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N,N'-다이페닐-파라-페닐렌다이아민

N,N'-Diphenyl-P-Phenylenediamine

HCID 6319
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인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
74-31-7
표준 SMILES
c1ccc(Nc2ccc(Nc3ccccc3)cc2)cc1
InChIKey
UTGQNNCQYDRXCH-UHFFFAOYSA-N
분자식
C18H16N2
평균 분자량
260.3 g/mol
단동위원소 질량
260.13134851

개요

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

이름 및 식별자

우선 이름
N,N'-Diphenyl-P-Phenylenediamine
IUPAC
1-N,4-N-diphenylbenzene-1,4-diamine
현지명
N,N'-다이페닐-파라-페닐렌다이아민
영어명
N,N-Diphenyl-p-phenylenediamine
분자식
C18H16N2
분자량
260.33

이름 및 동의어

74-31-7N,N'-Diphenyl-p-phenylenediamineN,N'-Diphenyl-1,4-phenylenediamineDPPDDiphenyl-p-phenylenediamineAgeRite DPPD1,4-DianilinobenzeneFlexamine GNonflex HDiafen FFNonox DPPDAntioxidant H
이름 더 보기
N,N""""-다이페닐-파라-페닐렌다이아민N,N'-다이페닐-파라-페닐렌다이아민JZFDiafennaugardjnocracdpnonflexhantagedpdiafenffusafgy-2
DFFDStabilizer DPPDAltofane DIP1,4-Bis(phenylamino)benzenePermanax 18Usaf gy-2p-PhenylaminodiphenylamineAntigene P

데이터베이스 식별자

CAS
74-31-7
PubChem CID
6319
DTXSID
DTXSID9020538
ChEMBL
CHEMBL1333512
ChEBI
CHEBI:34860
UNII
DD517SCM92
EC Number
200-806-4
Nikkaji
J11.021C

물성

구조 계산 물성

XLogP
5
극성 표면적
24.1 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
4
무거운 원자 수
20
형식 전하
0
복잡도
231

실험 및 물리화학적 성질

PolymersNitrogen Compounds -> Amines, Polyaromatic
SpringerMaterials PropertiesDensity
Density · 3건

1.21 (NTP, 1992) - Denser than water; will sink

1.20

Relative density (water = 1): 1.2

Viscosity5.48X10-1 Pa.s (liquid)
Color/Form · 3건

Colorless leaflets from alcohol; commercial grades are greenish-brown

Gray powder

White solid

Solubility · 3건

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: none

Flash Point · 2건

400 °F (NTP, 1992)

232 °C c.c.

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 2건

428 to 437 °F at 0.5 mmHg (NTP, 1992)

220-225 °C @ 0.5 mm Hg

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Warning

H317: 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)

Warning

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)

유해성 정보

Regulatory Information · 4건

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/22932

1,4-Benzenediamine, N,N'-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelPoison
Fire Hazards · 2건

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.

Fire Potential · 2건

COMBUSTIBLE.

SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the eyes and skin sensitization.
Hazards Summary · 1건

화학 및 산업

약리 정보

FDA Pharmacological Classification · 6건

DD517SCM92

N,N'-DIPHENYL-1,4-PHENYLENEDIAMINE

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

용도 및 제조

Uses · 6건

Used as antioxidant (rubber, polyethylene, feedstuffs, petroleum, vegetable oils, animal fats, and oils), polymerization inhibitor, copper degradation inhibitor, and as an intermediate (dyes, drugs, plastics, and detergents); [HSDB]

Petroleum Production and Refining [Category: Industry]

ANTIOXIDANT FOR RUBBER, POLYETHYLENE, FEEDSTUFFS, PETROLEUM, VEGETABLE OILS, ANIMAL FATS & OILS; POLYMERIZATION INHIBITOR

Polymerization inhibitor, antioxidant for rubber, petr oils, feedstuffs.

THERAP CAT (VET): Antioxidant for feedstuffs

Flex-resistant antioxidant in rubbers; stabilizer; polymerization inhibitor; retards copper degradation; intermediate for dyes, drugs, plastics and detergents.

U.S. Production · 3건

2023: <75,000 lb

(1972) 8.13X10+8 GRAMS

(1975) 4.85X10+8 GRAMS

Consumer UsesLubricating agent
Industry UsesOther
Methods of Manufacturing · 2건

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).

