3081-14-9

Basic information

• Product Name: N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE
• Synonyms: 77PD;N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE;SANTOFLEX(R) 77;(1,4-dimethylpentyl)phenylenediamine;4-Benzenediamine,N,N’-bis(1,4-dimethylpentyl)-1;77ppd;antioxidant4030;eastozone
• CAS NO: 3081-14-9
• Molecular Formula: C₂₀H₃₆N₂
• Molecular Weight: 304.51
• EINECS: 221-375-9
• Mol File: 3081-14-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 435.32°C (rough estimate)
• Flash Point: 234.8°C
• Appearance: /
• Density: 0.9452 (rough estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.6450 (estimate)
• PKA: 8.59±0.50(Predicted)
• Water Solubility: 800μg/L at 22℃
• CAS DataBase Reference: N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE(3081-14-9)
• EPA Substance Registry System: N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE(3081-14-9)

Safety Data

• Hazardous Substances Data: 3081-14-9(Hazardous Substances Data)

Usage

Uses

N-Cyclohexyl-2-benzothiazyl sulphenamide is an intermediate in organic synthesis; an accelerator in natural and styrene-butadienethiazyl sulfenamide rubber.

General Description

Deep red slightly viscous liquid with an aromatic odor.

Air & Water Reactions

N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE may be sensitive to heat, air and moisture during long term storage. Insoluble in water.

Reactivity Profile

N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE may react with oxidizing agents . 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.

Health Hazard

SYMPTOMS: Symptoms of exposure to N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE may include eye or skin irritation.

Fire Hazard

N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE is probably combustible.

Flammability and Explosibility

Nonflammable

Synthetic route

5-Methyl-2-hexanone (110-12-3) + 1,4-phenylenediamine (106-50-3) → N-(1,4-dimethylpentyl)-p-phenylenediamine (63302-43-2) + N,N'-bis-(1,4-dimethylpentyl)-1,4-phenylenediamine (3081-14-9) + N-(1,4-dimethyl-pentylidene)-benzene-1,4-diamine + N,N'-bis-(1,4-dimethyl-pentylidene)-benzene-1,4-diamine

Conditions	Yield
With hydrogen; (η4-1,5-cyclooctadiene)bis(triphenylphosphine)iridium hexafluorophosphate; Montmorillonite K10 at 80℃; under 7600 Torr; for 24h; Condensation; reduction;	A 10% B 48% C 19% D 23%
With hydrogen; Shrock-Osborn catalyst; Montmorillonite K10 at 80℃; under 7600 Torr; for 24h; Condensation; reduction;	A 20 % Spectr. B 75 % Spectr. C 3 % Spectr. D 2 % Spectr.

5-Methyl-2-hexanone (110-12-3) + 1,4-phenylenediamine (106-50-3) → N,N'-bis-(1,4-dimethylpentyl)-1,4-phenylenediamine (3081-14-9) + N,N'-bis-(1,4-dimethyl-pentylidene)-benzene-1,4-diamine

Conditions	Yield
With hydrogen; Shrock-Osborn catalyst; Montmorillonite K10 at 80℃; under 7600 Torr; for 24h; Condensation; reduction;	A 99 % Spectr. B 1 % Spectr.

5-Methyl-2-hexanone (110-12-3) + 1,4-phenylenediamine (106-50-3) → N,N'-bis-(1,4-dimethylpentyl)-1,4-phenylenediamine (3081-14-9)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 10 - 30℃; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;

5-Methyl-2-hexanone (110-12-3) + 4-nitro-aniline (100-01-6) → N,N'-bis-(1,4-dimethylpentyl)-1,4-phenylenediamine (3081-14-9)

Conditions	Yield
Stage #1: 5-Methyl-2-hexanone; 4-nitro-aniline at 120 - 124℃; for 24h; Autoclave; Stage #2: With palladium on activated charcoal; hydrogen at 155 - 160℃; under 15001.5 Torr; for 1.5h; Reagent/catalyst; Pressure;

Upstream product

• 110-12-3 5-Methyl-2-hexanone 
• 100-01-6 4-nitro-aniline 
• 106-50-3 1,4-phenylenediamine 

Relevant articles and documents

Preparation method of anti-aging agent TAPDT and intermediate thereof

The invention discloses a preparation method of an anti-aging agent TAPDT and an intermediate thereof. The preparation method comprises the following steps: carrying out a condensation dehydration reaction on melamine and formic acid to generate 2,4,6-tri(formamido)-1,3,5-triazine, then subjecting 2,4,6-tri(formamido)-1,3,5-triazine to reacting with parachloronitrobenzene under the catalysis of sodium carbonate to generate 2,4,6-tri(4-nitrophenyl)-1,3,5-triazine, and carrying out a hydrogenation reversion reaction on 2,4,6-tri(4-nitrophenyl)-1,3,5-triazine and methyl isoamyl ketone under the catalysis of a catalyst to obtain the anti-aging agent TAPDT. The method has the advantages of usage of easily available raw materials, low cost, high reaction selectivity and yield, few byproducts, low cost and good quality.

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.

Polymerisation inhibitor

A monomer composition, stabilized against premature polymerization, comprising: a) an ethylenically unsaturated monomer or mixture of monomers polymerizable by free radical initiation, and b) an effective amount, sufficient to inhibit premature polymerization of component (a) of a mixture of: i) 1 to 99% by weight, based on the total weight of components (i) and (ii), of a mixture of at least one aromatic amine and at least one organic acid in a molar ratio of 10:1 to 1:10, and ii) 99 to 1% by weight, based on the total weight of components (i) and (ii), of at least one stable radical compound.