101-96-2

Basic information

• Product Name: N,N'-Bis(1-methylpropyl)-1,4-phenylenediamine
• Synonyms: 1,4-Benzenediamine, N,N'-bis(1-methylpropyl)-;4-Benzenediamine,N,N’-bis(1-methylpropyl)-1;Antioxidant 22;antioxidant22;cp40182;Du Pont Gasoline Antioxidant No. 22;dupontgasolineantioxidantno22;Kerobit BPD
• CAS NO: 101-96-2
• Molecular Formula: C₁₄H₂₄N₂
• Molecular Weight: 220.35
• EINECS: 202-992-2
• Product Categories: Amines;C11 to C38;Nitrogen Compounds;efficiency antioxidant of gasoline
• Mol File: 101-96-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 17.8°C
• Boiling Point: 159 °C / 7mmHg
• Flash Point: 100°C
• Appearance: dark red liquid
• Density: 0.942 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.05Pa at 25℃
• Refractive Index: n20/D 1.539
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.67±0.50(Predicted)
• Water Solubility: <0.1 g/100 mL at 20 oC
• Stability: Stable. Combustible.
• BRN: 2805827
• CAS DataBase Reference: N,N'-Bis(1-methylpropyl)-1,4-phenylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Bis(1-methylpropyl)-1,4-phenylenediamine(101-96-2)
• EPA Substance Registry System: N,N'-Bis(1-methylpropyl)-1,4-phenylenediamine(101-96-2)

Safety Data

• Hazard Codes: C,N,T
• Statements: 25-34-43-50/53-41-38
• Safety Statements: 26-36/37/39-45-61-60
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• RTECS: SS9040000
• F: 10-23
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 101-96-2(Hazardous Substances Data)

Usage

Chemical Properties

dark red liquid

Uses

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

General Description

Amber to red or dark reddish black liquid.

Air & Water Reactions

N,N'-Bis(1-methylpropyl)-1,4-phenylenediamine may be sensitive to prolonged exposure to air or light. Insoluble in water.

Reactivity Profile

N,N'-Bis(1-methylpropyl)-1,4-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.

Fire Hazard

N,N'-Bis(1-methylpropyl)-1,4-phenylenediamine is combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion. Moderately toxic by inhalation and sh contact. Corrosive to skin. A mild allergen. Symptoms of exposure are sweating, flushmg, shortness of breath, and slow pulse. Combustible when exposed to heat or flame; can react with oxidzing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

Synthetic route

4-nitro-aniline (100-01-6) + butanone (78-93-3) → N,N'-di-sec-butyl p-phenylenediamine (101-96-2)

Conditions	Yield
With copper oxide-chromium oxide at 180℃; under 36775.4 Torr; Hydrogenation;
With platinum on activated charcoal at 160℃; under 29420.3 - 36775.4 Torr; Hydrogenation;

N-sec-butyl-4-phenylazo-aniline (101423-88-5) + butanone (78-93-3) → N,N'-di-sec-butyl p-phenylenediamine (101-96-2)

Conditions	Yield
With platinum on activated charcoal at 160℃; under 73550.8 Torr; Hydrogenation;

N-sec-butyl-N-nitroso-4-phenylazo-aniline (101289-90-1) + butanone (78-93-3) → N,N'-di-sec-butyl p-phenylenediamine (101-96-2)

Conditions	Yield
With platinum on activated charcoal at 160℃; under 73550.8 Torr; Hydrogenation;

butanone (78-93-3) + 1,4-phenylenediamine (106-50-3) → N,N'-di-sec-butyl p-phenylenediamine (101-96-2)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0 - 30℃; Temperature; Inert atmosphere;

N,N'-di-sec-butyl p-phenylenediamine (101-96-2) → N-(sec-butyl)-4-nitroaniline (4138-37-8) + [1,4]benzoquinone-bis-(N-sec-butyl oxime ) (109104-66-7)

