10081-67-1

Basic information

• Product Name: Bis[4-(2-phenyl-2-propyl)phenyl]amine
• Synonyms: 4-(1-methyl-1-phenylethyl)-n-[4-(1-methyl-1-phenylethyl)phenyl]-benzenamin;4-(1-methyl-1-phenylethyl)-N-[4-(1-methyl-1-phenylethyl)phenyl]-Benzenamine;4,4’Bis(pehnylisopropyl)diphenylamine;4,4’-Dicumyl-diphenylamine;antioxidantky-405;Benzenamine,4-(1-methyl-1-phenylethyl)-N-[4-(1-methyl-1-phenylethyl)phenyl]-;4,4'-BIS(ALPHA,ALPHA-DIMETHYLBENZYL)DIPHENYLAMINE;4-(1-methyl-1-phenylethyl)-N-[4-(1-methyl-1-phenylethyl)phenyl]aniline
• CAS NO: 10081-67-1
• Molecular Formula: C₃₀H₃₁N
• Molecular Weight: 405.57
• EINECS: 233-215-5
• Product Categories: Industrial/Fine Chemicals;Organics;It is especially effective in polyisoprene, Neoprene, nitrile, EPDM, HNBR and acrylic rubbers
• Mol File: 10081-67-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 100°C
• Boiling Point: 535.2 °C at 760 mmHg
• Flash Point: 292 °C
• Appearance: /
• Density: 1.061 g/cm³
• Vapor Pressure: 1.58E-11mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Practically insoluble in water
• PKA: 1.59±0.50(Predicted)
• Water Solubility: 6.7μg/L at 20℃
• CAS DataBase Reference: Bis[4-(2-phenyl-2-propyl)phenyl]amine(CAS DataBase Reference)
• NIST Chemistry Reference: Bis[4-(2-phenyl-2-propyl)phenyl]amine(10081-67-1)
• EPA Substance Registry System: Bis[4-(2-phenyl-2-propyl)phenyl]amine(10081-67-1)

Safety Data

• Statements: 36/37/38-53
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 10081-67-1(Hazardous Substances Data)

Usage

Description

4,4'-Diphenylisopropyl diphenylamine (Antioxidant HS-911) is a kind of high-efficient nontoxic Antioxidant to replace D, A, RD and so on which are carcinogenic. HS-911 can be used in NR, IIR, SBR, NBR, BR, CR and their blend, and is especially efficient in protecting CR from thermal aging. It can also be used in plastic industry. HS-911 not only can protect vulcanized rubber from thermal aging, light aging, ozone aging and damage caused by repeating deformation, but also has a passivating effect on heavy metal and transition metal.

Uses

Because of its light contamination, HS-911 can be used in insulative and protective rubber sheeting for color wires and cables as well as common color rubber products in place of Antioxidant 264, SP, 2264, MB, DNP, etc, to greatly reduce the production cost. In carbon black rubber, it has oxidation resistance of amine type, and will not pollute products. HS-911 can be exclusively used or used together with other Antioxidant . Normal dosage in rubber is 2-3 phr.

Application

Diphenylamine antioxidant CAPOX 445, 4, 4'-Bis (alpha, alpha-dimethylbenzyl) diphenylamine, is a highly effective non-discoloring aromatic amine type antioxidant finding utility as a thermal stabilizer in a wide variety of applications, including polyolefins, styrenics, polyols, hot melt adhesives, lubricants and polyamides. Excellent performance at processing temperatures, and strong synergy with other types of antioxidants such as phenolics and phosphites, makes CAPOX 445 an excellent choice as a component of your thermal stabilizer package.

Flammability and Explosibility

Nonflammable

Industrial uses

This product is one of the few kinds of antioxidant, which is non-toxic, tasteless, light colored. The anti- oxygen effect is similar America in Uniroyal. It is widely used in various kinds of elastomers. It can be used in polyethylene, polypropylene, polyvinyl chloride and other color master batch. It can also be used as antioxidant in polyurethane foam, rubber wire, cable, food package and adhesive, especially in neoprene colorful cable's jacket for its excellent resistance to heat, light, and aging. In polyether this product can be used as light-resistant and anti-aging antioxidant, also as antioxidant for lubricating oil.It is especially effective to be used in neoprene acrylate rubber, polyether polyalcohol for its resistance to aging caused by high temperature and light. When used together with sulfur-contained antioxidant, it has operational effect.

