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N,N'-Di-sec-butyl-p-phenylendiamin

N,N'-Di-sec-butyl-p-phenylenediamine

HCID 7589
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Grundinformationen

CAS
101-96-2
Standard-SMILES
CCC(C)Nc1ccc(NC(C)CC)cc1
InChIKey
FSWDLYNGJBGFJH-UHFFFAOYSA-N
Summenformel
C14H24N2
Durchschnittliche Molmasse
220,35 g/mol
Monoisotopische Masse
220,19394877

Überblick

N,n'-di-sec-butyl-p-phenylenediamine appears as amber to red or dark reddish black liquid. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
N,N'-Di-sec-butyl-p-phenylenediamine
IUPAC
1-N,4-N-di(butan-2-yl)benzene-1,4-diamine
Lokaler Name
N,N'-Di-sec-butyl-p-phenylendiamin
Englischer Name
N,N'-Di-sec-butyl-p-phenylenediamine
Summenformel
C14H24N2
Molmasse
220.35

Namen und Synonyme

101-96-2N,N'-Di-sec-butyl-p-phenylenediamineAntioxidant 22Tenamene 2Topanol MKerobit BPDSantoflex 44N,N'-Di-sec-butyl-1,4-phenylenediamineN,N'-DI-SEC-BUTYL-P-PHENYLDIAMINEN,N'-Di-sec-butylparaphenylenediamineN,N'-Di-s-butyl-p-phenylenediamineDu Pont Gasoline Antioxidant No. 22
Weitere Namen anzeigen
44PDAntioxidant 44PDuop5Kerobcp40182topanolm
UOP 5p-Phenylenediamine, N,N'-di-sec-butyl-1,4-Benzenediamine, N,N'-bis(1-methylpropyl)-NSC 68417CCRIS 4603DTXSID7024956HSDB 5343N,N'-Bis(1-methylpropyl)-1,4-benzenediamine

Datenbank-Bezeichner

CAS
101-96-2
PubChem CID
7589
DTXSID
DTXSID7024956
ChEMBL
CHEMBL1409985

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,5
Polarare Oberfläche (TPSA)
24,1 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
6
Schwere Atome
16
Formalladung
0
Komplexität
154

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
SpringerMaterials PropertiesBoiling point
Density · 2 Einträge

0.94 to 0.95 at 75 °F (NTP, 1992)

0.94 kg/l @ 20 °C

Color/Form · 3 Einträge

Amber to red liquid

Reddish-brown liquid

Pale yellow oil

Solubility · 3 Einträge

less than 1 mg/mL at 68 °F (NTP, 1992)

Soluble in gasoline, absolute ethanol and benzene; insoluble in water or caustic solutions

Insoluble in water; soluble in hydrocarbon solvents

Flash Point · 2 Einträge

285 °F (NTP, 1992)

270 °F (132 °C) (CLOSED CUP)

Boiling Point98 °C @ 26.6 Pa
Melting Point · 2 Einträge

64 °F (NTP, 1992)

18 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 0.4% (5 of 1132) of reports.

Danger

H301 (99%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1132 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 1,4-Benzenediamine, N,N'-bis(1-methylpropyl)-

1,4-Benzenediamine, N1,N4-bis(1-methylpropyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediamine, N1,N4-bis(1-methylpropyl)- 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: N,N'-di-sec-butyl-p-phenylenediamine (EC: 202-992-2)

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

DOT LabelCorrosive
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of tissues, skin burns, sweating, flushing of the face, shortness of breath and slow pulse.
Hazards Summary · 1 Eintrag

Chemie und Industrie

Verwendung und Herstellung

Uses · 6 Einträge

Used in gasoline (gum inhibitor, antioxidant, and stabilizer) and styrene-butadiene rubbers (antioxidant and antiozonant); [HSDB]

Petroleum Production and Refining [Category: Industry]

GASOLINE GUM INHIBITOR

ANTIOXIDANT & STABILIZER IN GASOLINE

ANTIOXIDANT & ANTIOZONANT IN STYRENE-BUTADIENE RUBBERS

Antioxidant (motor fuels)

U.S. Production · 3 Einträge

2023: 1,000,000 - <2,500,000 lb

(1979) 1.50X10+9 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Consumer UsesStabilizing agent
Industry UsesStabilizing agent
Methods of Manufacturing · 3 Einträge

