HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
N,N'-Diphenyl-p-phenylendiamin
DPPD · JZF · DFFD · Diafen · naugardj · nocracdp · nonflexh · antagedp
Identifikatoren & physikalische Daten
| CAS No. | 74-31-7 |
|---|---|
| Summenformel | C18H16N2 |
| Durchschnittliche Molmasse | 260,3 g/mol |
| Monoisotopische Masse | 260,13134851 g/mol |
| SMILES | c1ccc(Nc2ccc(Nc3ccccc3)cc2)cc1 |
| InChIKey | UTGQNNCQYDRXCH-UHFFFAOYSA-N |
| PubChem CID | 6319 |
| ChEMBL | CHEMBL1333512 |
| ChEBI | CHEBI:34860 |
| EC No. | 200-806-4 |
| DTXSID | DTXSID9020538 |
| Lokaler Name | N,N'-Diphenyl-p-phenylendiamin |
Chemische & physikalische Eigenschaften
| XLogP | 5 |
|---|---|
| Polarare Oberfläche (TPSA) | 24,1 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 231 |
| Polymers | Nitrogen Compounds -> Amines, Polyaromatic |
| SpringerMaterials Properties | Density |
| Dichte | 1.21 (NTP, 1992) - Denser than waterwill sink1.20Relative density (water = 1): 1.2 |
| Viscosity | 5.48X10-1 Pa.s (liquid) |
| Color/Form | Colorless leaflets from alcoholcommercial grades are greenish-brownGray powderWhite solid |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)Sol in monochlorobenzene, benzene, DMF, ether, chloroform, acetone, ethyl acetate, isopropyl acetate, glacial acetic acid. Slightly sol in alcohol. Almost insol in petr ether, water.Solubility in water: noneDMSO (Slightly), Methanol (Slightly)<0.1 g/100 mL at 20 ºC |
| Flammpunkt | 400 °F (NTP, 1992)232 °C c.c.220-225°C/1mm |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 428 to 437 °F at 0.5 mmHg (NTP, 1992)220-225 °C @ 0.5 mm Hg220-225 °C0.5 mm Hg(lit.) |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES... |
| Schmelzpunkt | 293 to 306 °F (NTP, 1992)150-151 °CSpecific gravity: 1.28melting point: 145-152 °C143-145 °C(lit.) |
| Dampfdichte | 9 (NTP, 1992) - Heavier than airwill sink (Relative to Air)9.0 (Air= 1)Relative vapor density (air = 1): 9.0 |
| Brechungsindex | 1.6300 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 1.85±0.20(Predicted) |
| Farbe | Pale Grey to Very Dark Grey |
| Merck | 14,3329 |
| BRN | 2215944 |
| Henry-Konstante | 4.7×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong acids, strong oxidizing agents |
| InChI | 1S/C18H16N2/c1-3-7-15(8-4-1)19-17-11-13-18(14-12-17)20-16-9-5-2-6-10-16/h1-14,19-20H |
| InChIKey | UTGQNNCQYDRXCH-UHFFFAOYSA-N |
| SMILES | N(c1ccccc1)c2ccc(Nc3ccccc3)cc2 |
| LogP (Verteilungskoeffizient) | 4.536 (est) |
| CAS Datenbank | 74-31-7(CAS DataBase Reference) |
| NIST chemische Informationen | 1,4-Benzenediamine, N,N'-diphenyl-(74-31-7) |
| EPA chemische Informationen | N,N'-Diphenyl-p-phenylenediamine (74-31-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]P203, P261, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: 1,4-Benzenediamine, N,N'-diphenyl-1,4-Benzenediamine, N1,N4-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediamine, N1,N4-diphenyl- 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: 26-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/229321,4-Benzenediamine, N,N'-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | 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. |
| Brandpotenzial | COMBUSTIBLE.SLIGHT, WHEN EXPOSED TO HEAT OR FLAME. |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the eyes and skin sensitization. |
| Gefahrenübersicht | May cause skin sensitization[ICSC] Danger of skin sensitization[MAK] Food concentrations as low as 0.005% increase frequency of stillbirths in pregnant ratsEmergency treatment: ParaphenylenediamineIn sensitized individuals, paraphenylenediamine may cause allergic contact dermatitis following application as a hair dye and asthma following inhalationFollowing ingestion, can cause angioneurotic edema, methemoglobinemia, acute tubular necrosis, and hepatotoxicityAn adult died after ingestion of 3 grams of p-phenylenediamineAnother adult who ingested 1800 mg developed angioneurotic edema and acute renal failure[HSDB] May cause skin sensitization[eChemPortal: ESIS] A mild eye irritantCauses changes in liver weight, renal tubules, and clotting factors in repeated feeding studies of rats[RTECS] See p-Phenylenediamine. |
| FDA-Anforderungen | ...ITS DISTRIBUTION WAS...STOPPED IN 1956 BY US FDA. |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| Reactivity Profile | 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. |
| Chemical Dangers | Decomposes on heating. This produces toxic fumes including carbon monoxide and nitrogen oxides. Reacts with oxidants. This generates fire and explosion hazard. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Air and Water Reactions | Insoluble in water. |
| Brandbekämpfung | 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. |
| Erste-Hilfe-Maßnahmen | 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).Rinse mouth. |
| Erste Hilfe | 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. |
| Sichere Lagerung | Separated from strong oxidants. Keep in a well-ventilated room. |
| Lagerbedingungen | ...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT, MOISTURE, ACID, OR ACID FUMES, SHOULD BE STORED IN COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD & SHOULD BE PERIODICALLY INSPECTED & MONITORED. |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | 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. |
| Verschüttetes entsorgen | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear face shield. |
| Fire Prevention | NO open flames. Prevent deposition of dust. |
| Inhalation Risk | A nuisance-causing concentration of airborne particles can be reached quickly when dispersed. |
| Wechselwirkungen | /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. |
| Umweltverhalten | 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). |
| Unerwünschte Wirkungen | 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. |
| Expositionspfade | The substance can be absorbed into the body by inhalation. |
| ICSC Environmental Data | Avoid release to the environment in circumstances different to normal use. Bioaccumulation of this chemical may occur along the food chain, for example in fish. Environmental effects from the substance have not been investigated adequately. |
| Soil Adsorption/Mobility | 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). |
| Human Toxicity Excerpts | LOW TOXICITY. |
| Artificial Pollution Sources | 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). |
| Environmental Biodegradation | AEROBIC: N,N'-diphenyl-p-phenylenediamine, present at 100 mg/l, reached 0.2% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/l in the Japanese MITI test(1). |
| Environmental Bioconcentration | 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. |
| Volatilization from Water/Soil | 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). |
| Non-Human Toxicity Excerpts | IT WAS SHOWN THAT DPPD IN CONCN IN FOOD OF AS LOW AS 0.005% COULD LEAD TO HIGH INCIDENCE OF STILLBIRTHS IN PREGNANT RATS... |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2921 51 90 |
| RTECS-Nr. | ST2275000 |
| R-Sätze (R) | 43-52/53 |
| Toxizität | LD50 orally in Rabbit: 2370 mg/kg LD50 dermal Rat 4500 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24-37-61 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 74-31-7(Hazardous Substances Data) |
| Gefahrenklasse | Aquatic Chronic 3Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
N,N'-Diphenyl-4-phenylenediamine (DPPD) is a rubber accelerant, formerly contained in the "black rubber mix". The most frequent occupational categories are in metal industry, homemakers, health services and laboratories, and building industries.
Verwenden
Polymerization inhibitor. Antioxidant for rubber, petroleum oils, feedstuffs.