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Home > Encyclopedia > 4,4′-Diaminodiphenyl ether

4,4′-Diaminodiphenyl ether

4,4′-Diaminodiphenyl ether structure

4,4′-Diaminodiphenyl ether 

structure
  • CAS No:

    101-80-4

  • Formula:

    C12H12N2O

  • Chemical Name:

    4,4′-Diaminodiphenyl ether

  • Synonyms:

    Benzenamine,4,4′-oxybis-;Aniline,4,4′-oxydi-;4,4′-Oxybis[benzenamine];4,4′-Diaminophenyl ether;p,p′-Oxydianiline;4,4′-Diaminodiphenyl ether;Oxybis(4-aminobenzene);Oxydi-p-phenylenediamine;4,4′-Oxydianiline;Bis(4-aminophenyl) ether;p,p′-Oxybis[aniline];p,p′-Diaminodiphenyl ether;Bis(p-aminophenyl) ether;4,4′-Diaminobiphenyl oxide;Oxydianiline;4-Aminophenyl ether;4,4′-Oxybis(aniline);p-Aminophenyl ether;4,4′-Oxydiphenylamine;ODA;4,4′-Diaminobiphenyl ether;4,4′-Diaminodiphenyl oxide;NSC 37075;NSC 6089;4-(4-Aminophenoxy)phenylamine;DPE;DPE (amine);Di(4-aminophenyl) ether;1-Amino-4-(4-aminophenoxy)benzene;DDE;4-(4′-Aminophenoxy)benzenamine;4-(4-Aminophenoxy)aniline;121509-79-3;928208-61-1

  • Categories:

    Organic Chemistry  >  Ethers and Derivatives

Description

Colorless crystalline 4-Aminophenyl ether is a resin used in the manufacture of a variety of industrial products. For example as, insulating varnishes, flame-retardant fi bers, wire enamels, coatings, and fi lms. It is also used for the manufacture of other fi re-resistant products. 4,40′-Oxydianiline is a white crystalline solid,or a beige powder.Odorless colorless crystals or an odorless fine, beige powder.


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


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

4,4′-Diaminodiphenyl ether Basic Attributes

200.24

200.24

475735

202-977-0

28DLB4Z70T

37075|6089

3077

DTXSID0021094

Colorless crystals

29222900

Characteristics

61.3

1.36

White Solid

1.1131 (rough estimate)

186-187 °C

>300 °C

426 °F

1.6660 (estimate)

H2O: <0.01 g/100 mL at 15 ºC;Insoluble in water, benzene, carbon tetrachloride and ethanol; soluble in acetone

Store below +30°C.

10 mm Hg ( 240 °C)

LD50 orl-rat: 725 mg/kg HYSAAV 33,137,68

Henry's Law constant = 1.5X10-11 atm-cu m/mole at 25 °C (est)

pKa1 = 3.96 (amine) (est)

Hydroxyl radical reaction rate constant = 2.1X10-10 cu cm/molecule-sec at 25 °C

Insoluble in water.

Ethers

Peroxidizable Compound

4,4'-DIAMINODIPHENYL ETHER oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. A mixture of liquid air and diethyl ether exploded spontaneously [MCA Case History 616(1960)].

914 °F (NTP, 1992)|490 °C

Safety Information

III

6.1

UN 3077 9/PG 3

3

45-46-23/24/25-51/53-62-36/37/38-22-50/53-43

53-45-61-36/37-26-20-60

BY7900000

T,N

Stable. Combustible. Incompatible with strong oxidizing agents. Hygroscopic.

P201-P261-P273-P280-P301 + P310-P311

H301 + H311 + H331-H317-H340-H350-H361-H410

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.

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]

This chemical is combustible. (NTP, 1992)

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H301+H311+H331 (29.08%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 282 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P308+P313, P314, P321, P330, P333+P313, P363, P391, P405, and P501|Warning|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P308+P313, P314, P321, P330, P333+P313, P363, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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)

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. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

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/

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.

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/

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.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Toxicity

LD50 Rat oral 725 mg/kg|LD50 Rat intragastric 725 (+ or - 50) mg/kg|LD50 Rat ip 365 (+ or - 25) mg/kg|LD50 Mouse oral 685 mg/kg|For more Non-Human Toxicity Values (Complete) data for BIS(4-AMINOPHENYL) ETHER (9 total), please visit the HSDB record page.

