1,2-フェニレンジアミン

log Kow = 0.15

0.15 (calculated)

Brownish-yellow leaflets from water; plates from chloroform

Tan crystals or leaflets from water

White crystalline solid when pure

less than 1 mg/mL at 68 °F (NTP, 1992)

Because of ... limited solubility in cold water/o-phenylenediamine/ can be recrystalized from water

Freely soluble in alcohol, chloroform, ether

Soluble in water, ethyl ether, benzene, chloroform; very soluble in ethanol

In water, 4.07X10+4 mg/L at 35 °C

Solubility in water, g/100ml at 35 °C: 0.4

313 °F (NFPA, 2010)

313 °F; 156 °C (Closed cup)

156 °C c.c.

313 °F

493 to 496 °F at 760 mmHg (NTP, 1992)

257 °C

256-258 °C

493-496 °F

257 °C @760 [mm Hg]

216 to 219 °F (NTP, 1992)

219 °F

102.1 °C

103-104 °C

216-219 °F

104 °C

2.06X10-3 mm Hg at 25 °C

Vapor pressure, kPa at 20 °C: 0.0013

1,2-phenylenediamine appears as colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.

Dry Powder; Liquid

Colorless to brownish-yellow solid that darkens on exposure to light and air; [CHEMINFO]

BROWN-TO-YELLOW CRYSTALS. TURNS DARK ON EXPOSURE TO LIGHT.

Colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]；H312: Harmful in contact with skin [Warning Acute toxicity, dermal]；H317: May cause an allergic skin reaction [Warning Sensitization, Skin]；H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332: Harmful if inhaled [Warning Acute toxicity, inhalation]；H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]；H351: Suspected of causing cancer [Warning Carcinogenicity]；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]

P203, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P330, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

Chemical: 1,2-Benzenediamine

Hazard Traits - Carcinogenicity；Authoritative List - IARC Carcinogens - 2B; Prop 65；Report - regardless of intended function of ingredient in the product

1,2-Benzenediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenediamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 02-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2001；Status: Active Update: 31-10-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1268；Status: Active Update: 30-07-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1399

1,2-Phenylenediamine: HSNO Approval: HSR003048 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.)

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

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

SYMPTOMS: Symptoms of exposure to this chemical may include skin and eye irritation, headache, drowsiness, mental confusion and liver damage.；ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. It is highly toxic by inhalation and skin absorption. (NTP, 1992)

At lethal concentrations, exposed animals have seizures and paralysis without anesthesia. [ChemIDplus] Methemoglobinemia is observed in acute animal studies. In subchronic studies, rats have anemia and elevated liver enzymes. Critical Effects are irritation; liver; blood; [ACGIH]

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. 1,2-Benzenediamine is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.

All persons who manufacture (including import or by-product manufacture) or process o -pda, or intend to manufacture or process ortho-phenylenediamine after the effective date of this rule to the end of the reimbursement period shall submit letters of intent to test, submit study plans, conduct tests, and submit data, or submit exemption applications as specified in paragraphs (c)(3), (d), and (e) of this section, subpart A of this part, and parts 790 and 792 of this chapter for single-phase rulemaking. Required testing: health efffects, chemical fate and environmental effects testing.

1,2-PHENYLENEDIAMINE a weak aromatic amine base neutralizes acids in exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Darkens on exposure to air (Roger Patrick, DuPont Engineer).

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

Use water spray, powder.

Fresh air, rest. Artificial respiration may be needed. 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. 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.；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)

Spillage Disposal. 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 let this chemical enter the environment. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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 keep this material in a tightly closed container under an inert atmosphere, protect it from light, and store it at refrigerated temperatures. (NTP, 1992)

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Recommendable method: Incineration. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

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.

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

LC50; Species: Brachydanio rerio (Zebrafish); Concentration: 24 mg/L for 96 hr /Conditions of bioassay not specified/

LC100; Species: Brachydanio rerio (Zebrafish); Concentration: 33 mg/L for 96 hr /Conditions of bioassay not specified/

LC50; Species: Pimephales promelas (Fathead minnow); Concentration: 44 mg/L for 96 hr /Conditions of bioassay not specified/

LC50; Species: Pimephales promelas (Fathead minnow); Concentration: 271 mg/L for 96 hr /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for O-PHENYLENEDIAMINE (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that o-phenylenediamine is expected to have very high mobility in soil(SRC). However, 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), suggesting that mobility may be much lower in some soils(SRC). Volatilization of o-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), based upon its vapor pressure, 2.06X10-3 mm Hg(5), and water solubility, 4.04X10+4 mg/L(6). o-Phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). A 100% of total decomposition required greater than 64 days using a soil inoculum(7), suggesting that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that o-phenylenediamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.06X10-3 mm Hg(4), and water solubility, 4.04X10+4 mg/L(5). The pKa values of <2 and 4.47(6) indicate o-phenylenediamine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(7), an estimated BCF of 3(SRC),from its log Kow of 0.15(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). o-Phenylenediamine exhibited 33% removal after 5 days incubation using acclimated activated sludge inoculum(10), suggesting that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-phenylenediamine, which has a vapor pressure of 2.06X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase o-phenylenediamine 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 0.7 hours(SRC), calculated from its rate constant of 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). o-Phenylenediamine absorbs light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect；IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.；ACGIH Carcinogen - Confirmed Animal.

