비스(4-아미노페닐) 에테르

log Kow = 1.36

1.36

less than 0.1 mg/mL at 59 °F (NTP, 1992)

Insoluble in water, benzene, carbon tetrachloride and ethanol; soluble in acetone

426 °F (NTP, 1992)

219 °C

219 °C (closed cup)

Sublimes (NTP, 1992)

>300 °C

367 to 369 °F (NTP, 1992)

189 °C (decomposes

187 °C

10 mmHg at 464 °F ; 15 mmHg at 482 °F (NTP, 1992)

0.00000436 [mmHg]

0.0000003 [mm Hg] @25 °C

4,4'-diaminodiphenyl ether appears as odorless colorless crystals or an odorless fine, beige powder. (NTP, 1992)

Dry Powder

Colorless solid; [HSDB] Colorless crystalline solid; [MSDSonline]

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Warning

H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Chemical: Benzenamine, 4,4'-oxybis-

Hazard Traits - Carcinogenicity; Genotoxicity

Benzenamine, 4,4'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 4,4'-oxybis- 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)

REACH registered substance: 4,4'-oxydianiline (EC: 202-977-0)

Substance: 4,4'-oxydianiline

4,4'-Diaminodiphenyl ether: Does not have an individual approval but may be used under an appropriate group standard

DHEW/NCI; Bioassay of 4,4'-Oxydianiline for Possible Carcinogenicity (1980) Technical Rpt Series No. 205 DHEW Pub No. (NIH) 80-1761

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 4,4'-Oxydianiline (101-80-4) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s141oxyd.pdf]

Acute toxicity - category 3

Acute toxicity (Oral) - Category 4

Germ cell mutagenicity - Category 2

Acute toxicity (Oral) - Category 4

Carcinogens

Carc. 1B

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.

Special protective equipment for fire-fighters Wear self contained breathing apparatus for fire fighting if necessary.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Stable under recommended storage conditions.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

ACCIDENTAL RELEASE MEASURES. Personal precautions. Wear respiratory protection. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

Product: Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

Incineration: Incineration with provision for NO(x) removal from flue gases by scrubber, catalytic or thermal device.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for BIS(4-AMINOPHENYL) ETHER (8 total), please visit the HSDB record page.

Provide appropriate exhaust ventilation at places where dust is formed.

Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for BIS(4-AMINOPHENYL) ETHER (11 total), please visit the HSDB record page.

2.2 [mg/m3]

24 [mg/m3]

140 [mg/m3]

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Handle with gloves.

Eye protection: Safety glasses. Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

LC50; Species: Ceriodaphnia dubia; Conditions: semi-static, pH 7.9-8.3, temp 24-25.5 °C, dissolved oxygen 7.12-8.2mg/L; Concentration: 223.6 ug/L 48 hr, end point: mortality, concn used: 0, 5, 50, 100, 500, 5000 mg/L

LC50; Species: Pimephales promelas (Fathead minnow); Conditions: semi-static, pH 7.3-8.3, temp 24-25.7 °C, dissolved oxygen 4.0-8.5 mg/L; Concentration: 22 mg/L for 96 hr, end point: mortality, concentrations used: 0, 6.25, 12.5, 25, 50, 100 mg/L

LC50; Species: Selenastrum capricornutum (Algae); Conditions: static, freshwater, pH 7.11-7.79, mean light intensity 7492 lumens/sq m (definitive), 7463 lumens/sq m (recovery), temp 24.0-24.8 °C; Concentration: 7.9 mg/L for 72 hr (end point: cell number), 21.7 mg/L for 72 hr (end point: growth rate), concentrations used: 0, 3.75, 7.5, 15, 30, 60 mg/L

