2,SRC). Abiotic degradation of 1,4-benzenediamine by photochemically produced peroxy radicals is an important environmental fate process in surface waters(3,SRC). The rate constant for this reaction has been estimated as 1X10+4 L/mol-s at 25 °C(3). This corresponds to a half-life of about 1 day for a solution concentration of 1X10-9 M of peroxy radicals(3). 1,4-Benzenediamine adsorbs UV light above 290 nm (UV maximum 308 nm(4)) and therefore may undergo direct photolysis in the environment by sunlight. 53.7% Photooxidation of a 1,4-diaminobenzene dihydrochloride sample (initial concentration unspecified) on a silica gel substrate was observed when irradiated with light above 290 nm for 17 hours(5).
An estimated BCF value of 0.3 was calculated for 1,4-benzenediamine(SRC), using a measured log Kow of -0.3(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC). An experimental BCF value of 450 was measured for algae exposed to 1,4-diaminobenzene dihydrochloride for 24 hours(4). An experimental BCF value of 6 was measured for fish (golden ide) exposed to 1,4-diaminobenzene dihydrochloride for 3 days(4).
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).
The Henry's Law constant for 1,4-benzenediamine is estimated as 6.7X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 1,4-benzenediamine will be essentially nonvolatile from water surfaces(2,SRC). 1,4-Benzenediamine is not expected to volatilize from dry soil surfaces based on an extrapolated vapor pressure of 0.005 mm Hg at 25 °C(3).
Occupational exposure to 1,4-benzenediamine may occur through inhalation and dermal contact with this compound at workplaces where 1,4-benzenediamine is produced or used(1,SRC). NIOSH (NOES Survey 1981-83) has statistically estimated that 104 workers are potentially exposed to 1,4-benzenediamine in the USA(2). The general population may be exposed to this compound by dermal contact, primarily through the use of hair dyes containing 1,4-benzenediamine(1,3).
Drug Information
Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)
PARAPHENYLENEDIAMINE HYDROCHLORIDE WAS APPLIED TO THE SKIN OF DOGS IN GELS AND FLUIDS, AS THEY ARE USED IN HAIR DYEING; ABSORPTION WAS DETERMINED BY COMPARING BLOOD CONCENTRATIONS WITH THAT OBTAINED AFTER IV INJECTION OF THE DIAMINE OVER A COMPARABLE PERIOD OF TIME. IT WAS CALCULATED THAT 16 MG WERE ABSORBED WHEN 50 ML OF A LAURYL SULFATE-BASED GEL CONTAINING 1.5 G PARAPHENYLENEDIAMINE WAS APPLIED FOR 3 HOURS AND FREE ACCESS TO AIR WAS ALLOWED (THE MAXIMAL BLOOD CONCENTRATION WAS 0.15 UG/ML). THIS AMOUNT ROSE TO 110 MG IF THE TREATED AREA WAS IMMEDIATELY COVERED WITH ALUMINUM FOIL (THE MAXIMAL BLOOD CONCENTRATION WAS 0.5 UG/ML). /P-PHENYLENEDIAMINE HYDROCHLORIDE/|THE DISTRIBUTION KINETICS OF THE (3)H-LABELED P-PHENYLENEDIAMINE HYDROCHLORIDE WAS STUDIED WHEN ADMINISTERED IV AND WHEN APPLIED PERCUTANEOUSLY IN MICE AND RABBITS. IN RABBITS, IV ADMINISTRATION LED TO A BIPHASIC BLOOD CLEARANCE WITH T/2 VALUES OF 24 MINUTES AND 43.5 HOURS AND QUICK PERCUTANEOUS ABSORPTION. THE TISSUE DISTRIBUTION PATTERN INVESTIGATED AFTER IV AND PERCUTANEOUS ADMINISTRATION IN 16 DIFFERENT TISSUES AND ALSO IN BLOOD DID NOT DEMONSTRATE ANY TARGET ORGAN FOR SELECTIVE LOCALIZATION OF THE DYE. NO GREATER THAN 0.06% OF THE IV ADMINISTERED RADIOACTIVITY WAS MEASURED PER 10 G OF ANY TISSUE AT THE 12TH DAY. /P-PHENYENEDIAMINE HYDROCHLORIDE/|After the /dog abdominal/ skin was washed, m-phenylenediamine concentration in the blood was observed to decline more rapidly than was the case with p-phenylenediamine and 2,5-diaminotoluene.