793-24-8

Basic information

• Product Name: N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine
• Synonyms: SANTOFLEX(R) 13 PASTILLES;N-(1,3-DIMETHYLBUTYL)-N'-PHENYL-P-PHENYLENEDIAMINE;N-(1,3-DIMETHYLBUTYL)-N'-PHENYL-1,4-PHENYLENEDIAMINE;N-(4-METHYL-2-PENTYL)-N'-PHENYL-1,4-PHENYLENEDIAMINE;ANTOZITE 67P;4-[(4-METHYL-2-PENTYL)AMINO]DIPHENYLAMINE;6PPD;4-Benzenediamine,N-(1,3-dimethylbutyl)-N’-phenyl-1
• CAS NO: 793-24-8
• Molecular Formula: C₁₈H₂₄N₂
• Molecular Weight: 268.4
• EINECS: 212-344-0
• Product Categories: Industrial/Fine Chemicals;ANTIDEGRADANTS;Indazoles
• Mol File: 793-24-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 45-46°C
• Boiling Point: 260°C
• Flash Point: 204°C
• Appearance: Purple flakes
• Density: 0.986~1.00g/cm3
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 6.73±0.32(Predicted)
• Water Solubility: <0.1 g/100 mL at 17 oC
• CAS DataBase Reference: N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine(793-24-8)
• EPA Substance Registry System: N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine(793-24-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-43-50/53
• Safety Statements: 36/37-60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• RTECS: ST0900000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 793-24-8(Hazardous Substances Data)

Usage

Chemical Properties

Gray purple to purplish brown flake or granular

General Description

Purple flakes.

Air & Water Reactions

N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

You should protect N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine from exposure to strong oxidizing agents such as chlorine or hydrogen peroxide. N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine will ignite if heated strongly.

Fire Hazard

N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine is combustible.

Synthetic route

4-methyl-2-pentanone (108-10-1) + N-phenylphenylene-1,4-diamine (101-54-2) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
With hydrogen at 99.84℃; under 18751.9 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Time; Autoclave;	100%
With hydrogen; pyrographite at 20 - 150℃; under 22052.2 Torr; for 0.1h; Autoclave;	99.4%
With platinum on activated charcoal; isopropyl alcohol at 50 - 150℃; under 36775.4 Torr; Hydrogenation;

C18H22N2 (63302-40-9) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
With palladium on activated charcoal; hydrogen In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; under 7500.75 Torr; Solvent; Temperature;	92.6%

p-nitrosodiphenylamine (156-10-5) + 4-methyl-2-pentanone (108-10-1) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
With platinum on activated charcoal; isopropyl alcohol at 50 - 150℃; under 25742.8 Torr; Hydrogenation;

4-ntrophenyl(phenyl)amine (836-30-6) + 4-methyl-2-pentanone (108-10-1) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
With platinum on activated charcoal; isopropyl alcohol at 50 - 150℃; under 25742.8 Torr; Hydrogenation;

N-[1,3-Dimethyl-but-(E)-ylidene]-N'-phenyl-benzene-1,4-diamine → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
With formic acid; palladium on activated charcoal at 85℃; Yield given;

4-ntrophenyl(phenyl)amine (836-30-6) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 5percent Pd/C 2: 5percent palladium-on-carbon / 85 °C 3: HCOOH / 5percent Pd/C / 85 °C View Scheme
Multi-step reaction with 3 steps 1: formic acid / 5percent Pd/C / 85 °C 2: 5percent palladium-on-carbon / 85 °C 3: HCOOH / 5percent Pd/C / 85 °C View Scheme

4-methyl-2-pentanone (108-10-1) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5percent palladium-on-carbon / 85 °C 2: HCOOH / 5percent Pd/C / 85 °C View Scheme

N-phenylphenylene-1,4-diamine (101-54-2) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5percent palladium-on-carbon / 85 °C 2: HCOOH / 5percent Pd/C / 85 °C View Scheme

2-amino-4-methylpentane (15761-50-9, 34017-11-3, 54548-48-0, 108-09-8) + 4-(phenylimino)cyclohexa-2,5-dienone (2406-04-4) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
In methanol

4-methyl-2-pentanone (108-10-1) + N-phenylphenylene-1,4-diamine (101-54-2) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) + C18H22N2 (63302-40-9)

Conditions	Yield
With palladium on activated charcoal; hydrogen at 200℃; under 30003 Torr; Reagent/catalyst;
With hydrogen at 160℃; under 22502.3 Torr; for 4h; Autoclave;

4-methyl-2-pentanone (108-10-1) + N-phenylphenylene-1,4-diamine (101-54-2) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) + aniline (62-53-3)

