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Bis[4-(2-phenyl-2-propyl)phenyl]amine, also known as Antioxidant HS-911, is a high-efficiency, non-toxic antioxidant used to replace carcinogenic antioxidants such as D, A, and RD. It is effective in protecting various types of rubber and plastics from thermal aging, light aging, ozone aging, and damage caused by repeated deformation. HS-911 also has a passivating effect on heavy metal and transition metal.

10081-67-1

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10081-67-1 Usage

Uses

Used in Rubber Industry:
Bis[4-(2-phenyl-2-propyl)phenyl]amine is used as an antioxidant in various types of rubber, including NR, IIR, SBR, NBR, BR, and CR, for its efficient protection against thermal aging. It is especially effective in protecting CR from thermal aging and can be used in insulative and protective rubber sheeting for color wires and cables, as well as common color rubber products, to reduce production costs.
Used in Plastic Industry:
Bis[4-(2-phenyl-2-propyl)phenyl]amine is used as a thermal stabilizer in a wide variety of applications, including polyolefins, styrenics, polyols, hot melt adhesives, lubricants, and polyamides. It provides excellent performance at processing temperatures and has strong synergy with other types of antioxidants such as phenolics and phosphites.
Used in Polyethylene, Polypropylene, and Polyvinyl Chloride:
Bis[4-(2-phenyl-2-propyl)phenyl]amine is used as an antioxidant in color masterbatch for polyethylene, polypropylene, and polyvinyl chloride.
Used in Polyurethane Foam, Rubber Wire, Cable, Food Package, and Adhesive:
Bis[4-(2-phenyl-2-propyl)phenyl]amine is used as an 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.
Used in Polyether and Lubricating Oil:
Bis[4-(2-phenyl-2-propyl)phenyl]amine is used as a light-resistant and anti-aging antioxidant in polyether and as an antioxidant for lubricating oil.
Used in Neoprene Acrylate Rubber and Polyether Polyalcohol:
Bis[4-(2-phenyl-2-propyl)phenyl]amine is used for its resistance to aging caused by high temperature and light in neoprene acrylate rubber and polyether polyalcohol.
Used with Sulfur-Contained Antioxidant:
When used together with sulfur-contained antioxidant, Bis[4-(2-phenyl-2-propyl)phenyl]amine has an operational effect.

Flammability and Explosibility

Nonflammable

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%

Check Digit Verification of cas no

The CAS Registry Mumber 10081-67-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,0,8 and 1 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 10081-67:
(7*1)+(6*0)+(5*0)+(4*8)+(3*1)+(2*6)+(1*7)=61
61 % 10 = 1
So 10081-67-1 is a valid CAS Registry Number.
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

10081-67-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Naugard 445

1.2 Other means of identification

Product number -
Other names 4-(2-phenylpropan-2-yl)-N-[4-(2-phenylpropan-2-yl)phenyl]aniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10081-67-1 SDS

10081-67-1Synthetic route

diphenylamine
122-39-4

diphenylamine

isopropenylbenzene
98-83-9

isopropenylbenzene

A

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

B

4-(α,α-dimethylbenzyl)diphenylamine

4-(α,α-dimethylbenzyl)diphenylamine

Conditions
ConditionsYield
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

diphenylamine

isopropenylbenzene
98-83-9

isopropenylbenzene

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

Conditions
ConditionsYield
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
N-phenyl-1-naphthylamine
90-30-2

N-phenyl-1-naphthylamine

diphenylamine
122-39-4

diphenylamine

isopropenylbenzene
98-83-9

isopropenylbenzene

A

4-nonyldiphenylamine

4-nonyldiphenylamine

B

4-α-methylstyryl-4'-nonyldiphenylamine

4-α-methylstyryl-4'-nonyldiphenylamine

C

4,4'-dinonyldiphenylamine

4,4'-dinonyldiphenylamine

D

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

E

4-(α,α-dimethylbenzyl)diphenylamine

4-(α,α-dimethylbenzyl)diphenylamine

Conditions
ConditionsYield
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;
diphenylamine
122-39-4

diphenylamine

isopropenylbenzene
98-83-9

isopropenylbenzene

A

4-nonyldiphenylamine

4-nonyldiphenylamine

B

4-α-methylstyryl-4'-nonyldiphenylamine

4-α-methylstyryl-4'-nonyldiphenylamine

C

4,4'-dinonyldiphenylamine

4,4'-dinonyldiphenylamine

D

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

E

4-(α,α-dimethylbenzyl)diphenylamine

4-(α,α-dimethylbenzyl)diphenylamine

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

ethyl 10-bromoanthracene-9-carboxylate

ethyl 10-bromoanthracene-9-carboxylate

ethyl 10-[bis[4-(1-methyl-1-phenylethyl)phenyl]amino]anthracene-9-carboxylate

ethyl 10-[bis[4-(1-methyl-1-phenylethyl)phenyl]amino]anthracene-9-carboxylate

Conditions
ConditionsYield
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

9,10-Dibromoanthracene

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

N9,N9,N10,N10-tetrakis(4-(2-phenylpropan-2-yl)phenyl)anthracene-9,10-diamine

N9,N9,N10,N10-tetrakis(4-(2-phenylpropan-2-yl)phenyl)anthracene-9,10-diamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In toluene for 10h; Reflux;80%
ethyl 2-bromoisobutyrate
600-00-0

ethyl 2-bromoisobutyrate

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

3,3-dimethyl-5-(2-phenylpropan-2-yl)-1-(4-(2-phenylpropan-2-yl)phenyl)indolin-2-one

3,3-dimethyl-5-(2-phenylpropan-2-yl)-1-(4-(2-phenylpropan-2-yl)phenyl)indolin-2-one

Conditions
ConditionsYield
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]

2-bromospiro[fluorenyl-9,8'-indolo[3,2,1-de]acridine]

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

C61H48N2

C61H48N2

Conditions
ConditionsYield
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

1-bromo-2,3-dichlorobenzene

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

C66H63ClN2

C66H63ClN2

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

bis[4-(2-phenyl-2-isopropyl)phenyl]-4-nitrophenylamine
1243278-12-7

bis[4-(2-phenyl-2-isopropyl)phenyl]-4-nitrophenylamine

Conditions
ConditionsYield
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

1.4-dibromobenzene

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

N-(4-bromophenyl)-4-(2-phenylpropan-2-yl)-N-(4-(2-phenylpropan-2-yl)phenyl)benzeneamine
1310961-36-4

N-(4-bromophenyl)-4-(2-phenylpropan-2-yl)-N-(4-(2-phenylpropan-2-yl)phenyl)benzeneamine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene at 120℃; for 7h; Inert atmosphere;62%
iodobenzene
591-50-4

iodobenzene

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

C36H35N
259218-10-5

C36H35N

Conditions
ConditionsYield
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

4,4,4-trifluorobutyric acid

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

4-(2-phenylpropan-2-yl)-N-(4-(2-phenylpropan-2-yl)phenyl)-N-(3,3,3-trifluoropropyl)aniline

4-(2-phenylpropan-2-yl)-N-(4-(2-phenylpropan-2-yl)phenyl)-N-(3,3,3-trifluoropropyl)aniline

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

7-bromo-10-hexyl-10H-phenothiazine-3-carbaldehyde
312924-97-3

7-bromo-10-hexyl-10H-phenothiazine-3-carbaldehyde

7-(bis(4-(2-phenylpropan-2-yl)phenyl)amino)-10-hexyl-10H-phenothiazine-3-carbaldehyde
1618093-71-2

7-(bis(4-(2-phenylpropan-2-yl)phenyl)amino)-10-hexyl-10H-phenothiazine-3-carbaldehyde

Conditions
ConditionsYield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene Reflux; Inert atmosphere;45%
carbon tetrabromide
558-13-4

carbon tetrabromide

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

2,7-bis(1-methyl-1-phenylethyl)-N,N-bis[4-(1-methyl-1-phenylethyl)phenyl]acridin-9-amine

2,7-bis(1-methyl-1-phenylethyl)-N,N-bis[4-(1-methyl-1-phenylethyl)phenyl]acridin-9-amine

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

Conditions
ConditionsYield
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-propyl)phenyl]amine

bis[4-(2-phenyl-2-isopropyl)phenyl]-4-aminophenylamine
1243278-14-9

bis[4-(2-phenyl-2-isopropyl)phenyl]-4-aminophenylamine

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

N,N-bis(4-nitrophenyl)-N',N'-bis[4-(2-phenyl-2-isopropyl)phenyl]-1,4-phenylenediamine
1246049-04-6

N,N-bis(4-nitrophenyl)-N',N'-bis[4-(2-phenyl-2-isopropyl)phenyl]-1,4-phenylenediamine

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

N,N-bis(4-aminophenyl)-N',N'-bis[4-(2-phenyl-2-isopropyl)phenyl]-1,4-phenylenediamine
1246048-80-5

N,N-bis(4-aminophenyl)-N',N'-bis[4-(2-phenyl-2-isopropyl)phenyl]-1,4-phenylenediamine

Conditions
ConditionsYield
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

1.4-dibromobenzene

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

C80H79N3

C80H79N3

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

C39H33N3O2S
1350319-91-3

C39H33N3O2S

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

C45H43N3O4S
1350319-92-4

C45H43N3O4S

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

C41H35N3O4S
1350319-94-6

C41H35N3O4S

Conditions
ConditionsYield
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

2-bromothiophene

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

C34H33NS
1350319-90-2

C34H33NS

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

7-bromo-10-hexyl-10H-phenothiazine-3-carbaldehyde
312924-97-3

7-bromo-10-hexyl-10H-phenothiazine-3-carbaldehyde

3-(7-(bis(4-(2-phenylpropan-2-yl)phenyl)amino)-10-hexyl-10H-phenothiazin-3-yl)-2-cyanoacrylic acid
1618093-69-8

3-(7-(bis(4-(2-phenylpropan-2-yl)phenyl)amino)-10-hexyl-10H-phenothiazin-3-yl)-2-cyanoacrylic acid