|A homologous series of hair dyes was selected for percutaneous absorption studies with excised human skin. The permeability constants obtained for the dyes were compared with octanol/water and skin membrane/water partition coefficients. The compounds examined were: p-phenylenediamine, o-phenylenediamine, 2-nitro-p-phenylenediamine, 2-amino-4-nitrophenol, 4-chloro-m-phenylenediamine, and 4-amino-2-nitrophenol. Skin absorption of the dyes was observed when they were applied in an aqueous solution. With one exception, the octanol/water partition coefficients were in the same rank order as the permeability constants. The determination of the partitioning of the hair dyes between water and either stratum corneum or epidermis was more complex. Preliminary stratum corneum/water partition studies resulted in values that were in the reverse order of skin permeation. When binding of the compounds to components of the membrane was saturated, the partition values more closely duplicated the rank order of permeability of the dyes. Prediction of percutaneous absorption of substances based on their partition coefficients may be confounded if these compounds are capable of binding to skin.
P-PHENYLENEDIAMINE YIELDS P-QUINONE PROBABLY IN MAN, MONKEY, PIG, HORSE, SHEEP, GOAT, CAT, RABBIT, GUINEA PIG, RAT, MOUSE, & HEN. /FROM TABLE/|P-PHENYLENEDIAMINE YIELDS P-QUINONE PROBABLY IN HORSERADISH ... WITH CERULOPLASMIN & LACCASE. /FROM TABLE/|P-PHENYLENEDIAMINE YIELDS P-QUINONE PROBABLY IN PERIPLANETA, ... IN CITRUS, ... IN TEA. /FROM TABLE/|N,N'-DIACETYL-PARA-PHENYLENEDIAMINE WAS IDENTIFIED AS A URINARY METABOLITE OF PARA-PHENYLENEDIAMINE IN DOGS.
FROM STUDIES OF THE INTRACUTANEOUS SENSITIZATION OF GUINEA-PIGS USING PARA-PHENYLENEDIAMINE, HYDROQUINONE, QUINHYDRONE AND BENZOQUINONE, IT HAS BEEN SUGGESTED THAT BENZOQUINONE FORMATION PLAYS AN IMPORTANT ROLE IN THE ALLERGIC ACTION OF PARA-PHENYLENEDIAMINE.
ORTHO-PHENYLENEDIAMINE (1,2-DIAMINOBENZENE) CONTENT, 0.1% MAXIMUM; AND IRON CONTENT, 50 MG/KG MAXIMUM.
Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation pharynx, larynx; bronchial asthma; sensitization dermatitis Target Organs: respiratory system, skin (NIOSH, 2016)
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)|(See procedures)
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.
Flush eyes with water. Wash contaminated areas of body with soap and water.|For immediate first aid: Ensure that adequate decontamination has been carried out. If victim is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Organic bases, amines, and related compounds/|For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Monitor for shock and treat if necessary ... Anticipate seizures and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... Cover skin burns with sterile dressings after decontamination ... . /Organic bases, amines, and related compounds/
EXPOSED WORKMEN ... SUFFER FROM ALLERGIC ASTHMA & FREQUENTLY SHOW INFLAMMATORY REACTIONS OF THE LARYNX & PHARYNX, EVIDENTLY CAUSED BY DIRECT IRRITATION. ... VERY SMALL QUANTITIES ... COULD CAUSE ASTHMA IN PERSONS AFTER 3 MO TO 10 YR OF EXPOSURE. THESE EPISODES WERE CVHARACTERIZED BY THE IMMEDIATE ONSET OF SYMPTOMS WHICH PROMPTLY DISAPPEARED UPON DISCONTINUATION OF THE EXPOSURE.|Potential symptoms of overexposure are irritation of pharynx and larynx; bronchial asthma; sensitization dermatitis.|/HYPERSENSITIVITY/ REACTIONS WHICH HAVE FOLLOWED APPLICATION OF DYES CONTAINING P-PHENYLENEDIAMINE TO HAIR ... CHARACTERISTICALLY HAVE CONSISTED OF DERMATITIS OF HEAD, FOREHEAD, & NECK, ASSOC WITH EDEMA OF LIDS & CONJUNCTIVA, WITH TEARING & EXOPHTHALMOS.|Produces severe local reactions and systemic effects from percutaneous absorption and from ingestion. Local actions incl severe dermatitis and urticaria; in the eye, chemosis, lacrimation, exophthalmos, ophthalmia, and even permanent blindness. Systemic actions incl asthma, gastritis (regardless of portal of entry), rise in blood pressure, transudation into serous cavities, vertigo, tremors, convulsions and coma. ... The ortho isomer (diolene) is less toxic than the para (orsin).|For more Human Toxicity Excerpts (Complete) data for 1,4-BENZENEDIAMINE (16 total), please visit the HSDB record page.