Synthesis

a, first raw material diphenylamine 50.0g into a reaction vessel equipped with a stirrer, reflux condenser, heated to diphenylamine added to melt;After completely melted, a mixed catalyst prepared from 1.5 g of magnesium chloride and 1.5 g of anhydrous stannous chloride was added, and heating and stirring were continued for mixing; b. After step a is mixed uniformly, 80.5 g of α-methylstyrene is added dropwise, and the dropwise addition time is 0.5 h. After the dropwise addition is completed, the reaction temperature is controlled to be 130-140° C., and the reaction is completed at this temperature for 1 h. The reaction is completed. ; c, after the end of the reaction, the resulting reaction solution was cooled, then add 60 of petroleum ether 140g and methanol 5g mixed solvent, dropped to 25 ± 2 °C cooling crystallization; d, after the end of crystallization, followed by filtration, petroleum ether and water washing, and then dried at 45 °C for 14 hours, dried to obtain the antioxidant 4,4 '- bis (α, α- dimethyl benzyl) diphenylamine . The product obtained in this example was white crystal with a yield of 85% and a purity of 98.24%

InChI:InChI=1/C30H31N/c1-29(2,23-11-7-5-8-12-23)25-15-19-27(20-16-25)31-28-21-17-26(18-22-28)30(3,4)24-13-9-6-10-14-24/h5-22,31H,1-4H3

Synthetic route

diphenylamine (122-39-4) + isopropenylbenzene (98-83-9) → bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) + 4-(α,α-dimethylbenzyl)diphenylamine

Conditions	Yield
With Al-MSU-G at 90℃; for 6h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time;	A 97.2% B n/a
With acid-treated clay catalyst Engelhard F-24 In o-xylene at 89.9℃; for 12h; Product distribution; Irradiation; other alkylating agent, var. catalyst, var. temp, var. solvent, var. time, also without sonication, and in air, also reused catalysts;

diphenylamine (122-39-4) + isopropenylbenzene (98-83-9) → bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1)

Conditions	Yield
With zinc(II) chloride In ethanol; 1,2-dichloro-ethane at 185℃; Solvent; Temperature; Reagent/catalyst; Flow reactor; regioselective reaction;	89%
Stage #1: diphenylamine With tin(ll) chloride; magnesium chloride Heating; Stage #2: isopropenylbenzene at 130 - 140℃; for 1.5h; Reagent/catalyst; Temperature;	85%
With 2-methylbenzene-1,4-diol In toluene at 60 - 125℃; Inert atmosphere;	38.5 g

2,4-dimethyl-1-heptene (19549-87-2, 127388-21-0, 127388-22-1) + N-phenyl-1-naphthylamine (90-30-2) + diphenylamine (122-39-4) + isopropenylbenzene (98-83-9) → 4-nonyldiphenylamine + 4-α-methylstyryl-4'-nonyldiphenylamine + 4,4'-dinonyldiphenylamine + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) + 4-(α,α-dimethylbenzyl)diphenylamine

Conditions	Yield
Stage #1: N-phenyl-1-naphthylamine; diphenylamine; Fulcat 22B at 220℃; under 15.0015 Torr; for 1h; Stage #2: 2,4-dimethyl-1-heptene at 130 - 220℃; for 6.5h; Stage #3: isopropenylbenzene at 130 - 134℃; for 3h; Product distribution / selectivity;

...Expand

2,4-dimethyl-1-heptene (19549-87-2, 127388-21-0, 127388-22-1) + diphenylamine (122-39-4) + isopropenylbenzene (98-83-9) → 4-nonyldiphenylamine + 4-α-methylstyryl-4'-nonyldiphenylamine + 4,4'-dinonyldiphenylamine + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) + 4-(α,α-dimethylbenzyl)diphenylamine