REACTION OF P-PHENYLENEDIAMINE & 2-BUTANONE TO FORM THE DIANIL DERIVATIVE, FOLLOWED BY CATALYTIC HYDROGENATION

s-Butylamine + hydroquinone (reductive amination)

Reductive alkylation of p-phenylenediamine

Formulations/Preparations"TENAMENE" /IS/ TRADEMARK FOR GROUP OF ADDITIVES FOR GASOLINE & OTHER PETROLEUM PRODUCTS. /TENAMENE/
General Manufacturing Information · 2 Einträge

Synthetic Rubber Manufacturing

1,4-Benzenediamine, N1,N4-bis(1-methylpropyl)-: ACTIVE

Anwendungen

VerwendenN,N''-di-sec-Butyl-p-phenylenediamine is used in method for preparing polyurethane adhesive.

Anbieter100 Anbieter

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
UNII
76251WU9I2
EC Number
202-992-2
Nikkaji
J23.256D
Vapor Pressure · 2 Einträge

85.3 mmHg at 100 °F (NTP, 1992)

0.00156 [mmHg]

Physical Description · 3 Einträge

N,n'-di-sec-butyl-p-phenylenediamine appears as amber to red or dark reddish black liquid. (NTP, 1992)

CBI; Liquid

Pale yellow or amber to red liquid; mp = 18 deg C; [HSDB] Dark red liquid; [MSDSonline]

Autoignition Temperature625 °F (329 °C)

Physikochemische Eigenschaften

Schmelzpunkt
17.8 °C · 17.8°C
Siedepunkt
159 °C · 159 °C / 7mmHg
Dichte
0.942 g/mL · 0.942 g/mL at 20 °C(lit.)
Dampfdruck
0.05 Pa · 0.05Pa at 25℃
Brechungsindex
20 · n20/D 1.539
Flammpunkt
100 °C · 100°C
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
pka
8.67 · 8.67±0.50(Predicted)
Aggregatzustand
clear liquid
Farbe
Light yellow to Brown to Dark red
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 20 ºC
BRN
2805827 · 2805827
Stabilität
Stable. Combustible.
InChI
1S/C14H24N2/c1-5-11(3)15-13-7-9-14(10-8-13)16-12(4)6-2/h7-12,15-16H,5-6H2,1-4H3
InChIKey
FSWDLYNGJBGFJH-UHFFFAOYSA-N
SMILES
CCC(C)Nc1ccc(NC(C)CC)cc1
LogP
0.59 · 0.59-3.7 at 25℃
CAS Datenbank
101 · 101-96-2(CAS DataBase Reference)
NIST chemische Informationen
N,N'-Di-sec-butyl-p-phenylenediamine(101-96-2)
EPA chemische Informationen
N,N'-di-sec-Butyl-p-phenylenediamine (101-96-2)

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] A strong irritant that may cause burns; [CAMEO] Highly irritating or corrosive to skin and eyes, based on animal studies; [eChemPortal: HPVIS] Causes burns; May cause skin sensitization; Toxic if swallowed; Absorbed through skin; [Aldrich MSDS] See p-Phenylenediamine.

Reactive GroupAmines, Aromatic
Reactivity Profile · 1 Eintrag

N,N'-DI-SEC-BUTYL-P-PHENYLENEDIAMINE reacts 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.

Air and Water ReactionsThis compound may be sensitive to prolonged exposure to air or light. Insoluble in water.
NFPA Hazard Classification · 3 Einträge

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and CategoriesAcute Tox. 3 (99%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

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.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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 · 1 Eintrag

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.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

Toxikologische Informationen

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.
Toxicity DataLCLo (rat) = 600 mg/m3/6h

Sicherheitsdaten

F
10-23
wgk
3
tsca
TSCA listed
ridadr
UN 2922 8/PG 2
hs_code
2921.51.5000
RTECS-Nr.
SS9040000
risk_code
25-34-43-50/53-41-38
Toxizität
LD50 oral in rat: 148mg/kg
hazard_code
C,N,T
safety_code
26-36/37/39-45-61-60
hazard_class
6.1(b)
packing_group
III
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten
101-96-2(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Irrit. 2Skin Sens. 1
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