Conditions	Yield
With 10% Pd/C; hydrogen at 160℃; under 22502.3 Torr; for 4h; Autoclave;

4-methyl-pent-3-en-2-one (141-79-7) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen 2: pyrographite; ; hydrogen / 0.1 h / 20 - 150 °C / 22052.2 Torr / Autoclave View Scheme

benzene (71-43-2) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / chloroform; benzene / 5 h / 50 °C / Industrial scale 2: tetramethyl ammoniumhydroxide; platinum on carbon; hydrogen / water / 80 °C / 11251.1 Torr 3: pyrographite; ; hydrogen / 0.1 h / 20 - 150 °C / 22052.2 Torr / Autoclave View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / chloroform; benzene / 5 h / 50 °C / Industrial scale 2: hydrogen / 200 °C / Industrial scale 3: tetramethyl ammoniumhydroxide; platinum on carbon; hydrogen / water / 80 °C / 11251.1 Torr 4: pyrographite; ; hydrogen / 0.1 h / 20 - 150 °C / 22052.2 Torr / Autoclave View Scheme

phenol (108-95-2) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonia / 450 °C / 760.05 Torr / Industrial scale 2: tetramethyl ammoniumhydroxide; platinum on carbon; hydrogen / water / 80 °C / 11251.1 Torr 3: pyrographite; ; hydrogen / 0.1 h / 20 - 150 °C / 22052.2 Torr / Autoclave View Scheme

nitrobenzene (98-95-3) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen / 200 °C / Industrial scale 2: tetramethyl ammoniumhydroxide; platinum on carbon; hydrogen / water / 80 °C / 11251.1 Torr 3: pyrographite; ; hydrogen / 0.1 h / 20 - 150 °C / 22052.2 Torr / Autoclave View Scheme
Multi-step reaction with 3 steps 1: tetramethyl ammoniumhydroxide / water / 2.1 h / 75 °C / 55 Torr / Dean-Stark 2: hydrogen; 5%-palladium/activated carbon / 0.5 h / 80 °C / 11251.1 Torr / Autoclave 3: 3 % platinum on carbon; hydrogen / 0.5 h / 155 °C / 26252.6 Torr / Autoclave View Scheme

aniline (62-53-3) → N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetramethyl ammoniumhydroxide / water / 2.1 h / 75 °C / 55 Torr / Dean-Stark 2: hydrogen; 5%-palladium/activated carbon / 0.5 h / 80 °C / 11251.1 Torr / Autoclave 3: 3 % platinum on carbon; hydrogen / 0.5 h / 155 °C / 26252.6 Torr / Autoclave View Scheme

oxalyl dichloride (79-37-8) + N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) → N,N'-bis(4-anilinophenyl)-N,N'-bis(4-methylpentan-2-yl)oxamide

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 48h; Cooling with ice;	86%

prop-2-ene-1-thiol (870-23-5) + N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) → 3-(allylsulfanyl)-N1-(4-methyl-2-pentyl)-N4-phenyl-1,4-benzenediamine

Conditions	Yield
Stage #1: N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine With magnesium sulfate; silver(l) oxide In toluene at 25℃; for 15h; Stage #2: prop-2-ene-1-thiol In ethanol at 25℃;	65%

ethene (74-85-1) + N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) → C22H32N2 (944727-84-8) + C24H36N2 + C24H36N2 (944727-85-9)

Conditions	Yield
diethylaluminium chloride In hexane for 12 - 16h; Product distribution / selectivity;	A 47.2% B n/a C n/a

Adipic acid (124-04-9) + N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) → N,N'-bis(4-anilinophenyl)-N,N'-bis(4-methylpentan-2-yl)adipamide

Conditions	Yield
Stage #1: Adipic acid With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran; chloroform for 8h; Reflux; Stage #2: N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine With pyridine In tetrahydrofuran at 20℃; Cooling with ice;	39%

N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) → 2-methyl-N4-(4-methyl-2-pentyl)-N7-phenyl-2,3-dihydro-1-benzothiophene-4,7-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Ag2O; MgSO4 / toluene / 15 h / 25 °C 1.2: 65 percent / ethanol / 25 °C 2.1: 75 percent / 150 - 155 °C View Scheme

thiophosgene (463-71-8) + N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) + potassium carbonate (584-08-7) → N-(4-anilinophenyl)-N-(1,3-dimethyl-butyl)-thiocarbamate-O-methyl ester (118745-60-1)

Conditions	Yield
In methanol; chloroform

N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) + methyl iodide (74-88-4) → N-(4-anilinophenyl)-N-(1,3-dimethyl-butyl)-dithiocarbamate methyl ester (118745-59-8)