Conditions	Yield
With Perbenzoic acid

N,N'-di-sec-butyl p-phenylenediamine (101-96-2) → N,N′-di-sec-butyl-N,N′-dinitroso-1,4-phenylenediamine (106476-75-9)

Conditions	Yield
With hydrogenchloride; sodium nitrite
With hydrogenchloride; sodium nitrite In water; hexan-1-ol at 20 - 40℃; for 2h;

pyrocatechol phosphorochloridite (1641-40-3) + N,N'-di-sec-butyl p-phenylenediamine (101-96-2) → N,N'-bis-benzo[1,3,2]dioxaphosphol-2-yl-N,N'-di-sec-butyl-benzene-1,4-diamine (10154-52-6)

Conditions	Yield
With triethylamine In benzene

d,l-2-ethylhexanal (123-05-7) + N,N'-di-sec-butyl p-phenylenediamine (101-96-2) + sodium tris(acetoxy)borohydride (56553-60-7) + sodium hydrogencarbonate (144-55-8) → N,N'-di-sec-butyl-N,N'-di-(2-ethylhexyl)-p-phenylenediamine (1295578-34-5)

Conditions	Yield
In n-heptane; dichloromethane

chloromethyltriethoxysilane (15267-95-5) + N,N'-di-sec-butyl p-phenylenediamine (101-96-2) → C28H56N2O6Si2

Conditions	Yield
In toluene at 80℃; for 2h; Reflux; Inert atmosphere;

Upstream product

• 78-93-3 butanone 
• 106-50-3 1,4-phenylenediamine 
• 101289-90-1 N-sec-butyl-N-nitroso-4-phenylazo-aniline 
• 101423-88-5 N-sec-butyl-4-phenylazo-aniline 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 4138-37-8 N-(sec-butyl)-4-nitroaniline 
• 109104-66-7 [1,4]benzoquinone-bis-(N-sec-butyl oxime ) 
• 106476-75-9 N,N′-di-sec-butyl-N,N′-dinitroso-1,4-phenylenediamine 
• 1295578-34-5 N,N'-di-sec-butyl-N,N'-di-(2-ethylhexyl)-p-phenylenediamine 

Relevant articles and documents

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Process for inhibiting the polymerization of vinyl aromatic compounds

A process is disclosed for inhibiting the polymerization of vinyl aromatic compounds, such as styrene, during its distillation. The process involves adding a mixture of at least two inhibitors to the vinyl aromatic compound. One such combination is N,N′-di-2-butyl-N,N′,4-dinitroso-1,4-diaminobenzene and dinitrocresol. A stabilizer such as N,N′-di-2-butyl-1,4-diaminobenzene can also be added.

Corrosion inhibiting composition

A composition, in contact with a corrodable metal surface, which composition comprises: (a) an aqueous-based or oil-based system; and (b) as inhibitor for protecting the metal surface against corrosion, at least one compound having the formula I: STR1 as well as salts or partial esters thereof wherein: n is 0 or an integer ranging from 1 to 20, R is a straight or branched chain C4 -C30 alkyl group, optionally interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C5 -C12 cycloalkyl group, a C6 -C10 aryl group optionally substituted by one, two or three C1 -C12 alkyl groups, or a C7 -C13 aralkyl group which is optionally substituted by a hydroxyl group; R1 is H or a straight- or branched chain C1 -C4 alkyl group; R2 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R3 is H, a straight or branched chain C1 -C4 alkyl group, --CH2 CO2 H or --CH2 CH2 CO2 H; R4 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R5 is H, a straight or branched chain C1 -C4 alkyl group, CH2 CO2 H or CH2 CH2 CO2 H; provided that at least one group R4 must be CO2 H, with the provisio, that compositions comprising an oil-based system and a compound having the formula STR2 wherein R, R1 and R2 are hydrogen or alkyl radicals, having a total from 10 to 38 C-atoms, are excluded.