CA1083606A - Preparation de diphenylamine p-styrenee. - Google Patents

Preparation de diphenylamine p-styrenee.

Info

Publication number: CA1083606A
Authority: CA; Canada
Prior art keywords: diphenylamine; styrene; catalyst; para; reaction temperature
Prior art date: 1975-04-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA247,913A

Other languages

English (en)

Inventor

Vipin M. Kothari

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Goodyear Tire and Rubber Co

Original Assignee

Goodyear Tire and Rubber Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-04-18

Filing date

1976-03-15

Publication date

1980-08-12

1976-03-15 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1980-08-12 Application granted granted Critical

1980-08-12 Publication of CA1083606A publication Critical patent/CA1083606A/fr

Status Expired legal-status Critical Current

Links

DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title claims abstract description 42
238000000034 method Methods 0.000 title claims abstract description 12
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 37
239000003054 catalyst Substances 0.000 claims abstract description 25
239000004927 clay Substances 0.000 claims abstract description 11
238000006243 chemical reaction Methods 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 2
229940035422 diphenylamine Drugs 0.000 claims 4
238000006467 substitution reaction Methods 0.000 abstract description 5
230000002378 acidificating effect Effects 0.000 abstract description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 7
239000000047 product Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
235000006708 antioxidants Nutrition 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
229910052681 coesite Inorganic materials 0.000 description 2
229910052906 cristobalite Inorganic materials 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
229910052901 montmorillonite Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910052682 stishovite Inorganic materials 0.000 description 2
229910052905 tridymite Inorganic materials 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
229920000459 Nitrile rubber Polymers 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
229920003244 diene elastomer Polymers 0.000 description 1
239000000539 dimer Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA247,913A 1975-04-18 1976-03-15 Preparation de diphenylamine p-styrenee. Expired CA1083606A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US56951675A	1975-04-18	1975-04-18
US569,516		1975-04-18

Publications (1)

Publication Number	Publication Date
CA1083606A true CA1083606A (fr)	1980-08-12

Family

ID=24275763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA247,913A Expired CA1083606A (fr)	1975-04-18	1976-03-15	Preparation de diphenylamine p-styrenee.

Country Status (6)

Country	Link
JP (1)	JPS51127053A (fr)
CA (1)	CA1083606A (fr)
DE (1)	DE2612060A1 (fr)
FR (1)	FR2307794A1 (fr)
GB (1)	GB1479263A (fr)
IT (1)	IT1058083B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN109369418A (zh) *	2018-10-10	2019-02-22	河南师范大学	一种节能环保型烷基苯胺类液体抗氧剂的连续合成工艺及合成装置

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4263456A (en) *	1976-12-02	1981-04-21	The Goodyear Tire & Rubber Company	Process of preparing styrenated diphenylamine
CA1106409A (fr) *	1977-10-07	1981-08-04	Richard M. D'sidocky	Catalyse modifie par une base de la styrenation de la diphenylamine
DE3067396D1 (en) *	1979-12-22	1984-05-10	British Petroleum Co Plc	Proton-catalysed reactions catalysed by hydrogen ion-exchanged layered clays
SG65759A1 (en) *	1997-06-06	1999-06-22	Ciba Sc Holding Ag	Nonylated diphenylamines
CN104725237A (zh) *	2015-03-25	2015-06-24	江苏飞亚化学工业有限责任公司	苯乙烯化二苯胺防老剂的制备方法

1976
- 1976-03-15 CA CA247,913A patent/CA1083606A/fr not_active Expired
- 1976-03-22 DE DE19762612060 patent/DE2612060A1/de not_active Withdrawn
- 1976-04-05 IT IT4887476A patent/IT1058083B/it active
- 1976-04-08 FR FR7610236A patent/FR2307794A1/fr active Granted
- 1976-04-09 GB GB1462876A patent/GB1479263A/en not_active Expired
- 1976-04-13 JP JP4175176A patent/JPS51127053A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN109369418A (zh) *	2018-10-10	2019-02-22	河南师范大学	一种节能环保型烷基苯胺类液体抗氧剂的连续合成工艺及合成装置

Also Published As

Publication number	Publication date
DE2612060A1 (de)	1976-10-28
FR2307794A1 (fr)	1976-11-12
GB1479263A (en)	1977-07-13
FR2307794B1 (fr)	1980-04-11
JPS51127053A (en)	1976-11-05
IT1058083B (it)	1982-04-10

Legal Events

Date	Code	Title	Description
1997-08-12	MKEX	Expiry

Publication	Publication Date	Title
CA1213614A (fr)	1986-11-04	Preparation d'amines cyclo-aliphatiques ou aromatiques
US4201880A (en)	1980-05-06	Preparation of ortho-alkylated phenols
DE69827893T2 (de)	2005-12-22	Verfahren zur Beseitigung von mehrfach alkylierten Phenolen bei der katalytischen Alkylierung von Phenol
EP0665826A1 (fr)	1995-08-09	Procede de cyclodimerisation de 1,3-butadienes en 4-vinylcyclohexenes.
US3305590A (en)	1967-02-21	Decomposition of alpha hydroperoxy derivatives of alkyl substituted aromatic hydrocarons
US4110253A (en)	1978-08-29	Method for the disproportionation of highly alkylated phenols with phenol
JPS59199644A (ja)	1984-11-12	置換フエノ−ルの製法
CN113004150B (zh)	2021-10-29	一种二苯胺类l57,l67的合成方法
US5097085A (en)	1992-03-17	Process for oligomerizing olefins using phosphorous-containing acid on montmorillonite clay
US4191844A (en)	1980-03-04	Hydrodealkylation process and catalyst
US2283465A (en)	1942-05-19	Treatment of phenols
JP3305102B2 (ja)	2002-07-22	フェノール類のオルソアルキル化触媒、その前駆体、及びそのような触媒を用いるオルソアルキル化フェノール類の製造方法。
CA1095086A (fr)	1981-02-03	Procede d'obtention de diphenylamine styrenee
US4060560A (en)	1977-11-29	Disproportionation of xylenols with phenol to form cresols
CA1106409A (fr)	1981-08-04	Catalyse modifie par une base de la styrenation de la diphenylamine
EP0028200A1 (fr)	1981-05-06	Alcoylation de 2,6-di-tert.-alcoylphénols par des alcanediols
US4407729A (en)	1983-10-04	Catalysts
CH551352A (de)	1974-07-15	Verfahren zur herstellung von 2,6 - dialkyl - und 2,6 diaralkylsubstituierten p - kresol.
US4331566A (en)	1982-05-25	Catalyst for hydrodealkylation process
CN114514069B (zh)	2024-06-21	苯酚烷基化催化剂前体和催化剂及苯酚烷基化方法
US3291847A (en)	1966-12-13	Catalytic alkylation of alkyl-substituted aromatics with monoolefins
US4205017A (en)	1980-05-27	Hydrodehydroxylation process using a rhenium-fluorided alumina catalyst
US4533768A (en)	1985-08-06	Zinc oxide catalyzed dealkylation of alkylated phenols
US2412230A (en)	1946-12-10	Alkylation of aromatic hydrocarbons
DE2612060A1 (de)	1976-10-28	Verfahren zur herstellung von mit styrol umgesetztem diphenylamin

CA1083606A - Preparation de diphenylamine p-styrenee. - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=24275763

Family Applications (1)

Country Status (6)

Cited By (1)

Families Citing this family (5)

Cited By (1)

Also Published As

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Legal Events