Conditions	Yield
With carbon disulfide; sodium hydroxide In tetrahydrofuran

1-Decene (872-05-9) + N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) → N'-phenyl-N-2-isohexyl-[2-(2-isodecyl)-p-phenylene]diamine

Conditions	Yield
With tetrabutylammomium bromide; aluminum (III) chloride at 160 - 170℃; for 27h; Friedel Crafts Alkylation;

N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) + 4-hydroxy-3,5-di-tert-butylphenylpropionic acid (20170-32-5) → 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-N-(1,3-dimethyl-butyl)-N-(4-phenylamino-phenyl)propionamide

Conditions	Yield
With boric acid In toluene for 15h; Dean-Stark; Inert atmosphere; Reflux;

N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) + methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate (6386-38-5) → 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-N-(1,3-dimethyl-butyl)-N-(4-phenylamino-phenyl)propionamide

Conditions	Yield
With boric acid In toluene for 15h; Dean-Stark; Inert atmosphere; Reflux; Molecular sieve;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4-(3-hydroxypropyl)-2,6-di-tert-butylphenol (36294-23-2) + N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (793-24-8) → 4-(3-{4,6-bis-[(1,3-dimethyl-butyl)-(4-phenylamino-phenyl)amino]-[1,3,5]triazin-2-yloxy}propyl)-2,6-di-tert-butyl-phenol

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 4-(3-hydroxypropyl)-2,6-di-tert-butylphenol With triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine In tetrahydrofuran at 65℃; for 15h; Inert atmosphere;

Upstream product

• 62-53-3 aniline 
• 108-10-1 4-methyl-2-pentanone 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 63302-40-9 C₁₈H₂₂N₂ 
• 98-95-3 nitrobenzene 
• 108-95-2 phenol 
• 71-43-2 benzene 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 15761-50-9 2-amino-4-methylpentane 
• 2406-04-4 4-(phenylimino)cyclohexa-2,5-dienone 
• 836-30-6 4-ntrophenyl(phenyl)amine 
• 156-10-5 p-nitrosodiphenylamine 

Downstream Products

• 944727-84-8 C₂₂H₃₂N₂ 
• 944727-85-9 C₂₄H₃₆N₂ 
• 118745-59-8 N-(4-anilinophenyl)-N-(1,3-dimethyl-butyl)-dithiocarbamate methyl ester 
• 118745-60-1 N-(4-anilinophenyl)-N-(1,3-dimethyl-butyl)-thiocarbamate-O-methyl ester 

Relevant articles and documents

Effects of pore structure of MgO-templated mesoporous carbon on its supported Pt catalysts for reductive alkylation of p-aminodiphenylamine with methyl isobutyl ketone

Mesoporous carbon (MC) was prepared by the nano-MgO template method and used as a support for the preparation of a Pt-based reductive alkylation catalyst. N2 physical adsorption-desorption, scanning electron microscopy, transmission electron microscopy and X-ray diffraction were used to characterize the carbon supports and supported Pt catalysts. The effects of the pore structure of the Pt/MC catalyst on its performance for reductive alkylation of p-aminodiphenylamine with methyl isobutyl ketone were investigated. The results show that the surface area and pore structure of the MgO-templated mesoporous carbons can be modulated directionally by varying the size of nano-MgO particles and the MgO/PF mass ratio. The catalytic activity and stability of the catalysts for N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine synthesis increases with an increase in the pore size of the mesoporous carbons. Complete conversion of p-ADPA and 100% selectivity to 6PPD were obtained over Pt/MC50(1/1) within 4 hours, which could maintain a high catalytic activity after being reused 10 times. The characterization results indicate that there was an obvious decrease in the BET specific surface area, pore volume and Pt specific surface area of all used catalysts compared with the fresh catalysts, and the trend was more obvious with the decrease of catalyst pore size, which should be the primary reason for the degradation of catalytic performance.

Method for preparation of anti-aging agent 6PPD by using micro-reactor

The invention discloses a method for preparation of an anti-aging agent 6PPD by using a micro-reactor; a homogeneous solution of p-aminodiphenyl amine and methyl isobutyl ketone and hydrogen gas are subjected to a reaction in a gas-liquid reactor, then are introduced into a solid-liquid reactor and are subjected to a reaction, and the obtained reaction liquid repeats the above operations. Compared with the prior art, the gas-liquid reactor and the solid-liquid reactor are connected in series, the gas-solid-liquid three-phase reaction is performed in a micro-channel, and eventually, the conversion rate of raw materials is improved and the reaction time is shortened. The micro-reactor has the advantages of large specific surface area and strong heat transfer and mass transfer abilities, and enables the reactions to be carried out efficiently; and the reaction temperature, time and material ratio and other conditions can be precisely controlled through the micro-channel reactor, by-products are reduced, and the security is improved.

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