Conditions	Yield
Stage #1: 2,4-dimethyl-1-heptene; diphenylamine; Fulcat 22B at 80 - 220℃; under 15.0015 Torr; for 5.5 - 7.5h; Stage #2: isopropenylbenzene at 130 - 134℃; for 3h; Product distribution / selectivity;

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) + ethyl 10-bromoanthracene-9-carboxylate → ethyl 10-[bis[4-(1-methyl-1-phenylethyl)phenyl]amino]anthracene-9-carboxylate

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 90℃; for 3h; Inert atmosphere;	90%

9,10-Dibromoanthracene (523-27-3) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → N9,N9,N10,N10-tetrakis(4-(2-phenylpropan-2-yl)phenyl)anthracene-9,10-diamine

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In toluene for 10h; Reflux;	80%

ethyl 2-bromoisobutyrate (600-00-0) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → 3,3-dimethyl-5-(2-phenylpropan-2-yl)-1-(4-(2-phenylpropan-2-yl)phenyl)indolin-2-one

Conditions	Yield
With [2,2]bipyridinyl; copper diacetate; potassium carbonate In acetonitrile at 120℃; for 12h; Schlenk technique; Inert atmosphere;	80%

2-bromospiro[fluorenyl-9,8'-indolo[3,2,1-de]acridine] + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C61H48N2

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Inert atmosphere; Heating;	70%

1-bromo-2,3-dichlorobenzene (56961-77-4) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C66H63ClN2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate at 130℃; Inert atmosphere;	66.2%

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) + 4-Fluoronitrobenzene (350-46-9) → bis[4-(2-phenyl-2-isopropyl)phenyl]-4-nitrophenylamine (1243278-12-7)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 120℃; for 24h;	63%
With sodium hydride In dimethyl sulfoxide at 120℃; for 48h;	50%
With sodium hydride In dimethyl sulfoxide at 120℃; for 48h;	50%

1.4-dibromobenzene (106-37-6) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → N-(4-bromophenyl)-4-(2-phenylpropan-2-yl)-N-(4-(2-phenylpropan-2-yl)phenyl)benzeneamine (1310961-36-4)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene at 120℃; for 7h; Inert atmosphere;	62%

iodobenzene (591-50-4) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C36H35N (259218-10-5)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 8h; Buchwald-Hartwig reaction; Reflux; Inert atmosphere;	55%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 8h; Inert atmosphere; Reflux;	55%

4,4,4-trifluorobutyric acid (406-93-9) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → 4-(2-phenylpropan-2-yl)-N-(4-(2-phenylpropan-2-yl)phenyl)-N-(3,3,3-trifluoropropyl)aniline

Conditions	Yield
With di-tert-butyl peroxide; copper(II) hexafluoroacetylacetonate; 9-mesitylacridine at 35℃; for 24h; Inert atmosphere; Irradiation;	51%

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) + 7-bromo-10-hexyl-10H-phenothiazine-3-carbaldehyde (312924-97-3) → 7-(bis(4-(2-phenylpropan-2-yl)phenyl)amino)-10-hexyl-10H-phenothiazine-3-carbaldehyde (1618093-71-2)

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene Reflux; Inert atmosphere;	45%

carbon tetrabromide (558-13-4) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → 2,7-bis(1-methyl-1-phenylethyl)-N,N-bis[4-(1-methyl-1-phenylethyl)phenyl]acridin-9-amine

Conditions	Yield
In toluene at 20℃; Rate constant; Irradiation; photoinduced reaction of diarylamines with CBr4; spectral study; intermediates formation; spectral and kinetic properties of intermediates;
In toluene at 20℃; Irradiation;
In hexane Irradiation;

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → BBTPA (1243278-16-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / dimethyl sulfoxide / 48 h / 120 °C 2: palladium on activated charcoal; hydrazine hydrate / 12 h / Reflux; Inert atmosphere 3: 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate / toluene / 10 h / Reflux; Inert atmosphere View Scheme