A bioassay of /4,4'-oxydianiline/ for possible carcinogenicity was conducted by feeding diets containing 200, 400, or 500 ppm test chemical to groups of 50 male or female F344 rats and 150, 300, or 800 ppm to groups of 50 male or female B6C3F1 mice for 104 weeks. Matched controls consisted of 50 untreated rats and 50 untreated mice of each sex. All surviving animals were killed at 104 to 105 weeks. ... In male and female rats, hepatocellular carcinomas or neoplastic nodules occurred at incidences that were dose related, and the incidences in all dosed groups (except low dose females) were higher than those in the controls. The occurence of follicular cell adenomas and carcinomas of the thyroid was dose related. Among groups of male and female rats, the incidences in the mid and high dose groups of either sex were significantly higher than those in the corresponding controls. In male and female mice, adenomas in the harderian glands occurred in all dosed groups at incidences that were significantly higher than the incidence in the matched controls. In low dose male mice and high dose female mice, hepatocellular adenomas and carcinomas occured at incidences significantly higher than those in the matched controls. In female mice follicular cell adenomas in the thyroid occurred with a positive linear trend, and in a direct comparison the incidence in the high dose group was also significantly higher than that in controls. ... Under the conditions of this bioassay, 4,4'-oxydianiline was carcinogenic for male and female F344 rats, including hepatocellular carcinomas or neoplastic nodules and follicular cell adenomas or carcinomas of the thyroid. 4,4-Oxydianiline was also carcinogenic for male and female B6C3F1 mice, inducing adenomas in the harderian glands, hepatocellular adenomas or carcinomas in both sexes, and follicular cell adenomas in the thyroid of females.

bis(4-Aminophenyl) ether is not known to occur as such in nature.

bis(4-Aminophenyl) ether's production and use as a chemical intermediate for polyimide and poly(ester-imide) resins(1) may result in its release to the environment through various waste streams(SRC).

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 rate constant for the vapor-phase reaction of bis(4-aminophenyl) ether with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-10 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 1.8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 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(2). bis(4-Aminophenyl) ether does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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).

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).

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).

NIOSH (NOHS Survey 1972-1974) has statistically estimated that 45 workers were potentially exposed to 4,4'-diaminodiphenyl ether in the USA(1,2). Occupational exposure to bis(4-aminophenyl) ether may occur through dermal contact with this compound at workplaces where bis(4-aminophenyl) ether is produced or used(SRC).

Drug Information

SYMPTOMS: Symptoms of exposure to this compound may include irritation. ACUTE/CHRONIC HAZARDS: This compound is harmful if ingested, inhaled or absorbed through the skin. It is an irritant. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (NTP, 1992)|Carcinogens

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. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as 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 patient quiet and maintain normal body temperature. Obtain medical attention. /Ethers and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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. Provide a low-stimulus environment. 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 0.9% saline (NS) 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 ... . Treat frostbite by rapid rewarming ... . /Ethers and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethers and related compounds/

4,4'-diaminodiphenyl ether

4,4′-Diaminodiphenyl ether Use and Manufacturing

Methods of Manufacturing

Reaction of 4,4'-diaminodiphenyl ether with tin and hydrochloric acid in the presence of ethanol.

Uses

Used as a monomer of polyimide, a high temperature resistant polymer material, also used as a dye intermediate in the plastic industry, and also used as a fragrance for resin synthesis. Dye intermediates. Resin synthesis. 1. It is one of the important raw materials for high temperature resistant resins such as new special engineering plastics polyimide, polyetherimide, polyesterimide, polymaleimide, and polyaramid; 2. It is also synthetic 3,3',4,4'-Tetraaminodiphenyl ether raw material, the latter is the main monomer for preparing a series of aromatic heterocyclic heat-resistant polymer materials. 3. It is also used as a raw material and crosslinking agent for synthetic polymers such as high-performance heat-resistant epoxy resin and polyurethane. 4. At the same time, it is also used to replace carcinogenic benzidine to produce azo dyes, reactive dyes and perfumes. At present, using diaminodiphenyl ether as a raw material has developed direct dyes of different color levels such as scarlet, brilliant red, sand red, yellow brown, green, gray, blue, brilliant orange, black, etc., which can be used for silk, wool, cotton, The dyeing of hemp and other fabrics is superior to benzidine dyes in terms of color fastness and exhaustion rate.


Intermediates


Electrical and electronic products

Production

1,000,000 - 10,000,000 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.

Minimal purity: 98%

Paint and coating manufacturing|Benzenamine, 4,4'-oxybis-: ACTIVE

Method: EPA-OSW 8270D; Procedure: gas chromatography/mass spectrometry; Analyte: 4,4'-oxydianiline; Matrix: solid waste matrices, soils, air sampling media and water samples; Detection Limit: 20 ug/L.

Health Hazards -> Carcinogens

Computed Properties

Molecular Weight:200.24
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:200.094963011
Monoisotopic Mass:200.094963011
Topological Polar Surface Area:61.3
Heavy Atom Count:15
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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