관련 반응

19건
반응 기록 만들기
HRID 2325 반응식
HRID 2325반응물로uspto-grants-1998_03
HRID 6575 반응식
HRID 6575반응물로uspto-grants-2006_08
HRID 249207 반응식
HRID 249207반응물로uspto-grants-1993_05
HRID 394823 반응식
HRID 394823반응물로uspto-grants-2003_08
HRID 697624 반응식
HRID 697624반응물로Training data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 704480 반응식
HRID 704480반응물로uspto-grants-1991_01
HRID 716594 반응식
HRID 716594반응물로uspto-grants-2015_11
HRID 851517 반응식
HRID 851517생성물로uspto-grants-1983_05
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화합물 노트

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DecompositionWHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES...
Melting Point · 4건

293 to 306 °F (NTP, 1992)

150-151 °C

Specific gravity: 1.28; melting point: 145-152 °C

150-151 °C

Vapor Density · 3건

9 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

9.0 (Air= 1)

Relative vapor density (air = 1): 9.0

물리화학적 성질

녹는점
143 · 143-145 °C(lit.)
끓는 점
220 · 220-225 °C0.5 mm Hg(lit.)
밀도
1.2 · 1.2
굴절률
1.63 · 1.6300 (estimate)
인화점
220 · 220-225°C/1mm
저장 조건
30 °C · Store below +30°C.
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
고체
산도 계수 (pKa)
1.85 · 1.85±0.20(Predicted)
색상
옅은 회색에서 매우 어두운 회색까지
수용성
20 °C에서 · 20°C에서 <0.1g/100mL
Merck
14 · 14,3329
BRN
2215944 · 2215944
Henry's Law Constant
4.7 · 4.7×104 mol/(m3Pa) at 25℃, HSDB (2015)
안정성
안정적인. 강산, 강산화제와 호환되지 않습니다.
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
4.536 · 4.536 (est)
NIST
1 · 1,4-Benzenediamine, N,N'-diphenyl-(74-31-7)
EPA
N,N'-Diphenyl-p-phenylenediamine (74-31-7)

화학적 성질

grey powder

May cause skin sensitization; [ICSC] Danger of skin sensitization; [MAK] Food concentrations as low as 0.005% increase frequency of stillbirths in pregnant rats; Emergency treatment: Paraphenylenediamine; In sensitized individuals, paraphenylenediamine may cause allergic contact dermatitis following application as a hair dye and asthma following inhalation; Following ingestion, can cause angioneurotic edema, methemoglobinemia, acute tubular necrosis, and hepatotoxicity; An adult died after ingestion of 3 grams of p-phenylenediamine; Another adult who ingested 1800 mg developed angioneurotic edema and acute renal failure; [HSDB] May cause skin sensitization; [eChemPortal: ESIS] A mild eye irritant; Causes changes in liver weight, renal tubules, and clotting factors in repeated feeding studies of rats; [RTECS] See p-Phenylenediamine.

FDA Requirements...ITS DISTRIBUTION WAS...STOPPED IN 1956 BY US FDA.
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity Profile · 1건

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 DangersDecomposes on heating. This produces toxic fumes including carbon monoxide and nitrogen oxides. Reacts with oxidants. This generates fire and explosion hazard.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
Air and Water ReactionsInsoluble in water.

안전 및 보호

Fire Fighting · 2건

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.

First Aid Measures · 4건

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.

First Aid · 1건

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.

Safe StorageSeparated from strong oxidants. Keep in a well-ventilated room.
Storage Conditions · 1건

...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.

Nonfire Spill Response · 1건

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.

Disposal Methods · 1건

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.

Spillage Disposal · 1건

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 EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear face shield.
Fire PreventionNO open flames. Prevent deposition of dust.
Inhalation RiskA nuisance-causing concentration of airborne particles can be reached quickly when dispersed.

독성 정보

Interactions/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.
Environmental Fate · 3건

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).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by inhalation.
ICSC Environmental DataAvoid 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 · 1건

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 ExcerptsLOW TOXICITY.
Artificial Pollution SourcesN,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 BiodegradationAEROBIC: 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 · 1건

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 · 1건

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 ExcerptsIT WAS SHOWN THAT DPPD IN CONCN IN FOOD OF AS LOW AS 0.005% COULD LEAD TO HIGH INCIDENCE OF STILLBIRTHS IN PREGNANT RATS...

규제 정보

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

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
ST2275000
독성
LD50 orally in Rabbit: 2370 mg/kg LD50 dermal Rat 4500 mg/kg
HS 번호
2921 51 90
risk_code
43-52/53
hazard_code
Xi
safety_code
24-37-61
기존화학 물질
KE-12056
Hazard Classifications
Aquatic Chronic 3Skin Sens. 1
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
74-31-7(Hazardous Substances Data)

... from hydroquinone and aniline, acid cat.

Formulations/Preparations · 2건

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/

General Manufacturing Information · 4건

Plastics 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%.

응용 분야 · 3건

개요N,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.

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

일반 설명Gray or dark gray powder or flakes.

상·하류 제품 정보

상류 원료

아닐린

하류 제품

14-비스(디페닐아미노)벤젠N,N'-Bis-(4-bromo-phenyl)-N,N'-diphenyl-benzene-1,4-diamine

추가 설명

정의ChEBI: An N-substituted diamine that is 1,4-phenylenediamine in which one hydrogen from each amino group is replaced by a phenyl group.