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → bis[4-(2-phenyl-2-isopropyl)phenyl]-4-aminophenylamine (1243278-14-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / dimethyl sulfoxide / 48 h / 120 °C 2: palladium on activated charcoal; hydrazine hydrate / 12 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / dimethyl sulfoxide / 48 h / 120 °C 2: hydrazine hydrate / palladium 10% on activated carbon / ethanol / 90 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / dimethyl sulfoxide / 24 h / 120 °C 2: palladium on activated charcoal; hydrazine hydrate / ethanol / 12 h / Reflux View Scheme

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → N,N-bis(4-nitrophenyl)-N',N'-bis[4-(2-phenyl-2-isopropyl)phenyl]-1,4-phenylenediamine (1246049-04-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / dimethyl sulfoxide / 48 h / 120 °C 2: hydrazine hydrate / palladium 10% on activated carbon / ethanol / 90 °C 3: cesium fluoride / dimethyl sulfoxide / 24 h / 120 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / dimethyl sulfoxide / 24 h / 120 °C 2: palladium on activated charcoal; hydrazine hydrate / ethanol / 12 h / Reflux 3: cesium fluoride / dimethyl sulfoxide / 24 h / 120 °C View Scheme

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → N,N-bis(4-aminophenyl)-N',N'-bis[4-(2-phenyl-2-isopropyl)phenyl]-1,4-phenylenediamine (1246048-80-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydride / dimethyl sulfoxide / 48 h / 120 °C 2: hydrazine hydrate / palladium 10% on activated carbon / ethanol / 90 °C 3: cesium fluoride / dimethyl sulfoxide / 24 h / 120 °C 4: hydrazine / palladium 10% on activated carbon / ethanol / 90 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydride / dimethyl sulfoxide / 24 h / 120 °C 2: palladium on activated charcoal; hydrazine hydrate / ethanol / 12 h / Reflux 3: cesium fluoride / dimethyl sulfoxide / 24 h / 120 °C 4: palladium on activated charcoal; hydrazine hydrate / ethanol / 12.5 h / 90 °C / Reflux View Scheme

1.4-dibromobenzene (106-37-6) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C80H79N3

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate / toluene / 7 h / 120 °C / Inert atmosphere 2: 1,1'-bis-(diphenylphosphino)ferrocene; tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate / toluene / 5 h / 110 °C / Inert atmosphere View Scheme

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C39H33N3O2S (1350319-91-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium t-butanolate; tri-tert-butyl phosphine; palladium diacetate / toluene; icosane / 2 h 2: acetonitrile / 4 h / 20 °C View Scheme

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C45H43N3O4S (1350319-92-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium t-butanolate; tri-tert-butyl phosphine; palladium diacetate / toluene; icosane / 2 h 2: acetonitrile / 4 h / 20 °C 3: potassium carbonate / acetonitrile / 2 h / 80 °C View Scheme

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C41H35N3O4S (1350319-94-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium t-butanolate; tri-tert-butyl phosphine; palladium diacetate / toluene; icosane / 2 h 2: acetonitrile / 4 h / 20 °C 3: potassium carbonate / acetonitrile / 2 h / 80 °C 4: toluene-4-sulfonic acid / toluene / 4 h / 80 °C View Scheme

2-bromothiophene (1003-09-4) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C34H33NS (1350319-90-2)

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In icosane; toluene for 2h;	43.3 g

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) + 7-bromo-10-hexyl-10H-phenothiazine-3-carbaldehyde (312924-97-3) → 3-(7-(bis(4-(2-phenylpropan-2-yl)phenyl)amino)-10-hexyl-10H-phenothiazin-3-yl)-2-cyanoacrylic acid (1618093-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; tri-tert-butyl phosphine; potassium tert-butylate / toluene / Reflux; Inert atmosphere 2: piperidine / acetonitrile; chloroform / 10 h / Reflux View Scheme

(S)-epichlorohydrin (67843-74-7) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C33H36ClNO

Conditions	Yield
With acetic acid at 60 - 65℃; for 48h;

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → (R)-3-(4,4'-bis(α,α-dimethylbenzyl))diphenylaminopropene oxide