Conditions
ConditionsYield
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

(S)-epichlorohydrin

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

C33H36ClNO

C33H36ClNO

Conditions
ConditionsYield
With acetic acid at 60 - 65℃; for 48h;
bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

(R)-3-(4,4'-bis(α,α-dimethylbenzyl))diphenylaminopropene oxide

(R)-3-(4,4'-bis(α,α-dimethylbenzyl))diphenylaminopropene oxide

Conditions
ConditionsYield
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

bis[4-(2-phenyl-2-propyl)phenyl]amine

(S)-3-(4,4'-bis(α,α-dimethylbenzyl))diphenylaminopropene oxide

(S)-3-(4,4'-bis(α,α-dimethylbenzyl))diphenylaminopropene oxide

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

bis[4-(2-phenyl-2-propyl)phenyl]amine
10081-67-1

bis[4-(2-phenyl-2-propyl)phenyl]amine

C33H36ClNO

C33H36ClNO

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

10081-67-1Relevant academic research and scientific papers

Mesostructured aluminosilicate alkylation catalysts for the production of aromatic amine antioxidants

Liu, Yu,Kim, Seong Su,Pinnavaia, Thomas J.

, p. 381 - 387 (2004)

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.

Alkylation of diphenylamine with α-methylstyrene and diisobutylene using acid-treated clay catalysts

Chitnis, Sandeep R.,Sharma, Man Mohan

, p. 84 - 94 (1996)

Alkylation of diphenylamine was carried out with α-methylstyrene and diisobutylene using acid-treated clay catalyst Engelhard F-24 to produce mono- and dialkylated diphenylamines. Dialkylated diphenylamines are industrially useful as antioxidants and heat stabilizers. Mono and dialkylated diphenylamines were separated in pure form from the reaction mixture and characterized by FTIR and 1H NMR. Reaction conditions for obtaining high selectivity of each of the alkylated products were studied. A comparative study of the reaction rates, with various other grades of acid-treated clay catalysts, was done for the reaction between diphenylamine and α-methylstyrene. The reaction between diphenylamine and α-methylstyrene was also studied in a continuous mode of operation in a fixed bed reactor. Deactivation of the catalyst occurred during the course of these reactions and reuse of the catalyst posed problems; alternative schemes were considered to regenerate the deactivated catalyst. The basic reasons for the deactivation of the catalyst were investigated in the case of reaction between diphenylamine and α-methylstyrene. The fresh and used catalysts were characterized using various spectroscopic and other techniques such as X-ray diffraction, X-ray photoelectron spectroscopy, UV-visible and nuclear magnetic resonance spectroscopy, surface area (BET) and surface acidity (TPD), pore size distribution, and pore volume. These studies indicated that the deactivation of the catalyst was due to irreversible adsorption on the surface, loss of microporous structure and loss of surface acidity. The adsorbed species appeared to be diphenylamine and/or alkylated product(s), coordinated to the surface oxygen of the catalyst through nitrogen, forming a nitro kind of species.

Zinc-Catalyzed Alkylation of Aromatic Amines in Continuous Flow

Bo, Xiaofan,Mao, Mengmei,Wan, Li,Xin, Zhong,Yao, Hanlin,Zhang, Le

, p. 2078 - 2084 (2020)

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.

Anti-oxidant 4, 4' - double (α, α - dimethyl benzyl) diphenylamine preparation method (by machine translation)

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Paragraph 0020; 0036-0070, (2018/04/01)

The invention discloses a method for antioxidant 4, 4' - double (α, α - dimethyl benzyl) diphenylamine preparation method. First of all the raw materials diphenylamine added to a reaction vessel, heating to melt; melting compound catalyst added after continued heating and stirring; after stir dropwise α - methyl styrene, after dropping the heating reaction; after the reaction, the temperature of the resulting reaction solution, then adding petroleum ether and methanol mixed solvent, cooling to room temperature to crystallize; filtering the final turn, petroleum ether washing, washing and drying, drying to obtain the anti-oxidant 4, 4' - double (α, α - dimethyl benzyl) diphenylamine. This invention adopts the disposable synthetic antioxidant, only need to filter after the reaction, washing can obtain high-quality antioxidant product, without the need of acidified, alkali neutralization, washing and other complex post-treatment process, not three wastes to produce, also saves the many complex steps. Therefore, the invention has obvious economic and social benefits. (by machine translation)

Preparation method of diphenylamine rubber aging inhibitor

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Paragraph 0041; 0059-0060, (2018/01/14)

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.

ALKYLATED PANA AND DPA COMPOSITIONS

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Page/Page column 26-29, (2010/02/14)

The invention relates to a composition comprising a mixture of alkylated N-α-naphthyl-N-phenylamine (PANA) and alkylated diphenylamine (DPA), the product obtainable by alkylat-ing PANA or a mixture of PANA and DPA with alkenes and the process for alkylating PANA or a mixture of PANA and DPA with alkenes. The compositions according to the present in-vention have an outstanding anti-oxidative action, which can be demonstrated by established test methods.

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