1,4-benzenediamine
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
irritation pharynx, larynx; bronchial asthma; sensitization dermatitis
Cough. Dizziness. Headache. Laboured breathing. See Ingestion.
MAY BE ABSORBED! Redness.
Redness. Pain. Swelling of the eyelids. Blurred vision. Loss of vision.
respiratory system, skin
p-Phenylenediamine Use and Manufacturing
It is obtained by reducing p-nitroaniline with iron powder in acidic medium. Put the iron powder into hydrochloric acid, heat to 90°C, and add p-nitroaniline with stirring. After the addition, the reaction was performed at 95-100°C for 0.5h, and then concentrated hydrochloric acid was added dropwise to complete the reduction reaction. After cooling, neutralize to pH 7-8 with saturated sodium carbonate solution, filter while hot, and wash the filter cake with hot water. The filtrate and the washing liquid are combined, concentrated under reduced pressure, cooled and crystallized or distilled under reduced pressure to obtain p-phenylenediamine in a yield of 95%.
It is an important dye intermediate, mainly used in the manufacture of azo dyes and sulfur dyes. It can also be used in the production of fur black D and rubber antioxidant DNP, etc.; used as a fluorescent indicator, analytical reagent and fur dyeing agent, and also used in dyes Synthesis; mainly used in the production of azo dyes and sulfur dyes, and also used in the production of fur black D, fur blue black DB, fur brown NZ and rubber antioxidants DNP, 288, DOP, DBP. P-phenylenediamine is also used as a raw material for cosmetic hair dye Ursi D, gasoline polymerization inhibitor and developer. Mainly used for fur dyeing, and can also be dyed together with other dyes, often used as mordant
Adhesives and sealant chemicals
Non-TSCA use
(1978) PROBABLY GREATER THAN 4.54X10+6 G|(1982) PROBABLY GREATER THAN 4.54X10+6 G
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.
All other basic organic chemical 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.
ELECTROCHEMICAL DETECTION AND HPLC ANALYSIS OF NONVOLATILE POLLUTANTS. /NONVOLATILE POLLUTANTS/|ION-EXCHANGE THIN LAYER CHROMATOGRAPHY ANALYSIS OF HAIR DYES. /HAIR DYES/|AROMATIC AMINES (INCLUDING 1,4-BENZENEDIAMINE) ARE DETECTED IN WATER BY ELECTROCHEMICAL DETECTION.|SEPARATION AND DETERMINATION OF PHENYLENEDIAMINE DERIVATIVES IN HAIR DYE PRODUCTS BY HPLC. /PHENYLENEDIAMINE DERIVATIVES/|Method No. 87; m-, o- and p-Phenylenediamine, HPLC, quantitation limit 2.1 ug/cu-m (based on a 100-L air volume).
Hazardous Air Pollutants (HAPs)|Cosmetics -> Hair dyeing
Computed Properties
Molecular Weight:108.14
XLogP3:-0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:108.068748264
Monoisotopic Mass:108.068748264
Topological Polar Surface Area:52
Heavy Atom Count:8
Complexity:54.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
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