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 450(SRC), determined from a structure estimation method(2), indicates that bis(4-aminophenyl) ether is expected to have moderate 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 bis(4-aminophenyl) ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(5). bis(4-Aminophenyl) ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-6 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 450(SRC), determined from a structure estimation method(2), indicates that bis(4-aminophenyl) ether is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.5X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 4(SRC), from its log Kow of 1.36(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). bis(4-Aminophenyl) ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(4-aminophenyl) ether, which has an estimated vapor pressure of 2.5X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bis(4-aminophenyl) ether 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 1.8 hours(SRC), calculated from its rate constant of 2.1X10-10 cu cm/molecule-sec at 25 °C(3). Particulate-phase bis(4-aminophenyl) ether may be removed from the air by wet or dry deposition(SRC). bis(4-Aminophenyl) ether does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=101-80-4]

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

Using a structure estimation method based on molecular connectivity indices(1), the Koc of bis(4-aminophenyl) ether can be estimated to be 450(SRC). According to a classification scheme(2), this estimated Koc value suggests that bis(4-aminophenyl) ether is expected to have moderate mobility in soil. However, aromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(3).

4,4'-Diaminodiphenyl ether

Group 2B: Possibly carcinogenic to humans

Volume 29: (1982) Some Industrial Chemicals and Dyestuffs

1987

1987

4,4'-Oxydianiline

An estimated BCF of 4 was calculated in fish for bis(4-aminophenyl) ether(SRC), using a log Kow of 1.36(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for bis(4-aminophenyl) ether is estimated as 1.5X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bis(4-aminophenyl) ether is expected to be essentially nonvolatile from water surfaces(2). bis(4-Aminophenyl) ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-6 mm Hg(SRC), determined from a fragment constant method(3).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Fischer 344 rats and B6C3F1 mice were fed diets that contained 4,4'-oxydianiline for 13 wk. A 0.1 to 0.2% diet caused 40-70% mortality in female rats. Although mice ate approx 3.5 times more than rats, no mice died.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Fischer 344 rats and B6C3F1 mice were fed diets that contained 4-4'-oxydianiline for 13 wk. Alopecia, dyspnea and cyanosis in rats, and lethargy in both species at 0.1-0.2% diet. Diffuse parenchymatous goiter was seen in most rats at 0.2% and in all animals at 0.06%.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Fischer 344 rats and B6C3F1 mice were fed diets that contained 4,4'-oxydianiline for 13 wk. In rats, thyroids had interstitial fibrosis and vascular degeneration, there was hyperplasia of pituitary basophils in both species, but incr cells that secrete thyrotropin in rats.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ There is sufficient evidence for the carcinogenicity of 4-aminophenyl ether (4,4-oxydianiline) in animals. When administered in the diet, the compound increased the incidence of adenomas of the Harderian gland and hepatocellular adenomas or carcinomas in mice of both sexes, follicular cell adenomas in female mice, and hepatocellular carcinomas and follicular cell adenomas or carcinomas of the thyroid in F344 rats of both sexes. The population of thyrotrophs (thyrotropin-producing cells) was increased in the pituitary glands of the rats with neoplasms of the thyroid gland. These cells were distinct from prolactin cells, and the increase in number suggested insufficient hormone production by the induced thyroid tumors. When administered by subcutaneous injection, the compound induced maligant and benign liver tumors in rats.

For more Non-Human Toxicity Excerpts (Complete) data for BIS(4-AMINOPHENYL) ETHER (29 total), please visit the HSDB record page.

Used as a chemical intermediate for polyimide and poly(ester-imide) resins; [HSDB]

Chem int for polyimide and poly(ester-imide) resins

Substance listed with specific concentration in tattoo ink and/or permanent make up according to EU Commission Regulation 2020/2081. The concentration limit (by weight) is 0.0005%.

2023: 75,000 - <500,000 lb

4-Aminophenyl ether was produced in relatively large volume (in the order of 100,000-1,000,000 lbs) in the 1970s but has since declined significantly.

(1976)Probably greater than 9.08x10+5 grams

(1978) Probably greater than 9.08x10+5 grams

Benzenamine, 4,4'-oxybis- 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).

For more U.S. Production (Complete) data for BIS(4-AMINOPHENYL) ETHER (6 total), please visit the HSDB record page.

Paint and Coating Manufacturing

Benzenamine, 4,4'-oxybis-: ACTIVE