CA1083606A - Process of preparing para styrenated diphenylamine. - Google Patents
Process of preparing para styrenated diphenylamine.Info
- Publication number
- CA1083606A CA1083606A CA247,913A CA247913A CA1083606A CA 1083606 A CA1083606 A CA 1083606A CA 247913 A CA247913 A CA 247913A CA 1083606 A CA1083606 A CA 1083606A
- Authority
- CA
- Canada
- Prior art keywords
- diphenylamine
- styrene
- catalyst
- para
- reaction temperature
- Prior art date
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 (en) | 1980-08-12 |
Family
ID=24275763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA247,913A Expired CA1083606A (en) | 1975-04-18 | 1976-03-15 | Process of preparing para styrenated diphenylamine. |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS51127053A (enrdf_load_stackoverflow) |
| CA (1) | CA1083606A (enrdf_load_stackoverflow) |
| DE (1) | DE2612060A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2307794A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1479263A (enrdf_load_stackoverflow) |
| IT (1) | IT1058083B (enrdf_load_stackoverflow) |
Cited By (1)
| 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)
| 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 (en) * | 1977-10-07 | 1981-08-04 | Richard M. D'sidocky | Base modified catalysis in the styrenation of diphenylamine |
| EP0031687B2 (en) * | 1979-12-22 | 1993-06-23 | The British Petroleum Company p.l.c. | 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/en 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)
| 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 |
|---|---|
| FR2307794B1 (enrdf_load_stackoverflow) | 1980-04-11 |
| GB1479263A (en) | 1977-07-13 |
| DE2612060A1 (de) | 1976-10-28 |
| FR2307794A1 (fr) | 1976-11-12 |
| IT1058083B (it) | 1982-04-10 |
| JPS51127053A (en) | 1976-11-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |