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Home > Encyclopedia > N,N′-Diphenyl-p-phenylenediamine

N,N′-Diphenyl-p-phenylenediamine

N,N′-Diphenyl-p-phenylenediamine structure

N,N′-Diphenyl-p-phenylenediamine 

structure
  • CAS No:

    74-31-7

  • Formula:

    C18H16N2

  • Chemical Name:

    N,N′-Diphenyl-p-phenylenediamine

  • Synonyms:

    1,4-Benzenediamine,N1,N4-diphenyl-;p-Phenylenediamine,N,N′-diphenyl-;1,4-Benzenediamine,N,N′-diphenyl-;N1,N4-Diphenyl-1,4-benzenediamine;AgeRite DPPD;1,4-Bis(phenylamino)benzene;1,4-Dianilinobenzene;N,N′-Diphenyl-p-phenylenediamine;4,4′-Diphenyl-p-phenylenediamine;DPPD;Flexamine G;JZF;Nonox DPPD;4-Phenylaminodiphenylamine;p-Phenylaminodiphenylamine;Diafen FF;Diphenyl-p-phenylenediamine;N,N′-Diphenyl-1,4-phenylenediamine;Altofane DIP;Nonflex H;Permanax 18;Stabilizer DPPD;p-Bis(phenylamino)benzene;Nocrac DP;Permanax DPPD;DFFD;Antage DP;Ekaland DPPD;Naugard J;Antigen P;Antigene P;Antioxidant H;N,N′-Diphenyl-1,4-benzenediamine;NSC 5761;Diafen FF-T;PPD;Antioxidant PPD;Antioxidant 7PPD;1,4-Benzenediamine N1,N4-diphenyl-;1-N,4-N-Diphenylbenzene-1,4-diamine;Vulkanox DPPD;DAPD;66746-42-7;72711-53-6;943443-44-5

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

grey powder


N,n'-diphenyl-p-phenylenediamine appears as gray or dark gray powder or flakes. (NTP, 1992)|DryPowder, PelletsLargeCrystals; OtherSolid|COLOURLESS CRYSTALS OR GREY POWDER.


N,n'-diphenyl-p-phenylenediamine appears as gray or dark gray powder or flakes. (NTP, 1992)|N,N'-diphenyl-1,4-phenylenediamine is an N-substituted diamine that is 1,4-phenylenediamine in which one hydrogen from each amino group is replaced by a phenyl group. It has a role as an antioxidant. It is a secondary amino compound and a N-substituted diamine. It derives from a p-aminodiphenylamine.|N,n'-diphenyl-1,4-phenylenediamine is a Standardized Chemical Allergen. The physiologic effect of n,n'-diphenyl-1,4-phenylenediamine is by means of Increased Histamine Release, and Cell-mediated Immunity.

N,N′-Diphenyl-p-phenylenediamine Basic Attributes

260.33

260.33

200-806-4

DD517SCM92

1181

5761

1673

DTXSID9020538

Colorless leaflets from alcohol; commercial grades are greenish-brown|Gray powder|White solid

2921590090

Characteristics

24.1

5

N,n'-diphenyl-p-phenylenediamine appears as gray or dark gray powder or flakes. (NTP, 1992)

1.20 g/cm3

150-151 °C

220-225 °C @ Press: 0.5 Torr

220-225°C/1mm

1.694

H2O: <0.1 g/100 mL at 20 ºC

2-8°C

6.35X10-9 mm Hg @ 25 deg C

Relative vapour density (air = 1): 9.0

Oral-rat LD50: 2370 mg/kg; Oral-Mouse LD50: 18000 mg/kg

When heated, open flame is more flammable; heated to decompose toxic nitrogen oxide fumes; teratogen

CAN REACT WITH OXIDIZING MATERIALS

Insoluble in water.

Amines, Phosphines, and Pyridines

N,N'-DIPHENYL-P-PHENYLENEDIAMINE may react with oxidizing materials (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

-9.34X10+9 J/kmol

Dust explosion possible if in powder or granular form, mixed with air.

1.10X10+8 J/kmol

Critical temperature: 906 K; critical pressure: 2.31X10+6 Pa

Safety Information

III

6.1

NONH for all modes of transport

1

43-52/53

24-37-61

ST2275000

Xi

Treasury is ventilated, low temperature and dry; stored and transported separately from oxidant

Reacts with oxidants; weak allergic agent

Stable. Incompatible with strong acids, strong oxidizing agents

P273-P280

H317-H412

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.

...ITS DISTRIBUTION WAS...STOPPED IN 1956 BY US FDA.

This chemical is combustible. This chemical may form explosive dust-air mixtures. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P201, P202, P261, P272, P273, P280, P281, P302+P352, P308+P313, P321, P333+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 307 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)|Use water spray, powder, foam, carbon dioxide.

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)

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 store this material in a refrigerator. (NTP, 1992)

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

COMBUSTIBLE.|SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. 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.

Separated from strong oxidants. Keep in a well-ventilated room.

A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.

Repeated or prolonged contact may cause skin sensitization.

NO open flames. Prevent deposition of dust.

PREVENT DISPERSION OF DUST! STRICT HYGIENE!

Use local exhaust.

Protective gloves. Protective clothing.

Wear face shield.

Toxicity

moderately toxic

/IN/ 1962.../IT WAS SHOWN THAT/ DIPHENYL-P-PHENYLENEDIAMINE (DPPD)...GAVE SOME MEASURE OF PROTECTION /TO CARBON TETRACHLORIDE LETHALITY IN RATS/. THE PROTECTIVE EFFECT OF DPPD WAS CONFIRMED.../IN/ 1965.