/AQUATIC SPECIES/ The static acute toxicities and degradative rates of the unsubstituted phenylenediamines (pdas) varied significantly among the ortho, para and meta isomers. With fathead minnows, the nominal 96 hr LC50s were 0.06, 44 and 1,600 mg/L for p-pda, o-pda and m-pda, respectively. In daphnid tests, the nominal 48 hr EC50s were 0.28, 0.87 and 5.9 mg/L for p-pda, o-pda and m-pda, respectively. The nominal 96 hr EC50s in algae were 0.28, 0.16, and 2.4 mg/L for p-pda, o-pda and m-pda, respectively. With oxygenation, the times to reach 1/2 initial concentrations were 4 to 9 hr for p-pda, 650 to 1,100 hr for o-pda and 3,200 to 8,100 hr for m-pda. Results suggest that acute toxicities of pdas are related to their chemical reactivities (degradative rates) and that pdas may degrade rapidly under environmental conditions.

/OTHER TERRESTRIAL SPECIES/ ...The toxicity of 10 benzamines was tested by the well diffusion assay technique against 18 common bacterial species including the nitrogen-fixing bacterium Azotobacter vinelandii. ... o-Phenylenediamine was inhibitory to Escherichia coli, Klebsiella pnemoniae, Salmonella enteritidis, and Shigella sonnei. ... Because many of these organisms are common soil and aquatic bacteria, the accumulation of these benzamine compounds in the environment may have an adverse impact on soil biochemical activities.

/PLANTS/ Three isomers of the promutagen phenylenediamine at mM concentrations were plant-activated and induced mutation in stamen hairs of Tradescantia clone 4430. The rank order of the mutagenicity of the isomers was: o-phenylenediamine > m-phenylenediamine > p-phenylenediamine with corresponding mutagenic potencies of 5.60, 1.43, and 0.46 mutant stamen hair cells/mumole, respectively. Diethyldithiocarbamate (DEDTC) and ammonium meta-vanadate (vanadate) repressed the mutagenic activity of o-phenylenediamine (o-PDA) in intact plants. Based on inhibition kinetics and reaction rates, the mechanism of DEDTC antimutagenicity was attributed to the inhibition of peroxidases that are required in the plant activation of o-PDA to mutagenic product(s). Spectrophotometric measurements of equimolar concentrations of o-PDA and vanadate demonstrated that the antimutagenic property of vanadate was mainly due to its reactivity with o-PDA.

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

Redness.

Redness. Pain.

See Inhalation.

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.[Available from, as of November 6, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=95-54-5]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of o-phenylenediamine can be estimated to be 34(SRC). According to a classification scheme(2), this estimated Koc value suggests that o-phenylenediamine is expected to have very high mobility in soil. However, 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), suggesting that mobility may be much lower in some soils(SRC).

1,2-Benzenediamine (CAS # 95-54-5) was evaluated for eye irritation in 3 albino rabbits administered undiluted ocular instillations of 100 mg. The treated eyes remained unrinsed during post-instillation observation. Ocular irritation was maximal in all 3 rabbits 1 hour after treatment. A mean irritation score was 31.7/110. One rabbit remained unimproved at 72nd hour observation, developing corneal ulceration and vascularization by the 7th day, while Day 7 found complete resolution of all irritative signs in the other 2 treated rabbits. By 14th day observation period, one rabbit continued to show corneal vascularization and ulceration with slight conjunctival redness comprising an individual irritation score of 12/110 and a mean score (3 rabbits) of 4.0/110. Study investigators assigned a descriptive rating of "moderately irritating" to 1,2-benzenediamine.

o-Phenylenediamine (CAS # 95-54-5) was evaluated for oral neurotoxicity in Crl:CDBR rats (12/sex/group) administered single gavage doses of 0, 225, 450, and 900 mg/kg (10 mL/kg in methyl cellulose). Bodyweight, feed consumption, clinical signs, functional observational battery performance, fore- and hindlimb grip strength, foot splay and motor activity were assessed prior to treatment (baseline values), and at 1 hour, 24 hours, and 4 days post-treatment. Toxicity was demonstrated at all dose levels. High-dose rats, 2 males and 4 females were found dead prior to scheduled sacrifice and significant weight loss within one day of dosing was common to all treatment groups, persisting throughout Day 4. Significant reductions in feed consumption were pronounced initially, but transient in all but the high-dose group. Clinical signs were most severe 2-4 days after treatment and included initial discolored urine, abnormal respiration with gasping, congestion, and sneezing (450, 900 mg/kg), dose-related malaise, postural changes, palpebral closure, and decreased arousal. The functional observational battery, fore-, and hindlimb grip strength and foot splay assessments were not indicative of a neurotoxicity at any treatment level. Motor activity was significantly depressed following treatment in all treatment groups relative to control. Study investigators attributed these findings to a general condition of dose-related malaise and reported no evidence of specific toxic effects on the central nervous system.

