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

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

Uses

Used in Adhesive Industry:
N,N'-Bis(1-methylpropyl)-1,4-phenylenediamine is used as a curing agent for preparing polyurethane adhesives. Its presence in the adhesive formulation enhances the curing process, leading to improved adhesive strength and performance.

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

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

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

N, N'-dialkyl phenylenediamine preparation method and application

The present invention discloses a N, N'-dialkyl phenylenediamine preparation method and application. The preparation method comprises the following steps: in a protective atmosphere, phenylenediamine and / or a phenylenediamine derivative is pre-reacted with a ketone and / or an aldehyde under acidic conditions, then a reducing agent is added for continued reaction to obtain a crude reaction product, and the crude reaction product is post processed to obtain N, N'-dialkyl phenylenediamine. According to the preparation method, no hydrogen, alkyl halide, high activity noble metal catalyst and the like are used, the safety is increased substantially, meanwhile the cost of raw materials can be effectively reduced, and the reaction conditions are very mild, energy consumption is low, the reaction efficiency is high, post processing is simple, a target product is high in purity, less in by-products and free of waste acid, and the obtained product N, N'-dialkyl phenylenediamine can be used as an anti-aging agent, an antioxidant, and the like, and can be widely used in fuel oil.

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.

2-Propanol derivatives as corrosion inhibitors

New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) STR1 or a derivative thereof in which R1, R2 and R3 are, independently, hydrogen, a C1 -C15 straight or branched chain alkyl residue, a C5 -C12 cycloalkyl residue, a C6 -C15 aryl residue or C7 -C12 alkaryl residue, and R4 and R5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that (a) R4 and R5 are not simultaneously hydrogen, (b) when R4 and R5 are each --CH2 --CH2 --OH, R1 and R2 are not simultaneously hydrogen and R3 is not a pentyl residue and (c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent; as well as salts thereof. Some of the compounds of formula I are new.

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.

Triazole-organodithiophosphate reaction product additives for functional fluids

New reaction products, useful as additives for functional fluids, are obtained by reacting, at elevated temperature, (A) a triazole having the formula IA or IB: STR1 wherein R7 is hydrogen or a C1 -C20 alkyl residue; R8 and R9 are the same or different and each is C1 -C20 alkyl, C3 -C20 alkenyl, C5 -C12 cycloalkyl, C7 -C13 aralkyl, C6 -C10 aryl or R8 and R9, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic residue or R8 and R9 is each a residue of formula: wherein X is O, S or N(R12), R12 is hydrogen or C1 -C20 alkyl, "alkylene" is a C1 -C12 alkylene residue and n is 0 or an integer from 1 to 6; R10 is hydrogen, C1 -C20 alkyl or C6 -C10 aryl or C7 -C18 alkyl phenyl; and R11 is hydrogen, C1 -C20 alkyl or a residue --CH2 NR8 R9 wherein R8 and R9 have their previous significance; with (B) an organodithiophosphate having the formula: STR2 in which R13 is a C1 -C20 alkyl or C7 -C18 alkyl phenyl or C7 -C13 aralkyl group, M is a metal ion of Group IA, IB, IIA, IIB, VB, VIB, VIIB or VIII of the Periodic System of Elements, and y is the valency of M.

Nickel stabilizers for synthetic polymers

New complexes of nickel salts of hydroxybenzoic acids are stabilizers for polymers. The complexes are prepared by reacting a nickel benzoate with a corresponding alcohol.

Piperidine derivatives

A composition comprising an organic material and, as stabiliser, a compound having the formula SPC1 And salts thereof, wherein R1 and R2 are the same or different and each is an alkyl residue having from 1 to 12 carbon atoms or R1 and R2, together with the carbon atom to which they are bound, form a cycloalkyl residue having from 5 to 12 carbon atoms in the ring, Y is O, hydrogen, a straight or branched alkyl residue having from 1 to 20 carbon atoms, an alkenyl or alkynyl residue having from 3 to 12 carbon atoms, an aralkyl residue having from 7 to 12 carbon atoms or a group having the formula EQU1 wherein R is hydrogen, or a methyl or phenyl residue and R3 is hydrogen or a straight- or branched chain alkyl residue having from 1 to 12 carbon atoms.