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 48 h / 60 - 65 °C 2: sodium hydroxide / diethyl ether / 2 h / Reflux View Scheme

bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → (S)-3-(4,4'-bis(α,α-dimethylbenzyl))diphenylaminopropene oxide

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 48 h / 60 - 65 °C 2: sodium hydroxide / diethyl ether / 2 h / Reflux View Scheme

(R)-(-)-epichlorohydrin (51594-55-9) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C33H36ClNO

Conditions	Yield
With acetic acid at 60 - 65℃; for 48h;

Upstream product

• 19549-87-2 2,4-dimethyl-1-heptene 
• 90-30-2 N-phenyl-1-naphthylamine 
• 122-39-4 diphenylamine 
• 98-83-9 isopropenylbenzene 

Downstream Products

• 1350319-91-3 C₃₉H₃₃N₃O₂S 
• 1350319-92-4 C₄₅H₄₃N₃O₄S 
• 1350319-94-6 C₄₁H₃₅N₃O₄S 
• 1350319-90-2 C₃₄H₃₃NS 
• 1618093-69-8 3-(7-(bis(4-(2-phenylpropan-2-yl)phenyl)amino)-10-hexyl-10H-phenothiazin-3-yl)-2-cyanoacrylic acid 
• 1618093-71-2 7-(bis(4-(2-phenylpropan-2-yl)phenyl)amino)-10-hexyl-10H-phenothiazine-3-carbaldehyde 

Relevant articles and documents

Mesostructured aluminosilicate alkylation catalysts for the production of aromatic amine antioxidants

The conversion of diphenylamine (DPA) and α-methylstyrene (AMS) to the antioxidants mono- and dicumenyldiphenylamine was carried out over mesostructured aluminosilicate catalysts with hexagonal (2% Al-MCM-41), wormhole (2% Al-HMS), and lamellar/vesicular (2% Al-MSU-G) framework structures. A commercial acid-treated clay catalyst, Engelhard F-20, was included for comparison perposes. The yields of the desired antioxidant, namely dicumenyldiphenylamine (DCDPA), increased in the order F-20 (～57%)3PW12O40·xH2O (PW 12) supported on mesostructured wormhole HMS and lamellar/vesicular MSU-G silica, also was examined as a catalyst for DCDPA production. The supported catalyst systems, however, afforded lower maximum yields of DCDPA (～73-80%) in comparison to the mesostructured aluminosilicate catalysts. The exceptionally high yields of alkylated products obtained with the mesoporous aluminosilicate catalysts in comparison to the F-20 clay and the supported PW12 catalysts are attributable in part to intermediate acid strengths that minimize completing dimerization reactions of the AMS alkylating agent. Also, the pore structures of the mesostructured catalysts facilitate access to active sites on the framework walls and provide more efficient transport of reagents to framework reaction centers. Also, the regular mesoporosity of the aluminosilicate catalysts makes these structures less prone to pore plugging and to the masking of acidity through the adsorption of the high molecular weight reaction products.

Zinc-Catalyzed Alkylation of Aromatic Amines in Continuous Flow

A practical approach to the synthesis of antioxidant 4,4′-dicumyldiphenylamine (DCDPA) and its derivatives by Friedel-Crafts alkylation of aromatic amines was developed under continuous flow conditions. Because of the enhanced mass and heat transfer features of the microreactor, the reaction time was significantly reduced in contrast to a batch mode. The reaction was carried out using a 1:6 v/v ethanol/Cl(CH2)2Cl cosolvent system with ZnCl2 as the catalyst to achieve satisfactory yields. This is an effective method for the synthesis of DCDPA and its derivatives with excellent para selectivity that has the merits of shorter reaction time, easy operation, and straightforward scale-up.

Preparation method of diphenylamine rubber aging inhibitor

The invention relates to a preparation method of a diphenylamine rubber aging inhibitor. An immobilized catalyst is prepared from a Lewis acidic ionic liquid by supporting the Lewis acidic ionic liquid on the surface of a molecular sieve and is applied to an alkylation reaction of diphenylamine. The method can have remarkable progress in the aspects of yield, purity, service life of the catalyst and other aspects as compared with the prior art.