N,N'-Diphenyl-p-phenylenediamine's production and use as an flex-resistant antioxidant in rubbers(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 1.3X10+5(SRC), determined from a structure estimation method(2), indicates that N,N'-diphenyl-p-phenylenediamine is expected to be immobile in soil(SRC). Volatilization of N,N'-diphenyl-p-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-10 atm-cu m/mole(3), using a fragment constant estimation method(3). N,N'-Diphenyl-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.35X10-9 mm Hg(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.3X10+5(SRC), determined from an estimation method(2), indicates that N,N'-diphenyl-p-phenylenediamine 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 2.1X10-10 atm-cu m/mole(4), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 260(SRC), from an estimated log Kow of 4.0(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate. BCFs for N,N'-diphenyl-p-phenylenediamine were determined to be greater than 100(8,9). N,N'-Diphenyl-p-phenylenediamine was determined to be non-biodegradable using the Japanese MITI test(9), attaining 0.2% of its theoretical BOD in 2 weeks(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N'-diphenyl-p-phenylenediamine, which has a vapor pressure of 6.35X10-9 mm Hg at 25 °C(2) is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase N,N'-diphenyl-p-phenylenediamine may be removed from the air by wet and dry deposition. N,N'-Diphenyl-p-phenylenediamine absorbs light in the environmental UV spectrum, and has the potential for direct photolysis(3).

The rate constant for the vapor-phase reaction of N,N'-diphenyl-p-phenylenediamine with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of approximately 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). N,N'-Diphenyl-p-phenylenediamine absorbs light in the environmental UV spectrum (>290 nm), and has the potential for direct photolysis(2).

1.32e+03|An estimated BCF of 260 was calculated for N,N'-diphenyl-p-phenylenediamine(SRC), using an estimated log Kow of 4.0(1) and a regression-derived equation(2). The BCF for N,N'-diphenyl-p-phenylenediamine was determined to be greater than 100(4). The bioconcentration of N,N'-diphenyl-p-phenylenediamine in the lipids of fish (8 week exposure period) were between 264-1418 and 495-2146 for test concentrations of 0.1 mg/l and 0.01 mg/l, respectively(5). According to a classification scheme(3), BCF values of 500 to 2000 are low and from 50 to 150 are high.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for N,N'-diphenyl-p-phenylenediamine can be estimated to be 1.3X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that N,N'-diphenyl-p-phenylenediamine is expected to be immobile in soil(SRC).

The Henry's Law constant for N,N'-diphenyl-p-phenylenediamine is estimated as 2.1X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that N,N'-diphenyl-p-phenylenediamine is expected to be essentially nonvolatile from water surfaces(2). N,N'-Diphenyl-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.35X10-9 mm Hg(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 7680 workers are potentially exposed to N,N'-diphenyl-p-phenylenediamine in the US(1). Occupational exposure to N,N'-diphenyl-p-phenylenediamine may occur through inhalation and dermal contact with this compound at workplaces where N,N'-diphenyl-p-phenylenediamine is produced or used(SRC).

Drug Information

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the eyes and skin sensitization. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides, carbon oxides, aniline and other related amines. It may be absorbed through the skin. (NTP, 1992)

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)


Fresh air, rest.


Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap.


Rinse with plenty of water (remove contact lenses if easily possible).

LOW TOXICITY.

DDPD

The substance can be absorbed into the body by inhalation.

N,N′-Diphenyl-p-phenylenediamine Use and Manufacturing

Methods of Manufacturing

Prepd by condensing hydroquinone or p-aminophenol with aniline: Calm, Ber 16, 2805 (1883); Clemens, Magoffin, US patent 2,503,712 (1950 to Kodak). Purification: Pecherer, US patent 2,833,824 (1958 to Hoffmann-La Roche).|... from hydroquinone and aniline, acid cat.

Uses

Polymerization inhibitor.Antioxidant for rubber, petroleum oils, feedstuffs.


Antioxidants / Stabilisers


Plastic and rubber products not covered elsewhere

Production

100,000 - 500,000 lb|(1972) 8.13X10+8 GRAMS|(1975) 4.85X10+8 GRAMS

Purity: 9.2% (min)|Flexamine G /is/ trademark for mixt of N,N'-diphenyl-para-phenylenediamine and complex diarylamine-ketone reaction product. Uses: antioxidant used in tires, camelback, wire insulation, neoprene belting and soles. /Flexamine G/

Plastic material and resin manufacturing|1,4-Benzenediamine, N1,N4-diphenyl-: ACTIVE|...ITS DISTRIBUTION WAS...STOPPED IN 1956 BY US FDA.|IN ORDER TO PREVENT OXIDATION OF VITAMIN E & TO STABILIZE VITAMIN A & CAROTENE IN MIXED ANIMAL FEEDS IT.../BECAME/ COMMERCIAL PRACTICE TO ADD ANTIOXIDANTS. PROBABLY MOST WIDELY USED COMPD WAS DPPD...WHICH WAS USUALLY ADDED TO POULTRY FEEDS IN CONCN OF 0.025%.

Computed Properties

Molecular Weight:260.3
XLogP3:5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:260.131348519
Monoisotopic Mass:260.131348519
Topological Polar Surface Area:24.1
Heavy Atom Count:20
Complexity:231
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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