Acute dermal toxicity was evaluated in single New Zealand female rabbits receiving one occluded application of o-phenylenediamine to abraded skin at dose levels of 300, 1000, or 3000 mg/kg body weight for 24 hours. Mortality was not observed in any animal at any dose level, and the LD50 was reported to be greater than 3000 mg/kg. Clinical signs of toxicity were not observed, and the test article was not irritating to rabbit skin. Gross necropsy did not reveal any evidence of pathological effects.

Acute inhalation toxicity was evaluated in 10 BR rats (5 male and 5 female) exposed to o-phenylene diamine vapor at a nominal concentration of 1340.0 mg/cu m for 4 hours. The atmosphere was generated by passing a stream of air through the test material in a gas wash bottle. Mortality was not observed in any animal during exposure or a 14 day observation period, and the LC50 was reported to be greater than 1340 mg/cu m. Clinical indications of toxicity were not observed, and necropsy of animals at 14 days did not reveal gross pathologic alterations.

For more TSCA Test Submissions (Complete) data for O-PHENYLENEDIAMINE (8 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Produces severe local reactions and systemic effects from percutaneous absorption and from ingestion. Local actions include severe dermatitis and urticaria; in the eye, chemosis, lacrimation, exophthalmos, ophthalmia, and even permanent blindness. Systemic actions include 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). Neither is believed to be capable of inducing significant methemoglobinemia.

/GENOTOXICITY/ Chromosomal aberration tests that were performed ... in peripheral human lymphocytes were ... positive with metabolic activation.

o-Phenylenediamine occurs as degradation product of thiophanate methyl & benomyl (benzimidazole fungicides).

o-Phenylenediamine's production and use as a chemical intermediate in the manufacture of dyes, photographic developing agent, organic synthesis, and as a laboratory reagent(1) may result in its release to the environment through various waste streams(SRC).

Chemical: 1,2-Benzenediamine

Hazard Traits - Carcinogenicity；Authoritative List - IARC Carcinogens - 2B; Prop 65；Report - regardless of intended function of ingredient in the product

1,2-Benzenediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenediamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 02-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2001；Status: Active Update: 31-10-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1268；Status: Active Update: 30-07-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1399

1,2-Phenylenediamine: HSNO Approval: HSR003048 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.)

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. 1,2-Benzenediamine is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.

All persons who manufacture (including import or by-product manufacture) or process o -pda, or intend to manufacture or process ortho-phenylenediamine after the effective date of this rule to the end of the reimbursement period shall submit letters of intent to test, submit study plans, conduct tests, and submit data, or submit exemption applications as specified in paragraphs (c)(3), (d), and (e) of this section, subpart A of this part, and parts 790 and 792 of this chapter for single-phase rulemaking. Required testing: health efffects, chemical fate and environmental effects testing.

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.

Used as a chemical intermediate, analytical reagent, and photographic developer; [CHEMINFO]

Photographic Processing [Category: Other]

Hair-dye substance banned by the European Union (September 2007)

Manufacture of dyes, photographic developing agent, organic synthesis, laboratory reagent.

Used for the preparation of benzimidazole-derived agricultural fungicides such as benomyl; other fungicide uses include thiophanate methyl (Topsin), a turf fungicide and fuberidazole; in the preparation of a variety of benzimidazoles used as veterinarian anthelmintics.

Fluorescent indicator, pH range 3.1-4.4, green fluorescence-nonfluorescence

(1974) 5.42X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1975) 7.28X10+7 GRAMS (PRINCPL CUSTMS DISTS)

2023: 1,000,000 - <5,000,000 lb；2022: 1,000,000 - <5,000,000 lb；2021: 1,000,000 - <5,000,000 lb；2020: 1,000,000 - <5,000,000 lb

(1972) PROBABLY GREATER THAN 1.36X10+6 GRAMS

(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS

1,2-Benzenediamine is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4277]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,2-Benzenediamine. Aggregated National Production Volume: 1 to < 10 million pounds.

The principal route to o-phenylenediamine is by the reduction of 2-nitroaniline, which is produced by the amination of 2-chloronitrobenzene with ammonia. Hydrogenation can be achieved with a variety of reducing agents, such as iron powder, hydrazine, or hydrogen sulfide, but commercially it is performed catalytically in the liquid phase over a palladium catalyst.

AMMONOLYSIS FOLLOWED BY REDUCTION OF O-CHLORONITROBENZENE; REDUCTION OF O-NITROANILINE WITH SODIUM SULFIDE IN AN AUTOCLAVE

Made by reducing o-nitroaniline with Zn and NaOH.

Reduction of ortho-dinitrobenzene or nitroaniline with iron and hydrochloric acid. Method of purification: crystallization.

All Other Chemical Product and Preparation Manufacturing

1,2-Benzenediamine: ACTIVE